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!

Wind Surf

Windstar Cruises

Dec 12, 2027 - Dec 27, 2027 (15 Nights)

Philipsburg, St. Maarten • Charlestown, Nevis • Roseau, Dominica • Mayreau Island, Saint Vincent and the Grenadines • Les Saintes, F.W.I. • Basseterre, St. Kitts and Nevis • Gustavia, St. Barts • Philipsburg, St. Maarten • St John's, Antigua • Gustavia, St. Barts • Road Bay, Anguilla • Soper's Hole, Tortola • Great Harbor Jost Van Dyke, British Virgin Islands • Great Harbor Jost Van Dyke, British Virgin Islands • Virgin Gorda, British Virgin Islands • Charlestown, Nevis • Philipsburg, St. Maarten

Average Starting Price

Feb 26, 2028 - Mar 4, 2028 (7 Nights)

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

Average Starting Price

Jan 4, 2027 - Jan 15, 2027 (11 Nights)

Bridgetown, Barbados • Castries, St. Lucia • Fort-De-France, Martinique • St John's, Antigua • Oranjestad, Aruba • Willemstad, Curacao • Kralendijk, Bonaire • Canouan, Saint Vincent and the Grenadines • Bequia Island, Saint Vincent • Bridgetown, Barbados

Average Starting Price

Nov 20, 2027 - Nov 27, 2027 (7 Nights)

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

Average Starting Price

Jan 26, 2027 - Feb 5, 2027 (10 Nights)

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

Average Starting Price

30% OFF

Mar 13, 2027 - Mar 20, 2027 (7 Nights)

Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • Philipsburg, St. Maarten • St John's, Antigua • St. Kitts • Roseau, Dominica • Fort-De-France, Martinique

Average Starting Price

Jan 17, 2027 - Jan 31, 2027 (14 Nights)

San Juan, Puerto Rico • Philipsburg, St. Maarten • Martinique • Grenada • St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico

Average Starting Price

Feb 5, 2027 - Feb 15, 2027 (10 Nights)

Fort Lauderdale • Philipsburg, St. Maarten • Castries, St. Lucia • Grenada • Roseau, Dominica • St John's, Antigua • Fort Lauderdale

Average Starting Price

$1,806pp

Jim's Onboard Credit

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