Explore over 320 cruise vacations

+ $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,744

per Cabin

Departing on:

Sat, Jan 25 - Sun, Feb 02

from $1,744

Sat, Dec 14 - Sun, Dec 22

from $1,904

Sat, Jan 11 - Sun, Jan 19

from $2,224

Saint (Isles) & Seas of the Caribbean

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

Insider cabins from

$1,668

per Cabin

7 nights

Resilient Lady & Valiant Lady

Sat, Dec 14 - Sat, Dec 21

+ $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,668

per Cabin

Departing on:

2024Best Rate

from $1,668

Sat, Mar 08 - Sat, Mar 15

from $2,786

Sat, Nov 08 - Sat, Nov 15

SAVINGS TO WRITE HOME ABOUT

80% off your 2nd Sailor + free drinks

Always Included Luxury covers your WiFi, tips & gratuities, all dining, & more.

Dominican Daze

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

Insider cabins from

$1,286

per Cabin

5 nights

Valiant Lady & Scarlet Lady

+ $100 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,286

per Cabin

Departing on:

Fri, Feb 28 - Wed, Mar 05

from $1,286

Sun, Dec 15 - Fri, Dec 20

from $1,870

Fri, Jan 03 - Wed, Jan 08

from $2,500

Fire & Sunset Soirées

Miami, Florida • Key West, Florida • Beach Club at Bimini • Miami, Florida

Insider cabins from

$1,192

per Cabin

4 nights

Valiant Lady & Scarlet Lady

+ $100 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,192

per Cabin

Departing on:

Wed, Feb 19 - Sun, Feb 23

from $1,192

Thu, Dec 26 - Mon, Dec 30

from $10,678

Only suites remaining

Wed, Jan 08 - Sun, Jan 12

from $5,200

Only suites remaining

Scarlet New Year's Ahoy!

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

Sea View cabins from

$4,786

per Cabin

8 nights

Scarlet Lady

+ $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Sea View cabins from

$4,786

per Cabin

Departing on:

Sat, Dec 28 - Sun, Jan 05

from $4,786

Valiant New Year's Ahoy!

Miami, Florida • Key West, Florida • Beach Club at Bimini • Miami, Florida

Sea View cabins from

$3,202

per Cabin

4 nights

Valiant Lady

+ $100 in drinks — on us

Getaways for 80% off 2nd Sailor

Sea View cabins from

$3,202

per Cabin

Departing on:

Mon, Dec 30 - Fri, Jan 03

from $3,202

Sunsets in the Lesser Antilles

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

Insider cabins from

$1,806

per Cabin

7 nights

Resilient Lady & Valiant Lady

+ $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,806

per Cabin

Departing on:

Sat, Jan 04 - Sat, Jan 11

from $1,806

Sat, Feb 01 - Sat, Feb 08

from $2,926

Sat, Feb 15 - Sat, Feb 22

from $2,660

Western Caribbean Charm

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

Insider cabins from

$1,428

per Cabin

6 nights

Scarlet Lady & Resilient Lady

+ $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,428

per Cabin

Departing on:

Sun, Feb 02 - Sat, Feb 08

from $1,428

Sun, Jan 05 - Sat, Jan 11

from $9,864

Only suites remaining

Sun, Jan 19 - Sat, Jan 25

from $2,640

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

San Juan, St. Vincent, Barbados & More

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

Sea View cabins from

$3,402

per Cabin

10 nights

Resilient Lady

+ $300 in drinks — on us

Getaways for 80% off 2nd Sailor

Sea View cabins from

$3,402

per Cabin

Departing on:

Sat, Jan 11 - Tue, Jan 21

from $3,402

Riviera Maya

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

Insider cabins from

$1,288

per Cabin

5 nights

Valiant Lady & Scarlet Lady

+ $100 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,288

per Cabin

Departing on:

Sun, Feb 09 - Fri, Feb 14

from $1,288

Sun, Jan 12 - Fri, Jan 17

from $1,990

Sun, Jan 26 - Fri, Jan 31

from $1,990

Idyllic Caribbean Isles & Colombia

San Juan • Cartagena • Willemstad • Oranjestad • Castries • St. John's • Philipsburg • San Juan

Insider cabins from

$2,310

per Cabin

11 nights

Resilient Lady

+ $300 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,310

per Cabin

Departing on:

Tue, Jan 21 - Sat, Feb 01

from $2,310

Resilient Valentine's Voyage

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

Sea View cabins from

$3,206

per Cabin

7 nights

Resilient Lady

+ $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Sea View cabins from

$3,206

per Cabin

Departing on:

Sat, Feb 08 - Sat, Feb 15

from $3,206

Scarlet Valentine's Voyage

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

Insider cabins from

$2,320

per Cabin

8 nights

Scarlet Lady

+ $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,320

per Cabin

Departing on:

