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Cruise Dates

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October 2026

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Rotterdam

Holland America Line

Feb 23, 2027 - Mar 16, 2027 (21 Nights)

Fort Lauderdale • Philipsburg, St. Maarten • St John's, Antigua • Roseau, Dominica • Fort-De-France, Martinique • St. Kitts • San Juan, Puerto Rico • Relaxaway Half Moon Cay • Fort Lauderdale • Relaxaway Half Moon Cay • Falmouth, Jamaica • George Town, Cayman Islands • Mahogany Bay, Honduras • Belize City • Cozumel • Fort Lauderdale

Average Starting Price

$3,989pp

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!

Norwegian Aqua

Norwegian Cruise Line

Aug 1, 2027 - Aug 8, 2027 (7 Nights)

Port Canaveral (Orlando), Florida • Great Stirrup Cay • Falmouth, Jamaica • George Town, Cayman Islands • Cozumel • Port Canaveral (Orlando), Florida

Average Starting Price

Oct 24, 2027 - Oct 30, 2027 (6 Nights)

Fort Lauderdale • Perfect Day Cococay • Falmouth, Jamaica • Labadee, Haiti • Fort Lauderdale

Average Starting Price

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

Miami • George Town, Cayman Islands • Falmouth, Jamaica • Oranjestad, Aruba • Willemstad, Curacao • Castries, St. Lucia • Pointe-à-Pitre, Guadeloupe • Tortola • Miami

Average Starting Price

$6,599pp

Jim's Onboard Credit

Norwegian Joy

Norwegian Cruise Line

Jan 31, 2028 - Feb 9, 2028 (9 Nights)

Miami • Nassau • Cabo Rojo, Dominican Republic • Oranjestad, Aruba • Willemstad, Curacao • Falmouth, Jamaica • Miami

Average Starting Price

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

Port Canaveral (Orlando), Florida • Cozumel • George Town, Cayman Islands • Falmouth, Jamaica • Disney Castaway Cay, Bahamas • Port Canaveral (Orlando), Florida

Average Starting Price

$2,707pp

Jim's Onboard Credit

Adventure of the Seas

Royal Caribbean

Jan 24, 2027 - Jan 30, 2027 (6 Nights)

Fort Lauderdale • Falmouth, Jamaica • George Town, Cayman Islands • Nassau • Fort Lauderdale

Average Starting Price

$600pp

Jim's Onboard Credit

FREE Specialty Dining Meal

28% OFF

Seven Seas Prestige

Regent Seven Seas Cruises

Mar 2, 2028 - Mar 14, 2028 (12 Nights)

Miami • Key West, Florida • George Town, Cayman Islands • Falmouth, Jamaica • Cabo Rojo, Dominican Republic • Cartagena, Colombia • Limon, Costa Rica • Panama Canal, Panama • Panama City (Fuerte Amador), Panama

Average Starting Price

Mar 27, 2027 - Apr 3, 2027 (7 Nights)

New Orleans • Cozumel • George Town, Cayman Islands • Falmouth, Jamaica • New Orleans

Average Starting Price

$763pp

Jim's Onboard Credit

FREE Specialty Dining Meal

Norwegian Sun

Norwegian Cruise Line

Jan 13, 2027 - Jan 25, 2027 (12 Nights)

Miami • George Town, Cayman Islands • Falmouth, Jamaica • Cartagena, Colombia • Panama Canal, Panama • Colon, Panama • Limon, Costa Rica • Harvest Caye, Belize • Cozumel • Miami

Average Starting Price

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

Fort Lauderdale • Relaxaway Half Moon Cay • Falmouth, Jamaica • George Town, Cayman Islands • Cozumel • Fort Lauderdale

Average Starting Price

$1,024pp

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!

Explorer of the Seas

Royal Caribbean

Dec 18, 2027 - Dec 26, 2027 (8 Nights)

Fort Lauderdale • Falmouth, Jamaica • George Town, Cayman Islands • Costa Maya • Nassau • Fort Lauderdale

Average Starting Price

$1,172pp

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!

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