Explore 395 cruise vacations

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,864

per Cabin

‌

Departing on:

Sat, Apr 05 - Sun, Apr 13

from (US$)$2,864

Sat, Mar 22 - Sun, Mar 30

from (US$)$4,320

Sat, Apr 19 - Sun, Apr 27

from (US$)$3,026

Western Caribbean Charm

Miami, Florida • Costa Maya • Roatán • Beach Club at Bimini • Miami, Florida

Insider cabins from

$2,100

per Cabin

‌

6 nights

Scarlet Lady & Resilient Lady

+ up to $100 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,100

per Cabin

‌

Departing on:

Sun, Nov 09 - Sat, Nov 15

Sun, Mar 30 - Sat, Apr 05

from (US$)$2,118

Sun, Apr 13 - Sat, Apr 19

from (US$)$2,628

* Port changes in place on select sailings — see full cruise details

Grand Cayman, Costa Maya & More

Miami, Florida • George Town • Costa Maya • Beach Club at Bimini • Miami, Florida

Insider cabins from

$3,230

per Cabin

‌

7 nights

Valiant Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$3,230

per Cabin

‌

Departing on:

Sun, Jul 13 - Sun, Jul 20

from (US$)$3,230

Grand Turk, Puerto Plata & More

Miami, Florida • Puerto Plata • Grand Turk • Beach Club at Bimini • Miami, Florida

Sea View cabins from

$3,852

per Cabin

‌

7 nights

Valiant Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Sea View cabins from

$3,852

per Cabin

‌

Departing on:

Sun, Jul 20 - Sun, Jul 27

from (US$)$3,852

RED HOT

Brilliant Lady Miami MerMaiden

Miami, Florida • Philipsburg, St. Maarten • Tortola • Beach Club at Bimini • Miami, Florida

Insider cabins from

$3,200

per Cabin

‌

8 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$3,200

per Cabin

‌

Departing on:

Fri, Oct 17 - Sat, Oct 25

from (US$)$3,200

Honduras, Mexico & Bahamas

Miami, Florida • Roatán • Costa Maya • Cozumel (Playa del Carmen) • Beach Club at Bimini • Miami, Florida

Insider cabins from

$2,452

per Cabin

‌

7 nights

Scarlet Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,452

per Cabin

‌

Departing on:

Fri, Oct 31 - Fri, Nov 07

from (US$)$2,452

Western Caribbean: From Miami to Bimini

Miami, Florida • Ocho Rios • George Town • Beach Club at Bimini • Miami, Florida

Insider cabins from

$2,170

per Cabin

‌

7 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,170

per Cabin

‌

Departing on:

Sat, Nov 01 - Sat, Nov 08

from (US$)$2,170

One-way to SJ: DR, St. Maarten & BVI

Miami, Florida • Puerto Plata • Philipsburg, St. Maarten • Tortola • San Juan

Insider cabins from

$2,100

per Cabin

‌

6 nights

Valiant Lady

+ up to $100 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,100

per Cabin

‌

Departing on:

Sun, Nov 02 - Sat, Nov 08

Colorful Curaçao to the Charming Caymans

Miami, Florida • Oranjestad • Willemstad • Cartagena • Ocho Rios • George Town • Miami, Florida

Insider cabins from

$3,136

per Cabin

‌

12 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

+ up to $300 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$3,136

per Cabin

‌

Departing on:

Sat, Nov 08 - Thu, Nov 20

from (US$)$3,136

Saint (Isles) & Seas of the Caribbean

San Juan • Tortola • Bridgetown • Castries • St. John's • Philipsburg, St. Maarten • San Juan

Insider cabins from

$2,156

per Cabin

‌

7 nights

Valiant Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,156

per Cabin

‌

Departing on:

Sat, Jan 02 - Sat, Jan 09

Sat, Nov 08 - Sat, Nov 15

from (US$)$2,928

Sat, Mar 21 - Sat, Mar 28

San Juan Sunrises & Dominican Dreams

Miami, Florida • San Juan • Puerto Plata • Beach Club at Bimini • Miami, Florida

Insider cabins from

$1,946

per Cabin

‌

7 nights

Resilient Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,946

per Cabin

‌

Departing on:

Sunny Miles of Tropical Isles

San Juan • Philipsburg, St. Maarten • Bridgetown • Castries • Fort-de-France • Basseterre • San Juan

Insider cabins from

$2,086

per Cabin

‌

7 nights

Valiant Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,086

per Cabin

‌

Departing on:

Sat, Nov 07 - Sat, Nov 14

Sunny San Juan & Isles of Beach Miles

Miami, Florida • Puerto Plata • San Juan • Philipsburg, St. Maarten • St. Croix • Miami, Florida

Insider cabins from

$2,384

per Cabin

‌

8 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,384

per Cabin

‌

Departing on:

Thu, Feb 12 - Fri, Feb 20

from (US$)$2,384

Thu, Nov 20 - Fri, Nov 28

from (US$)$2,402

Cayman Coves & Jamaican Waterfalls

Miami, Florida • Ocho Rios • George Town • Beach Club at Bimini • Miami, Florida

Insider cabins from

$1,948

per Cabin

‌

7 nights

Resilient Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,948

per Cabin

‌

Departing on:

Sat, Dec 06 - Sat, Dec 13

Thanksgiving in the Lesser Antilles

San Juan • Tortola • Basseterre • St. John's • Castries • St. Thomas • San Juan

Insider cabins from

$2,086

per Cabin

‌

7 nights

Valiant Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,086

per Cabin

‌

Departing on:

Antigua Waves & Grand Turk Caves

Miami, Florida • Grand Turk • St. John's • Basseterre • San Juan • Miami, Florida

Insider cabins from

$2,322

per Cabin

‌

9 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

+ up to $300 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,322

per Cabin

‌

Departing on:

Fri, Feb 20 - Sun, Mar 01

Fri, Nov 28 - Sun, Dec 07

from (US$)$2,370

Fri, Jan 23 - Sun, Feb 01

from (US$)$3,210

San Juan to Barbados & the St. Isles

San Juan • Philipsburg, St. Maarten • Basseterre • Roseau • Bridgetown • San Juan

