Explore 421 cruise vacations

+ instant savings applied*

SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sat, Mar 21 - Sat, Mar 28

Sat, Nov 08 - Sat, Nov 15

Fire & Sunset Soirées

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

Insider cabins from

per Cabin

4 nights

Scarlet Lady

+ instant savings applied*

SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Wed, Feb 04 - Sun, Feb 08

Wed, Nov 12 - Sun, Nov 16

Wed, Nov 26 - Sun, Nov 30

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

+ instant savings applied*

SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

Insider cabins from

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, 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

+ instant savings applied*

SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sat, Feb 28 - Sat, Mar 07

Sat, Nov 15 - Sat, Nov 22

Riviera Maya

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

Insider cabins from

per Cabin

5 nights

Scarlet Lady

+ instant savings applied*

SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sun, Jan 11 - Fri, Jan 16

Sun, Nov 16 - Fri, Nov 21

Sun, Dec 14 - Fri, Dec 19

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

+ instant savings applied*

SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Thu, Nov 20 - Fri, Nov 28

Thu, Feb 12 - Fri, Feb 20

Miami, Grand Turk (& back)

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

Sea View cabins from

per Cabin

5 nights

Scarlet Lady

+ instant savings applied*

SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

Sea View cabins from

per Cabin

Departing on:

Sun, Nov 30 - Fri, Dec 05

Fri, Nov 21 - Wed, Nov 26

Fri, Dec 19 - Wed, Dec 24

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

+ instant savings applied*

SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sat, Nov 22 - Sat, Nov 29

Sat, Dec 06 - Sat, Dec 13

Sat, Dec 13 - Sat, Dec 20

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

+ instant savings applied*

SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sat, Nov 22 - Sat, Nov 29

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

Sea View cabins from

per Cabin

9 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

+ instant savings applied*

SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

Sea View cabins from

per Cabin

Departing on:

Fri, Nov 28 - Sun, Dec 07

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

+ instant savings applied*

SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sat, Nov 29 - Fri, Dec 05

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

+ instant savings applied*

SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sat, Jan 17 - Sat, Jan 24

Sat, Nov 29 - Sat, Dec 06

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

+ instant savings applied*

SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Fri, Dec 05 - Sat, Dec 13

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

+ instant savings applied*

SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sun, Dec 07 - Thu, Dec 18

Sun, Mar 01 - Thu, Mar 12

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

+ instant savings applied*

SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

Sea View cabins from

per Cabin

Departing on:

Sat, Dec 13 - Sat, Dec 20

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

+ instant savings applied*

SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sat, Dec 20 - Sat, Dec 27

Scarlet Caribbean Holidays

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

Sea Terrace cabins from

per Cabin

4 nights

Scarlet Lady

+ instant savings applied*

SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

Sea Terrace cabins from

per Cabin

Departing on:

Wed, Dec 24 - Sun, Dec 28

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

+ instant savings applied*

SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sat, Dec 27 - Sat, Jan 03

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

+ instant savings applied*

SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

Insider cabins from

per Cabin

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

+ instant savings applied*

SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sat, Jan 03 - Sat, Jan 10

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

+ instant savings applied*

SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sat, Jan 03 - Sat, Jan 10

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

+ instant savings applied*

SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sun, Jan 04 - Thu, Jan 15

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

+ instant savings applied*

SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sat, Jan 10 - Sat, Jan 17

Sat, Mar 07 - Sat, Mar 14

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

+ instant savings applied*

SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

Insider cabins from

per Cabin

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

+ instant savings applied*

SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

Insider cabins from

per Cabin

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

+ instant savings applied*

SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

Insider 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

+ instant savings applied*

SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Mon, Jan 26 - Sun, Feb 01

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

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

+ instant savings applied*

SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sun, Feb 01 - Thu, Feb 12

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

+ instant savings applied*

SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

Insider cabins from

per Cabin

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

+ instant savings applied*

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

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

+ instant savings applied*

SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Thu, Mar 12 - Sat, Mar 21

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

RED HOT

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

+ instant savings applied*

SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Fri, Mar 20 - Sat, Mar 28

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

+ instant savings applied*

SAIL INTO DEEPER SAVINGS: 75% Off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sun, Apr 19 - Sun, Apr 26