Cruise Search | Caribbean Breeze Travel

Phyllis' Holiday Pick
Best time of the year to cruise! I love spending the holidays cruising with my family! The ships are beautifully decorated, and ringing in New Year’s Eve at sea is an experience I’ll never forget!

40% OFF

Marina

Oceania Cruises

Dec 10, 2026 - Dec 22, 2026 (12 Nights)

Miami • St. Thomas • Gustavia, St. Barts • St John's, Antigua • Fort-De-France, Martinique • Basseterre, St. Kitts and Nevis • Philipsburg, St. Maarten • Tortola • Miami

Average Starting Price

Feb 28, 2027 - Mar 14, 2027 (14 Nights)

Miami • St. John • St John's, Antigua • Terre de Haut, Guadeloupe • St. Thomas • San Juan, Puerto Rico • Philipsburg, St. Maarten • Gustavia, St. Barts • Gustavia, St. Barts • Basseterre, St. Kitts and Nevis • Grand Turk • Miami

Average Starting Price

$10,725pp

Jim's Onboard Credit

Luke's Port Pick
Grand Turk has it all - stunning ship views, a pool, great snorkeling, and crystal-clear water! This port will always be my favorite!

Celebrity Constellation

Celebrity Cruises

Feb 6, 2027 - Feb 13, 2027 (7 Nights)

San Juan, Puerto Rico • St. Thomas • St John's, Antigua • Roseau, Dominica • Castries, St. Lucia • Grenada • San Juan, Puerto Rico

Average Starting Price

Feb 10, 2028 - Feb 19, 2028 (9 Nights)

San Juan, Puerto Rico • Virgin Gorda, British Virgin Islands • Road Bay, Anguilla • Gustavia, St. Barts • St. Kitts • Deshaies, Guadeloupe • Fort-De-France, Martinique • St John's, Antigua • St. John • San Juan, Puerto Rico

Average Starting Price

Nov 21, 2026 - Dec 5, 2026 (14 Nights)

San Juan, Puerto Rico • Virgin Gorda, British Virgin Islands • St John's, Antigua • St. Pierre • Port Elizabeth (Bequia), Saint Vincent and the Grenadines • Grenada • Scarborough (Tobago), Trinidad and Tobago • Bridgetown, Barbados • Castries, St. Lucia • Roseau, Dominica • Basseterre, St. Kitts and Nevis • Charlestown, Nevis • Philipsburg, St. Maarten • Gustavia, St. Barts • San Juan, Puerto Rico

Average Starting Price

Mar 20, 2027 - Apr 12, 2027 (23 Nights)

Fort Lauderdale • San Juan, Puerto Rico • Marigot Bay, St. Martin, French West Indies • St John's, Antigua • Santa Cruz de la Palma, Spain • Santa Cruz de Tenerife, Spain • Canary Islands • San Sebastian (La Gomera), Canary Islands, Spain • Arrecife (Lanzarote), Spain • Funchal, Portugal • Funchal, Portugal • Agadir, Morocco • Casablanca, Morocco • Cadiz, Spain • Portimão, Portugal • Lisbon, Portugal

Average Starting Price

Feb 14, 2027 - Mar 6, 2027 (20 Nights)

Miami • Relaxaway Half Moon Cay • San Juan, Puerto Rico • St. Thomas • Tortola • Philipsburg, St. Maarten • St John's, Antigua • Castries, St. Lucia • Scenic Cruising Soufriere Bay • Roseau, Dominica • Bridgetown, Barbados • Grenada • Scarborough (Tobago), Trinidad and Tobago • Kralendijk, Bonaire • Oranjestad, Aruba • Willemstad, Curacao • Falmouth, Jamaica • Miami

Average Starting Price

$4,444pp

Jim's Onboard Credit

Jim's Port Pick
Half Moon Cay is one of my all-time favorite private islands - the sand is unbelievably soft, hands-down the best I’ve ever felt!

Silver Spirit

Silversea

Nov 3, 2028 - Nov 12, 2028 (9 Nights)

Miami • St. John • Gustavia, St. Barts • St John's, Antigua • Grand Turk • Miami

Average Starting Price

$3,700pp

Jim's Onboard Credit

Luke's Port Pick
Grand Turk has it all - stunning ship views, a pool, great snorkeling, and crystal-clear water! This port will always be my favorite!