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 - 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...

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...

8 Night - Relax the Caribbean Way
Starting in Bridgetown, Port Elizabeth VC / Bequia, Tobago Cays, St Vincent and the Grenadines, St Georges, Saint-Pierre, Soufriere, Bridgetown
2026 Sails: Dec 8, Dec 15, More...

16 Night - Caribbean Christmas Cruise : Barbados, St. Lucia & St. Thomas
Starting in Bridgetown, Castries, Roseau, Basseterre, St Kitts, Charlestown, Nevis, Philipsburg, San Juan, Charlotte Amalie, St Thomas, Virgin Gorda, St Johns AG, Gustavia, Saint-Pierre, Port Elizabeth VC, Bequia, Scarborough, Tobago, Mayreau, Grenadines, Bridgetown
2026 Sails: Dec 12, More...

7 Night - Bridgetown to Bridgetown
Starting in Bridgetown, Castries, St Lucia, Fort-de-France, Deshaies, St Johns, Les Saintes, Bequia, Bridgetown
2026 Sails: Dec 12, More...

7 Night - Grenadine Islands
Starting in Bridgetown, Barbados, Captains Best, Grenadines, St Georges, Grenada, Tobago Cays, Grenadines, Kingstown, St Vincent (Morning), Admiralty Bay, Bequia (Pm), Fort-de-France, Martinique (Morning), Beach, Martinique (Afternoon), Marigot Bay, St Lucia (Am), Soufriere, St Lucia (Pm), Bridgetown, Barbados
2026 Sails: Dec 12, Dec 26, 2027: Jan 9, Jan 23, Feb 6, Feb 20, Mar 6, Mar 20, More...

10 Night - Carribean Christmas Cruise : Antigua, Martinique & Saint Barthelemy
Starting in San Juan, Charlotte Amalie, St Thomas, Virgin Gorda, St Johns AG, Gustavia, Saint-Pierre, Port Elizabeth VC, Bequia, Scarborough, Tobago, Mayreau, Grenadines, Bridgetown
2026 Sails: Dec 18, More...

18 Night - Caribbean Holiday Cruise : San Juan, St. Barts & Curacao
Starting in San Juan, Charlotte Amalie, St Thomas, Virgin Gorda, St Johns AG, Gustavia, Saint-Pierre, Port Elizabeth VC, Bequia, Scarborough, Tobago, Mayreau, Grenadines, Bridgetown, Oranjestad, Willemstad AN, Castries, Charlestown, Nevis, Frederiksted, Saint Croix, San Juan
2026 Sails: Dec 18, More...