Insider cabins from

$1,548

per Cabin

‌

6 nights

Valiant Lady

+ up to $100 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,548

per Cabin

‌

Departing on:

Sat, Nov 29 - Fri, Dec 05

from (US$)$1,548

San Juan, Samaná & Bimini

Miami, Florida • San Juan • Samaná • Beach Club at Bimini • Miami, Florida

Insider cabins from

$1,946

per Cabin

‌

7 nights

Resilient Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,946

per Cabin

‌

Departing on:

Sat, Nov 29 - Sat, Dec 06

Aruba, Curaçao and the Lesser Antilles

San Juan • Willemstad • Oranjestad • Roseau • St. John's • Philipsburg, St. Maarten • San Juan

Insider cabins from

$2,064

per Cabin

‌

8 nights

Valiant Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,064

per Cabin

‌

Departing on:

Fri, Dec 05 - Sat, Dec 13

from (US$)$2,064

Aruban Sunsets & Calm Cayman Days

Miami, Florida • Oranjestad • Cartagena • Ocho Rios • George Town • Miami, Florida

Insider cabins from

$2,838

per Cabin

‌

11 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

+ up to $300 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,838

per Cabin

‌

Departing on:

Sun, Mar 01 - Thu, Mar 12

from (US$)$2,838

Sun, Dec 07 - Thu, Dec 18

from (US$)$2,868

St. Lucia, St. Maarten, Barbados & More

San Juan • Basseterre • Castries • Roseau • Bridgetown • Philipsburg, St. Maarten • San Juan

Insider cabins from

$2,382

per Cabin

‌

7 nights

Valiant Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,382

per Cabin

‌

Departing on:

Sat, Dec 13 - Sat, Dec 20

from (US$)$2,382

Brilliant Caribbean Holidays

Miami, Florida • Grand Turk • Puerto Plata • San Juan • Samaná • Miami, Florida

Insider cabins from

$3,134

per Cabin

‌

8 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$3,134

per Cabin

‌

Departing on:

Thu, Dec 18 - Fri, Dec 26

from (US$)$3,134

Resilient Caribbean Holidays

Miami, Florida • San Juan • Puerto Plata • Beach Club at Bimini • Miami, Florida

Insider cabins from

$2,786

per Cabin

‌

7 nights

Resilient Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,786

per Cabin

‌

Departing on:

Sun, Dec 20 - Sun, Dec 27

from (US$)$2,788

Valiant Caribbean Holidays

San Juan • Philipsburg, St. Maarten • Basseterre • St. John's • Castries • Tortola • San Juan

Insider cabins from

$2,730

per Cabin

‌

7 nights

Valiant Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,730

per Cabin

‌

Departing on:

from (US$)$2,730

Brilliant New Year's Ahoy!

Miami, Florida • Grand Turk • St. John's • Basseterre • San Juan • Miami, Florida

Insider cabins from

$4,680

per Cabin

‌

9 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

+ up to $300 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$4,680

per Cabin

‌

Departing on:

Fri, Dec 26 - Sun, Jan 04

from (US$)$4,680

Resilient New Year's Ahoy!

Miami, Florida • Ocho Rios • George Town • Beach Club at Bimini • Miami, Florida

Insider cabins from

$3,766

per Cabin

‌

7 nights

Resilient Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$3,766

per Cabin

‌

Departing on:

from (US$)$3,766

Sun, Dec 27 - Sun, Jan 03

from (US$)$3,906

Valiant New Year’s Ahoy!

San Juan • Philipsburg, St. Maarten • Basseterre • Castries • Bridgetown • St. Croix • San Juan

Insider cabins from

$3,768

per Cabin

‌

7 nights

Valiant Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$3,768

per Cabin

‌

Departing on:

from (US$)$3,768

Aruban Sights & Antiguan Nights

San Juan • Oranjestad • Willemstad • St. John's • Philipsburg, St. Maarten • San Juan

Insider cabins from

$2,086

per Cabin

‌

7 nights

Valiant Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,086

per Cabin

‌

Departing on:

Sat, Feb 06 - Sat, Feb 13

Cozumel, Grand Cayman & Bimini

Miami, Florida • George Town • Cozumel (Playa del Carmen) • Beach Club at Bimini • Miami, Florida

Insider cabins from

$1,946

per Cabin

‌

7 nights

Resilient Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,946

per Cabin

‌

Departing on:

Aruba, Bonaire, Colombia, Jamaica & More

Miami, Florida • Oranjestad • Kralendijk • Cartagena • Ocho Rios • George Town • Miami, Florida

Insider cabins from

$2,840

per Cabin

‌

11 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

+ up to $300 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,840

per Cabin

‌

Departing on:

Sun, Jan 04 - Thu, Jan 15

Cayman Isles & Jamaican Miles

Miami, Florida • George Town • Ocho Rios • Beach Club at Bimini • Miami, Florida

Insider cabins from

$1,948

per Cabin

‌

7 nights

Resilient Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,948

per Cabin

‌

Departing on:

Sun, Nov 01 - Sun, Nov 08

Virgin Island Views & Saint Isle Blues

San Juan • Tortola • Bridgetown • Kingstown • Basseterre • St. Croix • San Juan

Insider cabins from

$1,946

per Cabin

‌

7 nights

Valiant Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,946

per Cabin

‌

Departing on:

RED HOT

Grand Turk Tranquility & St. Croix Charm

Miami, Florida • Grand Turk • Puerto Plata • San Juan • St. Croix • Miami, Florida

Insider cabins from

$3,222

per Cabin

‌

8 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$3,222

per Cabin

‌

Departing on:

Thu, Jan 15 - Fri, Jan 23

from (US$)$3,222

St. Kitts, Barbados, Martinique & More

San Juan • Basseterre • Bridgetown • Fort-de-France • St. John's • Philipsburg, St. Maarten • San Juan

Insider cabins from

$1,946

per Cabin

‌

7 nights

Valiant Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,946

per Cabin

‌

Departing on:

Barbados, Antigua, BVI & More

San Juan • Tortola • Bridgetown • Fort-de-France • St. John's • Philipsburg, St. Maarten • San Juan

Insider cabins from

$1,946

per Cabin

‌

7 nights

Valiant Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,946

per Cabin

‌

Departing on:

