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 - Caribbean Yachting Discovery
Starting in St Johns AG, Antigua, Barbuda, Antigua and Barbuda, Iles des Saintes, Guadeloupe, Deshaies, Guadeloupe, Gustavia, Saint Barthelemy, Virgin Gorda, British Virgin Islands, Norman Island, British Virgin Islands, San Juan, Puerto Rico
2025 Sails: Dec 13, 2026: Jan 10, Feb 7, More...

8 Night - Yachtsman's Caribbean
Starting in San Juan, Puerto Rico, Sopers Hole (Frenchmans Cay), Carambola Beach, Saint Kitts and Nevis, Terre-de-Haut, Iles des Saintes, Guadeloupe, Saint Pierre, Martinique, Port Elizabeth VC, Bequia, St Vincent and the Grenadines, Saint Georges, Grenada, Bridgetown, Barbados
2025 Sails: Dec 14, More...

7 Night - Eastern Caribbean with St. Barths
Starting in Bridgetown, Barbados, Soufriere, Saint Lucia, Iles des Saintes, Guadeloupe, Falmouth Harbour, Antigua and Barbuda, Charlestown / Cades Bay, Saint Kitts and Nevis, Gustavia, Saint Barthelemy, Prickly Pear Cays, Anguilla, Marigot, Saint Martin
2025 Sails: Dec 20, 2026: Mar 28, 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...

15 Night - Happy Sunny Holidays
Starting in Philipsburg, North Sound / Virgin Gorda, The Bight Bay / Norman Island, Charlestown, Nevis, Terre-De-Haut, Iles Des Saintes, Soufriere, Chatham Bay / Union Island, St Georges, Saint-Pierre, Gustavia, Philipsburg
2025 Sails: Dec 21, More...