7 Night - St. Maarten to Barbados
Starting in Philipsburg, Gustavia, Carambola Beach, Pointe-a-Pitre, Cabrits (Portsmouth DM), Dominica, Fort-de-France, Port Elizabeth VC (Bequia), Bridgetown
2026 Sails: Oct 14, More...

7 Night - Classic Yachtsman's
Starting in St Johns AG, Terre De Haut, Iles des Saintes, Cabrits, Dominica, Beach Stop, Martinique, St Georges, Grenada, Tobago Cays, Grenadines, Marigot Bay, St Lucia (Morning), Soufriere, St Lucia (Afternoon), Bridgetown, Barbados
2026 Sails: Nov 28, More...

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 (Beach), St Kitts (Pm), Terre De Haut, Iles des Saintes, Beach, Martinique, Bridgetown, Barbados
2026 Sails: Dec 5, Dec 19, 2027: Jan 2, Jan 16, Jan 30, Feb 13, Feb 27, Mar 13, More...

7 Night - Leeward Islands
Starting in Philipsburg, St Maarten, Charlestown, Nevis, Sail with Royal Clipper South of Iles Des Saintes, Cabrits, Dominica, Terre-De-Haut, Iles Des Saintes, Deshaies, Guadeloupe, Falmouth Harbour, Antigua, Basseterre, St Kitts (Morning), South Friars Bay, St Kitts, Philipsburg, St Maarten
2026 Sails: Dec 5, More...

9 Night - Pirates Islands and Sailors' Haunts
Starting in Philipsburg, Cabrits, Saint-Pierre, Soufriere, Terre-De-Haut, Iles Des Saintes, Charlestown, Nevis, Road Bay (Sandy Ground), Philipsburg
2026 Sails: Dec 6, More...

7 Night - Leeward Islands
Starting in Philipsburg, St Maarten, Charlestown, Nevis, Sail with Royal Clipper South of Iles Des Saintes, Cabrits, Dominica, Terre-De-Haut, Iles Des Saintes, Deshaies, Guadeloupe, Falmouth Harbour, Antigua, Gustavia, St Barts, Philipsburg, St Maarten
2026 Sails: Dec 19, 2027: Jan 16, Jan 30, Feb 13, Feb 27, Mar 13, More...

15 Night - Holiday Season with Your Toes in the Sand
Starting in Philipsburg, North Sound / Virgin Gorda, Sail Through the Sir Francis Drake Channel, Great Harbour / Jost Van Dyke, The Bight Bay / Norman Island, Cabrits, Saint-Pierre, Soufriere, Terre-De-Haut, Iles Des Saintes, Gustavia, Philipsburg
2026 Sails: Dec 21, More...

7 Night - Leeward Islands
Starting in Philipsburg, St Maarten, Charlestown, Nevis, Sail with Royal Clipper South of Iles Des Saintes, Cabrits, Dominica, Deshaies, Guadeloupe, Terre-De-Haut, Iles Des Saintes, Falmouth Harbour, Antigua, Gustavia, St Barts, Philipsburg, St Maarten
2027 Sails: Jan 2, More...

8 Night - Caribbean Roundtrip from St Maarten (Philipsburg)
Starting in Philipsburg, Saint-Pierre, Soufriere, Cabrits, Charlestown, Nevis, Road Bay (Sandy Ground), Philipsburg
2027 Sails: Jan 11, Jan 25, More...

7 Night - Grenada to Antigua
Starting in St Georges, Grenada, Admiralty Bay, Bequia, Grenadines, Tobago Cays, Grenadines, Soufriere, St Lucia, Beach, Martinique, Cabrits, Dominica, Basseterre, St Kitts (Morning), South Friars Bay, St Kitts, St Johns AG
2027 Sails: Feb 27, More...