7 Night - Jewels of the Windward Islands
Starting in Bridgetown, Barbados, Anse Mitan, Martinique, Rodney Bay, Castries, St Lucia, Sunset Cruising Pitons, Mayreau, St Georges, Grenada, Bequia, Bridgetown, Barbados
2026 Sails: Nov 27, More...

14 Night - Exotic Caribbean in Depth
Starting in Bridgetown, Barbados, Rodney Bay, Saint Lucia, Little Bay, Montserrat, St Johns AG, Antigua, Carambola Beach, Saint Kitts and Nevis, Spanish Town, Virgin Gorda, British Virgin Islands, Philipsburg, Sint Maarten, Sopers Hole (Frenchmans Cay), British Virgin Islands, Carambola Beach, Saint Kitts and Nevis, Trois Ilets, Martinique, Port Elizabeth VC, Bequia, St Vincent and the Grenadines, Saint Georges, Grenada, Bridgetown, Barbados
2026 Sails: Nov 28, More...

7 Night - West Indies Explorer Cruise
Starting in Bridgetown, Barbados, Port Elizabeth VC, Bequia, Mayreau, Soufriere Bay, Terre De Haut, Iles des Saintes, Philipsburg, Simpson Bay, Gustavia, St Johns AG
2026 Sails: Nov 28, More...

14 Night - Discover Eastern Caribbean & Grenadines
Starting in Bridgetown, Barbados, Speightstown, Barbados, Bequia Island, Saint Vincent and the Grenadines, Kingstown, Saint Vincent and the Grenadines, Mayreau Island / Union Island, Saint Vincent and the Grenadines, Union Island, Saint Vincent and the Grenadines, Union Island / Tobago Cays, Saint Vincent and the Grenadines, Bridgetown, Barbados, Soufriere, Saint Lucia, Iles des Saintes, Guadeloupe, Falmouth Bay (English Harbour), Antigua and Barbuda, Charlestown / Cades Bay, Saint Kitts and Nevis, Gustavia, Saint Barthelemy, Norman Island, British Virgin Islands, Marigot, Saint Martin
2026 Sails: Nov 29, More...

7 Night - Grenadines & Windwards Yachting
Starting in Bridgetown, Barbados, Speightstown, Barbados, Bequia Island, Saint Vincent and the Grenadines, Kingstown, Saint Vincent and the Grenadines, Mayreau Island / Union Island, Saint Vincent and the Grenadines, Union Island, Saint Vincent and the Grenadines, Union Island / Tobago Cays, Saint Vincent and the Grenadines, Bridgetown, Barbados
2026 Sails: Nov 29, More...

14 Night - Star Collector : Lovely Leewards
Starting in San Juan, Cruz Bay, St John VI, Gustavia, St Barthelemy, Basseterre, St Kitts, Philipsburg, St Maarten, Great Harbour, Jost Van Dyke, Virgin Gorda / Prickly Pear, San Juan, St Georges, Grenada, Bequia, Mayreau, Deshaies, Marigot Bay, San Juan
2026 Sails: Nov 29, Dec 13, Dec 27, More...

16 Night - Star Collector : Windward Islands & Spanish New World
Starting in Bridgetown, Barbados, Rodney Bay, Sunset Cruising Pitons, Scarborough, Tobago, Bequia, Mayreau, St Georges, Grenada, Willemstad AN, Curacao, Oranjestad, Aruba, Cartagena CO, Bocas del Toro, San Blas Islands, Panama, Panama Canal Transit, Fuerte Amador, Panama City
2026 Sails: Dec 4, More...

8 Night - Windward Ways & Tobago Cays
Starting in Bridgetown, Barbados, Rodney Bay, Sunset Cruising Pitons, Scarborough, Tobago, Bequia, Mayreau, St Georges, Grenada, Willemstad AN, Curacao, Oranjestad, Aruba
2026 Sails: Dec 4, More...

7 Night - Yachtsman's Caribbean
Starting in Philipsburg, Sint Maarten, Sopers Hole (Frenchmans Cay), British Virgin Islands, Carambola Beach, Saint Kitts and Nevis, Trois Ilets, Martinique, Port Elizabeth VC, Bequia, St Vincent and the Grenadines, Saint Georges, Grenada, Bridgetown, Barbados
2026 Sails: Dec 5, Dec 26, 2027: Jan 16, Jan 30, Feb 20, Mar 6, Mar 20, Dec 4, 2028: Jan 22, Feb 5, Feb 19, Mar 4, Mar 18, More...

14 Night - Yachtsman's Caribbean in Depth
Starting in Philipsburg, Sint Maarten, Sopers Hole (Frenchmans Cay), British Virgin Islands, Carambola Beach, Saint Kitts and Nevis, Trois Ilets, Martinique, Port Elizabeth VC, Bequia, St Vincent and the Grenadines, Saint Georges, Grenada, Bridgetown, Barbados, Carambola Beach, Saint Kitts and Nevis, Terre-de-Haut, Iles des Saintes, Guadeloupe, Saint Pierre, Martinique, Roseau, Dominica, Rodney Bay, Saint Lucia, Bridgetown, Barbados
2026 Sails: Dec 5, More...