10 Night - Cruise Roundtrip from Bridgetown
Starting in Bridgetown, Barbados, Rodney Bay, South Friars Bay, Philipsburg, Gustavia, Terre De Haut, Iles des Saintes, Mayreau, Tobago Cays, Port Elizabeth VC, Bequia, Bridgetown, Barbados
2026 Sails: Feb 1, More...

12 Night - The Essentials of the Caribbean
Starting in Fort-de-France, Antigua, South Friars Bay, Saint-Kitts, Jost Van Dyke, Gustavia, Les Saintes, Portsmouth UK, Pigeon Island Beach, Soufriere, Tobago Cays, Mayreau Island, Port Elizabeth VC, Bequia Island, Union Island, Fort-de-France
2026 Sails: Feb 10, More...

11 Night - Barbados & Caribbean Gems Cruise
Starting in Bridgetown, Barbados, Rodney Bay, Portsmouth UK, Gustavia, Philipsburg, South Friars Bay, Terre De Haut, Iles des Saintes, Tobago Cays, Port Elizabeth VC, Bequia, Mayreau, Bridgetown, Barbados
2026 Sails: Feb 11, More...

14 Night - Exotic Caribbean Isles
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, 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
2026 Sails: 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: Feb 21, More...

7 Night - Yachtsman's 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
2026 Sails: Feb 21, More...

7 Night - Windward Islands Explorer Cruise
Starting in Bridgetown, Barbados, Port Elizabeth VC, Bequia, Mayreau, Rodney Bay, Le Marin, Terre De Haut, Iles des Saintes, Falmouth Bay, Philipsburg
2026 Sails: Feb 22, More...

8 Night - Cruising the Caribbean's Windward Islands - with Smithsonian Journeys
Starting in Vieux Fort, Portsmouth UK, Les Saintes, Port Elizabeth VC, Bequia Island, Mayreau Island, Saint Georges, Grenada, Tobago Cays, Bridgetown, Vieux Fort
2026 Sails: Feb 28, More...

7 Night - Gliding the Waters of the Windward Islands
Starting in Pointe-a-Pitre, Grande Anse dArlet, Tobago Cays, Sandy Island, Carriacou, Port Elizabeth VC, Bequia Island, Sailing by les Pitons, Soufriere, Portsmouth UK, Marie-Galante, Pointe-a-Pitre
2026 Sails: Feb 28, More...

14 Night - Yachtsman's Island Jewels
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, Carambola Beach, Saint Kitts and Nevis, Pointe-a-Pitre, Guadeloupe, Trois Ilets, Martinique, Roseau, Dominica, Rodney Bay, Saint Lucia, Bridgetown, Barbados
2026 Sails: Mar 7, More...