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, St Kitts, Terre De Haut, Iles des Saintes, Beach, Martinique, Bridgetown, Barbados
2025 Sails: Dec 27, 2026: Jan 10, Jan 24, Feb 7, Feb 21, Mar 7, Mar 21, More...

14 Night - Discover the Yachting Islands of the Caribbean
Starting in San Juan, Puerto Rico, Culebra Island, Puerto Rico, St John VI, US Virgin Islands / Jost Van Dyke, British Virgin Islands, Norman Island, British Virgin Islands, Philipsburg, Sint Maarten, Gustavia, Saint Barthelemy, Little Bay, Montserrat, St Johns AG, Antigua, Barbuda, Antigua and Barbuda, Iles des Saintes, Guadeloupe, Deshaies, Guadeloupe, Gustavia, Saint Barthelemy, Virgin Gorda, British Virgin Islands, Norman Island, British Virgin Islands, San Juan, Puerto Rico
2026 Sails: Jan 3, More...

14 Night - Discover the Yachting Islands of the Caribbean
Starting in St Johns AG, Antigua, Barbuda, Antigua and Barbuda, Iles des Saintes, Guadeloupe, Deshaies, Guadeloupe, Gustavia, Saint Barthelemy, Virgin Gorda, British Virgin Islands, Norman Island, British Virgin Islands, San Juan, Puerto Rico, Culebra Island and Vieques Island, Puerto Rico, St John VI, US Virgin Islands / Jost Van Dyke, British Virgin Islands, Norman Island, British Virgin Islands, Philipsburg, Sint Maarten, Gustavia, Saint Barthelemy, Little Bay, Montserrat, St Johns AG, Antigua
2026 Sails: Jan 10, More...

10 Night - the Best of the Secluded Caribbean Cruise
Starting in San Juan, St John VI (Cruz Bay), US Virgin Islands, Prickly Pear, Sandy Ground, Gustavia, Philipsburg, Terre De Haut, Iles des Saintes, Port Elizabeth VC, Bequia, Tobago Cays, Bridgetown, Barbados
2026 Sails: Jan 10, More...

14 Night - Discover the Yachting Islands of the Caribbean
Starting in San Juan, Puerto Rico, Culebra Island and Vieques Island, Puerto Rico, St John VI, US Virgin Islands / Jost Van Dyke, British Virgin Islands, Norman Island, British Virgin Islands, Philipsburg, Sint Maarten, Gustavia, Saint Barthelemy, Little Bay, Montserrat, St Johns AG, Antigua, Gustavia, Saint Barthelemy, Iles des Saintes, Guadeloupe, Deshaies, Guadeloupe, Barbuda, Antigua and Barbuda, Virgin Gorda, British Virgin Islands, Norman Island, British Virgin Islands, San Juan, Puerto Rico
2026 Sails: Jan 17, More...

7 Night - St. Barths & Caribbean Gems Cruise
Starting in Philipsburg, Falmouth Bay, Charlestown, Nevis, Terre De Haut, Iles des Saintes, Saba, Gustavia, White Bay, Jost van Dyke, San Juan
2026 Sails: Jan 18, More...

11 Night - the Best of the Secluded Caribbean Cruise
Starting in Bridgetown, Barbados, St Georges, Mayreau, Tobago Cays, Port Elizabeth VC, Bequia, Terre De Haut, Iles des Saintes, Charlestown, Nevis, South Friars Bay, Gustavia, Spanish Town, Virgin Gorda, Norman Island, St John VI (Cruz Bay), US Virgin Islands, San Juan
2026 Sails: Jan 20, More...

7 Night - Caribbean Yachting Discovery
Starting in St Johns AG, Antigua, Gustavia, Saint Barthelemy, Iles des Saintes, Guadeloupe, Deshaies, Guadeloupe, Barbuda, Antigua and Barbuda, Virgin Gorda, British Virgin Islands, Norman Island, British Virgin Islands, San Juan, Puerto Rico
2026 Sails: Jan 24, More...

7 Night - Windward & Leeward Islands Cruise
Starting in San Juan, White Bay, Jost van Dyke, Sint Eustatius, Gustavia, Falmouth Bay, Terre De Haut, Iles des Saintes, Le Marin, Bridgetown, Barbados
2026 Sails: Jan 25, More...

10 Night - Antigua to Grenada
Starting in St Johns AG, Gustavia, St Barts, Sailing Sir Francis Drake Channel, The Bight / Norman Island, British Virgin Islands, White Bay, Jost Van Dyke, Sopers Hole, Tortola, Spanish Town, Virgin Gorda, Beach, Captains Best, British Virgin Islands, Basseterre, St Kitts (Morning), South Friars Bay, St Kitts, Terre De Haut, Iles des Saintes, Beach, Martinique, Admiralty Bay, Bequia, Grenadines, Tobago Cays, Grenadines, St Georges, Grenada
2026 Sails: Jan 28, More...