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October 2026

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41% OFF

MSC Poesia

MSC Cruises

Jan 14, 2027 - Jan 24, 2027 (10 Nights)

Miami • Willemstad, Curacao • Oranjestad, Aruba • Ocho Rios, Jamaica • George Town, Cayman Islands • Cozumel • Miami

Average Starting Price

Feb 23, 2028 - Mar 15, 2028 (21 Nights)

Fort Lauderdale • Relaxaway Half Moon Cay • Cabo Rojo, Dominican Republic • Kralendijk, Bonaire • Willemstad, Curacao • Oranjestad, Aruba • Fort Lauderdale • Relaxaway Half Moon Cay • Ocho Rios, Jamaica • George Town, Cayman Islands • Mahogany Bay, Honduras • Belize City • Cozumel • Nassau • Fort Lauderdale

Average Starting Price

$5,089pp

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!

Norwegian Epic

Norwegian Cruise Line

Jan 17, 2027 - Jan 24, 2027 (7 Nights)

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

Average Starting Price

Apr 9, 2028 - Apr 15, 2028 (6 Nights)

Fort Lauderdale • Key West, Florida • George Town, Cayman Islands • Nassau • Fort Lauderdale

Average Starting Price

Oct 30, 2028 - Nov 13, 2028 (14 Nights)

New York, New York • Nassau • Puerto Plata, Dominican Republic • Kralendijk, Bonaire • Willemstad, Curacao • Oranjestad, Aruba • Falmouth, Jamaica • George Town, Cayman Islands • Miami

Average Starting Price

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

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

Average Starting Price

$1,253pp

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!

Rotterdam

Holland America Line

Dec 12, 2026 - Jan 2, 2027 (21 Nights)

Fort Lauderdale • Relaxaway Half Moon Cay • Falmouth, Jamaica • George Town, Cayman Islands • Mahogany Bay, Honduras • Belize City • Cozumel • Fort Lauderdale • Philipsburg, St. Maarten • St. Kitts • Roseau, Dominica • Castries, St. Lucia • St John's, Antigua • St. Thomas • Relaxaway Half Moon Cay • Fort Lauderdale

Average Starting Price

$3,604pp

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!

42% OFF

Carnival Horizon

Carnival Cruise Line

Sep 9, 2028 - Sep 16, 2028 (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

Jan 17, 2027 - Feb 7, 2027 (21 Nights)

Fort Lauderdale • Relaxaway Half Moon Cay • Oranjestad, Aruba • Cartagena, Colombia • Enter Panama Canal at Cristobal • Cruising Panama Canal And Gatun Lake • Gatun Lake, Panama • Cruising Gatun Lake And Panama Canal • Panama Canal, Panama • Colon, Panama • Limon, Costa Rica • George Town, Cayman Islands • Fort Lauderdale • St John's, Antigua • St. Thomas • Tortola • San Juan, Puerto Rico • Relaxaway Half Moon Cay • Fort Lauderdale

Average Starting Price

$4,264pp

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!

50% OFF

Carnival Legend

Carnival Cruise Line

Dec 19, 2026 - Dec 27, 2026 (8 Nights)

Tampa • Fun Day at Sea • George Town, Cayman Islands • Fun Day at Sea • Isla Tropicale, Roatan • Belize City • Cozumel • Fun Day at Sea • Tampa

Average Starting Price

$778pp

Jim's Onboard Credit

57% OFF

Margaritaville at Sea Islander

Margaritaville at Sea

Jan 9, 2027 - Jan 16, 2027 (7 Nights)

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

Average Starting Price

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

Miami • George Town, Cayman Islands • Ocho Rios, Jamaica • Nassau • Bimini • Miami

Average Starting Price

$903pp

Jim's Onboard Credit

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