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October 2026

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Eurodam

Holland America Line

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

Fort Lauderdale • Relaxaway Half Moon Cay • Philipsburg, St. Maarten • Roseau, Dominica • Fort-De-France, Martinique • St. Kitts • St. Thomas • Fort Lauderdale

Average Starting Price

$3,034pp

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!

29% OFF

Seven Seas Prestige

Regent Seven Seas Cruises

Jan 19, 2029 - Jan 29, 2029 (10 Nights)

Miami • Tortola • St John's, Antigua • Castries, St. Lucia • Roseau, Dominica • St. Thomas • Miami

Average Starting Price

$7,499pp

Jim's Onboard Credit

Celebrity Constellation

Celebrity Cruises

Jan 30, 2027 - Feb 6, 2027 (7 Nights)

San Juan, Puerto Rico • Tortola • Basseterre, St. Kitts and Nevis • Roseau, Dominica • Castries, St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico

Average Starting Price

Feb 2, 2027 - Feb 13, 2027 (11 Nights)

Fort Lauderdale • Philipsburg, St. Maarten • St John's, Antigua • Roseau, Dominica • Fort-De-France, Martinique • St. Kitts • Tortola • Relaxaway Half Moon Cay • Fort Lauderdale

Average Starting Price

$2,419pp

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

Jan 18, 2028 - Jan 28, 2028 (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

Nov 22, 2026 - Dec 6, 2026 (14 Nights)

Miami • San Juan, Puerto Rico • Road Bay, Anguilla • St. Kitts • Roseau, Dominica • Fort-De-France, Martinique • Little Bay, Montserrat • Terre de Haut, Guadeloupe • Virgin Gorda, British Virgin Islands • Great Harbor Jost Van Dyke, British Virgin Islands • Miami

Average Starting Price

Jan 27, 2028 - Feb 6, 2028 (10 Nights)

Average Starting Price

Jan 16, 2027 - Jan 23, 2027 (7 Nights)

San Juan, Puerto Rico • St. Thomas • St. Croix • Philipsburg, St. Maarten • St John's, Antigua • Roseau, Dominica • San Juan, Puerto Rico

Average Starting Price

$532pp

Jim's Onboard Credit

FREE Specialty Dining Meal

Vista

Oceania Cruises

Mar 2, 2029 - Mar 13, 2029 (11 Nights)

Miami • San Juan, Puerto Rico • St John's, Antigua • Castries, St. Lucia • Bridgetown, Barbados • Roseau, Dominica • Tortola • Miami

Average Starting Price

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

San Juan, Puerto Rico • Tortola • St John's, Antigua • Roseau, Dominica • St. Croix • Basseterre, St. Kitts and Nevis • San Juan, Puerto Rico

Average Starting Price

$689pp

Jim's Onboard Credit

FREE Specialty Dining Meal

Celebrity Eclipse

Celebrity Cruises

Dec 3, 2026 - Dec 12, 2026 (9 Nights)

Fort Lauderdale • Basseterre, St. Kitts and Nevis • Castries, St. Lucia • Roseau, Dominica • St John's, Antigua • Fort Lauderdale

Average Starting Price

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

San Juan, Puerto Rico • Tortola • Bridgetown, Barbados • Castries, St. Lucia • Roseau, Dominica • Philipsburg, St. Maarten • San Juan, Puerto Rico

Average Starting Price

$973pp

Jim's Onboard Credit

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