Antigua & the St. Isles

San Juan • Philipsburg, St. Maarten • Basseterre • St. John's • Castries • St. Thomas • San Juan

Insider cabins from

$1,876

per Cabin

‌

7 nights

Valiant Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,876

per Cabin

‌

Departing on:

from (US$)$1,876

Magnetic Miami to Gorgeous George Town

Miami, Florida • Willemstad • Oranjestad • Cartagena • Ocho Rios • George Town • Miami, Florida

Insider cabins from

$2,840

per Cabin

‌

11 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

+ up to $300 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,840

per Cabin

‌

Departing on:

Sun, Feb 01 - Thu, Feb 12

St. Lucia, Barbados & More

San Juan • Philipsburg, St. Maarten • Basseterre • Castries • Bridgetown • St. Thomas • San Juan

Insider cabins from

$2,016

per Cabin

‌

7 nights

Valiant Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,016

per Cabin

‌

Departing on:

Sat, Feb 07 - Sat, Feb 14

Aruba, Curaçao and the St. Isles

San Juan • Oranjestad • Willemstad • St. Croix • Philipsburg, St. Maarten • San Juan

Insider cabins from

$2,016

per Cabin

‌

7 nights

Valiant Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,016

per Cabin

‌

Departing on:

Sat, Feb 14 - Sat, Feb 21

Antigua, Martinique, & Barbados & More

San Juan • Philipsburg, St. Maarten • Bridgetown • Fort-de-France • St. John's • Tortola • San Juan

Insider cabins from

$2,086

per Cabin

‌

7 nights

Valiant Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,086

per Cabin

‌

Departing on:

Sat, Feb 21 - Sat, Feb 28

Quaint Castries to Elegant Antigua

San Juan • Basseterre • Castries • Fort-de-France • St. John's • Tortola • San Juan

Insider cabins from

$2,228

per Cabin

‌

7 nights

Valiant Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,228

per Cabin

‌

Departing on:

Gorgeous Antigua, St. Kitts & Bimini

Miami, Florida • Puerto Plata • St. John's • Basseterre • Beach Club at Bimini • Miami, Florida

Insider cabins from

$2,322

per Cabin

‌

9 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

+ up to $300 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,322

per Cabin

‌

Departing on:

Thu, Mar 12 - Sat, Mar 21

Costa Mayan Caves & Honduran Waves

Miami, Florida • Costa Maya • Roatán • Cozumel (Playa del Carmen) • Miami, Florida

Insider cabins from

$2,006

per Cabin

‌

6 nights

Resilient Lady

+ up to $100 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,006

per Cabin

‌

Departing on:

Sat, Mar 14 - Fri, Mar 20

from (US$)$2,006

Sunsets in the Lesser Antilles

San Juan • Oranjestad • Willemstad • Fort-de-France • Basseterre • San Juan

Insider cabins from

$2,156

per Cabin

‌

7 nights

Valiant Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,156

per Cabin

‌

Departing on:

Sat, Jan 09 - Sat, Jan 16

Sat, Mar 14 - Sat, Mar 21

Sat, Dec 05 - Sat, Dec 12

RED HOT

Puerto Rican Nights & St. Croix Delights

Miami, Florida • Puerto Plata • San Juan • St. Croix • Beach Club at Bimini • Miami, Florida

Insider cabins from

$2,544

per Cabin

‌

8 nights

Resilient Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,544

per Cabin

‌

Departing on:

Fri, Mar 20 - Sat, Mar 28

Tortola, Charleston, Newport & More

San Juan • Tortola • Puerto Plata • Charleston, South Carolina • Newport, Rhode Island • New York City, New York

Insider cabins from

$2,144

per Cabin

‌

9 nights

Valiant Lady

+ up to $300 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,144

per Cabin

‌

Departing on:

Sat, Mar 28 - Mon, Apr 06

from (US$)$2,144

Puerto Plata, San Juan & Tortola

Miami, Florida • Puerto Plata • San Juan • Tortola • Miami, Florida

Insider cabins from

$2,228

per Cabin

‌

7 nights

Scarlet Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,228

per Cabin

‌

Departing on:

Sun, Apr 19 - Sun, Apr 26

Miami to Grand Turk: Halloween Edition

Miami, Florida • Grand Turk • Puerto Plata • Beach Club at Bimini • Miami, Florida

Insider cabins from

$1,846

per Cabin

‌

6 nights

Scarlet Lady

+ up to $100 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,846

per Cabin

‌

Departing on:

Sun, Oct 25 - Sat, Oct 31

from (US$)$1,846

Mexico & Bimini: Halloween Edition

Miami, Florida • Cozumel (Playa del Carmen) • Costa Maya • Beach Club at Bimini • Miami, Florida

Insider cabins from

$1,968

per Cabin

‌

6 nights

Resilient Lady

+ up to $100 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,968

per Cabin

‌

Departing on:

Mon, Oct 26 - Sun, Nov 01

Valiant's Haunted Halloween Soirée

San Juan • Willemstad • Oranjestad • Fort-de-France • Basseterre • San Juan

Insider cabins from

$2,366

per Cabin

‌

7 nights

Valiant Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,366

per Cabin

‌

Departing on:

Sat, Oct 31 - Sat, Nov 07

from (US$)$2,366

November Nights in the Eastern Caribbean

Miami, Florida • Puerto Plata • San Juan • Tortola • Beach Club at Bimini • Miami, Florida

Insider cabins from

$2,544

per Cabin

‌

8 nights

Resilient Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,544

per Cabin

‌

Departing on:

Sun, Nov 08 - Mon, Nov 16

Caribbean East: Virgin & Saint Isles

San Juan • Tortola • Basseterre • St. John's • Castries • San Juan

Insider cabins from

$1,850

per Cabin

‌

6 nights

Valiant Lady

+ up to $100 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,850

per Cabin

‌

Departing on:

Sat, Jan 23 - Fri, Jan 29

from (US$)$1,850

Sat, Nov 14 - Fri, Nov 20

Sat, Mar 13 - Fri, Mar 19

from (US$)$2,090

St. Isles & Sun-soaked Seas

Miami, Florida • Philipsburg, St. Maarten • Tortola • Basseterre • St. John's • Beach Club at Bimini • Miami, Florida

