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!

Viking Sea

Viking

Dec 17, 2027 - Dec 27, 2027 (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

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!

Harmony of the Seas

Royal Caribbean

Sep 25, 2027 - Oct 2, 2027 (7 Nights)

Port Canaveral (Orlando), Florida • Philipsburg, St. Maarten • San Juan, Puerto Rico • Perfect Day Cococay • Port Canaveral (Orlando), Florida

Average Starting Price

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

San Juan, Puerto Rico • Tortola • Castries, St. Lucia • Bridgetown, Barbados • Roseau, Dominica • Philipsburg, St. Maarten • San Juan, Puerto Rico

Average Starting Price

Dec 19, 2027 - Dec 29, 2027 (10 Nights)

Average Starting Price

Jan 29, 2028 - Feb 7, 2028 (9 Nights)

Fort Lauderdale • St. Thomas • St John's, Antigua • Castries, St. Lucia • Philipsburg, St. Maarten • Fort Lauderdale

Average Starting Price

$1,191pp

Jim's Onboard Credit

Norwegian Prima

Norwegian Cruise Line

Nov 27, 2027 - Dec 4, 2027 (7 Nights)

San Juan, Puerto Rico • Tortola • St. Kitts • St John's, Antigua • Bridgetown, Barbados • Philipsburg, St. Maarten • St. Thomas • San Juan, Puerto Rico

Average Starting Price

Jul 25, 2027 - Aug 1, 2027 (7 Nights)

Port Canaveral (Orlando), Florida • Perfect Day Cococay • St. Thomas • Philipsburg, St. Maarten • Port Canaveral (Orlando), Florida

Average Starting Price

$1,922pp

Jim's Onboard Credit

Jim's Ship Pick
This is the BEST ship I’ve EVER sailed on! It rarely felt crowded, the food was incredible, the shows were absolutely phenomenal, and there’s something for everyone!