3 Night - San Juan / San Juan
Starting in San Juan, Gustavia, Virgin Gorda, San Juan
2025 Sails: Dec 18, More...

8 Night - Southern Caribbean Cruise : Antigua, Martinique & Bequia
Starting in San Juan, Charlotte Amalie, St Thomas, Virgin Gorda, St Johns AG, Saint-Pierre, Port Elizabeth VC, Bequia, Scarborough, Tobago, Bridgetown
2025 Sails: Dec 19, More...

7 Night - Reverie Under Sail in the Heart of the Lesser Antilles
Starting in Marigot, Sandy Island, Anguilla, Virgin Gorda, Norman Island, Cooper Island, Jost Van Dyke, Beef Island, Dog Island, Anguilla, Philipsburg
2025 Sails: Dec 20, More...

15 Night - Christmas Caribbean Style
Starting in Philipsburg, North Sound / Virgin Gorda, Sail Through the Sir Francis Drake Channel, White Bay, Jost Van Dyke, Charlestown, Nevis, Chatham Bay / Union Island, Soufriere, Saint-Pierre, Terre-De-Haut, Iles Des Saintes, St Johns AG, Antigua, Gustavia, Philipsburg
2025 Sails: Dec 20, More...

7 Night - Treasure Islands
Starting in Philipsburg, St Maarten, Road Bay, Anguilla, White Bay, Jost Van Dyke, Sopers Hole, Tortola, Sailing Sir Francis Drake Channel, The Bight / Norman Island, British Virgin Islands, Spanish Town, Virgin Gorda, Beach, Captains Best, British Virgin Islands, Basseterre, St Kitts (Morning), South Friars Bay, St Kitts, Gustavia, St Barts, Philipsburg, St Maarten
2025 Sails: Dec 20, 2026: Jan 3, Jan 17, Jan 31, Feb 14, Feb 28, Mar 14, Nov 28, Dec 12, Dec 26, 2027: Jan 9, Jan 23, Feb 6, Feb 20, Mar 6, Mar 20, More...

7 Night - San Juan / San Juan
Starting in San Juan, Virgin Gorda, St Johns AG, Soufriere, Gustavia, St John VI, San Juan
2025 Sails: Dec 21, More...

15 Night - Happy Sunny Holidays
Starting in Philipsburg, North Sound / Virgin Gorda, The Bight Bay / Norman Island, Charlestown, Nevis, Terre-De-Haut, Iles Des Saintes, Soufriere, Chatham Bay / Union Island, St Georges, Saint-Pierre, Gustavia, Philipsburg
2025 Sails: Dec 21, More...

7 Night - Leeward Islands Celebration Cruise
Starting in Charlotte Amalie, St Thomas, St John VI (Cruz Bay), US Virgin Islands, Charlestown, Nevis, Gustavia, Prickly Pear, Spanish Town, Virgin Gorda, Norman Island, San Juan
2025 Sails: Dec 21, More...

14 Night - An Extended Journey of Caribbean Festivities and West Indies Coastal Wonders
Starting in Miami, Ocean Cay, Charlotte Amalie (Saint Thomas), Spanish Town (Virgin Gorda), Marigot, San Juan, Road Bay, St John VI (Cruz Bay), US Virgin Islands, New Year Fireworks Sju, Puerto Plata, Dominican Republic, Key West, Miami
2025 Sails: Dec 22, More...

7 Night - A Journey of Holiday Festivities and Unwrapping Gifts of Sand and Sun
Starting in Miami, Ocean Cay, Charlotte Amalie (Saint Thomas), Spanish Town (Virgin Gorda), Marigot, San Juan
2025 Sails: Dec 22, More...