Sat, Feb 08 - Sun, Feb 16

from $2,320

Valiant Valentine's Voyage

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

Sea View cabins from

$1,690

per Cabin

5 nights

Valiant Lady

+ $100 in drinks — on us

Getaways for 80% off 2nd Sailor

Sea View cabins from

$1,690

per Cabin

Departing on:

Fri, Feb 14 - Wed, Feb 19

from $1,690

San Juan, Barbados & Beyond

San Juan • Philipsburg • Castries • Bridgetown • Fort-de-France • Basseterre • San Juan

Insider cabins from

$2,506

per Cabin

7 nights

Resilient Lady

+ $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,506

per Cabin

Departing on:

Sat, Mar 01 - Sat, Mar 08

from $2,506

Puerto Rican Daze & Caribbean Nights

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

Insider cabins from

$2,182

per Cabin

10 nights

Resilient Lady

+ $300 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,182

per Cabin

Departing on:

Sat, Mar 22 - Tue, Apr 01

from $2,182

Colombia & Caribbean Islands

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

Insider cabins from

$2,824

per Cabin

11 nights

Resilient Lady

+ $300 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,824

per Cabin

Departing on:

Tue, Apr 01 - Sat, Apr 12

from $2,824

Sunny Daze in Puerto Plata & Nassau

Miami, Florida • Puerto Plata • Nassau • Miami, Florida

Sea View cabins from

$2,190

per Cabin

5 nights

Valiant Lady

+ $100 in drinks — on us

Getaways for 80% off 2nd Sailor

Sea View cabins from

$2,190

per Cabin

Departing on:

Fri, Apr 11 - Wed, Apr 16

from $2,190

A Virgin Celebration Voyage (Miami)

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

Insider cabins from

$1,690

per Cabin

5 nights

Valiant Lady

+ $100 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,690

per Cabin

Departing on:

Sun, May 04 - Fri, May 09

from $1,690

Mayan Sol

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

Insider cabins from

$1,490

per Cabin

5 nights

Valiant Lady

+ $100 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,490

per Cabin

Departing on:

Sun, Sep 07 - Fri, Sep 12

from $1,490

Sun, May 18 - Fri, May 23

from $1,890

Sun, Jun 15 - Fri, Jun 20

from $1,890

Grand Cayman, Costa Maya & More

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

Insider cabins from

$2,788

per Cabin

7 nights

Valiant Lady

+ $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,788

per Cabin

Departing on:

Sun, Jul 13 - Sun, Jul 20

from $2,788

Grand Turk, Puerto Plata & More

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

Insider cabins from

$3,290

per Cabin

7 nights

Valiant Lady

+ $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$3,290

per Cabin

Departing on:

Sun, Jul 20 - Sun, Jul 27

from $3,290

Virgin Voyages Comedy Fest from Miami

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

Insider cabins from

$1,692

per Cabin

5 nights

Valiant Lady

+ $100 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,692

per Cabin

Departing on:

Sun, Aug 10 - Fri, Aug 15

from $1,692

Brilliant Lady Miami MerMaiden

Miami, Florida • Philipsburg • Tortola • Beach Club at Bimini • Miami, Florida

Insider cabins from

$3,186

per Cabin

8 nights

Brilliant Lady

+ $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$3,186

per Cabin

Departing on:

Fri, Oct 17 - Sat, Oct 25

from $3,186

Riviera Maya: Halloween Edition

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

Insider cabins from

$1,490

per Cabin

5 nights

Valiant Lady

+ $100 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,490

per Cabin

Departing on:

Sun, Oct 19 - Fri, Oct 24

from $1,490

Dominican Daze: Halloween Edition

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

Insider cabins from

$1,590

per Cabin

5 nights

Valiant Lady

+ $100 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,590

per Cabin

Departing on:

Fri, Oct 24 - Wed, Oct 29

from $1,590

Valiant's Haunted Halloween Soirée

Miami, Florida • Key West, Florida • Beach Club at Bimini • Miami, Florida

Insider cabins from

$1,280

per Cabin

4 nights

Valiant Lady

+ $100 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,280

per Cabin

Departing on:

Wed, Oct 29 - Sun, Nov 02

from $1,280

Honduras, Mexico & Bahamas

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

Insider cabins from

$2,088

per Cabin

7 nights

Scarlet Lady

+ $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,088

per Cabin

Departing on:

Fri, Oct 31 - Fri, Nov 07

from $2,088

Western Caribbean: From Miami to Bimini

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

Insider cabins from

$2,086

per Cabin

7 nights

Brilliant Lady

+ $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,086

per Cabin

Departing on:

Sat, Nov 01 - Sat, Nov 08

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

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

Insider cabins from

$1,788

per Cabin

6 nights

Valiant Lady

+ $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,788

per Cabin

Departing on:

Sun, Nov 02 - Sat, Nov 08

from $1,788

Colorful Curacao to the Charming Caymans

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

Insider cabins from

$3,096

per Cabin

12 nights

Brilliant Lady

+ $300 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$3,096

per Cabin

Departing on:

Sat, Nov 08 - Thu, Nov 20

from $3,096

San Juan Sunrises & Dominican Dreams

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

Insider cabins from

$2,086

per Cabin

7 nights

Resilient Lady

+ $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,086

per Cabin

Departing on:

Sat, Nov 15 - Sat, Nov 22

Sat, Jan 31 - Sat, Feb 07

Sat, Feb 28 - Sat, Mar 07

Sunny Miles of Tropical Isles

San Juan • Philipsburg • Bridgetown • Castries • Fort-de-France • Basseterre • San Juan

Insider cabins from

$1,948

per Cabin

7 nights

Valiant Lady

+ $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,948

per Cabin

Departing on:

Sat, Nov 15 - Sat, Nov 22

Sat, Feb 28 - Sat, Mar 07

From Miami to St. Croix

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

Insider cabins from

$2,384

per Cabin

8 nights

Brilliant Lady

+ $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 $2,384

Thu, Nov 20 - Fri, Nov 28

from $2,386

Miami, Grand Turk (& back)

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

Insider cabins from

$1,590

per Cabin

5 nights

Scarlet Lady & Resilient Lady

+ $100 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,590

per Cabin

Departing on:

Fri, Dec 19 - Wed, Dec 24

from $1,590

Fri, Nov 21 - Wed, Nov 26

from $1,592

Fri, Jan 16 - Wed, Jan 21

from $1,690

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

+ $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,948

per Cabin

Departing on:

Sat, Jan 24 - Sat, Jan 31

Sat, Nov 22 - Sat, Nov 29

from $2,228

Sat, Dec 06 - Sat, Dec 13

Sun-Soaked Seas & Saint Isles

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

Insider cabins from

$2,780

per Cabin

10 nights

Valiant Lady

+ $300 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,780

per Cabin

Departing on:

Sat, Nov 22 - Tue, Dec 02

from $2,780

Miami to San Juan

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

Insider cabins from

$2,324

per Cabin

9 nights

Brilliant Lady

+ $300 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,324

per Cabin

Departing on:

Fri, Nov 28 - Sun, Dec 07

from $2,324

Fri, Jan 23 - Sun, Feb 01

from $2,502

Fri, Feb 20 - Sun, Mar 01

from $2,502

San Juan, Samaná & Bimini

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

Insider cabins from

$1,948

per Cabin

7 nights

Resilient Lady

+ $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,948

per Cabin

Departing on:

Sat, Jan 17 - Sat, Jan 24

Sat, Nov 29 - Sat, Dec 06

Cartagena & Caribbean Faves

San Juan • Cartagena • Willemstad • Oranjestad • Fort-de-France • St. John's • Philipsburg • San Juan

Insider cabins from

$3,060

per Cabin

11 nights

Valiant Lady

+ $300 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$3,060

per Cabin

Departing on:

Tue, Dec 02 - Sat, Dec 13

from $3,060

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

+ $300 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,838

per Cabin

Departing on:

Sun, Dec 07 - Thu, Dec 18

from $2,838

Sun, Mar 01 - Thu, Mar 12

from $2,838

St. Lucia, St. Maarten, Barbados & More

San Juan • Basseterre • Castries • Roseau • Bridgetown • Philipsburg • San Juan

Insider cabins from

$1,946

per Cabin

7 nights

Valiant Lady

+ $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,946

per Cabin

Departing on:

Sat, Dec 13 - Sat, Dec 20

Brilliant Caribbean Holidays

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

Insider cabins from

$3,186

per Cabin

8 nights

Brilliant Lady

+ $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$3,186

per Cabin

Departing on:

Thu, Dec 18 - Fri, Dec 26

from $3,186

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

+ $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,786

per Cabin

Departing on:

Sat, Dec 20 - Sat, Dec 27

from $2,786

Valiant Caribbean Holidays

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

Insider cabins from

$2,368

per Cabin

7 nights

Valiant Lady

+ $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,368

per Cabin

Departing on:

Sat, Dec 20 - Sat, Dec 27

from $2,368

Scarlet Caribbean Holidays

Miami, Florida • Nassau • Beach Club at Bimini • Miami, Florida

Insider cabins from

$1,512

per Cabin

4 nights

Scarlet Lady

+ $100 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,512

per Cabin

Departing on:

Wed, Dec 24 - Sun, Dec 28

from $1,512

Brilliant New Year's Ahoy!