Insider cabins from

$2,682

per Cabin

‌

10 nights

Brilliant Lady

+ up to $300 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,682

per Cabin

‌

Departing on:

Mon, Jan 25 - Thu, Feb 04

from (US$)$2,682

Sun, Nov 15 - Wed, Nov 25

Mon, Feb 22 - Thu, Mar 04

from (US$)$2,982

Captivating Costa Maya & Cozumel Charm

Miami, Florida • Costa Maya • Cozumel (Playa del Carmen) • Beach Club at Bimini • Miami, Florida

Insider cabins from

$1,908

per Cabin

‌

6 nights

Resilient Lady

+ up to $100 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,908

per Cabin

‌

Departing on:

Mon, Nov 16 - Sun, Nov 22

from (US$)$1,908

Thanksgiving: St. Isles, Aruba & Curaçao

San Juan • St. Thomas • Willemstad • Oranjestad • Basseterre • Philipsburg, St. Maarten • San Juan

Insider cabins from

$2,866

per Cabin

‌

8 nights

Valiant Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,866

per Cabin

‌

Departing on:

Fri, Nov 20 - Sat, Nov 28

from (US$)$2,866

Antiguan Elegance & Sunny St. Isles

San Juan • St. Thomas • Tortola • Basseterre • St. John's • Philipsburg, St. Maarten • San Juan

Insider cabins from

$2,296

per Cabin

‌

7 nights

Valiant Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,296

per Cabin

‌

Departing on:

Sat, Nov 28 - Sat, Dec 05

St. Maarten, Tortola, San Juan & more

Miami, Florida • Philipsburg, St. Maarten • Tortola • St. Croix • San Juan • Puerto Plata • Beach Club at Bimini • Miami, Florida

Insider cabins from

$2,680

per Cabin

‌

10 nights

Brilliant Lady

+ up to $300 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,680

per Cabin

‌

Departing on:

Mon, Jan 11 - Thu, Jan 21

from (US$)$2,680

Mon, Nov 30 - Thu, Dec 10

Mon, Mar 08 - Thu, Mar 18

from (US$)$3,082

Pre-Holiday Caribbean Getaway

Miami, Florida • Philipsburg, St. Maarten • Tortola • San Juan • Beach Club at Bimini • Miami, Florida

Insider cabins from

$2,322

per Cabin

‌

9 nights

Brilliant Lady

+ up to $300 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,322

per Cabin

‌

Departing on:

Mon, Dec 14 - Wed, Dec 23

Valiant Caribbean Holidays

San Juan • Basseterre • Fort-de-France • Oranjestad • Willemstad • San Juan

Insider cabins from

$2,786

per Cabin

‌

7 nights

Valiant Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,786

per Cabin

‌

Departing on:

Sat, Dec 19 - Sat, Dec 26

Valiant New Year's Ahoy!

San Juan • Philipsburg, St. Maarten • Fort-de-France • Bridgetown • Castries • St. John's • San Juan

Insider cabins from

$4,186

per Cabin

‌

7 nights

Valiant Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$4,186

per Cabin

‌

Departing on:

Sat, Dec 26 - Sat, Jan 02

from (US$)$4,186

Brilliant New Year's Ahoy!

Miami, Florida • Philipsburg, St. Maarten • Basseterre • Tortola • St. John's • Beach Club at Bimini • Miami, Florida

Insider cabins from

$5,380

per Cabin

‌

10 nights

Brilliant Lady

+ up to $300 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$5,380

per Cabin

‌

Departing on:

Mon, Dec 28 - Thu, Jan 07

from (US$)$5,380

Puerto Rico to Aruba, Bonaire & More

San Juan • Oranjestad • Willemstad • Kralendijk • Fort-de-France • Philipsburg, St. Maarten • San Juan

Insider cabins from

$2,624

per Cabin

‌

8 nights

Valiant Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,624

per Cabin

‌

Departing on:

Fri, Jan 29 - Sat, Feb 06

from (US$)$2,624

San Juan & St. Isles: Valentine’s Voyage

Miami, Florida • Philipsburg, St. Maarten • Tortola • St. Croix • San Juan • Puerto Plata • Beach Club at Bimini • Miami, Florida

Insider cabins from

$2,980

per Cabin

‌

10 nights

Brilliant Lady

+ up to $300 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,980

per Cabin

‌

Departing on:

Mon, Feb 08 - Thu, Feb 18

from (US$)$2,980

Lesser Antilles: Valentine's Day

San Juan • Oranjestad • Willemstad • Fort-de-France • Basseterre • San Juan

Insider cabins from

$2,438

per Cabin

‌

7 nights

Valiant Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,438

per Cabin

‌

Departing on:

Sat, Feb 13 - Sat, Feb 20

from (US$)$2,438

PR, DR & Bimini: Valentine’s Voyage

Miami, Florida • San Juan • Puerto Plata • Beach Club at Bimini • Miami, Florida

Insider cabins from

$2,660

per Cabin

‌

7 nights

Resilient Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,660

per Cabin

‌

Departing on:

Sun, Feb 14 - Sun, Feb 21

from (US$)$2,660

Saint Isles & The Greater Antilles

San Juan • Tortola • Castries • Bridgetown • Roseau • Philipsburg, St. Maarten • San Juan

Insider cabins from

$2,296

per Cabin

‌

7 nights

Valiant Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,296

per Cabin

‌

Departing on:

Sat, Feb 20 - Sat, Feb 27

Barbados, Dominica & St. Isle Spring

San Juan • St. Thomas • Bridgetown • Kingstown • Roseau • Philipsburg, St. Maarten • San Juan

Insider cabins from

$2,786

per Cabin

‌

8 nights

Valiant Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,786

per Cabin

‌

Departing on:

Fri, Mar 19 - Sat, Mar 27

Colorful Curaçao, Aruba & Antigua

San Juan • Willemstad • Oranjestad • St. John's • Philipsburg, St. Maarten • San Juan

Insider cabins from

$2,436

per Cabin

‌

7 nights

Valiant Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,436

per Cabin

‌

Departing on:

Sat, Mar 27 - Sat, Apr 03

from (US$)$2,436

‌

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Showing 130 cruise vacations that match your search

