Cruise Search | Caribbean Breeze Travel

Ocean & RiverAllOcean OnlyOceanRiver OnlyRiver

Cruise Dates



October 2026



1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31

Nights

Clear All Filters

Enchanted Princess

Princess Cruises

Dec 27, 2026 - Jan 6, 2027 (10 Nights)

Fort Lauderdale • Grand Turk • Amber Cove, Dominican Republic • San Juan, Puerto Rico • St John's, Antigua • Philipsburg, St. Maarten • St. Kitts • Fort Lauderdale

Average Starting Price

$1,089pp

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!

49% OFF

MSC Opera

MSC Cruises

Jan 10, 2028 - Jan 17, 2028 (7 Nights)

La Romana, Dominican Republic • Catalina Island, Dominican Republic • Virgin Gorda, British Virgin Islands • Philipsburg, St. Maarten • St. Kitts • St John's, Antigua • La Romana, Dominican Republic

Average Starting Price

Feb 4, 2029 - Feb 18, 2029 (14 Nights)

Fort Lauderdale • Amber Cove, Dominican Republic • San Juan, Puerto Rico • St. Kitts • Fort Lauderdale • Relaxaway Half Moon Cay • San Juan, Puerto Rico • Amber Cove, Dominican Republic • Grand Turk • Fort Lauderdale

Average Starting Price

$1,634pp

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!

Rhapsody of the Seas

Royal Caribbean

Nov 14, 2026 - Nov 21, 2026 (7 Nights)

San Juan, Puerto Rico • Philipsburg, St. Maarten • St John's, Antigua • Roseau, Dominica • Basseterre, St. Kitts and Nevis • St. Croix • San Juan, Puerto Rico

Average Starting Price

29% OFF

Feb 9, 2027 - Feb 23, 2027 (14 Nights)

Bridgetown, Barbados • Kingstown, Saint Vincent Island, Saint Vincent • Grenada • Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • Philipsburg, St. Maarten • St John's, Antigua • St. Kitts • Roseau, Dominica • Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • Castries, St. Lucia • Bridgetown, Barbados

Average Starting Price

49% OFF

Feb 8, 2028 - Feb 22, 2028 (14 Nights)

Bridgetown, Barbados • Kingstown, Saint Vincent Island, Saint Vincent • Castries, St. Lucia • Grenada • Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • Roseau, Dominica • Philipsburg, St. Maarten • St John's, Antigua • St. Kitts • Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • Roseau, Dominica • Bridgetown, Barbados

Average Starting Price

$2,299pp

Jim's Onboard Credit

Norwegian Prima

Norwegian Cruise Line

Jan 24, 2027 - Jan 31, 2027 (7 Nights)

San Juan, Puerto Rico • Tortola • St. Kitts • Bridgetown, Barbados • St. Lucia • Philipsburg, St. Maarten • St. Thomas • San Juan, Puerto Rico

Average Starting Price

Oct 2, 2028 - Oct 10, 2028 (8 Nights)

Halifax, Nova Scotia • St. Kitts • Little Bay, Montserrat • Rodney Bay, Saint Lucia • Bridgetown, Barbados

Average Starting Price

Dec 10, 2028 - Dec 20, 2028 (10 Nights)

San Juan, Puerto Rico • St. Thomas • Basseterre, St. Kitts and Nevis • Castries, St. Lucia • Bridgetown, Barbados • Roseau, Dominica • St John's, Antigua • Philipsburg, St. Maarten • St. Croix • San Juan, Puerto Rico

Average Starting Price

Dec 18, 2027 - Jan 8, 2028 (21 Nights)

Bridgetown, Barbados • Grenada • Bequia Island, Saint Vincent • St. Pierre • Terre de Haut, Guadeloupe • St John's, Antigua • St. Kitts • Great Harbor Jost Van Dyke, British Virgin Islands • Road Bay, Anguilla • Philipsburg, St. Maarten • Soper's Hole, Tortola • Road Bay, Anguilla • Falmouth (English Harbour), Antigua & Barbuda • St. Kitts • Terre de Haut, Guadeloupe • Kralendijk, Bonaire • Willemstad, Curacao • Rodney Bay, Saint Lucia • Bridgetown, Barbados

Average Starting Price

$14,468pp

Jim's Onboard Credit

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!