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Cruise Dates

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October 2026

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Scarlet Lady

Virgin Voyages

Mar 29, 2027 - Apr 3, 2027 (5 Nights)

Miami • George Town, Cayman Islands • Bimini • Miami

Average Starting Price

Dec 6, 2027 - Jan 4, 2028 (29 Nights)

Miami • Oranjestad, Aruba • Willemstad, Curacao • Kralendijk, Bonaire • Grenada • Bridgetown, Barbados • Castries, St. Lucia • Pointe-à-Pitre, Guadeloupe • Tortola • Miami • George Town, Cayman Islands • Cartagena, Colombia • Panama Canal, Panama • Puntarenas, Costa Rica • Puerto Quetzal, Guatemala • Zihuatanejo (Ixtapa), Mexico • Manzanillo, Mexico • Ensenada • Los Angeles

Average Starting Price

Dec 11, 2027 - Jan 2, 2028 (22 Nights)

Fort Lauderdale • Philipsburg, St. Maarten • St. Kitts • Fort-De-France, Martinique • Roseau, Dominica • St John's, Antigua • San Juan, Puerto Rico • Relaxaway Half Moon Cay • Fort Lauderdale • George Town, Cayman Islands • Cartagena, Colombia • Oranjestad, Aruba • Willemstad, Curacao • Relaxaway Half Moon Cay • Fort Lauderdale

Average Starting Price

$5,709pp

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!

Volendam

Holland America Line

Dec 11, 2027 - Dec 23, 2027 (12 Nights)

Fort Lauderdale • Relaxaway Half Moon Cay • Willemstad, Curacao • 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

Average Starting Price

$3,234pp

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!

51% OFF

Carnival Magic

Carnival Cruise Line

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

Miami • Celebration Key • Fun Day at Sea • Ocho Rios, Jamaica • George Town, Cayman Islands • Fun Day at Sea • Miami

Average Starting Price

Mar 21, 2027 - Apr 2, 2027 (12 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

Average Starting Price

$2,629pp

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!

44% OFF

Carnival Sunshine

Carnival Cruise Line

Jan 17, 2028 - Jan 27, 2028 (10 Nights)

Galveston • Fun Day at Sea • Fun Day at Sea • George Town, Cayman Islands • Montego Bay, Jamaica • Fun Day at Sea • Isla Tropicale, Roatan • Belize City • Cozumel • Fun Day at Sea • Galveston

Average Starting Price

Mar 6, 2027 - Mar 16, 2027 (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

$2,024pp

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!

Resilient Lady

Virgin Voyages

Apr 11, 2027 - Apr 18, 2027 (7 Nights)

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

Average Starting Price

$1,043pp

Jim's Onboard Credit

27% OFF

Seven Seas Prestige

Regent Seven Seas Cruises

Dec 28, 2027 - Jan 7, 2028 (10 Nights)

Miami • Cozumel • Santo Tomas de Castilla, Guatemala • Harvest Caye, Belize • Roatan, Honduras • Falmouth, Jamaica • George Town, Cayman Islands • Miami

Average Starting Price

$8,249pp

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!

Norwegian Aqua

Norwegian Cruise Line

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

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

Average Starting Price

47% OFF

Oct 10, 2027 - Oct 16, 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

$472pp

Jim's Onboard Credit

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