Explore 426 cruise vacations

Showing cruise vacations: Caribbean, August 2025 - April 2027

70% off 2nd Sailor + Free balcony upgrade ends in…

Mayan Sol

Miami, Florida
Costa Maya, Mexico
The Beach Club at Bimini, Bahamas
Miami, Florida

Insider cabins from

$1,292~~$1,726~~

per Cabin

5 nights

Valiant Lady, Resilient Lady & Scarlet Lady

BOOK NOW

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

$1,292~~$1,726~~

per Cabin

Departing on:

2025Best Rate

Sun, Sep 07 - Fri, Sep 12

from (US$)$1,292

2025

Sun, Oct 05 - Fri, Oct 10

from (US$)$1,490

2026

Mon, Jun 22 - Sat, Jun 27

from (US$)$1,990

Dominican Daze

Miami, Florida
Puerto Plata, Dominican Republic
The Beach Club at Bimini, Bahamas
Miami, Florida

Insider cabins from

$1,490~~$2,086~~

per Cabin

5 nights

Valiant Lady, Scarlet Lady, Resilient Lady & Brilliant Lady

BOOK NOW

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

$1,490~~$2,086~~

per Cabin

Departing on:

2026Best Rate

Mon, Sep 28 - Sat, Oct 03

from (US$)$1,490

2025

Fri, Sep 12 - Wed, Sep 17

from (US$)$1,590

2025

Fri, Sep 26 - Wed, Oct 01

from (US$)$1,590

Fire & Sunset Soirées

Miami, Florida
Key West, Florida
The Beach Club at Bimini, Bahamas
Miami, Florida

Insider cabins from

$1,114~~$1,492~~

per Cabin

4 nights

Valiant Lady, Scarlet Lady, Resilient Lady & Brilliant Lady

BOOK NOW

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

$1,114~~$1,492~~

per Cabin

Departing on:

2025Best Rate

Wed, Sep 17 - Sun, Sep 21

from (US$)$1,114

2025

Wed, Nov 12 - Sun, Nov 16

from (US$)$2,280

2025

Wed, Nov 26 - Sun, Nov 30

from (US$)$1,834

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

Riviera Maya

Miami, Florida
Cozumel, Mexico
The Beach Club at Bimini, Bahamas
Miami, Florida

Insider cabins from

$1,290~~$1,716~~

per Cabin

5 nights

Valiant Lady, Scarlet Lady & Resilient Lady

BOOK NOW

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

$1,290~~$1,716~~

per Cabin

Departing on:

2025Best Rate

Sun, Sep 21 - Fri, Sep 26

from (US$)$1,290

2025

Sun, Nov 16 - Fri, Nov 21

from (US$)$1,490

2025

Sun, Dec 14 - Fri, Dec 19

from (US$)$1,490

True Crime Voyage

Miami, Florida
Puerto Plata, Dominican Republic
The Beach Club at Bimini, Bahamas
Miami, Florida

Sea View cabins from

$1,590~~$2,236~~

per Cabin

5 nights

Valiant Lady

BOOK NOW

+ Balcony upgrades

70% off 2nd Sailor

Sea View cabins from

$1,590~~$2,236~~

per Cabin

Departing on:

2025

Fri, Oct 10 - Wed, Oct 15

from (US$)$1,590

Scarlet's Haunted Halloween Soirée

Barcelona
Palma de Mallorca, Spain
Casablanca, Morocco
Funchal, Madeira, Portugal
Santa Cruz de Tenerife, Spain
Miami, Florida

Sea Terrace cabins from

$4,050~~$6,068~~

per Cabin

15 nights

Scarlet Lady

BOOK NOW

+ Balcony upgrades

70% off 2nd Sailor

Sea Terrace cabins from

$4,050~~$6,068~~

per Cabin

Departing on:

2025

Thu, Oct 16 - Fri, Oct 31

from (US$)$4,050

★

ONBOARD CREDIT

Brilliant Lady Miami MerMaiden

Miami, Florida
Philipsburg, St. Maarten
Tortola, British Virgin Islands
The Beach Club at Bimini, Bahamas
Miami, Florida

Insider cabins from

$2,544~~$3,682~~

per Cabin

8 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

BOOK NOW

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

$2,544~~$3,682~~

per Cabin

Departing on:

2025

Fri, Oct 17 - Sat, Oct 25

from (US$)$2,544

Riviera Maya: Halloween Edition

Miami, Florida
Cozumel, Mexico
The Beach Club at Bimini, Bahamas
Miami, Florida

Sea View cabins from

$1,690~~$2,320~~

per Cabin

5 nights

Valiant Lady

BOOK NOW

+ Balcony upgrades

70% off 2nd Sailor

Sea View cabins from

$1,690~~$2,320~~

per Cabin

Departing on:

2025

Sun, Oct 19 - Fri, Oct 24

from (US$)$1,690

Dominican Daze: Halloween Edition

Miami, Florida
Puerto Plata, Dominican Republic
The Beach Club at Bimini, Bahamas
Miami, Florida

Sea View cabins from

$1,792~~$2,542~~

per Cabin

5 nights

Valiant Lady

BOOK NOW

+ Balcony upgrades

70% off 2nd Sailor

Sea View cabins from

$1,792~~$2,542~~

per Cabin

Departing on:

2025

Fri, Oct 24 - Wed, Oct 29

from (US$)$1,792

Valiant's Haunted Halloween Soirée

Miami, Florida
Key West, Florida
The Beach Club at Bimini, Bahamas
Miami, Florida

Sea View cabins from

$1,834~~$2,596~~

per Cabin

4 nights

Valiant Lady

BOOK NOW

+ Balcony upgrades

70% off 2nd Sailor

Sea View cabins from

$1,834~~$2,596~~

per Cabin

Departing on:

2025

Wed, Oct 29 - Sun, Nov 02

from (US$)$1,834

Scarlet's Haunted Halloween Soirée

Miami, Florida
Roatán, Honduras
Costa Maya, Mexico
Cozumel, Mexico
The Beach Club at Bimini, Bahamas
Miami, Florida

Sea View cabins from

$1,948~~$2,662~~

per Cabin

7 nights

Scarlet Lady

BOOK NOW

+ Balcony upgrades

70% off 2nd Sailor

Sea View cabins from

$1,948~~$2,662~~

per Cabin

Departing on:

2025

Fri, Oct 31 - Fri, Nov 07

from (US$)$1,948

★

ONBOARD CREDIT

Western Caribbean: From Miami to Bimini

Miami, Florida
Ocho Rios, Jamaica
George Town, Grand Cayman
The Beach Club at Bimini, Bahamas
Miami, Florida

Sea View cabins from

$2,226~~$3,172~~

per Cabin

7 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

BOOK NOW

+ Balcony upgrades

70% off 2nd Sailor

Sea View cabins from

$2,226~~$3,172~~

per Cabin

Departing on:

2025

Sat, Nov 01 - Sat, Nov 08

from (US$)$2,226

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

Miami, Florida
Puerto Plata, Dominican Republic
Philipsburg, St. Maarten
Tortola, British Virgin Islands
San Juan, Puerto Rico

Insider cabins from

$1,428~~$2,018~~

per Cabin

6 nights

Valiant Lady

BOOK NOW

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

$1,428~~$2,018~~

per Cabin

Departing on:

2025

Sun, Nov 02 - Sat, Nov 08

from (US$)$1,428

★

ONBOARD CREDIT

Colorful Curaçao to the Charming Caymans

Miami, Florida
Oranjestad, Aruba
Willemstad, Curaçao
Cartagena, Colombia
Ocho Rios, Jamaica
George Town, Grand Cayman
Miami, Florida

Insider cabins from

$3,096~~$4,498~~

per Cabin

12 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

BOOK NOW

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

$3,096~~$4,498~~

per Cabin

Departing on:

2025

Sat, Nov 08 - Thu, Nov 20

from (US$)$3,096

Saint (Isles) & Seas of the Caribbean

San Juan, Puerto Rico
Tortola, British Virgin Islands
Bridgetown, Barbados
Castries, St. Lucia
St. John's, Antigua
Philipsburg, St. Maarten
San Juan, Puerto Rico

Insider cabins from

$2,364~~$3,378~~

per Cabin

7 nights

Valiant Lady

BOOK NOW

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

$2,364~~$3,378~~

per Cabin

Departing on:

2027Best Rate

Sat, Jan 02 - Sat, Jan 09

from (US$)$2,364

2025

Sat, Nov 08 - Sat, Nov 15

from (US$)$2,926

2026

Sat, Mar 21 - Sat, Mar 28

from (US$)$3,362

Western Caribbean Charm

Miami, Florida
Costa Maya, Mexico
Roatán, Honduras
The Beach Club at Bimini, Bahamas
Miami, Florida

Sea Terrace cabins from

$1,788~~$2,446~~

per Cabin

6 nights

Resilient Lady

BOOK NOW

+ Balcony upgrades

70% off 2nd Sailor

Sea Terrace cabins from

$1,788~~$2,446~~

per Cabin

Departing on:

2025

Sun, Nov 09 - Sat, Nov 15

from (US$)$1,788

★

ONBOARD CREDIT

San Juan Sunrises & Dominican Dreams

Miami, Florida
San Juan, Puerto Rico
Puerto Plata, Dominican Republic
The Beach Club at Bimini, Bahamas
Miami, Florida

Insider cabins from

$1,808~~$2,536~~

per Cabin

7 nights

Resilient Lady

BOOK NOW

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

$1,808~~$2,536~~

per Cabin

Departing on:

2025Best Rate

Sat, Nov 15 - Sat, Nov 22

from (US$)$1,808

2026

Sat, Mar 28 - Sat, Apr 04

from (US$)$2,590

2026

Sat, Apr 18 - Sat, Apr 25

from (US$)$2,590

Sunny Miles of Tropical Isles

San Juan, Puerto Rico
Philipsburg, St. Maarten
Bridgetown, Barbados
Castries, St. Lucia
Fort-de-France, Martinique
Basseterre, St. Kitts and Nevis
San Juan, Puerto Rico

Sea View cabins from

$1,948~~$2,846~~

per Cabin

7 nights

Valiant Lady

BOOK NOW

+ Balcony upgrades

70% off 2nd Sailor

Sea View cabins from

$1,948~~$2,846~~

per Cabin

Departing on:

2025Best Rate

Sat, Nov 15 - Sat, Nov 22

from (US$)$1,948

2026

Sat, Feb 28 - Sat, Mar 07

from (US$)$2,088

2026

Sat, Nov 07 - Sat, Nov 14

from (US$)$2,508

★

ONBOARD CREDIT

Sunny San Juan & Isles of Beach Miles

Miami, Florida
Puerto Plata, Dominican Republic
San Juan, Puerto Rico
Philipsburg, St. Maarten
St. Croix, U.S. Virgin Islands
Miami, Florida

Sea View cabins from

$2,226~~$3,220~~

per Cabin

8 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

BOOK NOW

+ Balcony upgrades

70% off 2nd Sailor

Sea View cabins from

$2,226~~$3,220~~

per Cabin

Departing on:

2025

Thu, Nov 20 - Fri, Nov 28

from (US$)$2,226

Miami, Grand Turk (& back)

Miami, Florida
Grand Turk, Turks and Caicos
The Beach Club at Bimini, Bahamas
Miami, Florida

Insider cabins from

$1,492~~$2,024~~

per Cabin

5 nights

Scarlet Lady & Resilient Lady

BOOK NOW

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

$1,492~~$2,024~~

per Cabin

Departing on:

2026Best Rate

Sat, Oct 17 - Thu, Oct 22

from (US$)$1,492

2025

Fri, Nov 21 - Wed, Nov 26

from (US$)$1,892

2025

Sun, Nov 30 - Fri, Dec 05

from (US$)$2,250

★

ONBOARD CREDIT

Cayman Coves & Jamaican Waterfalls

Miami, Florida
Ocho Rios, Jamaica
George Town, Grand Cayman
The Beach Club at Bimini, Bahamas
Miami, Florida

Insider cabins from

$1,946~~$2,748~~

per Cabin

7 nights

Resilient Lady

BOOK NOW

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

$1,946~~$2,748~~

per Cabin

Departing on:

2026Best Rate

Sat, Jan 24 - Sat, Jan 31

from (US$)$1,946

2025

Sat, Nov 22 - Sat, Nov 29

from (US$)$2,382

2025

Sat, Dec 06 - Sat, Dec 13

from (US$)$1,948

Thanksgiving in the Lesser Antilles

San Juan, Puerto Rico
Tortola, British Virgin Islands
Basseterre, St. Kitts and Nevis
St. John's, Antigua
Castries, St. Lucia
Charlotte Amalie, St. Thomas
San Juan, Puerto Rico

