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!

Crown Princess

Princess Cruises

Feb 21, 2027 - Mar 7, 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 • Dominica • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico

Average Starting Price

Feb 23, 2027 - Mar 6, 2027 (11 Nights)

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

$2,269pp

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!

19% OFF

Zuiderdam

Holland America Line

Dec 5, 2026 - Dec 12, 2026 (7 Nights)

Miami • Grand Turk • San Juan, Puerto Rico • St. Thomas • Relaxaway Half Moon Cay • Miami

Average Starting Price

$579pp

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!

Star Pride

Windstar Cruises

Nov 15, 2027 - Nov 22, 2027 (7 Nights)

San Juan, Puerto Rico • St. John • Basseterre, St. Kitts and Nevis • Gustavia, St. Barts • Philipsburg, St. Maarten • Great Harbor Jost Van Dyke, British Virgin Islands • Virgin Gorda, British Virgin Islands • San Juan, Puerto Rico

Average Starting Price

Nov 29, 2026 - Dec 20, 2026 (21 Nights)

Fort Lauderdale • Philipsburg, St. Maarten • Fort-De-France, Martinique • Bridgetown, Barbados • Scarborough (Tobago), Trinidad and Tobago • Castries, St. Lucia • St. Kitts • Key West, Florida • Fort Lauderdale • Philipsburg, St. Maarten • St John's, Antigua • Tortola • San Juan, Puerto Rico • Relaxaway Half Moon Cay • Fort Lauderdale

Average Starting Price

$3,164pp

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!

Brilliant Lady

Virgin Voyages

Nov 30, 2026 - Dec 10, 2026 (10 Nights)

Miami • Philipsburg, St. Maarten • Tortola • St. Croix • San Juan, Puerto Rico • Puerto Plata, Dominican Republic • Bimini • Miami

Average Starting Price

Jan 30, 2028 - Feb 6, 2028 (7 Nights)

Port Canaveral (Orlando), Florida • Celebration Key • Amber Cove, Dominican Republic • San Juan, Puerto Rico • Grand Turk • Port Canaveral (Orlando), Florida

Average Starting Price

$569pp

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!