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Annapolis Bay Yacht Charter, Sailing Chesapeake Bay: Spotlight on St. Michaels

Sailing by yacht charter from Annapolis Bay in Maryland, you can go in any direction and have a fabulous summer adventure, but some of the most charming places are to be found along the Eastern Shore. Make your way over to Eastern Bay and into the Miles River to visit St. Michaels. Although you could continue cruising, once you get to St. Michaels, you might just want to stay most of the week. At 25 nautical miles from Annapolis, it can be just a day’s sail and is an ideal destination for families.Set out this summer from Annapolis Bay yacht charter and discover beautiful St. Michaels on Maryland’s Eastern Shore for a family vacation.

Note that in summer, marinas in the area tend to fill up quickly so booking ahead is highly advised. Experienced cruisers say that a good alternative is to anchor in San Domingo Creek or out in Miles River, rather than in the town marinas.

Annapolis Bay yacht charter
Photo by: Forsaken Photos

Annapolis Bay Yacht Charter, Sailing Chesapeake Bay: Spotlight on St. Michaels

Learn About the Water and Its Ways of Annapolis Bay yacht charter

St. Michaels is home to the Chesapeake Bay Maritime Museum, a sprawling complex that is both educational for visitors and a cultural touchstone for locals. Covering 18 acres on the town waterfront, this should definitely be your first stop. Among the permanent exhibits are a working boatyard and the Mitchell House. The boatyard is a must for cruisers, with its ongoing restoration and preservation projects, which the staff of shipwrights and apprentices are happy to discuss at length with visitors. The Mitchell House is the former home of Eliza Bailey Mitchell, sister to Frederick Douglass; both lived as slaves in St. Michaels from 1833 to 1836.

The museum also owns a “floating fleet” of restored historic vessels and replicas as well as the Hooper Strait lighthouse, a beautiful structure that is open for tours.

Eat On Land of Annapolis Bay yacht charter

A unique attraction in this area is walking-and-eating tours. You’ll walk about a mile over the course of 3 hours, eating and drinking at the best spots along the way and learning history and folklore all the while. Tours depart from the Maritime Museum. Tickets are reasonably priced and kids are welcome. Also done in the Eastern Shore towns of Cambridge, on the Choptank River, and Easton, a bit inland from St. Michaels, you could make this sailing trip mostly about the food.

Relax Back at the Marina

Having kids on your yacht charter can be incredible fun, but it can also be a bit stressful if they’re young, and this is another reason why you might want to limit your destinations. If you plan sufficiently in advance, you could score a slip at St. Michaels Marina. With a new pool, spa, bike rentals, and full services for cruisers, you’ll find yourself with the perfect combination of a home base for day sails and land-based comfort.

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