15 Night - Southern Caribbean in Depth
Starting in Miami, Florida, San Juan, Puerto Rico, Great Harbour, Jost van Dyke, British Virgin Islands, Carambola Beach, Saint Kitts and Nevis, Roseau, Dominica, Port Elizabeth VC, Bequia, St Vincent and the Grenadines, Bridgetown, Barbados, Rodney Bay, Saint Lucia, Little Bay, Montserrat, St Johns AG, Antigua, Carambola Beach, Saint Kitts and Nevis, Spanish Town, Virgin Gorda, British Virgin Islands, Philipsburg, Sint Maarten
2026 Sails: Nov 20, More...

8 Night - Southern Caribbean Gems
Starting in Miami, Florida, San Juan, Puerto Rico, Great Harbour, Jost van Dyke, British Virgin Islands, Carambola Beach, Saint Kitts and Nevis, Roseau, Dominica, Port Elizabeth VC, Bequia, St Vincent and the Grenadines, Bridgetown, Barbados
2026 Sails: Nov 20, More...

7 Night - Southern Caribbean Cruise : Bequia, Grenada & Tobago
Starting in San Juan, Virgin Gorda, St Johns AG, Saint-Pierre, Port Elizabeth VC, Bequia, Saint Georges, Grenada, Scarborough, Tobago, Bridgetown
2026 Sails: Nov 21, More...

7 Night - the Glorious Grenadines Cruise
Starting in Bridgetown, Barbados, Soufriere Bay, Kingstown, Port Elizabeth VC, Bequia, Tobago Cays, St Georges, Mayreau, Bridgetown, Barbados
2026 Sails: Nov 21, More...

14 Night - Exotic Caribbean in Depth
Starting in Bridgetown, Barbados, Rodney Bay, Saint Lucia, Little Bay, Montserrat, St Johns AG, Antigua, Carambola Beach, Saint Kitts and Nevis, Spanish Town, Virgin Gorda, British Virgin Islands, Philipsburg, Sint Maarten, Sopers Hole (Frenchmans Cay), British Virgin Islands, 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: Nov 28, More...

7 Night - West Indies Explorer Cruise
Starting in Bridgetown, Barbados, Port Elizabeth VC, Bequia, Mayreau, Soufriere Bay, Terre De Haut, Iles des Saintes, Philipsburg, Simpson Bay, Gustavia, St Johns AG
2026 Sails: Nov 28, More...

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

14 Night - Caribbean Yacht Explorer
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), British Virgin Islands, 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, Nov 27, 2028: Jan 15, Jan 29, Feb 12, Feb 26, More...