Find a passage from Annapolis
Captains post passages that leave from Annapolis, United States. Browse what is open, read the route, the dates and the cost terms, then apply. This page also sets out what we have checked about sailing from Annapolis.
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Open passages from Annapolis
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Sailing from Annapolis
- ARC Europe 2027 is due to start on 8 May 2027 with a Sint Maarten fleet and a Chesapeake fleet, sailing via Bermuda and the Azores to a finish in Lagos, Portugal.Source: World Cruising Club (organiser or official source), seen 1 October 2026. Check with World Cruising Club: ARC Europe before you rely on it.
- Reported The Caribbean 1500 sails from Hampton on the Chesapeake to Nanny Cay, Tortola, in the British Virgin Islands. It usually departs around the first week of November each year. Any cruising yacht can enter without racing certificates. It is listed among World Cruising Club's rallies.Source: Sail Magazine (article or trade press), seen 1 October 2026. Check with World Cruising Club before you rely on it.
- Salty Dawg's 16th Caribbean Rally anticipates leaving Hampton on 1 November 2026, weather permitting, for Marsh Harbour in the Abacos or for Antigua. A Newport, Rhode Island fleet is due to leave in late October for Antigua, and the Hampton gathering runs from 26 October to 1 November.Source: Salty Dawg Sailing Association (organiser or official source), seen 1 October 2026. Check with Salty Dawg Sailing Association: Caribbean Rally before you rely on it.
Organisers and authorities to check with:
Last checked 1 October 2026. We have not opened every source page ourselves: confirm dates, fees, deadlines and entry rules with the organiser or the authority before you rely on them.
Rallies
How to get a berth
What counts as Annapolis
On Global Crew Finder a boat, a passage or a crew member counts as at Annapolis when it is within 30 nautical miles of 39.0 N, 76.5 W, or when its port or city is given as one of: Annapolis, Chesapeake Bay, Eastport.