Explore 400 cruise vacations

+ Balcony upgrades

70% off 2nd Sailor

Sea Terrace cabins from

per Cabin

Departing on:

Sun, Jul 13 - Sun, Jul 20

DEAL

Brilliant Lady Miami MerMaiden

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

Insider cabins from

per Cabin

8 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Fri, Oct 17 - Sat, Oct 25

DEAL

Honduras, Mexico & Bahamas

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

Insider cabins from

per Cabin

7 nights

Scarlet Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Fri, Oct 31 - Fri, Nov 07

DEAL

Western Caribbean: From Miami to Bimini

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

Insider cabins from

per Cabin

7 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sat, Nov 01 - Sat, Nov 08

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

per Cabin

6 nights

Valiant Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sun, Nov 02 - Sat, Nov 08

DEAL

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

per Cabin

12 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sat, Nov 08 - Thu, Nov 20

DEAL

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

per Cabin

7 nights

Valiant Lady

Sat, Jan 02 - Sat, Jan 09

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

2027Best Rate

Sat, Nov 08 - Sat, Nov 15

Sat, Mar 21 - Sat, Mar 28

Western Caribbean Charm

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

Insider cabins from

per Cabin

6 nights

Resilient Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sun, Nov 09 - Sat, Nov 15

DEAL

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

per Cabin

7 nights

Resilient Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sat, Mar 28 - Sat, Apr 04

Sat, Nov 15 - Sat, Nov 22

Sat, Apr 18 - Sat, Apr 25

DEAL

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

Insider cabins from

per Cabin

7 nights

Valiant Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sat, Feb 28 - Sat, Mar 07

Sat, Nov 15 - Sat, Nov 22

Sat, Nov 07 - Sat, Nov 14

DEAL

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

Insider cabins from

per Cabin

8 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Thu, Nov 20 - Fri, Nov 28

DEAL

Cayman Coves & Jamaican Waterfalls

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

Insider cabins from

per Cabin

7 nights

Resilient Lady

Sat, Dec 06 - Sat, Dec 13

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

2025Best Rate

Sat, Nov 22 - Sat, Nov 29

Sat, Dec 13 - Sat, Dec 20

DEAL

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

per Cabin

7 nights

Valiant Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sat, Nov 22 - Sat, Nov 29

DEAL

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

per Cabin

9 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

Fri, Nov 28 - Sun, Dec 07

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

2025Best Rate

Fri, Feb 20 - Sun, Mar 01

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

per Cabin

6 nights

Valiant Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sat, Nov 29 - Fri, Dec 05

DEAL

San Juan, Samaná & Bimini

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

Insider cabins from

per Cabin

7 nights

Resilient Lady

Sat, Nov 29 - Sat, Dec 06

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

2025Best Rate

Sat, Jan 17 - Sat, Jan 24

DEAL

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

per Cabin

8 nights

Valiant Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Fri, Dec 05 - Sat, Dec 13

DEAL

Aruban Sunsets & Calm Cayman Days

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

Insider cabins from

per Cabin

11 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sun, Mar 01 - Thu, Mar 12

Sun, Dec 07 - Thu, Dec 18

DEAL

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

per Cabin

7 nights

Valiant Lady

+ Balcony upgrades

70% off 2nd Sailor

Sea View cabins from

per Cabin

Departing on:

Sat, Dec 13 - Sat, Dec 20

DEAL

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

per Cabin

8 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Thu, Dec 18 - Fri, Dec 26

DEAL

Resilient Caribbean Holidays

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

Insider cabins from

per Cabin

7 nights

Resilient Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sat, Dec 20 - Sat, Dec 27

DEAL

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

per Cabin

7 nights

Valiant Lady

+ Balcony upgrades

70% off 2nd Sailor

Sea View cabins from

per Cabin

Departing on:

Sat, Dec 20 - Sat, Dec 27

DEAL

Brilliant New Year's Ahoy!

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

per Cabin

9 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Fri, Dec 26 - Sun, Jan 04

DEAL

Resilient New Year's Ahoy!

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

Insider cabins from

per Cabin

7 nights

Resilient Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sat, Dec 27 - Sat, Jan 03

DEAL

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

Insider cabins from

per Cabin

7 nights

Valiant Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sat, Dec 27 - Sat, Jan 03

DEAL

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

per Cabin

7 nights

Valiant Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sat, Jan 03 - Sat, Jan 10

Sat, Feb 06 - Sat, Feb 13

DEAL

Cozumel, Grand Cayman & Bimini

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

Insider cabins from

per Cabin

7 nights

Resilient Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sat, Jan 03 - Sat, Jan 10

DEAL

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

per Cabin

11 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sun, Jan 04 - Thu, Jan 15

DEAL

Cayman Isles & Jamaican Miles

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

Insider cabins from

per Cabin

7 nights

Resilient Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sun, Dec 13 - Sun, Dec 20

Sat, Jan 10 - Sat, Jan 17

Sat, Mar 07 - Sat, Mar 14

DEAL

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

per Cabin

7 nights

Valiant Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sat, Jan 10 - Sat, Jan 17

DEAL

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

Insider cabins from

per Cabin

7 nights

Valiant Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sat, Jan 17 - Sat, Jan 24

DEAL

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 View cabins from

per Cabin

7 nights

Valiant Lady

+ Balcony upgrades

70% off 2nd Sailor

Sea View cabins from

per Cabin

Departing on:

Sat, Jan 24 - Sat, Jan 31

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

per Cabin

6 nights

Brilliant Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Mon, Jan 26 - Sun, Feb 01

DEAL

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

Insider cabins from

per Cabin

7 nights

Valiant Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sat, Jan 31 - Sat, Feb 07

DEAL

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

per Cabin

7 nights

Resilient Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sat, Jan 31 - Sat, Feb 07

Sat, Feb 28 - Sat, Mar 07

Sun, Dec 06 - Sun, Dec 13

DEAL

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

per Cabin

11 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sun, Feb 01 - Thu, Feb 12

DEAL

Cayman Coves & Jamaican Waterfalls

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

Insider cabins from

per Cabin

7 nights

Resilient Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sat, Feb 07 - Sat, Feb 14

DEAL

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

Insider cabins from

per Cabin

7 nights

Valiant Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sat, Feb 07 - Sat, Feb 14

DEAL

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

Sea View cabins from

per Cabin

8 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

+ Balcony upgrades

70% off 2nd Sailor

Sea View cabins from

per Cabin

Departing on:

Thu, Feb 12 - Fri, Feb 20

DEAL

Resilient Valentine's Voyage

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

Insider cabins from

per Cabin

7 nights

Resilient Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sat, Feb 14 - Sat, Feb 21

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

Insider cabins from

per Cabin

7 nights

Valiant Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sat, Feb 14 - Sat, Feb 21

DEAL

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

Insider cabins from

per Cabin

7 nights

Valiant Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sat, Feb 21 - Sat, Feb 28

DEAL

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

Insider cabins from

per Cabin

7 nights

Valiant Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sat, Mar 07 - Sat, Mar 14

DEAL

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

per Cabin

9 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Thu, Mar 12 - Sat, Mar 21

Costa Mayan Caves & Honduran Waves

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

Insider cabins from

per Cabin

6 nights

Resilient Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sat, Mar 14 - Fri, Mar 20

DEAL

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

per Cabin

7 nights

Valiant Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sat, Dec 05 - Sat, Dec 12

Sat, Mar 14 - Sat, Mar 21

Sat, Jan 09 - Sat, Jan 16

DEAL

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

per Cabin

8 nights

Resilient Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Fri, Mar 20 - Sat, Mar 28

Tortola, Charleston, Newport & More

San Juan, Puerto Rico
Tortola, British Virgin Islands
Puerto Plata, Dominican Republic
Charleston, South Carolina
Newport, Rhode Island
New York City, New York

