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October 2026

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Sky Princess

Princess Cruises

Jan 2, 2028 - Jan 9, 2028 (7 Nights)

Fort Lauderdale • Relaxaway Half Moon Cay • San Juan, Puerto Rico • Amber Cove, Dominican Republic • Grand Turk • Fort Lauderdale

Average Starting Price

$559pp

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!

59% OFF

Carnival Magic

Carnival Cruise Line

Mar 6, 2027 - Mar 14, 2027 (8 Nights)

Miami • Relaxaway Half Moon Cay • Fun Day at Sea • San Juan, Puerto Rico • Philipsburg, St. Maarten • St. Thomas • Fun Day at Sea • Fun Day at Sea • Miami

Average Starting Price

$454pp

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!

18% OFF

Nieuw Statendam

Holland America Line

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

Fort Lauderdale • Grand Turk • San Juan, Puerto Rico • St. Thomas • Relaxaway Half Moon Cay • Fort Lauderdale

Average Starting Price

$634pp

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!

59% OFF

Margaritaville at Sea Beachcomber

Margaritaville at Sea

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

Miami • St. Thomas • San Juan, Puerto Rico • Puerto Plata, Dominican Republic • Miami

Average Starting Price

46% OFF

Jun 12, 2027 - Jun 19, 2027 (7 Nights)

Miami • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • Ocean Cay • Miami

Average Starting Price

$1,194pp

Jim's Onboard Credit

Jim Sr's Ship Pick
This ship never felt crowded - and the Pizza & Burger spot was a total win!

Grandeur of the Seas

Royal Caribbean

Jun 26, 2027 - Jul 3, 2027 (7 Nights)

San Juan, Puerto Rico • St. Thomas • St. Croix • Philipsburg, St. Maarten • Castries, St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico

Average Starting Price

Jan 29, 2028 - Feb 5, 2028 (7 Nights)

San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • St. Croix • Basseterre, St. Kitts and Nevis • San Juan, Puerto Rico

Average Starting Price

Nov 21, 2026 - Dec 5, 2026 (14 Nights)

Fort Lauderdale • Relaxaway Half Moon Cay • Amber Cove, Dominican Republic • Grand Turk • Key West, Florida • Fort Lauderdale • Grand Turk • San Juan, Puerto Rico • St. Thomas • Relaxaway Half Moon Cay • Fort Lauderdale

Average Starting Price

$2,104pp

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!

Zuiderdam

Holland America Line

Dec 5, 2026 - Dec 19, 2026 (14 Nights)

Miami • Grand Turk • San Juan, Puerto Rico • St. Thomas • Relaxaway Half Moon Cay • Miami • Relaxaway Half Moon Cay • Ocho Rios, Jamaica • George Town, Cayman Islands • Cozumel • Miami

Average Starting Price

$2,034pp

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!

Star Pride

Windstar Cruises

Nov 22, 2027 - Dec 13, 2027 (21 Nights)

San Juan, Puerto Rico • Grenada • Bequia Island, Saint Vincent • Mayreau Island, Saint Vincent and the Grenadines • Les Saintes, F.W.I. • Marigot Bay, St. Martin, French West Indies • San Juan, Puerto Rico • Catalina Island, Dominican Republic • Santa Domingo, Dominican Republic • Cartagena, Colombia • Cartagena, Colombia • Panama Canal, Panama • Colon, Panama • Panama Canal, Panama • Panama City (Fuerte Amador), Panama • Panama City (Fuerte Amador), Panama • Isla Parida, Panama • Puerto Jimenez (Golfo Dulce), Costa Rica • Quepos, Costa Rica • Puerto Caldera, Costa Rica

Average Starting Price

Jan 22, 2028 - Jan 29, 2028 (7 Nights)

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

Average Starting Price

Feb 15, 2028 - Feb 22, 2028 (7 Nights)

Fort Lauderdale • San Juan, Puerto Rico • Samana, Dominican Republic • Grand Turk • Fort Lauderdale

Average Starting Price

$679pp

Jim's Onboard Credit

Luke's Port Pick
Grand Turk has it all - stunning ship views, a pool, great snorkeling, and crystal-clear water! This port will always be my favorite!

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