Eastern Caribbean Antilles

Miami, Florida • Puerto Plata • San Juan • St. Croix • Beach Club at Bimini • Miami, Florida

Insider cabins from

$2,864

per Cabin

‌

8 nights

Scarlet Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,864

per Cabin

‌

Departing on:

Sat, Apr 05 - Sun, Apr 13

from (US$)$2,864

Sat, Mar 22 - Sun, Mar 30

from (US$)$4,320

Sat, Apr 19 - Sun, Apr 27

from (US$)$3,026

Western Caribbean Charm

Miami, Florida • Costa Maya • Roatán • Beach Club at Bimini • Miami, Florida

Insider cabins from

$2,100

per Cabin

‌

6 nights

Scarlet Lady & Resilient Lady

+ up to $100 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,100

per Cabin

‌

Departing on:

Sun, Nov 09 - Sat, Nov 15

Sun, Mar 30 - Sat, Apr 05

from (US$)$2,118

Sun, Apr 13 - Sat, Apr 19

from (US$)$2,628

* Port changes in place on select sailings — see full cruise details

Grand Cayman, Costa Maya & More

Miami, Florida • George Town • Costa Maya • Beach Club at Bimini • Miami, Florida

Insider cabins from

$3,230

per Cabin

‌

7 nights

Valiant Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$3,230

per Cabin

‌

Departing on:

Sun, Jul 13 - Sun, Jul 20

from (US$)$3,230

Grand Turk, Puerto Plata & More

Miami, Florida • Puerto Plata • Grand Turk • Beach Club at Bimini • Miami, Florida

Sea View cabins from

$3,852

per Cabin

‌

7 nights

Valiant Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Sea View cabins from

$3,852

per Cabin

‌

Departing on:

Sun, Jul 20 - Sun, Jul 27

from (US$)$3,852

RED HOT

Brilliant Lady Miami MerMaiden

Miami, Florida • Philipsburg, St. Maarten • Tortola • Beach Club at Bimini • Miami, Florida

Insider cabins from

$3,200

per Cabin

‌

8 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$3,200

per Cabin

‌

Departing on:

Fri, Oct 17 - Sat, Oct 25

from (US$)$3,200

Honduras, Mexico & Bahamas

Miami, Florida • Roatán • Costa Maya • Cozumel (Playa del Carmen) • Beach Club at Bimini • Miami, Florida

Insider cabins from

$2,452

per Cabin

‌

7 nights

Scarlet Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,452

per Cabin

‌

Departing on:

Fri, Oct 31 - Fri, Nov 07

from (US$)$2,452

Western Caribbean: From Miami to Bimini

Miami, Florida • Ocho Rios • George Town • Beach Club at Bimini • Miami, Florida

Insider cabins from

$2,170

per Cabin

‌

7 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,170

per Cabin

‌

Departing on:

Sat, Nov 01 - Sat, Nov 08

from (US$)$2,170

One-way to SJ: DR, St. Maarten & BVI

Miami, Florida • Puerto Plata • Philipsburg, St. Maarten • Tortola • San Juan

Insider cabins from

$2,100

per Cabin

‌

6 nights

Valiant Lady

+ up to $100 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,100

per Cabin

‌

Departing on:

Sun, Nov 02 - Sat, Nov 08

Colorful Curaçao to the Charming Caymans

Miami, Florida • Oranjestad • Willemstad • Cartagena • Ocho Rios • George Town • Miami, Florida

Insider cabins from

$3,136

per Cabin

‌

12 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

+ up to $300 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$3,136

per Cabin

‌

Departing on:

Sat, Nov 08 - Thu, Nov 20

from (US$)$3,136

Saint (Isles) & Seas of the Caribbean

San Juan • Tortola • Bridgetown • Castries • St. John's • Philipsburg, St. Maarten • San Juan

Insider cabins from

$2,156

per Cabin

‌

7 nights

Valiant Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,156

per Cabin

‌

Departing on:

Sat, Jan 02 - Sat, Jan 09

Sat, Nov 08 - Sat, Nov 15

from (US$)$2,928

Sat, Mar 21 - Sat, Mar 28

San Juan Sunrises & Dominican Dreams

Miami, Florida • San Juan • Puerto Plata • Beach Club at Bimini • Miami, Florida

Insider cabins from

$1,946

per Cabin

‌

7 nights

Resilient Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,946

per Cabin

‌

Departing on:

Sunny Miles of Tropical Isles

San Juan • Philipsburg, St. Maarten • Bridgetown • Castries • Fort-de-France • Basseterre • San Juan

Insider cabins from

$2,086

per Cabin

‌

7 nights

Valiant Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,086

per Cabin

‌

Departing on:

Sat, Nov 07 - Sat, Nov 14

Sunny San Juan & Isles of Beach Miles

Miami, Florida • Puerto Plata • San Juan • Philipsburg, St. Maarten • St. Croix • Miami, Florida

Insider cabins from

$2,384

per Cabin

‌

8 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,384

per Cabin

‌

Departing on:

Thu, Feb 12 - Fri, Feb 20

from (US$)$2,384

Thu, Nov 20 - Fri, Nov 28

from (US$)$2,402

Cayman Coves & Jamaican Waterfalls

Miami, Florida • Ocho Rios • George Town • Beach Club at Bimini • Miami, Florida

Insider cabins from

$1,948

per Cabin

‌

7 nights

Resilient Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,948

per Cabin

‌

Departing on:

Sat, Dec 06 - Sat, Dec 13

Thanksgiving in the Lesser Antilles

San Juan • Tortola • Basseterre • St. John's • Castries • St. Thomas • San Juan

Insider cabins from

$2,086

per Cabin

‌

7 nights

Valiant Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,086

per Cabin

‌

Departing on:

Antigua Waves & Grand Turk Caves

Miami, Florida • Grand Turk • St. John's • Basseterre • San Juan • Miami, Florida

Insider cabins from

$2,322

per Cabin

‌

9 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

+ up to $300 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,322

per Cabin

‌

Departing on:

Fri, Feb 20 - Sun, Mar 01

Fri, Nov 28 - Sun, Dec 07

from (US$)$2,370

Fri, Jan 23 - Sun, Feb 01

from (US$)$3,210

San Juan to Barbados & the St. Isles

San Juan • Philipsburg, St. Maarten • Basseterre • Roseau • Bridgetown • San Juan