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

Insider cabins from

$4,664

per Cabin

9 nights

Brilliant Lady

+ $300 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$4,664

per Cabin

Departing on:

Fri, Dec 26 - Sun, Jan 04

from $4,664

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

+ $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$3,766

per Cabin

Departing on:

Sat, Dec 27 - Sat, Jan 03

from $3,766

Valiant New Year’s Ahoy!

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

Insider cabins from

$3,768

per Cabin

7 nights

Valiant Lady

+ $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$3,768

per Cabin

Departing on:

Sat, Dec 27 - Sat, Jan 03

from $3,768

Scarlet New Year's Ahoy!

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

Insider cabins from

$2,918

per Cabin

5 nights

Scarlet Lady

+ $100 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,918

per Cabin

Departing on:

Sun, Dec 28 - Fri, Jan 02

from $2,918

Aruban Sights & Antiguan Nights

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

Insider cabins from

$2,086

per Cabin

7 nights

Valiant Lady

+ $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,086

per Cabin

Departing on:

Sat, Jan 03 - Sat, Jan 10

Cozumel, Grand Cayman & Bimini

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

Insider cabins from

$1,948

per Cabin

7 nights

Resilient Lady

+ $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,948

per Cabin

Departing on:

Sat, Jan 03 - Sat, Jan 10

Miami to the Cayman Islands

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

Insider cabins from

$2,840

per Cabin

11 nights

Brilliant Lady

+ $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

from $2,840

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

+ $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,948

per Cabin

Departing on:

Sat, Jan 10 - Sat, Jan 17

Sat, Mar 07 - Sat, Mar 14

from $2,226

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

+ $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,946

per Cabin

Departing on:

Sat, Jan 10 - Sat, Jan 17

Grand Turk Tranquility & St. Croix Charm

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

Insider cabins from

$2,384

per Cabin

8 nights

Brilliant Lady

+ $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,384

per Cabin

Departing on:

Thu, Jan 15 - Fri, Jan 23

from $2,384

St. Kitts, Barbados, Martinique & More

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

Insider cabins from

$1,946

per Cabin

7 nights

Valiant Lady

+ $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,946

per Cabin

Departing on:

Sat, Jan 17 - Sat, Jan 24

Barbados, Antigua, BVI & More

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

Insider cabins from

$1,946

per Cabin

7 nights

Valiant Lady

+ $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,946

per Cabin

Departing on:

Sat, Jan 24 - Sat, Jan 31

Quintessential Caribbean Highlights

San Juan • Philipsburg • Basseterre • St. John's • Fort-de-France • Castries • Kingstown • Bridgetown • San Juan

Insider cabins from

$2,780

per Cabin

10 nights

Valiant Lady

+ $300 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,780

per Cabin

Departing on:

Sat, Jan 31 - Tue, Feb 10

from $2,780

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

+ $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

from $2,840

Cartagena, Aruba, Antigua & More

San Juan • Cartagena • Willemstad • Oranjestad • St. John's • St. Croix • Philipsburg • San Juan

Insider cabins from

$3,058

per Cabin

11 nights

Valiant Lady

+ $300 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$3,058

per Cabin

Departing on:

Tue, Feb 10 - Sat, Feb 21

from $3,058

Antigua, Martinique, & Barbados & More

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

Insider cabins from

$2,086

per Cabin

7 nights

Valiant Lady

+ $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

+ $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,228

per Cabin

Departing on:

Sat, Mar 07 - Sat, Mar 14

from $2,228

Gorgeous Antigua, St. Kitts & Bimini

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

Insider cabins from

$2,682

per Cabin

9 nights

Brilliant Lady

+ $300 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,682

per Cabin

Departing on:

Thu, Mar 12 - Sat, Mar 21

from $2,682

Costa Mayan Caves & Honduran Waves

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

Insider cabins from

$1,910

per Cabin

6 nights

Resilient Lady

+ $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$1,910

per Cabin

Departing on:

Sat, Mar 14 - Fri, Mar 20

from $1,910

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

+ $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

from $2,544

Panama Canal & Pacific Wonders

Miami, Florida • Cartagena • Colón • Panama Canal (Cruising) • Puntarenas • Puerto Quetzal • Cabo San Lucas • Los Angeles, California

Insider cabins from

$6,370

per Cabin

16 nights

Brilliant Lady

+ $300 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$6,370

per Cabin

Departing on:

Sat, Mar 21 - Mon, Apr 06

from $6,370

Tortola, Charleston, Newport & More

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

Insider cabins from

$2,684

per Cabin

9 nights

Valiant Lady

+ $300 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,684

per Cabin

Departing on:

Sat, Mar 28 - Mon, Apr 06

from $2,684

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

+ $200 in drinks — on us

Getaways for 80% off 2nd Sailor

Insider cabins from

$2,228

per Cabin

Departing on: