It offers sailors protected waters, great anchorages, a forgiving bottom, gorgeous natural scenery, and unique towns and villages steeped in history. Annapolis is the crown jewel of the Mid Atlantic, and the best sailing destination on the East coast. It is the perfect place for you to begin your exploration of the Chesapeake Bay. Eat oysters and crabs that were until just a few hours ago living in the waters beneath your keel. Whether you want the quiet seclusion of a deserted anchorage, or the hustle and bustle of a metropolitan harbour the Chesapeake Bay has something for you.
Protected waters, great anchorages, gorgeous natural scenery and unique towns and villages make the Chesapeake an excellent choice for sailors, novice and expert alike.
Winds are usually between 7 and 20 knots year round. Navigation can be difficult due to numerous reefs. Best time to visit is between June and November.
We recommend you fly into Baltimore-Washington International Airport (45 min) or Dulles International Airport (80 min). British Airways flies direct from LHR to BWI. To get to the marina you can use Super Shuttle(800-258-3826) or get a taxi, or alternatively hire a car.
If you live in the States and want to drive, see below:
*Driving SOUTH from New Jersey/Pennsylvania, follow I-95 South to Baltimore, then I-695 East toward
Glen Burnie, then I-97 South toward Annapolis and Route 50 East and follow directions below.
*Driving EAST from Washington D.C. take Route 50 and follow the directions below.
*Driving WEST from Delaware/Maryland Eastern Shore take Route 50/301 West to the Bay Bridge.
Day 1: Herrington Harbour
Located on the western shore of the Chesapeake Bay, the harbour offers many amenities.
Day 2: Oxford
Oxford’s allure is the quiet small town where townspeople make visitors feel like old friends. Oxford works hard to maintain its serene, boaterfriendly atmosphere and boasts a small, easily walk-able downtown with enough shops, restaurants, and attractions to satisfy most visitors.
Day 3: Cambridge
The elegant 19th century homes lining Cambridge’s shaded streets hail from a time when the town was an economic and social center—a heritage also proudly preserved in its maritime museums.
Day 4: St. Leonard’s Creek
St. Leonard Creek, about seven miles upriver from Solomons, has been said to be the most beautiful on the Patuxent. This five-mile-long creek is on the river’s northern shore.
Day 5: Solomons
“Solomons Island is picturesque island town nestled in the joining of the Patuxent River and the Chesapeake Bay in Calvert County Maryland.Solomons remains a fishing village—alive with work-boats and an active
charter fishing fleet—but it’s also a place to escape and to learn about the Bay’s
past, present and future. ”
Day 6: St. Michaels
St Michaels, Maryland is a quaint waterfront village on the Eastern Shore, situated on a picturesque peninsula between Tilghman Island, Easton, and Oxford. St. Michaels became an important shipbuilding center especially noted for its “Baltimore Clippers,” the fastest sailing vessels of their time.
Day 7: Back to Annapolis Bay
Expect a sail time between five and seven hours
Chesapeake Deal Finder
- July 2018
- August 2018
- September 2018
- October 2018
- November 2018
- December 2018
- January 2019
- February 2019
- April 2019
- May 2019
- June 2019
- July 2019
- August 2019
- September 2019
- October 2019
- November 2019
- December 2019
- January 2020
- February 2020
- March 2020
- April 2020
- May 2020
- June 2020
- July 2020