Insider cabins from

$1,806~~$2,616~~

per Cabin

7 nights

Valiant Lady

BOOK NOW

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

$1,806~~$2,616~~

per Cabin

Departing on:

2025

Sat, Nov 22 - Sat, Nov 29

from (US$)$1,806

★

ONBOARD CREDIT

Antigua Waves & Grand Turk Caves

Miami, Florida
Grand Turk, Turks and Caicos
St. John's, Antigua
Basseterre, St. Kitts and Nevis
San Juan, Puerto Rico
Miami, Florida

Insider cabins from

$2,322~~$3,354~~

per Cabin

9 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

BOOK NOW

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

$2,322~~$3,354~~

per Cabin

Departing on:

2025Best Rate

Fri, Nov 28 - Sun, Dec 07

from (US$)$2,322

2026

Fri, Feb 20 - Sun, Mar 01

from (US$)$2,504

San Juan to Barbados & the St. Isles

San Juan, Puerto Rico
Philipsburg, St. Maarten
Basseterre, St. Kitts and Nevis
Roseau, Dominica
Bridgetown, Barbados
San Juan, Puerto Rico

Insider cabins from

$1,550~~$2,252~~

per Cabin

6 nights

Valiant Lady

BOOK NOW

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

$1,550~~$2,252~~

per Cabin

Departing on:

2025

Sat, Nov 29 - Fri, Dec 05

from (US$)$1,550

★

ONBOARD CREDIT

San Juan, Samaná & Bimini

Miami, Florida
San Juan, Puerto Rico
Samaná, Dominican Republic
The Beach Club at Bimini, Bahamas
Miami, Florida

Insider cabins from

$1,806~~$2,546~~

per Cabin

7 nights

Resilient Lady

BOOK NOW

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

$1,806~~$2,546~~

per Cabin

Departing on:

2025Best Rate

Sat, Nov 29 - Sat, Dec 06

from (US$)$1,806

2026

Sat, Jan 17 - Sat, Jan 24

from (US$)$2,366

Nicky Jam x Virgin Voyages

San Juan, Puerto Rico
Willemstad, Curaçao
Oranjestad, Aruba
Roseau, Dominica
St. John's, Antigua
Philipsburg, St. Maarten
San Juan, Puerto Rico

Insider cabins from

$2,066~~$3,014~~

per Cabin

8 nights

Valiant Lady

BOOK NOW

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

$2,066~~$3,014~~

per Cabin

Departing on:

2025

Fri, Dec 05 - Sat, Dec 13

from (US$)$2,066

★

ONBOARD CREDIT

Aruban Sunsets & Calm Cayman Days

Miami, Florida
Oranjestad, Aruba
Cartagena, Colombia
Ocho Rios, Jamaica
George Town, Grand Cayman
Miami, Florida

Insider cabins from

$2,838~~$4,130~~

per Cabin

11 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

BOOK NOW

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

$2,838~~$4,130~~

per Cabin

Departing on:

2026Best Rate

Sun, Mar 01 - Thu, Mar 12

from (US$)$2,838

2025

Sun, Dec 07 - Thu, Dec 18

from (US$)$2,840

★

ONBOARD CREDIT

Cayman Coves & Jamaican Waterfalls

Miami, Florida
Ocho Rios, Jamaica
George Town, Grand Cayman
The Beach Club at Bimini, Bahamas
Miami, Florida

Sea View cabins from

$1,948~~$2,742~~

per Cabin

7 nights

Resilient Lady

BOOK NOW

+ Balcony upgrades

70% off 2nd Sailor

Sea View cabins from

$1,948~~$2,742~~

per Cabin

Departing on:

2025Best Rate

Sat, Dec 13 - Sat, Dec 20

from (US$)$1,948

2026

Sat, Feb 07 - Sat, Feb 14

from (US$)$2,508

St. Lucia, St. Maarten, Barbados & More

San Juan, Puerto Rico
Basseterre, St. Kitts and Nevis
Castries, St. Lucia
Roseau, Dominica
Bridgetown, Barbados
Philipsburg, St. Maarten
San Juan, Puerto Rico

Sea View cabins from

$1,948~~$2,848~~

per Cabin

7 nights

Valiant Lady

BOOK NOW

+ Balcony upgrades

70% off 2nd Sailor

Sea View cabins from

$1,948~~$2,848~~

per Cabin

Departing on:

2025

Sat, Dec 13 - Sat, Dec 20

from (US$)$1,948

★

ONBOARD CREDIT

Brilliant Caribbean Holidays

Miami, Florida
Grand Turk, Turks and Caicos
Puerto Plata, Dominican Republic
San Juan, Puerto Rico
Samaná, Dominican Republic
Miami, Florida

Insider cabins from

$2,384~~$3,468~~

per Cabin

8 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

BOOK NOW

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

$2,384~~$3,468~~

per Cabin

Departing on:

2025

Thu, Dec 18 - Fri, Dec 26

from (US$)$2,384

★

ONBOARD CREDIT

Resilient Caribbean Holidays

Miami, Florida
San Juan, Puerto Rico
Puerto Plata, Dominican Republic
The Beach Club at Bimini, Bahamas
Miami, Florida

Insider cabins from

$3,012~~$4,388~~

per Cabin

7 nights

Resilient Lady

BOOK NOW

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

$3,012~~$4,388~~

per Cabin

Departing on:

2025

Sat, Dec 20 - Sat, Dec 27

from (US$)$3,012

Valiant Caribbean Holidays

San Juan, Puerto Rico
Philipsburg, St. Maarten
Basseterre, St. Kitts and Nevis
St. John's, Antigua
Castries, St. Lucia
Tortola, British Virgin Islands
San Juan, Puerto Rico

Sea View cabins from

$2,788~~$4,128~~

per Cabin

7 nights

Valiant Lady

BOOK NOW

+ Balcony upgrades

70% off 2nd Sailor

Sea View cabins from

$2,788~~$4,128~~

per Cabin

Departing on:

2025

Sat, Dec 20 - Sat, Dec 27

from (US$)$2,788

Scarlet Caribbean Holidays

Miami, Florida
Nassau, Bahamas
The Beach Club at Bimini, Bahamas
Miami, Florida

Sea Terrace cabins from

$1,912~~$2,734~~

per Cabin

4 nights

Scarlet Lady

BOOK NOW

+ Balcony upgrades

70% off 2nd Sailor

Sea Terrace cabins from

$1,912~~$2,734~~

per Cabin

Departing on:

2025Best Rate

Wed, Dec 24 - Sun, Dec 28

from (US$)$1,912

2026

Mon, Dec 21 - Sat, Dec 26

from (US$)$1,992

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

★

ONBOARD CREDIT

Brilliant New Year's Ahoy!

Miami, Florida
Grand Turk, Turks and Caicos
Philipsburg, St. Maarten
Basseterre, St. Kitts and Nevis
San Juan, Puerto Rico
Miami, Florida

Insider cabins from

$4,482~~$6,710~~

per Cabin

9 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

BOOK NOW

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

$4,482~~$6,710~~

per Cabin

Departing on:

2025

Fri, Dec 26 - Sun, Jan 04

from (US$)$4,482

★

ONBOARD CREDIT

Resilient New Year's Ahoy!

Miami, Florida
Ocho Rios, Jamaica
George Town, Grand Cayman
The Beach Club at Bimini, Bahamas
Miami, Florida

Sea View cabins from

$4,830~~$7,178~~

per Cabin

7 nights

Resilient Lady

BOOK NOW

+ Balcony upgrades

70% off 2nd Sailor

Sea View cabins from

$4,830~~$7,178~~

per Cabin

Departing on:

2025

Sat, Dec 27 - Sat, Jan 03

from (US$)$4,830

Valiant New Year’s Ahoy!

San Juan, Puerto Rico
Philipsburg, St. Maarten
Basseterre, St. Kitts and Nevis
Castries, St. Lucia
Bridgetown, Barbados
St. Croix, U.S. Virgin Islands
San Juan, Puerto Rico

Sea View cabins from

$4,188~~$6,304~~

per Cabin

7 nights

Valiant Lady

BOOK NOW

+ Balcony upgrades

70% off 2nd Sailor

Sea View cabins from

$4,188~~$6,304~~

per Cabin

Departing on:

2025

Sat, Dec 27 - Sat, Jan 03

from (US$)$4,188

Scarlet New Year's Ahoy!

Miami, Florida
Puerto Plata, Dominican Republic
The Beach Club at Bimini, Bahamas
Miami, Florida

Insider cabins from

$3,090~~$4,530~~

per Cabin

5 nights

Scarlet Lady

BOOK NOW

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

$3,090~~$4,530~~

per Cabin

Departing on:

2026Best Rate

Wed, Dec 30 - Mon, Jan 04

from (US$)$3,090

2025

Sun, Dec 28 - Fri, Jan 02

from (US$)$3,492

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

Aruban Sights & Antiguan Nights

San Juan, Puerto Rico
Oranjestad, Aruba
Willemstad, Curaçao
St. John's, Antigua
Philipsburg, St. Maarten
San Juan, Puerto Rico

Insider cabins from

$2,504~~$3,604~~

per Cabin

7 nights

Valiant Lady

BOOK NOW

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

$2,504~~$3,604~~

per Cabin

Departing on:

2027Best Rate

Sat, Feb 06 - Sat, Feb 13

from (US$)$2,504

2026

Sat, Jan 03 - Sat, Jan 10

from (US$)$2,928

★

ONBOARD CREDIT

Cozumel, Grand Cayman & Bimini

Miami, Florida
George Town, Grand Cayman
Cozumel, Mexico
The Beach Club at Bimini, Bahamas
Miami, Florida

Sea Terrace cabins from

$2,506~~$3,548~~

per Cabin

7 nights

Resilient Lady

BOOK NOW

+ Balcony upgrades

70% off 2nd Sailor

Sea Terrace cabins from

$2,506~~$3,548~~

per Cabin

Departing on:

2026

Sat, Jan 03 - Sat, Jan 10

from (US$)$2,506

Aruba, Bonaire, Colombia, Jamaica & More

Miami, Florida
Oranjestad, Aruba
Kralendijk, Bonaire
Cartagena, Colombia
Ocho Rios, Jamaica
George Town, Grand Cayman
Miami, Florida

Insider cabins from

$3,632~~$5,334~~

per Cabin

11 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

BOOK NOW

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

$3,632~~$5,334~~

per Cabin

Departing on:

2026

Sun, Jan 04 - Thu, Jan 15

from (US$)$3,632

★

ONBOARD CREDIT

Cayman Isles & Jamaican Miles

Miami, Florida
George Town, Grand Cayman
Ocho Rios, Jamaica
The Beach Club at Bimini, Bahamas
Miami, Florida

Insider cabins from

$2,086~~$2,962~~

per Cabin

7 nights

Resilient Lady

BOOK NOW

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

$2,086~~$2,962~~

per Cabin

Departing on:

2026Best Rate

Sun, Dec 13 - Sun, Dec 20

from (US$)$2,086

2026

Sat, Jan 10 - Sat, Jan 17

from (US$)$2,366

2026

Sat, Mar 07 - Sat, Mar 14

from (US$)$2,592

Virgin Island Views & Saint Isle Blues

San Juan, Puerto Rico
Tortola, British Virgin Islands
Bridgetown, Barbados
Kingstown, St. Vincent
Basseterre, St. Kitts and Nevis
St. Croix, U.S. Virgin Islands
San Juan, Puerto Rico

Insider cabins from

$1,948~~$2,864~~

per Cabin

7 nights

Valiant Lady

BOOK NOW

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

$1,948~~$2,864~~

per Cabin

Departing on:

2026

Sat, Jan 10 - Sat, Jan 17

from (US$)$1,948

St. Kitts, Barbados, Martinique & More

San Juan, Puerto Rico
Basseterre, St. Kitts and Nevis
Bridgetown, Barbados
Fort-de-France, Martinique
St. John's, Antigua
Philipsburg, St. Maarten
San Juan, Puerto Rico

Sea View cabins from

$2,366~~$3,496~~

per Cabin

7 nights

Valiant Lady

BOOK NOW

+ Balcony upgrades

70% off 2nd Sailor

Sea View cabins from

$2,366~~$3,496~~

per Cabin

Departing on:

2026

Sat, Jan 17 - Sat, Jan 24

from (US$)$2,366

Barbados, Antigua, BVI & More

San Juan, Puerto Rico
Tortola, British Virgin Islands
Bridgetown, Barbados
Fort-de-France, Martinique
St. John's, Antigua
Philipsburg, St. Maarten
San Juan, Puerto Rico

Sea Terrace cabins from

$2,786~~$4,138~~

per Cabin

7 nights

Valiant Lady

BOOK NOW

+ Balcony upgrades

70% off 2nd Sailor

Sea Terrace cabins from

$2,786~~$4,138~~

per Cabin

Departing on:

2026

Sat, Jan 24 - Sat, Jan 31

from (US$)$2,786

Grand Turk, Puerto Plata & Bimini

Miami, Florida
The Beach Club at Bimini, Bahamas
Puerto Plata, Dominican Republic
Grand Turk, Turks and Caicos
Miami, Florida

Insider cabins from

$2,160~~$3,098~~

per Cabin

6 nights

Brilliant Lady

BOOK NOW

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

$2,160~~$3,098~~

per Cabin

Departing on:

2026

Mon, Jan 26 - Sun, Feb 01

from (US$)$2,160

Antigua & the St. Isles

San Juan, Puerto Rico
Philipsburg, St. Maarten
Basseterre, St. Kitts and Nevis
St. John's, Antigua
Castries, St. Lucia
Charlotte Amalie, St. Thomas
San Juan, Puerto Rico

Sea View cabins from

$2,366~~$3,476~~

per Cabin

7 nights

Valiant Lady

BOOK NOW

+ Balcony upgrades

70% off 2nd Sailor

Sea View cabins from

$2,366~~$3,476~~

per Cabin

Departing on:

2026

Sat, Jan 31 - Sat, Feb 07

from (US$)$2,366

★

ONBOARD CREDIT

San Juan Sunrises & Dominican Dreams

Miami, Florida
Puerto Plata, Dominican Republic
San Juan, Puerto Rico
The Beach Club at Bimini, Bahamas
Miami, Florida

Insider cabins from

$1,666~~$2,334~~

per Cabin

7 nights

Resilient Lady

BOOK NOW

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

$1,666~~$2,334~~

per Cabin

Departing on:

2026Best Rate

Sat, Jan 31 - Sat, Feb 07

from (US$)$1,666

2026

Sat, Feb 28 - Sat, Mar 07

from (US$)$2,450

2026

Sun, Dec 06 - Sun, Dec 13

from (US$)$2,226

Magnetic Miami to Gorgeous George Town

Miami, Florida
Willemstad, Curaçao
Oranjestad, Aruba
Cartagena, Colombia
Ocho Rios, Jamaica
George Town, Grand Cayman
Miami, Florida

Insider cabins from

$2,838~~$4,112~~

per Cabin

11 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

BOOK NOW

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

$2,838~~$4,112~~

per Cabin

Departing on:

2026

Sun, Feb 01 - Thu, Feb 12

from (US$)$2,838

St. Lucia, Barbados & More

San Juan, Puerto Rico
Philipsburg, St. Maarten
Basseterre, St. Kitts and Nevis
Castries, St. Lucia
Bridgetown, Barbados
Charlotte Amalie, St. Thomas
San Juan, Puerto Rico

Sea View cabins from

$2,366~~$3,478~~

per Cabin

7 nights

Valiant Lady

BOOK NOW

+ Balcony upgrades

70% off 2nd Sailor

Sea View cabins from

$2,366~~$3,478~~

per Cabin

Departing on:

2026

Sat, Feb 07 - Sat, Feb 14

from (US$)$2,366

★

ONBOARD CREDIT

Brilliant Valentine's Voyage

Miami, Florida
Puerto Plata, Dominican Republic
San Juan, Puerto Rico
Philipsburg, St. Maarten
St. Croix, U.S. Virgin Islands
Miami, Florida

Insider cabins from

$2,384~~$3,472~~

per Cabin

8 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

BOOK NOW

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

$2,384~~$3,472~~

per Cabin

Departing on:

2026

Thu, Feb 12 - Fri, Feb 20

from (US$)$2,384

Scarlet Valentine's Voyage

Miami, Florida
Puerto Plata, Dominican Republic
The Beach Club at Bimini, Bahamas
Miami, Florida

Sea View cabins from

$1,992~~$2,856~~

per Cabin

5 nights

Scarlet Lady

BOOK NOW

+ Balcony upgrades

70% off 2nd Sailor

Sea View cabins from

$1,992~~$2,856~~

per Cabin

Departing on:

2026

Fri, Feb 13 - Wed, Feb 18

from (US$)$1,992

★

ONBOARD CREDIT

Resilient Valentine's Voyage

Miami, Florida
Ocho Rios, Jamaica
George Town, Grand Cayman
The Beach Club at Bimini, Bahamas
Miami, Florida

Insider cabins from

$2,592~~$3,740~~

per Cabin

7 nights

Resilient Lady

BOOK NOW

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

$2,592~~$3,740~~

per Cabin

Departing on:

2026

Sat, Feb 14 - Sat, Feb 21

from (US$)$2,592

Valiant Valentine's Voyage

San Juan, Puerto Rico
Oranjestad, Aruba
Willemstad, Curaçao
St. Croix, U.S. Virgin Islands
Philipsburg, St. Maarten
San Juan, Puerto Rico

Sea View cabins from

$2,366~~$3,500~~

per Cabin

7 nights

Valiant Lady

BOOK NOW

+ Balcony upgrades

70% off 2nd Sailor

Sea View cabins from

$2,366~~$3,500~~

per Cabin

Departing on:

2026

Sat, Feb 14 - Sat, Feb 21

from (US$)$2,366

Antigua, Martinique, & Barbados & More

San Juan, Puerto Rico
Philipsburg, St. Maarten
Bridgetown, Barbados
Fort-de-France, Martinique
St. John's, Antigua
Tortola, British Virgin Islands
San Juan, Puerto Rico

Sea View cabins from

$2,508~~$3,708~~

per Cabin

7 nights

Valiant Lady

BOOK NOW

+ Balcony upgrades

70% off 2nd Sailor

Sea View cabins from

$2,508~~$3,708~~

per Cabin

Departing on:

2026

Sat, Feb 21 - Sat, Feb 28

from (US$)$2,508

Quaint Castries to Elegant Antigua

San Juan, Puerto Rico
Basseterre, St. Kitts and Nevis
Castries, St. Lucia
Fort-de-France, Martinique
St. John's, Antigua
Tortola, British Virgin Islands
San Juan, Puerto Rico

Sea View cabins from

$2,226~~$3,286~~

per Cabin

7 nights

Valiant Lady

BOOK NOW

+ Balcony upgrades

70% off 2nd Sailor

Sea View cabins from

$2,226~~$3,286~~

per Cabin

Departing on:

2026

Sat, Mar 07 - Sat, Mar 14

from (US$)$2,226

Red Hot Sailing Club Voyage

Miami, Florida
Puerto Plata, Dominican Republic
St. John's, Antigua
Basseterre, St. Kitts and Nevis
The Beach Club at Bimini, Bahamas
Miami, Florida

Insider cabins from

$2,324~~$3,336~~

per Cabin

9 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

BOOK NOW

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

$2,324~~$3,336~~

per Cabin

Departing on:

2026

Thu, Mar 12 - Sat, Mar 21

from (US$)$2,324

Costa Mayan Caves & Honduran Waves

Miami, Florida
Roatán, Honduras
Costa Maya, Mexico
Cozumel, Mexico
Miami, Florida

Insider cabins from

$2,028~~$2,856~~

per Cabin

6 nights

Resilient Lady

BOOK NOW

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

$2,028~~$2,856~~

per Cabin

Departing on:

2026

Sat, Mar 14 - Fri, Mar 20

from (US$)$2,028

Sunsets in the Lesser Antilles

San Juan, Puerto Rico
Oranjestad, Aruba
Willemstad, Curaçao
Fort-de-France, Martinique
Basseterre, St. Kitts and Nevis
San Juan, Puerto Rico

Insider cabins from

$2,366~~$3,490~~

per Cabin

7 nights

Valiant Lady

BOOK NOW

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

$2,366~~$3,490~~

per Cabin

Departing on:

2026Best Rate

Sat, Dec 05 - Sat, Dec 12

from (US$)$2,366

2026

Sat, Mar 14 - Sat, Mar 21

from (US$)$2,648

2027

Sat, Jan 09 - Sat, Jan 16

from (US$)$2,366

Puerto Rican Nights & St. Croix Delights

Miami, Florida
Puerto Plata, Dominican Republic
San Juan, Puerto Rico
St. Croix, U.S. Virgin Islands
The Beach Club at Bimini, Bahamas
Miami, Florida

Insider cabins from

$2,960~~$4,318~~

per Cabin

8 nights

Resilient Lady

BOOK NOW

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

$2,960~~$4,318~~

per Cabin

Departing on:

2026

Fri, Mar 20 - Sat, Mar 28

from (US$)$2,960

Cayman Isles & Bimini Beach Miles

Miami, Florida
George Town, Grand Cayman
The Beach Club at Bimini, Bahamas
Miami, Florida

Insider cabins from

$1,590~~$2,202~~

per Cabin

5 nights

Resilient Lady & Scarlet Lady

BOOK NOW

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

$1,590~~$2,202~~

per Cabin

Departing on:

2026Best Rate

Mon, Nov 09 - Sat, Nov 14

from (US$)$1,590

2026

Mon, Jun 08 - Sat, Jun 13

from (US$)$1,992

2026

Sat, Jun 13 - Thu, Jun 18

from (US$)$2,192

Miami to Grand Turk: Halloween Edition

Miami, Florida
Grand Turk, Turks and Caicos
Puerto Plata, Dominican Republic
The Beach Club at Bimini, Bahamas
Miami, Florida

Insider cabins from

$2,102~~$3,000~~

per Cabin

6 nights

Scarlet Lady

BOOK NOW

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

$2,102~~$3,000~~

per Cabin

Departing on:

2026

Sun, Oct 25 - Sat, Oct 31

from (US$)$2,102

Mexico & Bimini: Halloween Edition

Miami, Florida
Cozumel, Mexico
Costa Maya, Mexico
The Beach Club at Bimini, Bahamas
Miami, Florida

Insider cabins from

$2,030~~$2,846~~

per Cabin

6 nights

Resilient Lady

BOOK NOW

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

$2,030~~$2,846~~

per Cabin

Departing on:

2026

Mon, Oct 26 - Sun, Nov 01

from (US$)$2,030

Scarlet's Haunted Halloween Soirée

Miami, Florida
Cozumel, Mexico
The Beach Club at Bimini, Bahamas
Miami, Florida

Insider cabins from

$1,690~~$2,330~~

per Cabin

5 nights

Scarlet Lady

BOOK NOW

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

$1,690~~$2,330~~

per Cabin

Departing on:

2026

Sat, Oct 31 - Thu, Nov 05

from (US$)$1,690

Valiant's Haunted Halloween Soirée

San Juan, Puerto Rico
Willemstad, Curaçao
Oranjestad, Aruba
Fort-de-France, Martinique
Basseterre, St. Kitts and Nevis
San Juan, Puerto Rico

Insider cabins from

$2,508~~$3,706~~

per Cabin

7 nights

Valiant Lady

BOOK NOW

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

$2,508~~$3,706~~

per Cabin

Departing on:

2026

Sat, Oct 31 - Sat, Nov 07

from (US$)$2,508

November Nights in the Eastern Caribbean

Miami, Florida
Puerto Plata, Dominican Republic
San Juan, Puerto Rico
Tortola, British Virgin Islands
The Beach Club at Bimini, Bahamas
Miami, Florida

Insider cabins from

$2,546~~$3,658~~

per Cabin

8 nights

Resilient Lady

BOOK NOW

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

$2,546~~$3,658~~

per Cabin

Departing on:

2026

Sun, Nov 08 - Mon, Nov 16

from (US$)$2,546

Caribbean East: Virgin & Saint Isles

San Juan, Puerto Rico
Tortola, British Virgin Islands
Basseterre, St. Kitts and Nevis
St. John's, Antigua
Castries, St. Lucia
San Juan, Puerto Rico

Insider cabins from

$2,028~~$2,804~~

per Cabin

6 nights

Valiant Lady

BOOK NOW

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

$2,028~~$2,804~~

per Cabin

Departing on:

2027Best Rate

Sat, Jan 23 - Fri, Jan 29

from (US$)$2,028

2026

Sat, Nov 14 - Fri, Nov 20

from (US$)$2,148

2027

Sat, Mar 13 - Fri, Mar 19

from (US$)$2,270

St. Isles & Sun-soaked Seas

Miami, Florida
Philipsburg, St. Maarten
Tortola, British Virgin Islands
Basseterre, St. Kitts and Nevis
St. John's, Antigua
The Beach Club at Bimini, Bahamas
Miami, Florida

