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Cruise Dates

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October 2026

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Disney Destiny

Disney Cruise Line

Jan 30, 2027 - Feb 6, 2027 (7 Nights)

Fort Lauderdale • Disney Lookout Cay at Lighthouse Point, Bahamas • San Juan, Puerto Rico • Philipsburg, St. Maarten • Fort Lauderdale

Average Starting Price

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

Fort Lauderdale • Relaxaway Half Moon Cay • San Juan, Puerto Rico • Amber Cove, Dominican Republic • Grand Turk • Fort Lauderdale

Average Starting Price

$949pp

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!

Sonata

Oceania Cruises

Feb 19, 2028 - Mar 1, 2028 (11 Nights)

Miami • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • St. Thomas • Basseterre, St. Kitts and Nevis • St John's, Antigua • Philipsburg, St. Maarten • Tortola • Miami

Average Starting Price

Nov 27, 2027 - Dec 5, 2027 (8 Nights)

Miami • Amber Cove, Dominican Republic • San Juan, Puerto Rico • Philipsburg, St. Maarten • Tortola • Miami

Average Starting Price

Nov 28, 2027 - Dec 5, 2027 (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

$649pp

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!

Disney Fantasy

Disney Cruise Line

Dec 3, 2027 - Dec 10, 2027 (7 Nights)

San Juan, Puerto Rico • Oranjestad, Aruba • Willemstad, Curacao • Roseau, Dominica • St John's, Antigua • San Juan, Puerto Rico

Average Starting Price

Dec 11, 2027 - Dec 18, 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

Dec 26, 2027 - Jan 2, 2028 (7 Nights)

Miami • Puerto Plata, Dominican Republic • Catalina Island, Dominican Republic • St. Croix • St. Thomas • New Year Fireworks SJU • New Year Fireworks SJU • Great Harbor Jost Van Dyke, British Virgin Islands • San Juan, Puerto Rico

Average Starting Price

$5,495pp

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!

52% OFF