7 Night - Classic Caribbean Yacht Harbors
Starting in Bridgetown, Barbados, Castries, Saint Lucia, Little Bay, Montserrat, St Johns AG, Antigua, Carambola Beach, Saint Kitts and Nevis, Great Harbour, Jost van Dyke, British Virgin Islands, Philipsburg, Sint Maarten
2026 Sails: Dec 19, 2027: Jan 23, Feb 13, Feb 27, Mar 13, Nov 27, 2028: Jan 15, Jan 29, Feb 12, Feb 26, More...

8 Night - Bridgetown to Bridgetown
Starting in Bridgetown, Bequia, Fort-de-France, Roseau, St Kitts (Basseterre), St John VI, Castries, St Lucia, Bridgetown
2026 Sails: Dec 19, More...

14 Night - Western Caribbean from Casa De Campo / La Romana
Starting in La Romana, Castries, St Lucia, Pointe-a-Pitre, St Johns AG, Antigua, Basseterre, Tortola (Road Harbour), La Romana, Catalina Island, Cabo Rojo, Puerto Plata, Dominican Republic, Grand Turk, Arroyo Barril (Samana), La Romana
2026 Sails: Dec 20, More...

7 Night - Caribbean Roundtrip from La Romana
Starting in La Romana, Castries, St Lucia, Pointe-a-Pitre, St Johns AG, Antigua, Basseterre, Tortola (Road Harbour), La Romana
2026 Sails: Dec 20, More...

7 Night - Eastern Caribbean with St. Barths
Starting in Marigot, Saint Martin, Marigot, Saint Martin / Prickly Pear Cays, Anguilla / Gustavia, Saint Barthelemy, Gustavia, Saint Barthelemy, Charlestown, Saint Kitts and Nevis / Cades Bay, Saint Kitts and Nevis, Falmouth Harbour, Antigua and Barbuda, Iles des Saintes, Guadeloupe, Soufriere, Saint Lucia, Bridgetown, Barbados
2026 Sails: Dec 20, 2027: Jan 16, Feb 13, Mar 13, More...

16 Night - Leeward Island Holiday
Starting in Miami, Florida, San Juan, Puerto Rico, Road Bay, Anguilla, Carambola Beach, Saint Kitts and Nevis, Marigot, St Martin, Terre-de-Haut, Iles des Saintes, Guadeloupe, Fort-De-France, Martinique, Rodney Bay, Saint Lucia, Roseau, Dominica, Little Bay, Montserrat, St Johns AG, Antigua, Great Harbour, Jost van Dyke, British Virgin Islands, Miami, Florida
2026 Sails: Dec 20, More...

7 Night - San Juan to San Juan
Starting in San Juan, Jost Van Dyke, British Virgin Islands, Little Bay, Montserrat, Castries, St Lucia, Fort-de-France, Sopers Hole, San Juan
2026 Sails: Dec 20, More...

14 Night - Caribbean Roundtrip from San Juan
Starting in San Juan, Jost Van Dyke, Little Bay, Castries, Fort-de-France, Sopers Hole, San Juan, St John VI, St Kitts, Les Saintes, Bequia, St Thomas, San Juan
2026 Sails: Dec 20, More...

15 Night - Holiday Season with Your Toes in the Sand
Starting in Philipsburg, North Sound / Virgin Gorda, Sail Through the Sir Francis Drake Channel, Great Harbour / Jost Van Dyke, The Bight Bay / Norman Island, Cabrits, Saint-Pierre, Soufriere, Terre-De-Haut, Iles Des Saintes, Gustavia, Philipsburg
2026 Sails: Dec 21, More...

8 Night - Bridgetown to San Juan
Starting in Bridgetown, Soufriere, St Lucia, Bequia, St Georges, Fort-de-France, St Kitts (Basseterre), St Thomas, San Juan
2026 Sails: Dec 21, More...