8 Night - A Tall Ship's Dream Destination
Starting in Philipsburg, St Johns AG, Antigua, Gustavia, North Sound / Virgin Gorda, Sail Through the Sir Francis Drake Channel, White Bay, Jost Van Dyke, Great Harbour / Jost Van Dyke, The Bight Bay / Norman Island, Philipsburg
2026 Sails: Jan 11, Nov 29, More...

8 Night - Christening Sailing
Starting in Miami, Puerto Plata, Dominican Republic, Samana, Jost Van Dyke, Great Harbour, Virgin Gorda / Prickly Pear, British Virgin Islands, Sopers Hole, San Juan
2026 Sails: Jan 15, 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 - Reverie Under Sail in the Heart of the Lesser Antilles
Starting in Marigot, Sandy Island, Anguilla, Virgin Gorda, Norman Island, Cooper Island, Beef Island, Jost Van Dyke, Beef Island, Dog Island, Anguilla, Philipsburg
2026 Sails: Jan 17, Feb 14, More...

11 Night - Jamaica to Antigua
Starting in Montego Bay, Jamaica, Port Antonio, Jamaica, Santo Domingo, Dominican Republic, 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, St Johns AG
2026 Sails: Jan 17, More...

7 Night - San Juan / San Juan
Starting in San Juan, Bridgetown, Les Anses-dArlet, Falmouth Harbour, Antigua, Virgin Gorda, Gustavia, San Juan
2026 Sails: Jan 18, Feb 15, 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 - San Juan & the Virgin Islands
Starting in San Juan, St John VI (Cruz Bay), US Virgin Islands, Basseterre, Gustavia, Philipsburg, St Maarten, Jost Van Dyke, Great Harbour, Virgin Gorda / Prickly Pear, British Virgin Islands, San Juan
2026 Sails: Jan 23, Feb 6, Mar 6, 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...

8 Night - Caribbean Roundtrip from St Maarten (Philipsburg)
Starting in Philipsburg, North Sound / Virgin Gorda, Sail Through the Sir Francis Drake Channel, White Bay, Jost Van Dyke, Great Harbour / Jost Van Dyke, The Bight Bay / Norman Island, St Johns AG, Antigua, Gustavia, Philipsburg
2026 Sails: Jan 25, More...