7 Night - Treasure Islands
Starting in Philipsburg, St Maarten, Road Bay, Anguilla, White Bay, Jost Van Dyke, Sopers Hole, Tortola, Sailing Sir Francis Drake Channel, The Bight / Norman Island, British Virgin Islands, Spanish Town, Virgin Gorda, Beach, Captains Best, British Virgin Islands, Basseterre, St Kitts (Morning), South Friars Bay, St Kitts, Gustavia, St Barts, Philipsburg, St Maarten
2026 Sails: Jan 3, Jan 17, Jan 31, Feb 14, Feb 28, Mar 14, Nov 28, Dec 12, Dec 26, 2027: Jan 9, Jan 23, Feb 6, Feb 20, Mar 6, Mar 20, More...

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...

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...

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...

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...

11 Night - Sailing On the Trade Winds
Starting in Philipsburg, Terre-De-Haut, Iles Des Saintes, Soufriere, Saint-Pierre, North Sound / Virgin Gorda, Sail Through the Sir Francis Drake Channel, Great Harbour / Jost Van Dyke, The Bight Bay / Norman Island, Gustavia, Philipsburg
2026 Sails: Mar 16, More...

7 Night - Antigua to Antigua
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, Philipsburg, St Maarten, Basseterre, St Kitts (Morning), South Friars Bay, St Kitts, St Johns AG
2026 Sails: Mar 21, More...

8 Night - A Tall Ship's Dream Destination
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, Gustavia, St Johns AG, Antigua, Philipsburg
2026 Sails: Dec 14, More...

8 Night - Caribbean Roundtrip from St Maarten (Philipsburg)
Starting in Philipsburg, Gustavia, St Johns AG, Antigua, 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
2027 Sails: Jan 4, Jan 18, More...

7 Night - Antigua Roundtrip
Starting in St Johns AG, Gustavia, St Barts, Sailing Sir Francis Drake Channel, The Bight / Norman Island, British Virgin Islands, Sopers Hole, Tortola, Spanish Town, Virgin Gorda, Beach, Captains Best, British Virgin Islands, White Bay, Jost Van Dyke, Road Bay, Anguilla, Basseterre, St Kitts (Morning), South Friars Bay, St Kitts, St Johns AG
2027 Sails: Mar 13, More...