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Cruise Dates

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October 2026

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Windstar Cruises

Jan 3, 2028 - Jan 10, 2028 (7 Nights)

San Juan, Puerto Rico • St. John • Gustavia, St. Barts • Basseterre, St. Kitts and Nevis • Philipsburg, St. Maarten • Great Harbor Jost Van Dyke, British Virgin Islands • Virgin Gorda, British Virgin Islands • San Juan, Puerto Rico

Average Starting Price

Nov 27, 2026 - Dec 2, 2026 (5 Nights)

San Juan, Puerto Rico • Great Harbor Jost Van Dyke, British Virgin Islands • Oranjestad, Aruba • Cartagena, Colombia • Cartagena, Colombia

Average Starting Price

Nov 7, 2026 - Nov 14, 2026 (7 Nights)

San Juan, Puerto Rico • Virgin Gorda, British Virgin Islands • St John's, Antigua • St. Pierre • Port Elizabeth (Bequia), Saint Vincent and the Grenadines • Grenada • Scarborough (Tobago), Trinidad and Tobago • Bridgetown, Barbados

Average Starting Price

Dec 5, 2027 - Dec 12, 2027 (7 Nights)

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

Average Starting Price

Dec 5, 2027 - Dec 12, 2027 (7 Nights)

San Juan, Puerto Rico • Bridgetown, Barbados • Grenada • Roseau, Dominica • St John's, Antigua • St. Thomas • San Juan, Puerto Rico

Average Starting Price

Nov 28, 2027 - Dec 12, 2027 (14 Nights)

San Juan, Puerto Rico • Tortola • St. Kitts • Dominica • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico

Average Starting Price

Jan 4, 2027 - Jan 11, 2027 (7 Nights)

San Juan, Puerto Rico • Philipsburg, St. Maarten • St John's, Antigua • Little Bay, Montserrat • Tortola • Miami

Average Starting Price

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

San Juan, Puerto Rico • St. Thomas • St John's, Antigua • Terre de Haut, Guadeloupe • Puerto Plata, Dominican Republic • Miami

Average Starting Price

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

San Juan, Puerto Rico • Philipsburg, St. Maarten • Terre de Haut, Guadeloupe • Road Bay, Anguilla • Ocean Cay • Miami

Average Starting Price

Dec 18, 2027 - Dec 24, 2027 (6 Nights)

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

Average Starting Price

$767pp

Jim's Onboard Credit

Phyllis' Holiday Pick
Best time of the year to cruise! I love spending the holidays cruising with my family! The ships are beautifully decorated, and ringing in New Year’s Eve at sea is an experience I’ll never forget!

Disney Fantasy

Disney Cruise Line

May 6, 2028 - May 13, 2028 (7 Nights)

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

Average Starting Price

Dec 18, 2027 - Dec 26, 2027 (8 Nights)

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

Average Starting Price

$1,192pp

Jim's Onboard Credit

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