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 - Southern Caribbean Adventurer
Starting in San Juan, Puerto Rico, St Maarten, Antigua, Dominica, Grenada, Barbados, San Juan, Puerto Rico, St Thomas, US Virgin Islands, St Maarten, Antigua, Dominica, Barbados, San Juan, Puerto Rico
2026 Sails: Mar 1, More...

7 Night - Southern Caribbean with Barbados and Antigua
Starting in San Juan, Puerto Rico, St Maarten, Antigua, Dominica, Grenada, Barbados, San Juan, Puerto Rico
2026 Sails: Mar 1, More...

15 Night - An Extended Journey Through Spectacular Nature and Historic Wonders
Starting in San Juan, St Georges, Grenada, Bequia, Bridgetown, Fort-de-France, Martinique, Gustavia, Basseterre, San Juan, Road Bay, St Johns AG, Antigua, St Maarten / Philipsburg, Spanish Town (Virgin Gorda), Miami
2026 Sails: Mar 3, More...

8 Night - A Journey from San Juan to San Juan
Starting in San Juan, St Georges, Grenada, Bequia, Bridgetown, Fort-de-France, Martinique, Gustavia, Basseterre, San Juan
2026 Sails: Mar 3, 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...

14 Night - Southern Caribbean Adventurer
Starting in San Juan, Puerto Rico, St Thomas, US Virgin Islands, St Maarten, Antigua, Dominica, Barbados, San Juan, Puerto Rico, Tortola, British Virgin Islands, St Kitts, Dominica, Grenada, Barbados, San Juan, Puerto Rico
2026 Sails: Mar 8, More...

10 Night - Grenada to Antigua
Starting in St Georges, Grenada, Charlotteville, Tobago, Englishmans Bay, Tobago, Saline Bay, Mayreau, Grenadines, Carriacou / Paradise Beach, Grenada, Tobago Cays, Grenadines, Admiralty Bay, Bequia, Grenadines, Fort-De-France, Martinique, Terre De Haut, Iles des Saintes, Basseterre, St Kitts (Morning), South Friars Bay, St Kitts, St Johns AG
2026 Sails: Mar 11, More...

14 Night - Southern Caribbean Adventurer
Starting in San Juan, Puerto Rico, Tortola, British Virgin Islands, St Kitts, Dominica, Grenada, Barbados, San Juan, Puerto Rico, St Thomas, US Virgin Islands, St Maarten, Antigua, Dominica, Barbados, San Juan, Puerto Rico
2026 Sails: Mar 15, More...