Insider cabins from

$1,548

per Cabin

‌

6 nights

Valiant Lady

+ up to $100 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,548

per Cabin

‌

Departing on:

Sat, Nov 29 - Fri, Dec 05

from (US$)$1,548

San Juan, Samaná & Bimini

Miami, Florida • San Juan • Samaná • Beach Club at Bimini • Miami, Florida

Insider cabins from

$1,946

per Cabin

‌

7 nights

Resilient Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,946

per Cabin

‌

Departing on:

Sat, Nov 29 - Sat, Dec 06

Aruba, Curaçao and the Lesser Antilles

San Juan • Willemstad • Oranjestad • Roseau • St. John's • Philipsburg, St. Maarten • San Juan

Insider cabins from

$2,064

per Cabin

‌

8 nights

Valiant Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,064

per Cabin

‌

Departing on:

Fri, Dec 05 - Sat, Dec 13

from (US$)$2,064

Aruban Sunsets & Calm Cayman Days

Miami, Florida • Oranjestad • Cartagena • Ocho Rios • George Town • Miami, Florida

Insider cabins from

$2,838

per Cabin

‌

11 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

+ up to $300 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,838

per Cabin

‌

Departing on:

Sun, Mar 01 - Thu, Mar 12

from (US$)$2,838

Sun, Dec 07 - Thu, Dec 18

from (US$)$2,868

St. Lucia, St. Maarten, Barbados & More

San Juan • Basseterre • Castries • Roseau • Bridgetown • Philipsburg, St. Maarten • San Juan

Insider cabins from

$2,382

per Cabin

‌

7 nights

Valiant Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,382

per Cabin

‌

Departing on:

Sat, Dec 13 - Sat, Dec 20

from (US$)$2,382

Brilliant Caribbean Holidays

Miami, Florida • Grand Turk • Puerto Plata • San Juan • Samaná • Miami, Florida

Insider cabins from

$3,134

per Cabin

‌

8 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$3,134

per Cabin

‌

Departing on:

Thu, Dec 18 - Fri, Dec 26

from (US$)$3,134

Resilient Caribbean Holidays

Miami, Florida • San Juan • Puerto Plata • Beach Club at Bimini • Miami, Florida

Insider cabins from

$2,786

per Cabin

‌

7 nights

Resilient Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,786

per Cabin

‌

Departing on:

Sun, Dec 20 - Sun, Dec 27

from (US$)$2,788

Valiant Caribbean Holidays

San Juan • Philipsburg, St. Maarten • Basseterre • St. John's • Castries • Tortola • San Juan

Insider cabins from

$2,730

per Cabin

‌

7 nights

Valiant Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,730

per Cabin

‌

Departing on:

from (US$)$2,730

Brilliant New Year's Ahoy!

Miami, Florida • Grand Turk • St. John's • Basseterre • San Juan • Miami, Florida

Insider cabins from

$4,680

per Cabin

‌

9 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

+ up to $300 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$4,680

per Cabin

‌

Departing on:

Fri, Dec 26 - Sun, Jan 04

from (US$)$4,680

Resilient New Year's Ahoy!

Miami, Florida • Ocho Rios • George Town • Beach Club at Bimini • Miami, Florida

Insider cabins from

$3,766

per Cabin

‌

7 nights

Resilient Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$3,766

per Cabin

‌

Departing on:

from (US$)$3,766

Sun, Dec 27 - Sun, Jan 03

from (US$)$3,906

Valiant New Year’s Ahoy!

San Juan • Philipsburg, St. Maarten • Basseterre • Castries • Bridgetown • St. Croix • San Juan

Insider cabins from

$3,768

per Cabin

‌

7 nights

Valiant Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$3,768

per Cabin

‌

Departing on:

from (US$)$3,768

Aruban Sights & Antiguan Nights

San Juan • Oranjestad • Willemstad • St. John's • Philipsburg, St. Maarten • San Juan

Insider cabins from

$2,086

per Cabin

‌

7 nights

Valiant Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,086

per Cabin

‌

Departing on:

Sat, Feb 06 - Sat, Feb 13

Cozumel, Grand Cayman & Bimini

Miami, Florida • George Town • Cozumel (Playa del Carmen) • Beach Club at Bimini • Miami, Florida

Insider cabins from

$1,946

per Cabin

‌

7 nights

Resilient Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,946

per Cabin

‌

Departing on:

Aruba, Bonaire, Colombia, Jamaica & More

Miami, Florida • Oranjestad • Kralendijk • Cartagena • Ocho Rios • George Town • Miami, Florida

Insider cabins from

$2,840

per Cabin

‌

11 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

+ up to $300 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,840

per Cabin

‌

Departing on:

Sun, Jan 04 - Thu, Jan 15

Cayman Isles & Jamaican Miles

Miami, Florida • George Town • Ocho Rios • Beach Club at Bimini • Miami, Florida

Insider cabins from

$1,948

per Cabin

‌

7 nights

Resilient Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,948

per Cabin

‌

Departing on:

Sun, Nov 01 - Sun, Nov 08

Virgin Island Views & Saint Isle Blues

San Juan • Tortola • Bridgetown • Kingstown • Basseterre • St. Croix • San Juan

Insider cabins from

$1,946

per Cabin

‌

7 nights

Valiant Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,946

per Cabin

‌

Departing on:

RED HOT

Grand Turk Tranquility & St. Croix Charm

Miami, Florida • Grand Turk • Puerto Plata • San Juan • St. Croix • Miami, Florida

Insider cabins from

$3,222

per Cabin

‌

8 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$3,222

per Cabin

‌

Departing on:

Thu, Jan 15 - Fri, Jan 23

from (US$)$3,222

St. Kitts, Barbados, Martinique & More

San Juan • Basseterre • Bridgetown • Fort-de-France • St. John's • Philipsburg, St. Maarten • San Juan

Insider cabins from

$1,946

per Cabin

‌

7 nights

Valiant Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,946

per Cabin

‌

Departing on:

Barbados, Antigua, BVI & More

San Juan • Tortola • Bridgetown • Fort-de-France • St. John's • Philipsburg, St. Maarten • San Juan

