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

Jan 9, 2028 - Jan 23, 2028 (14 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 • 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 • Gustavia, St. Barts • Philipsburg, St. Maarten

Average Starting Price

Jan 16, 2027 - Jan 26, 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

Jan 10, 2027 - Jan 24, 2027 (14 Nights)

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

Average Starting Price

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

Fort Lauderdale • Tortola • St John's, Antigua • Bridgetown, Barbados • Castries, St. Lucia • Basseterre, St. Kitts and Nevis • Fort Lauderdale

Average Starting Price

Jan 2, 2027 - Jan 23, 2027 (21 Nights)

Fort Lauderdale • Relaxaway Half Moon Cay • Falmouth, Jamaica • George Town, Cayman Islands • Belize City • Cozumel • Key West, Florida • Fort Lauderdale • Philipsburg, St. Maarten • St John's, Antigua • Roseau, Dominica • Fort-De-France, Martinique • St. Kitts • San Juan, Puerto Rico • Relaxaway Half Moon Cay • Fort Lauderdale

Average Starting Price

$3,709pp

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!

Celebrity Ascent

Celebrity Cruises

Jan 25, 2027 - Feb 5, 2027 (11 Nights)

Fort Lauderdale • Philipsburg, St. Maarten • St John's, Antigua • Castries, St. Lucia • Bridgetown, Barbados • Roseau, Dominica • Basseterre, St. Kitts and Nevis • Fort Lauderdale

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

29% OFF

Seven Seas Grandeur

Regent Seven Seas Cruises

Feb 14, 2028 - Feb 24, 2028 (10 Nights)

Bridgetown, Barbados • Grenada • Kingstown, Saint Vincent Island, Saint Vincent • Castries, St. Lucia • Fort-De-France, Martinique • Gustavia, St. Barts • Basseterre, St. Kitts and Nevis • St John's, Antigua • Roseau, Dominica • Bridgetown, Barbados

Average Starting Price

46% OFF

Jul 2, 2027 - Jul 9, 2027 (7 Nights)

Fort-De-France, Martinique • St John's, Antigua • La Romana, Dominican Republic • Catalina Island, Dominican Republic • Bridgetown, Barbados • Fort-De-France, Martinique

Average Starting Price

$1,027pp

Jim's Onboard Credit

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