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October 2026

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Norwegian Sun

Norwegian Cruise Line

Apr 5, 2027 - Apr 16, 2027 (11 Nights)

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

Average Starting Price

41% OFF

Nov 22, 2027 - Nov 28, 2027 (6 Nights)

Miami • Celebration Key • Fun Day at Sea • Montego Bay, Jamaica • George Town, Cayman Islands • Fun Day at Sea • Miami

Average Starting Price

Nov 23, 2027 - Dec 4, 2027 (11 Nights)

Fort Lauderdale • George Town, Cayman Islands • Oranjestad, Aruba • Willemstad, Curacao • Castries, St. Lucia • Basseterre, St. Kitts and Nevis • Fort Lauderdale

Average Starting Price

$1,336pp

Jim's Onboard Credit

Norwegian Jewel

Norwegian Cruise Line

Nov 19, 2027 - Nov 29, 2027 (10 Nights)

Miami • Great Stirrup Cay • Cabo Rojo, Dominican Republic • Willemstad, Curacao • Oranjestad, Aruba • Falmouth, Jamaica • George Town, Cayman Islands • Miami

Average Starting Price

$1,179pp

Jim's Onboard Credit

Norwegian Breakaway

Norwegian Cruise Line

Apr 4, 2027 - Apr 18, 2027 (14 Nights)

New Orleans • George Town, Cayman Islands • Oranjestad, Aruba • Willemstad, Curacao • Kralendijk, Bonaire • Grenada • St. Lucia • Tortola • Boston

Average Starting Price

$1,689pp

Jim's Onboard Credit

Brilliance of the Seas

Royal Caribbean

Nov 27, 2027 - Dec 5, 2027 (8 Nights)

Tampa • George Town, Cayman Islands • Cozumel • Roatan, Honduras • Costa Maya • Tampa

Average Starting Price

Nov 21, 2027 - Dec 1, 2027 (10 Nights)

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

Average Starting Price

$2,574pp

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!

Sirena

Oceania Cruises

Nov 6, 2027 - Nov 21, 2027 (15 Nights)

New York, New York • Tortola • St John's, Antigua • Basseterre, St. Kitts and Nevis • Kralendijk, Bonaire • Willemstad, Curacao • Oranjestad, Aruba • Ocho Rios, Jamaica • George Town, Cayman Islands • Miami

Average Starting Price

$4,149pp

Jim's Onboard Credit

Adventure of the Seas

Royal Caribbean

Mar 21, 2027 - Mar 27, 2027 (6 Nights)

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

Average Starting Price

$704pp

Jim's Onboard Credit

FREE Specialty Dining Meal

36% OFF

Carnival Dream

Carnival Cruise Line

Mar 20, 2027 - Mar 27, 2027 (7 Nights)

Galveston • Fun Day at Sea • Fun Day at Sea • Montego Bay, Jamaica • George Town, Cayman Islands • Cozumel • Fun Day at Sea • Galveston

Average Starting Price

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!

45% OFF

Carnival Legend

Carnival Cruise Line

Mar 21, 2027 - Mar 28, 2027 (7 Nights)

Tampa • Fun Day at Sea • Cozumel • Fun Day at Sea • Montego Bay, Jamaica • George Town, Cayman Islands • Fun Day at Sea • Tampa

Average Starting Price

$726pp

Jim's Onboard Credit

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