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 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 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 InShore Races Mount Gay Round Barbados Race Carlisle Bay 18/01/2023 OffShore Races RORC Caribbean 600 Race • Warm Water Offshore Race in shirts Fort Charlotte, Antigua & Barbuda 20/02/2023 InShore Races St.Maarten Heineken Regatta ∙ Serious Fun! Simpson Bay, St.Maarten 02/03/2023 InShore Races BVI Spring Regatta & Sailing Festival Nanny Cay 27/03/2023 InShore Races Les Voiles de Saint-Barth – St.Tropez of the Caribbean Gustavia, San Bartolomé 16/04/2023 InShore Races Round Antigua Race and Antigua Sailing Week Antigua y Barbuda 29/04/2023