8 Night - Bridgetown / San Juan
Starting in Bridgetown, St Georges, Canouan, Bequia, Fort-de-France, Terre-De-Haut (Marina Day), Falmouth Harbour, Antigua, Virgin Gorda, San Juan
2026 Sails: Feb 15, More...

10 Night - Grenada to Grenada
Starting in St Georges, Grenada, Charlotteville, Tobago, Englishmans Bay, Tobago, Tobago Cays, Grenadines, Carriacou / Paradise Beach, Grenada, Charlestown Bay, Canouan, Grenadines, Admiralty Bay, Bequia, Grenadines, Saint-Pierre, Martinique, Soufriere, St Lucia, Saline Bay, Mayreau, Grenadines, St Georges, Grenada
2026 Sails: Feb 18, 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...

20 Night - Caribbean from Bridgetown to Lisbon
Starting in Bridgetown, Bequia, Willemstad AN, Oranjestad, Kralendijk, Bridgetown, Mindelo, Santa Cruz de La Palma, Funchal, Lisbon
2026 Sails: Feb 23, More...

15 Night - An Extended Journey of Idyllic Coves and Captivating Cultures
Starting in Miami, Charlotte Amalie (Saint Thomas), Jost Van Dyke, St Johns AG, Antigua, Gustavia, San Juan, St Georges, Grenada, Bequia, Bridgetown, Fort-de-France, Martinique, Gustavia, Basseterre, San Juan
2026 Sails: Feb 24, More...

28 Night - Caribbean from San Juan to Lisbon
Starting in San Juan, St John VI, Gustavia, St Johns AG, Bequia, Soufriere, Bridgetown, Fort-de-France, Deshaies, St Kitts, Road Town, Fort Lauderdale, Royal Naval Dockyard, Funchal, Lisbon
2026 Sails: Feb 24, More...

7 Night - Windward Islands Surf & Sunsets
Starting in San Juan, Philipsburg, St Maarten, Les Saintes, Mayreau, Bequia, Soufriere, San Juan
2026 Sails: Feb 27, 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...