Caribbean races and cruising Choose from a variety of races and sailing holidays around the Caribbean Islands More Filters Please choose category to display filters Cancel Apply Distance Radius Disable Apply Default Order Highest Rated Most Reviewed Newest Listings Oldest Listings Featured Most Views Random On Request St. Maarten Sunset Sail Simpson Bay, Sint Maarten 01/01/2020 On Request St. Maarten Private Sunset Sail Simpson Bay, Sint Maarten 01/01/2020 On Request St. Maarten Day Sail Simpson Bay, Sint Maarten 01/01/2020 On Request St. Maarten Tintamare sail (day sail) Simpson Bay, Sint Maarten 01/01/2020 On Request St. Maarten Private Day Sail Simpson Bay, Sint Maarten 01/01/2020 On Request St. Maarten Private Tintamare Sail (day sail) Simpson Bay, Sint Maarten 01/01/2020 Cruising Cruising St.Maarten to Antigua Sint Maarten 13/03/2021 InShore Races Antigua Classic Yacht Regatta Antigua & Barbuda 31/03/2021 InShore Races Grenada Sailing Week International Regatta Saint George, Granada 30/01/2022 InShore Races St.Maarten Heineken Regatta ∙ Serious Fun! Simpson Bay, St.Maarten 03/03/2022 InShore Races BVI Spring Regatta & Sailing Festival Nanny Cay 28/03/2022 InShore Races Les Voiles de Saint-Barth – St.Tropez of the Caribbean Gustavia, San Bartolomé 17/04/2022 1 2