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5 minutes to book. Best day of our entire trip. Everything felt effortless from pickup to sunset.
Destination guide
U.S.A. — at a glance
4 boats are available to book across 1 departure base. Boats leave from Annapolis (4). The fleet is 2 catamarans and trimarans, 1 sailing boat, 1 motor yacht. Weekly prices start from €4,511 for a sailing boat; every price on this page is the boat’s own listed rate for 7 nights, before extras.
When to go
Chesapeake Bay sails from April to November: May, June, September and October are the sailing months with steady breezes and mild temperatures, July and August are hot and light with afternoon thunderstorms, and October has the Annapolis boat shows and the best colours on the Eastern Shore. The bay is shallow, sheltered and two hundred miles long, with a creek to anchor in every evening and crab houses on the docks.
Where to sail in U.S.A.
Yacht charter from Annapolis on Chesapeake Bay
Annapolis, the sailing capital of the East Coast and an hour from Washington and Baltimore, is the base for the boats on this page: St Michaels and Oxford on the Eastern Shore a day across the bay, the Choptank and the Wye rivers, Solomons Island to the south, and Baltimore's Inner Harbor to the north. A week loops the middle bay.
Boats leave from Annapolis 4
Sailing the Eastern Shore and the lower Chesapeake
A longer charter runs south past Tangier and Smith islands to the Potomac and the lower bay, or north to the Sassafras and Chester rivers; the water is flat, the distances short and the anchorages free, which is why the Chesapeake is where much of America learns to sail.
Boats leave from Annapolis 4
Bareboat, skippered or crewed
Bareboat charter on the Chesapeake is rented against a sailing résumé; skippers are added for a day or the week, and the motor yacht is rented crewed. Maryland asks anyone born on or after 1 July 1972 for a boating safety certificate, and the base issues a temporary one for the rental after its safety briefing.
Types of boats in U.S.A.
Two catamarans, a sailing monohull and a motor yacht at Annapolis - the whole US fleet on Adriavela.
- 2 catamarans and trimarans from €6,638 per week
- 1 sailing boat from €4,511 per week
- 1 motor yacht from €8,850 per week
Frequently asked questions
Do I need a licence to charter a boat in the U.S.A.?
Bareboat charter on the Chesapeake is rented against a sailing résumé; skippers are added for a day or the week, and the motor yacht is rented crewed. Maryland asks anyone born on or after 1 July 1972 for a boating safety certificate, and the base issues a temporary one for the rental after its safety briefing.
When is the best time to sail in the U.S.A.?
Chesapeake Bay sails from April to November: May, June, September and October are the sailing months with steady breezes and mild temperatures, July and August are hot and light with afternoon thunderstorms, and October has the Annapolis boat shows and the best colours on the Eastern Shore. The bay is shallow, sheltered and two hundred miles long, with a creek to anchor in every evening and crab houses on the docks.
Where can I sail in the U.S.A.?
2 sailing areas: Annapolis on Chesapeake Bay (from Annapolis); Eastern Shore and the lower Chesapeake (from Annapolis). Each has its own bases, and the boats on this page leave from all of them.
How many boats can I charter in the U.S.A.?
4 boats from 1 base: 2 catamarans and trimarans, 1 sailing boat, 1 motor yacht. Availability and prices are live from the charter companies.
How much does it cost to charter a boat in the U.S.A.?
On the boats listed here day rates start from €644 and a week (7 nights) from €4,511. These are the boats’ own listed rates before extras; fuel, marina fees on the route and local taxes are paid separately.