Explore 402 cruise vacations

Showing cruise vacations: Caribbean, December 2025 - January 2026

2 Sailors , 1 Cabin

Showing 8 cruise vacations that match your search

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 drinks

70% off 2nd Sailor + Balcony upgrades

Insider cabins from

per Cabin

Departing on:

Thu, Dec 18 - Fri, Dec 26

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 drinks

70% off 2nd Sailor + Balcony upgrades

Insider cabins from

per Cabin

Departing on:

Sat, Dec 20 - Sat, Dec 27

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 drinks

70% off 2nd Sailor + Balcony upgrades

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 drinks

70% off 2nd Sailor + Balcony upgrades

Sea View cabins from

per Cabin

Departing on:

Wed, Dec 24 - Sun, Dec 28

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 drinks

70% off 2nd Sailor + Balcony upgrades

Insider cabins from

per Cabin

Departing on:

Fri, Dec 26 - Sun, Jan 04

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 drinks

70% off 2nd Sailor + Balcony upgrades

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

+ free drinks

70% off 2nd Sailor + Balcony upgrades

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 drinks

70% off 2nd Sailor + Balcony upgrades

Sea View cabins from

per Cabin

Departing on:

Sun, Dec 28 - Fri, Jan 02