Explore 411 cruise vacations

Showing cruise vacations: All Destinations, December 2025 - February 2026

UP TO $300 IN ONBOARD CREDIT

On Caribbean sailings 7 nights or longer

On top of 70% off 2nd Sailor + balcony upgrades

Showing 41 cruise vacations that match your search

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

+ free balcony upgrade

SWING INTO SUMMER: 70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sun, Dec 07 - Thu, Dec 18

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

+ free balcony upgrade

SWING INTO SUMMER: 70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sat, Jan 24 - Sat, Jan 31

Sat, Dec 13 - Sat, Dec 20

Sat, Feb 14 - Sat, Feb 21

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

+ free balcony upgrade

SWING INTO SUMMER: 70% off 2nd Sailor

Sea View cabins from

per Cabin

Departing on:

Sat, Dec 13 - Sat, Dec 20

Riviera Maya

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

Insider cabins from

per Cabin

5 nights

Scarlet Lady

+ free balcony upgrade

SWING INTO SUMMER: 70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sun, Dec 14 - Fri, Dec 19

Sun, Jan 11 - Fri, Jan 16

Sun, Jan 25 - Fri, Jan 30

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

+ free balcony upgrade

SWING INTO SUMMER: 70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Thu, Dec 18 - Fri, Dec 26

Miami, Grand Turk (& back)

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

Insider cabins from

per Cabin

5 nights

Scarlet Lady

+ free balcony upgrade

SWING INTO SUMMER: 70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Fri, Jan 16 - Wed, Jan 21

Fri, Dec 19 - Wed, Dec 24

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

+ free balcony upgrade

SWING INTO SUMMER: 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

+ free balcony upgrade

SWING INTO SUMMER: 70% off 2nd Sailor

Sea View 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 View cabins from

per Cabin

4 nights

Scarlet Lady

+ free balcony upgrade

SWING INTO SUMMER: 70% off 2nd Sailor

Sea View cabins from

per Cabin

Departing on:

Wed, Dec 24 - Sun, Dec 28

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

+ free balcony upgrade

SWING INTO SUMMER: 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

+ free balcony upgrade

SWING INTO SUMMER: 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

+ free balcony upgrade

SWING INTO SUMMER: 70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sat, Dec 27 - Sat, Jan 03

Scarlet New Year's Ahoy!

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

Sea View cabins from

per Cabin

5 nights

Scarlet Lady

+ free balcony upgrade

SWING INTO SUMMER: 70% off 2nd Sailor

Sea View cabins from

per Cabin

Departing on:

Sun, Dec 28 - Fri, Jan 02

Dominican Daze

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

Insider cabins from

per Cabin

5 nights

Scarlet Lady

+ free balcony upgrade

SWING INTO SUMMER: 70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Fri, Jan 02 - Wed, Jan 07

Fri, Jan 30 - Wed, Feb 04

Fri, Feb 13 - Wed, Feb 18

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

+ free balcony upgrade

SWING INTO SUMMER: 70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sat, Jan 03 - Sat, Jan 10

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

+ free balcony upgrade

SWING INTO SUMMER: 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

+ free balcony upgrade

SWING INTO SUMMER: 70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sun, Jan 04 - Thu, Jan 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

+ free balcony upgrade

SWING INTO SUMMER: 70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Wed, Feb 04 - Sun, Feb 08

Wed, Jan 07 - Sun, Jan 11

Wed, Jan 21 - Sun, Jan 25

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

+ free balcony upgrade

SWING INTO SUMMER: 70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sat, Jan 10 - Sat, Jan 17

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

+ free balcony upgrade

SWING INTO SUMMER: 70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sat, Jan 10 - Sat, Jan 17

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

+ free balcony upgrade

SWING INTO SUMMER: 70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sat, Jan 17 - Sat, Jan 24

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

+ free balcony upgrade

SWING INTO SUMMER: 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

+ free balcony upgrade

SWING INTO SUMMER: 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

+ free balcony upgrade

SWING INTO SUMMER: 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

+ free balcony upgrade

SWING INTO SUMMER: 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

+ free balcony upgrade

SWING INTO SUMMER: 70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sat, Jan 31 - Sat, Feb 07

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

+ free balcony upgrade

SWING INTO SUMMER: 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

+ free balcony upgrade

SWING INTO SUMMER: 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

Sea View cabins from

per Cabin

7 nights

Valiant Lady

+ free balcony upgrade

SWING INTO SUMMER: 70% off 2nd Sailor

Sea View cabins from

per Cabin

Departing on:

Sat, Feb 07 - Sat, Feb 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

Sea View cabins from

per Cabin

8 nights

Brilliant Lady

Brilliant Lady's Inaugural Season

+ free balcony upgrade

SWING INTO SUMMER: 70% off 2nd Sailor

Sea View cabins from

per Cabin

Departing on:

Thu, Feb 12 - Fri, Feb 20

DEAL

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

+ free balcony upgrade

SWING INTO SUMMER: 70% off 2nd Sailor

Insider cabins from

per Cabin

Departing on:

Sat, Feb 14 - Sat, Feb 21