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October 2026

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Disney Fantasy

Disney Cruise Line

Dec 3, 2027 - Dec 10, 2027 (7 Nights)

San Juan, Puerto Rico • Oranjestad, Aruba • Willemstad, Curacao • Roseau, Dominica • St John's, Antigua • San Juan, Puerto Rico

Average Starting Price

$2,094pp

Jim's Onboard Credit

Norwegian Gem

Norwegian Cruise Line

Apr 3, 2027 - Apr 13, 2027 (10 Nights)

Tampa • Cabo Rojo, Dominican Republic • Willemstad, Curacao • Oranjestad, Aruba • Puerto Plata, Dominican Republic • Manhattan

Average Starting Price

Jul 17, 2027 - Jul 25, 2027 (8 Nights)

Miami • Oranjestad, Aruba • Willemstad, Curacao • Kralendijk, Bonaire • Miami

Average Starting Price

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

Mar 28, 2027 - Apr 4, 2027 (7 Nights)

San Juan, Puerto Rico • Philipsburg, St. Maarten • Oranjestad, Aruba • Willemstad, Curacao • Fort Lauderdale

Average Starting Price

Dec 22, 2027 - Jan 8, 2028 (17 Nights)

Fort Lauderdale • Grand Turk • San Juan, Puerto Rico • St. Thomas • Relaxaway Half Moon Cay • Fort Lauderdale • Relaxaway Half Moon Cay • Cabo Rojo, Dominican Republic • Willemstad, Curacao • Kralendijk, Bonaire • Oranjestad, Aruba • Fort Lauderdale

Average Starting Price

$4,794pp

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!

Nieuw Amsterdam

Holland America Line

Apr 2, 2027 - Apr 11, 2027 (9 Nights)

Fort Lauderdale • Kralendijk, Bonaire • Willemstad, Curacao • Cabo Rojo, Dominican Republic • Relaxaway Half Moon Cay • Fort Lauderdale

Average Starting Price

$1,829pp

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!

Scarlet Lady

Virgin Voyages

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

San Juan, Puerto Rico • Oranjestad, Aruba • Willemstad, Curacao • St John's, Antigua • Philipsburg, St. Maarten • San Juan, Puerto Rico

Average Starting Price

Dec 6, 2027 - Jan 3, 2028 (28 Nights)

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

Average Starting Price

37% OFF

Jan 22, 2028 - Jan 30, 2028 (8 Nights)

Port Canaveral (Orlando), Florida • Fun Day at Sea • Fun Day at Sea • Oranjestad, Aruba • Willemstad, Curacao • Fun Day at Sea • Fun Day at Sea • Celebration Key • Port Canaveral (Orlando), Florida

Average Starting Price

33% OFF

Jan 3, 2028 - Jan 15, 2028 (12 Nights)

Galveston • Fun Day at Sea • Fun Day at Sea • George Town, Cayman Islands • Fun Day at Sea • Oranjestad, Aruba • Kralendijk, Bonaire • Willemstad, Curacao • Fun Day at Sea • Montego Bay, Jamaica • Fun Day at Sea • Fun Day at Sea • Galveston

Average Starting Price

$1,206pp

Jim's Onboard Credit

26% OFF

Seven Seas Mariner

Regent Seven Seas Cruises

Apr 15, 2027 - Apr 29, 2027 (14 Nights)

Miami • Cruising the Caribbean Sea • Oranjestad, Aruba • Willemstad, Curacao • Kralendijk, Bonaire • Cruising the Caribbean Sea • Basseterre, St. Kitts and Nevis • Gustavia, St. Barts • St John's, Antigua • Tortola • Atlantic Ocean cruising • Atlantic Ocean cruising • Atlantic Ocean cruising • New York, New York

Average Starting Price

$9,799pp

Jim's Onboard Credit

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