Insider cabins from

per Cabin

9 nights

Valiant Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sat, Mar 28 - Mon, Apr 06

DEAL

Puerto Plata, San Juan & Tortola

Miami, Florida
Puerto Plata, Dominican Republic
San Juan, Puerto Rico
Tortola, British Virgin Islands
Miami, Florida

Insider cabins from

per Cabin

7 nights

Scarlet Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sun, Apr 19 - Sun, Apr 26

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

per Cabin

6 nights

Scarlet Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sun, Oct 25 - Sat, Oct 31

Mexico & Bimini: Halloween Edition

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

Insider cabins from

per Cabin

6 nights

Resilient Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Mon, Oct 26 - Sun, Nov 01

DEAL

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

per Cabin

7 nights

Valiant Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sat, Oct 31 - Sat, Nov 07

DEAL

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

per Cabin

8 nights

Resilient Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sun, Nov 08 - Mon, Nov 16

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

per Cabin

6 nights

Valiant Lady

Sat, Jan 23 - Fri, Jan 29

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

2027Best Rate

Sat, Nov 14 - Fri, Nov 20

Sat, Mar 13 - Fri, Mar 19

DEAL

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

per Cabin

10 nights

Brilliant Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sun, Nov 15 - Wed, Nov 25

Mon, Jan 25 - Thu, Feb 04

Mon, Feb 22 - Thu, Mar 04

Captivating Costa Maya & Cozumel Charm

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

Insider cabins from

per Cabin

6 nights

Resilient Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Mon, Nov 16 - Sun, Nov 22

DEAL

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

per Cabin

8 nights

Valiant Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Fri, Nov 20 - Sat, Nov 28

DEAL

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

per Cabin

7 nights

Valiant Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sat, Nov 28 - Sat, Dec 05

DEAL

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

per Cabin

10 nights

Brilliant Lady

Mon, Jan 11 - Thu, Jan 21

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

2027Best Rate

Mon, Nov 30 - Thu, Dec 10

Mon, Mar 08 - Thu, Mar 18

DEAL

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

per Cabin

9 nights

Brilliant Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Mon, Dec 14 - Wed, Dec 23

DEAL

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

per Cabin

7 nights

Valiant Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sat, Dec 19 - Sat, Dec 26

DEAL

Resilient Caribbean Holidays

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

Insider cabins from

per Cabin

7 nights

Resilient Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sun, Dec 20 - Sun, Dec 27

DEAL

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

per Cabin

7 nights

Valiant Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sat, Dec 26 - Sat, Jan 02

DEAL

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

per Cabin

7 nights

Resilient Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sun, Dec 27 - Sun, Jan 03

DEAL

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

per Cabin

10 nights

Brilliant Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Mon, Dec 28 - Thu, Jan 07

DEAL

Cayman Isles & Jamaican Miles

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

Insider cabins from

per Cabin

7 nights

Resilient Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sun, Jan 17 - Sun, Jan 24

DEAL

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

per Cabin

8 nights

Valiant Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Fri, Jan 29 - Sat, Feb 06

DEAL

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

per Cabin

10 nights

Brilliant Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Mon, Feb 08 - Thu, Feb 18

DEAL

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

per Cabin

7 nights

Valiant Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sat, Feb 13 - Sat, Feb 20

DEAL

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

per Cabin

7 nights

Resilient Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sun, Feb 14 - Sun, Feb 21

DEAL

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

per Cabin

7 nights

Valiant Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sat, Feb 20 - Sat, Feb 27

DEAL

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

per Cabin

7 nights

Valiant Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sat, Mar 06 - Sat, Mar 13

DEAL

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

per Cabin

8 nights

Valiant Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Fri, Mar 19 - Sat, Mar 27

DEAL

Colorful Curaçao, Aruba & Antigua

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

Insider cabins from

per Cabin

7 nights

Valiant Lady

+ Balcony upgrades

70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sat, Mar 27 - Sat, Apr 03