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Cruise Dates

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October 2026

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Celebrity Eclipse

Celebrity Cruises

Jan 17, 2028 - Jan 29, 2028 (12 Nights)

Fort Lauderdale • Oranjestad, Aruba • Willemstad, Curacao • Kralendijk, Bonaire • Philipsburg, St. Maarten • Castries, St. Lucia • St John's, Antigua • Fort Lauderdale

Average Starting Price

$1,610pp

Jim's Onboard Credit

Norwegian Prima

Norwegian Cruise Line

Nov 13, 2027 - Nov 20, 2027 (7 Nights)

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

Average Starting Price

Dec 11, 2026 - Dec 27, 2026 (16 Nights)

Fort Lauderdale • Philipsburg, St. Maarten • St John's, Antigua • Tortola • San Juan, Puerto Rico • Relaxaway Half Moon Cay • Fort Lauderdale • Relaxaway Half Moon Cay • Grand Turk • Amber Cove, Dominican Republic • Key West, Florida • Fort Lauderdale

Average Starting Price

$2,439pp

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!

Viking Sky

Viking

Dec 9, 2027 - Dec 19, 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

Sep 18, 2027 - Sep 25, 2027 (7 Nights)

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

Average Starting Price

Feb 19, 2027 - Feb 26, 2027 (7 Nights)

Fort Lauderdale • Philipsburg, St. Maarten • San Juan, Puerto Rico • Disney Castaway Cay, Bahamas • Fort Lauderdale

Average Starting Price

May 23, 2027 - May 30, 2027 (7 Nights)

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

Average Starting Price

$1,875pp

Jim's Onboard Credit

FREE Specialty Dining Meal

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!

37% OFF

Carnival Magic

Carnival Cruise Line

Jun 5, 2027 - Jun 13, 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

$929pp

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!

27% OFF

Seven Seas Prestige

Regent Seven Seas Cruises

Jan 17, 2028 - Jan 27, 2028 (10 Nights)

Miami • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • Philipsburg, St. Maarten • Gustavia, St. Barts • St John's, Antigua • Tortola • Miami

Average Starting Price

39% OFF

Jan 27, 2028 - Feb 5, 2028 (9 Nights)

Baltimore • Fun Day at Sea • Fun Day at Sea • Amber Cove, Dominican Republic • San Juan, Puerto Rico • Philipsburg, St. Maarten • Fun Day at Sea • Fun Day at Sea • Fun Day at Sea • Baltimore

Average Starting Price

36% OFF

Oct 30, 2027 - Nov 7, 2027 (8 Nights)

Port Canaveral (Orlando), Florida • Fun Day at Sea • Fun Day at Sea • Philipsburg, St. Maarten • San Juan, Puerto Rico • Amber Cove, Dominican Republic • Fun Day at Sea • Celebration Key • Port Canaveral (Orlando), Florida

Average Starting Price

Mar 8, 2027 - Mar 18, 2027 (10 Nights)

Miami • Philipsburg, St. Maarten • Tortola • St. Croix • San Juan, Puerto Rico • Puerto Plata, Dominican Republic • Bimini • Miami

Average Starting Price

$1,191pp

Jim's Onboard Credit

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