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Cruise Dates

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October 2026

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Norwegian Prima

Norwegian Cruise Line

Jan 8, 2028 - Jan 15, 2028 (7 Nights)

San Juan, Puerto Rico • Tortola • St. Kitts • Bridgetown, Barbados • St. Lucia • Philipsburg, St. Maarten • St. Thomas • San Juan, Puerto Rico

Average Starting Price

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

San Juan, Puerto Rico • St. Thomas • Basseterre, St. Kitts and Nevis • Castries, St. Lucia • Bridgetown, Barbados • Roseau, Dominica • St John's, Antigua • Philipsburg, St. Maarten • St. Croix • San Juan, Puerto Rico

Average Starting Price

Mar 19, 2028 - Mar 26, 2028 (7 Nights)

San Juan, Puerto Rico • St. Thomas • Basseterre, St. Kitts and Nevis • Willemstad, Curacao • Oranjestad, Aruba • San Juan, Puerto Rico

Average Starting Price

Mar 3, 2028 - Mar 14, 2028 (11 Nights)

Miami • San Juan, Puerto Rico • Soper's Hole, Tortola • Gustavia, St. Barts • St John's, Antigua • St. Kitts • Great Harbor Jost Van Dyke, British Virgin Islands • Miami

Average Starting Price

Jan 24, 2028 - Feb 7, 2028 (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 • St. John • Gustavia, St. Barts • Philipsburg, St. Maarten • Basseterre, St. Kitts and Nevis • Great Harbor Jost Van Dyke, British Virgin Islands • Virgin Gorda, British Virgin Islands • San Juan, Puerto Rico

Average Starting Price

Jan 12, 2027 - Feb 2, 2027 (21 Nights)

Fort Lauderdale • Philipsburg, St. Maarten • St John's, Antigua • Roseau, Dominica • Fort-De-France, Martinique • St. Kitts • San Juan, Puerto Rico • Relaxaway Half Moon Cay • Fort Lauderdale • Relaxaway Half Moon Cay • Falmouth, Jamaica • George Town, Cayman Islands • Mahogany Bay, Honduras • Belize City • Cozumel • Fort Lauderdale

Average Starting Price

$3,939pp

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!

Viking Sky

Viking

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

Average Starting Price

Dec 5, 2026 - Dec 12, 2026 (7 Nights)

Port Canaveral (Orlando), Florida • Puerto Plata, Dominican Republic • St. Thomas • Basseterre, St. Kitts and Nevis • Port Canaveral (Orlando), Florida

Average Starting Price

46% OFF

Jan 2, 2027 - Jan 16, 2027 (14 Nights)

Miami • Philipsburg, St. Maarten • St. Kitts • St. Thomas • Amber Cove, Dominican Republic • Miami • Grand Turk • Ocean Cay • Nassau • Miami

Average Starting Price

$1,345pp

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!

48% OFF

MSC Seashore

MSC Cruises

Jan 29, 2028 - Feb 12, 2028 (14 Nights)

Miami • Philipsburg, St. Maarten • St. Kitts • St. Thomas • Puerto Plata, Dominican Republic • Miami • Ocean Cay • Grand Turk • Nassau • Miami

Average Starting Price

$1,257pp

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!