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October 2026

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Sky Princess

Princess Cruises

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

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

Average Starting Price

$624pp

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

Nov 7, 2027 - Nov 14, 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 30, 2027 - Nov 6, 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

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

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

Average Starting Price

$528pp

Jim's Onboard Credit

FREE Specialty Dining Meal

Explorer of the Seas

Royal Caribbean

Mar 25, 2028 - Apr 2, 2028 (8 Nights)

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

Average Starting Price

$1,100pp

Jim's Onboard Credit

Norwegian Gem

Norwegian Cruise Line

Nov 28, 2026 - Dec 10, 2026 (12 Nights)

Tampa • San Juan, Puerto Rico • Tortola • St. Kitts • Philipsburg, St. Maarten • St. Thomas • Falmouth, Jamaica • George Town, Cayman Islands • Tampa

Average Starting Price

$909pp

Jim's Onboard Credit

Independence of the Seas

Royal Caribbean

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

Miami • Perfect Day Cococay • Nassau • Falmouth, Jamaica • George Town, Cayman Islands • Miami

Average Starting Price

$1,553pp

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!

10% OFF

Rotterdam

Holland America Line

Dec 12, 2026 - Dec 22, 2026 (10 Nights)

Fort Lauderdale • Relaxaway Half Moon Cay • Falmouth, Jamaica • George Town, Cayman Islands • Mahogany Bay, Honduras • Belize City • Cozumel • Fort Lauderdale

Average Starting Price

$864pp

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 Escape

Norwegian Cruise Line

Aug 13, 2028 - Aug 20, 2028 (7 Nights)

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

Average Starting Price

Feb 13, 2028 - Feb 27, 2028 (14 Nights)

Fort Lauderdale • Grand Turk • San Juan, Puerto Rico • Philipsburg, St. Maarten • Fort Lauderdale • Relaxaway Half Moon Cay • Falmouth, Jamaica • Cozumel • Fort Lauderdale

Average Starting Price

$1,193pp

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!

20% OFF

Seven Seas Prestige

Regent Seven Seas Cruises

Feb 22, 2027 - Mar 5, 2027 (11 Nights)

Panama City (Fuerte Amador), Panama • Panama Canal, Panama • Limon, Costa Rica • Roatan, Honduras • Harvest Caye, Belize • Santo Tomas de Castilla, Guatemala • Cozumel • George Town, Cayman Islands • Falmouth, Jamaica • Miami

Average Starting Price

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

Miami • Perfect Day Cococay • Nassau • Falmouth, Jamaica • Labadee, Haiti • Miami

Average Starting Price

$858pp

Jim's Onboard Credit

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