7 Night - Caribbean Yachting Hideaways
Starting in San Juan, Puerto Rico, Culebra Island and Vieques Island, Puerto Rico, St John VI, US Virgin Islands, Jost van Dyke, British Virgin Islands, Philipsburg, Sint Maarten, Gustavia, Saint Barthelemy, Little Bay, Montserrat, St Johns AG, Antigua
2025 Sails: Dec 20, 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...

13 Night - An Extended Celebration Journey Into New Caribbean Dawns
Starting in Bridgetown, Tobago / Scarborough, Fort-de-France, Martinique, St Johns AG, Antigua, St Maarten / Philipsburg, Tortola / Road Town, Miami, New Year Fireworks Sju, Jost Van Dyke, Deshaies, Bridgetown
2025 Sails: Dec 21, More...

7 Night - Tropical New Year's Ii Cruise
Starting in San Juan, White Bay, Jost van Dyke, Gustavia, Sandy Ground, St John VI (Cruz Bay), US Virgin Islands, Charlotte Amalie, St Thomas
2025 Sails: Dec 28, More...

7 Night - Beach Fun & Sun : a Remote Caribbean Getaway
Starting in Philipsburg, St Maarten, Falmouth Harbour, Road Bay, Sopers Hole, Jost Van Dyke, Great Harbour, Virgin Gorda / Prickly Pear, British Virgin Islands, Gustavia, Philipsburg, St Maarten
2025 Sails: Dec 28, 2026: Jan 4, 2027: Jan 2, Feb 13, Mar 13, More...

15 Night - An Extended Journey Into Shimmering New Dawns and Caribbean Secrets
Starting in Miami, New Year Fireworks Sju, Jost Van Dyke, Deshaies, Bridgetown, Fort-de-France, Martinique, Basseterre, San Juan, Gustavia, St Johns AG, Antigua, Tortola / Road Town, Road Bay, Miami
2025 Sails: Dec 29, More...

8 Night - A Journey from Miami to San Juan
Starting in Miami, New Year Fireworks Sju, Jost Van Dyke, Deshaies, Bridgetown, Fort-de-France, Martinique, Basseterre, San Juan
2025 Sails: Dec 29, More...

14 Night - Discover the Yachting Islands of the Caribbean
Starting in San Juan, Puerto Rico, Culebra Island, Puerto Rico, St John VI, US Virgin Islands / Jost Van Dyke, British Virgin Islands, Norman Island, British Virgin Islands, Philipsburg, Sint Maarten, Gustavia, Saint Barthelemy, Little Bay, Montserrat, St Johns AG, Antigua, Barbuda, Antigua and Barbuda, Iles des Saintes, Guadeloupe, Deshaies, Guadeloupe, Gustavia, Saint Barthelemy, Virgin Gorda, British Virgin Islands, Norman Island, British Virgin Islands, San Juan, Puerto Rico
2026 Sails: Jan 3, More...