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

13 Night - Caribbean Cruise : San Juan, Antigua & St. Lucia
Starting in San Juan, Virgin Gorda, St Johns AG, Saint-Pierre, Port Elizabeth VC, Bequia, Saint Georges, Grenada, Scarborough, Tobago, Bridgetown, Castries, Roseau, Basseterre, St Kitts, Charlestown, Nevis, Philipsburg, San Juan
2026 Sails: Dec 5, More...

7 Night - Southern Caribbean Cruise
Starting in San Juan, Puerto Rico, Charlotte Amalie, St Thomas, Philipsburg, St Maarten, St Johns AG, Antigua, Castries, St Lucia, Bridgetown, Barbados, San Juan, Puerto Rico
2026 Sails: Dec 5, Dec 26, 2027: Jan 23, Feb 20, Mar 6, More...

7 Night - South Caribbean
Starting in Fort-de-France, Martinique, Pointe-A-Pitre, Guadeloupe, St Johns AG, Antigua, Philipsburg, St Maarten, Basseterre, St Kitts and Nevis, Roseau, Dominica, Fort-de-France, Martinique
2026 Sails: Dec 5, 2027: Feb 27, More...

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, 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), 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...

7 Night - Cruise from St. Johns to San Juan
Starting in St Johns AG, Sint Eustatius, Gustavia, Charlestown, Nevis, Sandy Ground, White Bay, Jost van Dyke, Spanish Town, Virgin Gorda, Norman Island, San Juan
2026 Sails: Dec 5, More...

7 Night - Bridgetown to Bridgetown
Starting in Bridgetown, Bequia, Fort-de-France, Deshaies, Gustavia, St Barthelemy, St Johns, Castries, St Lucia, Bridgetown
2026 Sails: Dec 5, More...

7 Night - Windward Islands
Starting in Bridgetown, Barbados, Rodney Bay, St Lucia, Cabrits, Cabrits, Dominica, Falmouth Harbour, Antigua, Basseterre, St Kitts (Morning), South Friars Bay (Beach), St Kitts (Pm), Terre De Haut, Iles des Saintes, Beach, Martinique, Bridgetown, Barbados
2026 Sails: Dec 5, Dec 19, 2027: Jan 2, Jan 16, Jan 30, Feb 13, Feb 27, Mar 13, More...

14 Night - Barbados to Panama
Starting in Bridgetown, Barbados, Tobago Cays, Grenadines, St Georges, Grenada, Kralendijk, Bonaire, Willemstad AN, Curacao, Oranjestad, Aruba, Santa Marta, Colombia, Cartagena De Indias, Colombia, San Blas Archipelago, Panama, Panama Canal Transit, Balboa (Isla Flamenco), Panama
2026 Sails: Dec 5, More...