9 Night - Caribbean Flair Away from the Everyday
Starting in Philipsburg, Terre-De-Haut, Iles Des Saintes, Soufriere, Chatham Bay / Union Island, Port Elizabeth VC / Bequia, Cabrits, Philipsburg
2025 Sails: Nov 26, 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
2025 Sails: Nov 29, 2026: Nov 28, More...

7 Night - Leeward Islands
Starting in Philipsburg, St Maarten, River Bay, Barbuda, 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
2025 Sails: Nov 29, Dec 13, Dec 27, 2026: Jan 10, Jan 24, Feb 7, Feb 21, Mar 7, 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...

11 Night - Rendezvous of Two Windjammers
Starting in Philipsburg, North Sound / Virgin Gorda, The Bight Bay / Norman Island, Gustavia, Terre-De-Haut, Iles Des Saintes, Cabrits, Road Bay (Sandy Ground), Philipsburg
2025 Sails: Dec 11, 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, 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...

8 Night - Caribbean Roundtrip from St Maarten (Philipsburg)
Starting in Philipsburg, Saint-Pierre, Soufriere, Cabrits, Charlestown, Nevis, Road Bay (Sandy Ground), Philipsburg
2026 Sails: Jan 4, Jan 18, More...

8 Night - Sun, Sea, and Serenity
Starting in Philipsburg, Gustavia, Cabrits, Terre-De-Haut, Iles Des Saintes, Saint-Pierre, Road Bay (Sandy Ground), Philipsburg
2026 Sails: Feb 27, Mar 26, More...

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 - 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...