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, Norman Island, British Virgin Islands, Philipsburg, Sint Maarten, Gustavia, Saint Barthelemy, Little Bay, Montserrat, St Johns AG, Antigua
2026 Sails: Jan 17, Feb 28, 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, Beef Island, Jost Van Dyke, Beef Island, Dog Island, Anguilla, Philipsburg
2026 Sails: Jan 17, Feb 14, More...

14 Night - Gems of the Caribbean
Starting in Philipsburg, Sint Maarten, Sopers Hole (Frenchmans Cay), Carambola Beach, Saint Kitts and Nevis, Saint Pierre, Martinique, Port Elizabeth VC, Bequia, St Vincent and the Grenadines, Saint Georges, Grenada, 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: Jan 17, More...

11 Night - Jamaica to Antigua
Starting in Montego Bay, Jamaica, Port Antonio, Jamaica, Santo Domingo, Dominican Republic, Sailing Sir Francis Drake Channel, The Bight / Norman Island, British Virgin Islands, White Bay, Jost Van Dyke, Sopers Hole, Tortola, Spanish Town, Virgin Gorda, Beach, Captains Best, British Virgin Islands, Basseterre, St Kitts (Morning), South Friars Bay, St Kitts, St Johns AG
2026 Sails: Jan 17, More...

7 Night - San Juan & the Virgin Islands
Starting in San Juan, St John VI (Cruz Bay), US Virgin Islands, Basseterre, Gustavia, Philipsburg, St Maarten, Jost Van Dyke, Great Harbour, Virgin Gorda / Prickly Pear, British Virgin Islands, San Juan
2026 Sails: Jan 23, Feb 6, Mar 6, More...

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: Jan 24, Feb 14, Feb 28, Mar 21, Dec 19, 2027: Jan 23, Feb 13, Feb 27, Mar 13, More...

8 Night - Caribbean Roundtrip from St Maarten (Philipsburg)
Starting in Philipsburg, North Sound / Virgin Gorda, Sail Through the Sir Francis Drake Channel, White Bay, Jost Van Dyke, Great Harbour / Jost Van Dyke, The Bight Bay / Norman Island, St Johns AG, Antigua, Gustavia, Philipsburg
2026 Sails: Jan 25, More...

7 Night - Windward & Leeward Islands Cruise
Starting in San Juan, White Bay, Jost van Dyke, Sint Eustatius, Gustavia, Falmouth Bay, Terre De Haut, Iles des Saintes, Le Marin, Bridgetown, Barbados
2026 Sails: Jan 25, More...

10 Night - Antigua to Grenada
Starting in St Johns AG, Gustavia, St Barts, Sailing Sir Francis Drake Channel, The Bight / Norman Island, British Virgin Islands, White Bay, Jost Van Dyke, Sopers Hole, Tortola, Spanish Town, Virgin Gorda, Beach, Captains Best, British Virgin Islands, Basseterre, St Kitts (Morning), South Friars Bay, St Kitts, Terre De Haut, Iles des Saintes, Beach, Martinique, Admiralty Bay, Bequia, Grenadines, Tobago Cays, Grenadines, St Georges, Grenada
2026 Sails: Jan 28, More...

7 Night - Caribbean Yachting Hideaways
Starting in San Juan, Puerto Rico, Culebra 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
2026 Sails: Jan 31, More...