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Cruise Dates

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October 2026

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Norwegian Bliss

Norwegian Cruise Line

Jan 26, 2028 - Feb 7, 2028 (12 Nights)

Manhattan • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • Tortola • St. Thomas • St. Kitts • Philipsburg, St. Maarten • Manhattan

Average Starting Price

Feb 28, 2027 - Mar 7, 2027 (7 Nights)

San Juan, Puerto Rico • Philipsburg, St. Maarten • Martinique • Dominica • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico

Average Starting Price

Dec 11, 2026 - Dec 27, 2026 (16 Nights)

Fort Lauderdale • Philipsburg, St. Maarten • St John's, Antigua • Tortola • San Juan, Puerto Rico • Relaxaway Half Moon Cay • Fort Lauderdale • Relaxaway Half Moon Cay • Grand Turk • Amber Cove, Dominican Republic • Key West, Florida • Fort Lauderdale

Average Starting Price

$2,439pp

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!

Brilliant Lady

Virgin Voyages

Dec 14, 2026 - Dec 23, 2026 (9 Nights)

Miami • Philipsburg, St. Maarten • St. Thomas • San Juan, Puerto Rico • Bimini • Miami

Average Starting Price

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

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

Average Starting Price

$1,884pp

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 6, 2027 (14 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

Average Starting Price

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

Port Canaveral (Orlando), Florida • Celebration Key • Amber Cove, Dominican Republic • San Juan, Puerto Rico • Grand Turk • Port Canaveral (Orlando), Florida

Average Starting Price

$609pp

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!

29% OFF

Seven Seas Prestige

Regent Seven Seas Cruises

Jan 9, 2029 - Jan 19, 2029 (10 Nights)

Miami • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • Gustavia, St. Barts • Roseau, Dominica • St John's, Antigua • Tortola • Miami

Average Starting Price

Feb 25, 2027 - Mar 7, 2027 (10 Nights)

Fort Lauderdale • Relaxaway Half Moon Cay • Amber Cove, Dominican Republic • San Juan, Puerto Rico • Philipsburg, St. Maarten • St John's, Antigua • St. Kitts • Fort Lauderdale

Average Starting Price

$1,774pp

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!

Sun Princess

Princess Cruises

Mar 7, 2027 - Mar 21, 2027 (14 Nights)

Fort Lauderdale • Cozumel • Roatan, Honduras • Belize City • Fort Lauderdale • Grand Turk • San Juan, Puerto Rico • Amber Cove, Dominican Republic • Fort Lauderdale

Average Starting Price

$1,603pp

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!

36% OFF