7 Night - Yachtsman's Caribbean
Starting in Philipsburg, Sint Maarten, Sopers Hole (Frenchmans Cay), 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, More...

14 Night - Yachtsman's Caribbean in Depth
Starting in Philipsburg, Sint Maarten, Sopers Hole (Frenchmans Cay), 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...

14 Night - Exotic Caribbean in Depth
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, Trois Ilets, Martinique, Port Elizabeth VC, Bequia, St Vincent and the Grenadines, Saint Georges, Grenada, Bridgetown, Barbados
2026 Sails: Dec 19, 2027: Jan 23, Feb 13, Feb 27, Mar 13, More...

14 Night - Exotic Caribbean in Depth
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, Trois Ilets, Martinique, Port Elizabeth VC, Bequia, St Vincent and the Grenadines, Saint Georges, Grenada, Bridgetown, Barbados
2027 Sails: Jan 9, More...

10 Night - San Juan to Bridgetown
Starting in San Juan, Jost Van Dyke, British Virgin Islands, Gustavia, St Barthelemy, St Johns, Little Bay, Montserrat, Les Saintes, St Kitts (Basseterre), Trois Ilets, Castries, St Lucia, St Georges, Bridgetown
2027 Sails: Jan 10, More...

14 Night - Caribbean Gems in Depth
Starting in Philipsburg, Sint Maarten, Sopers Hole (Frenchmans Cay), Carambola Beach, Saint Kitts and Nevis, Trois Ilets, 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
2027 Sails: Jan 16, Feb 20, Mar 6, More...

10 Night - Bridgetown to San Juan
Starting in Bridgetown, Bequia, Castries, St Lucia, Trois Ilets, Roseau, Les Saintes, Little Bay, Montserrat, St Kitts (Basseterre), Gustavia, St Barthelemy, St John VI, San Juan
2027 Sails: Jan 20, More...

10 Night - San Juan to Bridgetown
Starting in San Juan, Jost Van Dyke, British Virgin Islands, Gustavia, St Barthelemy, St Kitts (Basseterre), Little Bay, Montserrat, Les Saintes, Roseau, Trois Ilets, Castries, St Lucia, St Georges, Bridgetown
2027 Sails: Feb 6, More...

10 Night - Bridgetown to San Juan
Starting in Bridgetown, Bequia, St Georges, Castries, St Lucia, Trois Ilets, Roseau, Les Saintes, St Kitts (Basseterre), Gustavia, St Barthelemy, Jost Van Dyke, British Virgin Islands, San Juan
2027 Sails: Feb 16, More...

19 Night - Yachtsman's Caribbean & Atlantic Passage
Starting in Philipsburg, Sint Maarten, Sopers Hole (Frenchmans Cay), Carambola Beach, Saint Kitts and Nevis, Trois Ilets, Martinique, Port Elizabeth VC, Bequia, St Vincent and the Grenadines, Saint Georges, Grenada, Bridgetown, Barbados, Castries, Saint Lucia, Funchal (Madeira), Portugal, Portimao, Portugal, Lisbon, Portugal
2027 Sails: Mar 20, More...