Insider cabins from

$2,780~~$4,006~~

per Cabin

10 nights

Brilliant Lady

BOOK NOW

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

$2,780~~$4,006~~

per Cabin

Departing on:

2026Best Rate

Sun, Nov 15 - Wed, Nov 25

from (US$)$2,780

2027

Mon, Jan 25 - Thu, Feb 04

from (US$)$2,780

2027

Mon, Feb 22 - Thu, Mar 04

from (US$)$2,980

Captivating Costa Maya & Cozumel Charm

Miami, Florida
Costa Maya, Mexico
Cozumel, Mexico
The Beach Club at Bimini, Bahamas
Miami, Florida

Insider cabins from

$1,908~~$2,660~~

per Cabin

6 nights

Resilient Lady

BOOK NOW

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

$1,908~~$2,660~~

per Cabin

Departing on:

2026

Mon, Nov 16 - Sun, Nov 22

from (US$)$1,908

Thanksgiving: St. Isles, Aruba & Curaçao

San Juan, Puerto Rico
Charlotte Amalie, St. Thomas
Willemstad, Curaçao
Oranjestad, Aruba
Basseterre, St. Kitts and Nevis
Philipsburg, St. Maarten
San Juan, Puerto Rico

Insider cabins from

$3,026~~$4,474~~

per Cabin

8 nights

Valiant Lady

BOOK NOW

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

$3,026~~$4,474~~

per Cabin

Departing on:

2026

Fri, Nov 20 - Sat, Nov 28

from (US$)$3,026

Jamaican Waves & Bimini Breeze

Miami, Florida
Ocho Rios, Jamaica
The Beach Club at Bimini, Bahamas
Miami, Florida

Insider cabins from

$1,690~~$2,306~~

per Cabin

5 nights

Scarlet Lady

BOOK NOW

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

$1,690~~$2,306~~

per Cabin

Departing on:

2027Best Rate

Mon, Feb 15 - Sat, Feb 20

from (US$)$1,690

2026

Mon, Nov 23 - Sat, Nov 28

from (US$)$1,892

Antiguan Elegance & Sunny St. Isles

San Juan, Puerto Rico
Charlotte Amalie, St. Thomas
Tortola, British Virgin Islands
Basseterre, St. Kitts and Nevis
St. John's, Antigua
Philipsburg, St. Maarten
San Juan, Puerto Rico

Insider cabins from

$2,506~~$3,636~~

per Cabin

7 nights

Valiant Lady

BOOK NOW

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

$2,506~~$3,636~~

per Cabin

Departing on:

2026

Sat, Nov 28 - Sat, Dec 05

from (US$)$2,506

St. Maarten, Tortola, San Juan & more

Miami, Florida
Philipsburg, St. Maarten
Tortola, British Virgin Islands
St. Croix, U.S. Virgin Islands
San Juan, Puerto Rico
Puerto Plata, Dominican Republic
The Beach Club at Bimini, Bahamas
Miami, Florida

Insider cabins from

$2,780~~$3,892~~

per Cabin

10 nights

Brilliant Lady

BOOK NOW

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

$2,780~~$3,892~~

per Cabin

Departing on:

2027Best Rate

Mon, Jan 11 - Thu, Jan 21

from (US$)$2,780

2026

Mon, Nov 30 - Thu, Dec 10

from (US$)$3,302

2027

Mon, Mar 08 - Thu, Mar 18

from (US$)$3,182

Pre-Holiday Caribbean Getaway

Miami, Florida
Philipsburg, St. Maarten
Tortola, British Virgin Islands
San Juan, Puerto Rico
The Beach Club at Bimini, Bahamas
Miami, Florida

Insider cabins from

$2,324~~$3,318~~

per Cabin

9 nights

Brilliant Lady

BOOK NOW

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

$2,324~~$3,318~~

per Cabin

Departing on:

2026

Mon, Dec 14 - Wed, Dec 23

from (US$)$2,324

Valiant Caribbean Holidays

San Juan, Puerto Rico
Basseterre, St. Kitts and Nevis
Fort-de-France, Martinique
Oranjestad, Aruba
Willemstad, Curaçao
San Juan, Puerto Rico

Insider cabins from

$2,928~~$4,352~~

per Cabin

7 nights

Valiant Lady

BOOK NOW

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

$2,928~~$4,352~~

per Cabin

Departing on:

2026

Sat, Dec 19 - Sat, Dec 26

from (US$)$2,928

Resilient Caribbean Holidays

Miami, Florida
Puerto Plata, Dominican Republic
San Juan, Puerto Rico
The Beach Club at Bimini, Bahamas
Miami, Florida

Insider cabins from

$2,786~~$4,050~~

per Cabin

7 nights

Resilient Lady

BOOK NOW

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

$2,786~~$4,050~~

per Cabin

Departing on:

2026

Sun, Dec 20 - Sun, Dec 27

from (US$)$2,786

Brilliant Caribbean Holidays

Miami, Florida
The Beach Club at Bimini, Bahamas
Puerto Plata, Dominican Republic
Miami, Florida

Insider cabins from

$2,192~~$3,158~~

per Cabin

5 nights

Brilliant Lady

BOOK NOW

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

$2,192~~$3,158~~

per Cabin

Departing on:

2026

Wed, Dec 23 - Mon, Dec 28

from (US$)$2,192

Valiant New Year's Ahoy!

San Juan, Puerto Rico
Philipsburg, St. Maarten
Fort-de-France, Martinique
Bridgetown, Barbados
Castries, St. Lucia
St. John's, Antigua
San Juan, Puerto Rico

Insider cabins from

$4,324~~$6,486~~

per Cabin

7 nights

Valiant Lady

BOOK NOW

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

$4,324~~$6,486~~

per Cabin

Departing on:

2026

Sat, Dec 26 - Sat, Jan 02

from (US$)$4,324

Resilient New Year's Ahoy!

Miami, Florida
George Town, Grand Cayman
Ocho Rios, Jamaica
The Beach Club at Bimini, Bahamas
Miami, Florida

Insider cabins from

$3,906~~$5,762~~

per Cabin

7 nights

Resilient Lady

BOOK NOW

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

$3,906~~$5,762~~

per Cabin

Departing on:

2026

Sun, Dec 27 - Sun, Jan 03

from (US$)$3,906

Brilliant New Year's Ahoy!