Insider cabins from

$1,946

per Cabin

‌

7 nights

Valiant Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,946

per Cabin

‌

Departing on:

Antigua & the St. Isles

San Juan • Philipsburg, St. Maarten • Basseterre • St. John's • Castries • St. Thomas • San Juan

Insider cabins from

$1,876

per Cabin

‌

7 nights

Valiant Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,876

per Cabin

‌

Departing on:

from (US$)$1,876

Magnetic Miami to Gorgeous George Town

Miami, Florida • Willemstad • Oranjestad • Cartagena • Ocho Rios • George Town • Miami, Florida

Insider cabins from

$2,840

per Cabin

‌

11 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

+ up to $300 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,840

per Cabin

‌

Departing on:

Sun, Feb 01 - Thu, Feb 12

St. Lucia, Barbados & More

San Juan • Philipsburg, St. Maarten • Basseterre • Castries • Bridgetown • St. Thomas • San Juan

Insider cabins from

$2,016

per Cabin

‌

7 nights

Valiant Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,016

per Cabin

‌

Departing on:

Sat, Feb 07 - Sat, Feb 14

Aruba, Curaçao and the St. Isles

San Juan • Oranjestad • Willemstad • St. Croix • Philipsburg, St. Maarten • San Juan

Insider cabins from

$2,016

per Cabin

‌

7 nights

Valiant Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,016

per Cabin

‌

Departing on:

Sat, Feb 14 - Sat, Feb 21

Antigua, Martinique, & Barbados & More

San Juan • Philipsburg, St. Maarten • Bridgetown • Fort-de-France • St. John's • Tortola • San Juan

Insider cabins from

$2,086

per Cabin

‌

7 nights

Valiant Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,086

per Cabin

‌

Departing on:

Sat, Feb 21 - Sat, Feb 28

Quaint Castries to Elegant Antigua

San Juan • Basseterre • Castries • Fort-de-France • St. John's • Tortola • San Juan

Insider cabins from

$2,228

per Cabin

‌

7 nights

Valiant Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,228

per Cabin

‌

Departing on:

Gorgeous Antigua, St. Kitts & Bimini

Miami, Florida • Puerto Plata • St. John's • Basseterre • Beach Club at Bimini • Miami, Florida

Insider cabins from

$2,322

per Cabin

‌

9 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

+ up to $300 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,322

per Cabin

‌

Departing on:

Thu, Mar 12 - Sat, Mar 21

Costa Mayan Caves & Honduran Waves

Miami, Florida • Costa Maya • Roatán • Cozumel (Playa del Carmen) • Miami, Florida

Insider cabins from

$2,006

per Cabin

‌

6 nights

Resilient Lady

+ up to $100 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,006

per Cabin

‌

Departing on:

Sat, Mar 14 - Fri, Mar 20

from (US$)$2,006

Sunsets in the Lesser Antilles

San Juan • Oranjestad • Willemstad • Fort-de-France • Basseterre • San Juan

Insider cabins from

$2,156

per Cabin

‌

7 nights

Valiant Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,156

per Cabin

‌

Departing on:

Sat, Jan 09 - Sat, Jan 16

Sat, Mar 14 - Sat, Mar 21

Sat, Dec 05 - Sat, Dec 12

RED HOT

Puerto Rican Nights & St. Croix Delights

Miami, Florida • Puerto Plata • San Juan • St. Croix • Beach Club at Bimini • Miami, Florida

Insider cabins from

$2,544

per Cabin

‌

8 nights

Resilient Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,544

per Cabin

‌

Departing on:

Fri, Mar 20 - Sat, Mar 28

Tortola, Charleston, Newport & More

San Juan • Tortola • Puerto Plata • Charleston, South Carolina • Newport, Rhode Island • New York City, New York

Insider cabins from

$2,144

per Cabin

‌

9 nights

Valiant Lady

+ up to $300 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,144

per Cabin

‌

Departing on:

Sat, Mar 28 - Mon, Apr 06

from (US$)$2,144

Puerto Plata, San Juan & Tortola

Miami, Florida • Puerto Plata • San Juan • Tortola • Miami, Florida

Insider cabins from

$2,228

per Cabin

‌

7 nights

Scarlet Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,228

per Cabin

‌

Departing on:

Sun, Apr 19 - Sun, Apr 26

Miami to Grand Turk: Halloween Edition

Miami, Florida • Grand Turk • Puerto Plata • Beach Club at Bimini • Miami, Florida

Insider cabins from

$1,846

per Cabin

‌

6 nights

Scarlet Lady

+ up to $100 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,846

per Cabin

‌

Departing on:

Sun, Oct 25 - Sat, Oct 31

from (US$)$1,846

Mexico & Bimini: Halloween Edition

Miami, Florida • Cozumel (Playa del Carmen) • Costa Maya • Beach Club at Bimini • Miami, Florida

Insider cabins from

$1,968

per Cabin

‌

6 nights

Resilient Lady

+ up to $100 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,968

per Cabin

‌

Departing on:

Mon, Oct 26 - Sun, Nov 01

Valiant's Haunted Halloween Soirée

San Juan • Willemstad • Oranjestad • Fort-de-France • Basseterre • San Juan

Insider cabins from

$2,366

per Cabin

‌

7 nights

Valiant Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,366

per Cabin

‌

Departing on:

Sat, Oct 31 - Sat, Nov 07

from (US$)$2,366

November Nights in the Eastern Caribbean

Miami, Florida • Puerto Plata • San Juan • Tortola • Beach Club at Bimini • Miami, Florida

Insider cabins from

$2,544

per Cabin

‌

8 nights

Resilient Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,544

per Cabin

‌

Departing on:

Sun, Nov 08 - Mon, Nov 16

Caribbean East: Virgin & Saint Isles

San Juan • Tortola • Basseterre • St. John's • Castries • San Juan

Insider cabins from

$1,850

per Cabin

‌

6 nights

Valiant Lady

+ up to $100 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,850

per Cabin

‌

Departing on:

Sat, Jan 23 - Fri, Jan 29

from (US$)$1,850

Sat, Nov 14 - Fri, Nov 20

Sat, Mar 13 - Fri, Mar 19

from (US$)$2,090

St. Isles & Sun-soaked Seas

Miami, Florida • Philipsburg, St. Maarten • Tortola • Basseterre • St. John's • Beach Club at Bimini • Miami, Florida

