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Cruise Dates

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October 2026

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Norwegian Jewel

Norwegian Cruise Line

Nov 28, 2026 - Dec 8, 2026 (10 Nights)

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

Average Starting Price

$759pp

Jim's Onboard Credit

Norwegian Escape

Norwegian Cruise Line

May 7, 2028 - May 14, 2028 (7 Nights)

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

Average Starting Price

Mar 6, 2027 - Mar 13, 2027 (7 Nights)

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

Average Starting Price

$699pp

Jim's Onboard Credit

FREE Specialty Dining Meal

46% OFF

Carnival Paradise

Carnival Cruise Line

Jan 17, 2028 - Jan 22, 2028 (5 Nights)

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

Average Starting Price

45% OFF

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

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

Average Starting Price

Jan 23, 2028 - Feb 6, 2028 (14 Nights)

Fort Lauderdale • Relaxaway Half Moon Cay • San Juan, Puerto Rico • Grand Turk • Amber Cove, Dominican Republic • Fort Lauderdale • Relaxaway Half Moon Cay • Falmouth, Jamaica • George Town, Cayman Islands • Cozumel • Fort Lauderdale

Average Starting Price

$1,228pp

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!

Sonata

Oceania Cruises

Mar 8, 2029 - Mar 15, 2029 (7 Nights)

Miami • Cozumel • Ocho Rios, Jamaica • George Town, Cayman Islands • Miami

Average Starting Price

$3,599pp

Jim's Onboard Credit

23% OFF

Seven Seas Prestige

Regent Seven Seas Cruises

Mar 5, 2029 - Mar 21, 2029 (16 Nights)

Los Angeles • Cabo San Lucas • Puerto Vallarta, Mexico • Puerto Quetzal, Guatemala • Puntarenas, Costa Rica • Panama Canal, Panama • Cartagena, Colombia • George Town, Cayman Islands • Miami

Average Starting Price

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

Port Canaveral (Orlando), Florida • Key West, Florida • Bimini • George Town, Cayman Islands • Cozumel • Port Canaveral (Orlando), Florida

Average Starting Price

$1,158pp

Jim's Onboard Credit

Independence of the Seas

Royal Caribbean

Feb 19, 2028 - Feb 26, 2028 (7 Nights)

Miami • Nassau • Falmouth, Jamaica • George Town, Cayman Islands • Cozumel • Miami

Average Starting Price

Feb 27, 2027 - Mar 6, 2027 (7 Nights)

Fort Lauderdale • Half Moon Cay • Ocho Rios, Jamaica • George Town, Cayman Islands • Cozumel • Fort Lauderdale

Average Starting Price

$2,089pp

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!

52% OFF

Margaritaville at Sea Beachcomber

Margaritaville at Sea

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

Miami • Key West, Florida • George Town, Cayman Islands • Ocho Rios, Jamaica • Nassau • Miami

Average Starting Price

$539pp

Jim's Onboard Credit

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