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Cruise Dates

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November 2026

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Vision of the Seas

Royal Caribbean

Dec 27, 2026 - Jan 3, 2027 (7 Nights)

San Juan, Puerto Rico • St. Thomas • St. Croix • St John's, Antigua • Roseau, Dominica • Philipsburg, St. Maarten • San Juan, Puerto Rico

Average Starting Price

$1,427pp

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!

Regal Princess

Princess Cruises

Nov 19, 2028 - Dec 3, 2028 (14 Nights)

Fort Lauderdale • Philipsburg, St. Maarten • St. Thomas • San Juan, Puerto Rico • Amber Cove, Dominican Republic • Fort Lauderdale • Relaxaway Half Moon Cay • Amber Cove, Dominican Republic • Grand Turk • Fort Lauderdale

Average Starting Price

$2,189pp

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!

Crown Princess

Princess Cruises

Mar 5, 2027 - Mar 12, 2027 (7 Nights)

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

Average Starting Price

Dec 19, 2026 - Dec 26, 2026 (7 Nights)

Port Canaveral (Orlando), Florida • Tortola • St. Thomas • Disney Castaway Cay, Bahamas • Port Canaveral (Orlando), Florida

Average Starting Price

$2,953pp

Jim's Onboard Credit

Norwegian Prima

Norwegian Cruise Line

Jan 10, 2027 - Jan 17, 2027 (7 Nights)

San Juan, Puerto Rico • Tortola • Philipsburg, St. Maarten • Bridgetown, Barbados • St. Lucia • St. Kitts • St. Thomas • San Juan, Puerto Rico

Average Starting Price

Apr 16, 2028 - Apr 23, 2028 (7 Nights)

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

Average Starting Price

$2,117pp

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!