Insider cabins from

$2,682

per Cabin

‌

10 nights

Brilliant Lady

+ up to $300 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,682

per Cabin

‌

Departing on:

Mon, Jan 25 - Thu, Feb 04

from (US$)$2,682

Sun, Nov 15 - Wed, Nov 25

Mon, Feb 22 - Thu, Mar 04

from (US$)$2,982

Captivating Costa Maya & Cozumel Charm

Miami, Florida • Costa Maya • Cozumel (Playa del Carmen) • Beach Club at Bimini • Miami, Florida

Insider cabins from

$1,908

per Cabin

‌

6 nights

Resilient Lady

+ up to $100 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,908

per Cabin

‌

Departing on:

Mon, Nov 16 - Sun, Nov 22

from (US$)$1,908

Thanksgiving: St. Isles, Aruba & Curaçao

San Juan • St. Thomas • Willemstad • Oranjestad • Basseterre • Philipsburg, St. Maarten • San Juan

Insider cabins from

$2,866

per Cabin

‌

8 nights

Valiant Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,866

per Cabin

‌

Departing on:

Fri, Nov 20 - Sat, Nov 28

from (US$)$2,866

Antiguan Elegance & Sunny St. Isles

San Juan • St. Thomas • Tortola • Basseterre • St. John's • Philipsburg, St. Maarten • San Juan

Insider cabins from

$2,296

per Cabin

‌

7 nights

Valiant Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,296

per Cabin

‌

Departing on:

Sat, Nov 28 - Sat, Dec 05

St. Maarten, Tortola, San Juan & more

Miami, Florida • Philipsburg, St. Maarten • Tortola • St. Croix • San Juan • Puerto Plata • Beach Club at Bimini • Miami, Florida

Insider cabins from

$2,680

per Cabin

‌

10 nights

Brilliant Lady

+ up to $300 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,680

per Cabin

‌

Departing on:

Mon, Jan 11 - Thu, Jan 21

from (US$)$2,680

Mon, Nov 30 - Thu, Dec 10

Mon, Mar 08 - Thu, Mar 18

from (US$)$3,082

Pre-Holiday Caribbean Getaway

Miami, Florida • Philipsburg, St. Maarten • Tortola • San Juan • Beach Club at Bimini • Miami, Florida

Insider cabins from

$2,322

per Cabin

‌

9 nights

Brilliant Lady

+ up to $300 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,322

per Cabin

‌

Departing on:

Mon, Dec 14 - Wed, Dec 23

Valiant Caribbean Holidays

San Juan • Basseterre • Fort-de-France • Oranjestad • Willemstad • San Juan

Insider cabins from

$2,786

per Cabin

‌

7 nights

Valiant Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,786

per Cabin

‌

Departing on:

Sat, Dec 19 - Sat, Dec 26

Valiant New Year's Ahoy!

San Juan • Philipsburg, St. Maarten • Fort-de-France • Bridgetown • Castries • St. John's • San Juan

Insider cabins from

$4,186

per Cabin

‌

7 nights

Valiant Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$4,186

per Cabin

‌

Departing on:

Sat, Dec 26 - Sat, Jan 02

from (US$)$4,186

Brilliant New Year's Ahoy!

Miami, Florida • Philipsburg, St. Maarten • Basseterre • Tortola • St. John's • Beach Club at Bimini • Miami, Florida

Insider cabins from

$5,380

per Cabin

‌

10 nights

Brilliant Lady

+ up to $300 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$5,380

per Cabin

‌

Departing on:

Mon, Dec 28 - Thu, Jan 07

from (US$)$5,380

Puerto Rico to Aruba, Bonaire & More

San Juan • Oranjestad • Willemstad • Kralendijk • Fort-de-France • Philipsburg, St. Maarten • San Juan

Insider cabins from

$2,624

per Cabin

‌

8 nights

Valiant Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,624

per Cabin

‌

Departing on:

Fri, Jan 29 - Sat, Feb 06

from (US$)$2,624

San Juan & St. Isles: Valentine’s Voyage

Miami, Florida • Philipsburg, St. Maarten • Tortola • St. Croix • San Juan • Puerto Plata • Beach Club at Bimini • Miami, Florida

Insider cabins from

$2,980

per Cabin

‌

10 nights

Brilliant Lady

+ up to $300 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,980

per Cabin

‌

Departing on:

Mon, Feb 08 - Thu, Feb 18

from (US$)$2,980

Lesser Antilles: Valentine's Day

San Juan • Oranjestad • Willemstad • Fort-de-France • Basseterre • San Juan

Insider cabins from

$2,438

per Cabin

‌

7 nights

Valiant Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,438

per Cabin

‌

Departing on:

Sat, Feb 13 - Sat, Feb 20

from (US$)$2,438

PR, DR & Bimini: Valentine’s Voyage

Miami, Florida • San Juan • Puerto Plata • Beach Club at Bimini • Miami, Florida

Insider cabins from

$2,660

per Cabin

‌

7 nights

Resilient Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,660

per Cabin

‌

Departing on:

Sun, Feb 14 - Sun, Feb 21

from (US$)$2,660

Saint Isles & The Greater Antilles

San Juan • Tortola • Castries • Bridgetown • Roseau • Philipsburg, St. Maarten • San Juan

Insider cabins from

$2,296

per Cabin

‌

7 nights

Valiant Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,296

per Cabin

‌

Departing on:

Sat, Feb 20 - Sat, Feb 27

Barbados, Dominica & St. Isle Spring

San Juan • St. Thomas • Bridgetown • Kingstown • Roseau • Philipsburg, St. Maarten • San Juan

Insider cabins from

$2,786

per Cabin

‌

8 nights

Valiant Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,786

per Cabin

‌

Departing on:

Fri, Mar 19 - Sat, Mar 27

Colorful Curaçao, Aruba & Antigua

San Juan • Willemstad • Oranjestad • St. John's • Philipsburg, St. Maarten • San Juan

Insider cabins from

$2,436

per Cabin

‌

7 nights

Valiant Lady

+ up to $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,436

per Cabin

‌

Departing on: