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
2025 Sails: Nov 22, Dec 6, Dec 20, 2026: 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 - Pirate Islands and Sailors' Haunts
Starting in Philipsburg, Gustavia, Road Bay (Sandy Ground), North Sound / Virgin Gorda, Sail Through the Sir Francis Drake Channel, Great Harbour / Jost Van Dyke, White Bay, Jost Van Dyke, Philipsburg
2025 Sails: Dec 4, More...

11 Night - A Sunny Break from Winter Blues
Starting in Philipsburg, Sail Through the Sir Francis Drake Channel, Great Harbour / Jost Van Dyke, The Bight Bay / Norman Island, North Sound / Virgin Gorda, Gustavia, Cabrits, Terre-De-Haut, Iles Des Saintes, Philipsburg
2025 Sails: Dec 10, More...

15 Night - Christmas Caribbean Style
Starting in Philipsburg, North Sound / Virgin Gorda, Sail Through the Sir Francis Drake Channel, White Bay, Jost Van Dyke, Charlestown, Nevis, Chatham Bay / Union Island, Soufriere, Saint-Pierre, Terre-De-Haut, Iles Des Saintes, St Johns AG, Antigua, Gustavia, Philipsburg
2025 Sails: Dec 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...