How to plan a 1-week Windward Islands sailing itinerary
To see the best of the Windward Islands in one week, focus exclusively on the St. Vincent and the Grenadines chain. Start in St. Vincent, sail south through the Tobago Cays, and end your trip in Union Island to minimize long open-water crossings.
- Book a one-way charter. Charter your boat starting at Barefoot Yacht Charters in St. Vincent (SVS) and ending in Union Island (UNI). This saves you a full day of sailing back against the wind at the end of your trip.
- Clear customs immediately. If you are hopping between St. Vincent and the Grenadines, your captain must clear out at the Kingstown customs office before leaving the main island. Have all passports and boat registration documents ready.
- Time your crossings. The channel between St. Vincent and Bequia is notoriously choppy. Plan to cross before 10:00 AM to catch calmer morning seas before the trade winds pick up.
- Do I need a sailing license to charter?
- Most charter companies require a resume of your sailing experience, but many offer 'skippered' charters where a professional captain handles the boat for you.
- What is the best way to get between islands if I'm not sailing?
- There are local ferries, but they are unreliable for a 1-week schedule. Use the SVG Air inter-island flights to move between major hubs.