Explore 423 cruise vacations

Sat, Mar 21 - Sat, Mar 28

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Departing on:

2026Best Rate

Sat, Nov 08 - Sat, Nov 15

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

Sat, Feb 28 - Sat, Mar 07

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SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

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Departing on:

2026Best Rate

Sat, Nov 15 - Sat, Nov 22

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

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SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

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Departing on:

Sat, Nov 22 - Sat, Nov 29

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

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SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

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Departing on:

Sat, Nov 29 - Fri, Dec 05

Nicky Jam's Caribbean Takeover

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

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per Cabin

8 nights

Valiant Lady

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SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

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Departing on:

Fri, Dec 05 - Sat, Dec 13

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

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SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

Sea View cabins from

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Departing on:

Sat, Dec 13 - Sat, Dec 20

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

Insider cabins from

per Cabin

7 nights

Valiant Lady

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SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

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Departing on:

Sat, Dec 20 - Sat, Dec 27

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

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SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

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Departing on:

Sat, Dec 27 - Sat, Jan 03

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

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SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

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Departing on:

Sat, Jan 03 - Sat, Jan 10

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

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SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

Insider cabins from

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Departing on:

Sat, Jan 10 - Sat, Jan 17

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

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SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

Insider cabins from

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Departing on:

Sat, Jan 17 - Sat, Jan 24

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

Insider cabins from

per Cabin

7 nights

Valiant Lady

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SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sat, Jan 24 - Sat, Jan 31

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

+ instant savings applied*

SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sat, Jan 31 - Sat, Feb 07

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

+ instant savings applied*

SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sat, Feb 07 - Sat, Feb 14

Aruba, Curaçao and the St. Isles

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

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SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

Insider cabins from

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Departing on:

Sat, Feb 14 - Sat, Feb 21

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

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SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sat, Feb 21 - Sat, Feb 28

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

+ instant savings applied*

SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sat, Mar 07 - Sat, Mar 14

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

+ instant savings applied*

SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sat, Mar 14 - Sat, Mar 21