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Cruise Dates

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October 2026

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Coral Princess

Princess Cruises

Dec 26, 2026 - Jan 6, 2027 (11 Nights)

Fort Lauderdale • St. Thomas • St. Kitts • Martinique • Bridgetown, Barbados • St. Lucia • Philipsburg, St. Maarten • Fort Lauderdale

Average Starting Price

$969pp

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!

Crown Princess

Princess Cruises

Mar 14, 2027 - Mar 21, 2027 (7 Nights)

San Juan, Puerto Rico • St. Thomas • St. Kitts • Dominica • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico

Average Starting Price

Dec 19, 2028 - Jan 2, 2029 (14 Nights)

Fort Lauderdale • Oranjestad, Aruba • Willemstad, Curacao • Kralendijk, Bonaire • Martinique • Bridgetown, Barbados • Dominica • St. Kitts • St. Thomas • Fort Lauderdale

Average Starting Price

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

Miami • Puerto Plata, Dominican Republic • Catalina Island, Dominican Republic • St. Thomas • Road Bay, Anguilla • St. John • San Juan, Puerto Rico

Average Starting Price

$3,655pp

Jim's Onboard Credit

Independence of the Seas

Royal Caribbean

Mar 7, 2027 - Mar 14, 2027 (7 Nights)

Miami • Perfect Day Cococay • San Juan, Puerto Rico • St. Thomas • Miami

Average Starting Price

$726pp

Jim's Onboard Credit

FREE Specialty Dining Meal

Azamara Quest

Azamara

Nov 6, 2027 - Nov 14, 2027 (8 Nights)

San Juan, Puerto Rico • Virgin Gorda, British Virgin Islands • St. Thomas • St John's, Antigua • St. Pierre • Port Elizabeth (Bequia), Saint Vincent and the Grenadines • Grenada • Scarborough (Tobago), Trinidad and Tobago • Bridgetown, Barbados

Average Starting Price

Aug 21, 2027 - Aug 28, 2027 (7 Nights)

San Juan, Puerto Rico • St. Thomas • St. Croix • Philipsburg, St. Maarten • Castries, St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico

Average Starting Price

Oct 17, 2027 - Oct 24, 2027 (7 Nights)

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

Average Starting Price

$1,383pp

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!