7 Day Annapolis & Chesapeake Bay Sailing Itinerary

A Fishing Pier in Chesapeake Bay to be seen on your Annapolis Yacht Charter
Sail around Chesapeake Bay

Head to Annapolis to start your charter in Chesapeake Bay. Be sure to allow some time before or after your charter to see Annapolis as well, with shops, restaurants, galleries, the market house and the US Naval Academy to be taken in. this itinerary sails south with north winds, but there are other options if southern winds are blowing instead.

Day 1: Annapolis to Herrington Harbour

Located on the western shore of the bay, Herrington Harbour South and North both offer overnight berths and also provide restaurants for your dinner. Herrington Harbour South is a popular choice, so it is worth reserving in advance. Try Mango’s on the Bay for a selection of steak, seafood accompanied by beer or martinis with a waterfront location.

Day 2: Herrington Harbour to Oxford

On the eastern shore of Chesapeake Bay, Oxford lies between Town Creek and the Tred Avon River. Town locals welcome visitors like old friends. The town is tranquil and perfect for boaters; downtown is easily accessible with enough to occupy visitors for the evening.

Day 3: Oxford to Cambridge

Situated 13 miles up river of the Choptank River, as county seat of Maryland’s Dorchester County, Cambridge is one of the oldest towns in Maryland. The town’s heritage is preserved in several maritime museums, and the Choptank River Fishing Pier State Park located directly across the river from Cambridge. Cambridge Creek provides a protected spot with plenty of room for anchoring boats.

Day 4: Cambridge to St Leonard Creek

St Leonard Creek flows off the Patuxent River, upriver from Solomons. The creek’s shore is a mixture of marshes, rolling hills and steep wooded banks. Vera’s Beach Club, at the mouth of Johns Creek is an ideally located marina and waterfront dining opportunity, which hosts a range of lively events throughout the year!

Day 5: St Leonard Creek to Solomons

South of St Leonard Creek, Solomons is tucked in to the shoreline where the Patuxent and Chesapeake Bay meet. The town is a fishing village with a working fishing fleet, but it is also a rather touristic town, where you can learn about the history of Chesapeake Bay. There are also plenty of shops and restaurants if you want to kick back and relax. Visit The Tiki Bar – it’s the first open air bar in Southern Maryland, and try one of their potent drinks – the house special is a Mai Tai.

Day 6: Solomons to St Michaels

This village lies on the waterfront of the eastern shore between Tilghman Island, Easton and Oxford. Once an important centre for shipbuilding, St Michaels is a popular yachting destination with plenty to see and do, including a visit to the Chesapeake Maritime Museum to learn about history, traditions and what goes on in the present day.

Day 7: St Michaels to Annapolis

Expect a relatively long sail back to Annapolis, but you may as well use the time wisely to take in the last of the sights and think about your return to sailing the east coast of America.

A selection of our Chesapeake Bay Bareboats

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