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Cruise Dates

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October 2026

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49% OFF

MSC World Asia

MSC Cruises

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

Pointe-à-Pitre, Guadeloupe • St John's, Antigua • Philipsburg, St. Maarten • St. Kitts • Roseau, Dominica • Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe

Average Starting Price

Nov 8, 2026 - Nov 15, 2026 (7 Nights)

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

Average Starting Price

41% OFF

Dec 26, 2026 - Jan 3, 2027 (8 Nights)

Miami • Relaxaway Half Moon Cay • Fun Day at Sea • San Juan, Puerto Rico • Philipsburg, St. Maarten • St. Thomas • Fun Day at Sea • Fun Day at Sea • Miami

Average Starting Price

$978pp

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 Princess

Princess Cruises

Dec 9, 2028 - Dec 23, 2028 (14 Nights)

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

Average Starting Price

$2,054pp

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!

Rotterdam

Holland America Line

Dec 1, 2026 - Dec 12, 2026 (11 Nights)

Fort Lauderdale • Philipsburg, St. Maarten • St John's, Antigua • Roseau, Dominica • Castries, St. Lucia • St. Kitts • St. Thomas • Relaxaway Half Moon Cay • Fort Lauderdale

Average Starting Price

$1,924pp

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

Jan 22, 2028 - Jan 29, 2028 (7 Nights)

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

Average Starting Price

$1,031pp

Jim's Onboard Credit

Norwegian Prima

Norwegian Cruise Line

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

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

Average Starting Price

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

Miami • Philipsburg, St. Maarten • St. Thomas • Perfect Day Cococay • Miami

Average Starting Price

$1,600pp

Jim's Onboard Credit

FREE Specialty Dining Meal

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!

Star of the Seas

Royal Caribbean

Jan 23, 2028 - Jan 30, 2028 (7 Nights)

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

Average Starting Price

$1,236pp

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!

46% OFF