Miami, Florida
Philipsburg, St. Maarten
Basseterre, St. Kitts and Nevis
Tortola, British Virgin Islands
St. John's, Antigua
The Beach Club at Bimini, Bahamas
Miami, Florida

Insider cabins from

$5,382~~$8,010~~

per Cabin

10 nights

Brilliant Lady

BOOK NOW

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

$5,382~~$8,010~~

per Cabin

Departing on:

2026

Mon, Dec 28 - Thu, Jan 07

from (US$)$5,382

Cayman Isles & Jamaican Miles

Miami, Florida
Ocho Rios, Jamaica
George Town, Grand Cayman
The Beach Club at Bimini, Bahamas
Miami, Florida

Insider cabins from

$2,228~~$3,110~~

per Cabin

7 nights

Resilient Lady

BOOK NOW

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

$2,228~~$3,110~~

per Cabin

Departing on:

2027

Sun, Jan 17 - Sun, Jan 24

from (US$)$2,228

Puerto Rico to Aruba, Bonaire & More

San Juan, Puerto Rico
Oranjestad, Aruba
Willemstad, Curaçao
Kralendijk, Bonaire
Fort-de-France, Martinique
Philipsburg, St. Maarten
San Juan, Puerto Rico

Insider cabins from

$2,864~~$4,140~~

per Cabin

8 nights

Valiant Lady

BOOK NOW

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

$2,864~~$4,140~~

per Cabin

Departing on:

2027

Fri, Jan 29 - Sat, Feb 06

from (US$)$2,864

San Juan & St. Isles: Valentine’s Voyage

Miami, Florida
Philipsburg, St. Maarten
Tortola, British Virgin Islands
St. Croix, U.S. Virgin Islands
San Juan, Puerto Rico
Puerto Plata, Dominican Republic
The Beach Club at Bimini, Bahamas
Miami, Florida

Insider cabins from

$2,980~~$4,200~~

per Cabin

10 nights

Brilliant Lady

BOOK NOW

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

$2,980~~$4,200~~

per Cabin

Departing on:

2027

Mon, Feb 08 - Thu, Feb 18

from (US$)$2,980

Key West & Bimini: Valentine’s Voyage

Miami, Florida
Key West, Florida
The Beach Club at Bimini, Bahamas
Miami, Florida

Insider cabins from

$1,432~~$1,942~~

per Cabin

4 nights

Scarlet Lady

BOOK NOW

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

$1,432~~$1,942~~

per Cabin

Departing on:

2027

Thu, Feb 11 - Mon, Feb 15

from (US$)$1,432

Lesser Antilles: Valentine's Day

San Juan, Puerto Rico
Oranjestad, Aruba
Willemstad, Curaçao
Fort-de-France, Martinique
Basseterre, St. Kitts and Nevis
San Juan, Puerto Rico

Insider cabins from

$2,644~~$3,834~~

per Cabin

7 nights

Valiant Lady

BOOK NOW

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

$2,644~~$3,834~~

per Cabin

Departing on:

2027

Sat, Feb 13 - Sat, Feb 20

from (US$)$2,644

PR, DR & Bimini: Valentine’s Voyage

Miami, Florida
San Juan, Puerto Rico
Puerto Plata, Dominican Republic
The Beach Club at Bimini, Bahamas
Miami, Florida

Insider cabins from

$2,660~~$3,786~~

per Cabin

7 nights

Resilient Lady

BOOK NOW

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

$2,660~~$3,786~~

per Cabin

Departing on:

2027

Sun, Feb 14 - Sun, Feb 21

from (US$)$2,660

Saint Isles & The Greater Antilles

San Juan, Puerto Rico
Tortola, British Virgin Islands
Castries, St. Lucia
Bridgetown, Barbados
Roseau, Dominica
Philipsburg, St. Maarten
San Juan, Puerto Rico

Insider cabins from

$2,508~~$3,608~~

per Cabin

7 nights

Valiant Lady

BOOK NOW

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

$2,508~~$3,608~~

per Cabin

Departing on:

2027

Sat, Feb 20 - Sat, Feb 27

from (US$)$2,508

Saint (Isles) & Seas of the Caribbean

San Juan, Puerto Rico
Philipsburg, St. Maarten
Bridgetown, Barbados
Castries, St. Lucia
St. John's, Antigua
Tortola, British Virgin Islands
San Juan, Puerto Rico

Insider cabins from

$2,506~~$3,594~~

per Cabin

7 nights

Valiant Lady

BOOK NOW

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

$2,506~~$3,594~~

per Cabin

Departing on:

2027

Sat, Mar 06 - Sat, Mar 13

from (US$)$2,506

Barbados, Dominica & St. Isle Spring

San Juan, Puerto Rico
Charlotte Amalie, St. Thomas
Bridgetown, Barbados
Kingstown, St. Vincent
Roseau, Dominica
Philipsburg, St. Maarten
San Juan, Puerto Rico

Insider cabins from

$3,024~~$4,400~~

per Cabin

8 nights

Valiant Lady

BOOK NOW

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

$3,024~~$4,400~~

per Cabin

Departing on:

2027

Fri, Mar 19 - Sat, Mar 27

from (US$)$3,024

Colorful Curaçao, Aruba & Antigua

San Juan, Puerto Rico
Willemstad, Curaçao
Oranjestad, Aruba
St. John's, Antigua
Philipsburg, St. Maarten
San Juan, Puerto Rico

Sea Terrace cabins from

$4,480~~$6,644~~

per Cabin

7 nights

Valiant Lady

BOOK NOW

+ Balcony upgrades

70% off 2nd Sailor

Sea Terrace cabins from

$4,480~~$6,644~~

per Cabin

Departing on:

2027

Sat, Mar 27 - Sat, Apr 03

from (US$)$4,480

San Juan to Miami: Dominican Daze

San Juan, Puerto Rico
Puerto Plata, Dominican Republic
The Beach Club at Bimini, Bahamas
Miami, Florida

Insider cabins from

$1,592~~$2,208~~

per Cabin

5 nights

Valiant Lady

BOOK NOW

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

$1,592~~$2,208~~

per Cabin

Departing on:

2027

Sat, Apr 10 - Thu, Apr 15

from (US$)$1,592