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Destination Highlight: St. Michaels

Sail to one of the most popular cruising destinations on the Chesapeake Bay. St. Michaels is rich with history, great restaurants and beautiful scenery.

Destination Highlight: St. Michaels, MD

Take a sail to one of our favorite cruising destinations in St. Michaels, Maryland.

St. Michaels is one of the most popular cruising destinations on the Chesapeake Bay for good reason. It is a historic and picturesque harbor town which lies on Maryland’s Eastern shore. Take the pleasant 25 nautical mile day sail from Annapolis and spend a few days exploring the area.

Along the St. Michaels waterfront, there are marinas with various levels of cruising amenities including the St. Michaels Marina, St. Michaels Harbour Inn and Marina and Higgins Yacht Yard. All the marinas are within walking distance from downtown. If you choose to stay a marina, calling ahead for reservations is a good idea in the summer season. If you prefer, anchoring is an option outside the main harbor or in the Miles River, and is still close to town. Be sure to book a dinghy with your charter reservation, or take advantage of the Harbor Shuttle water taxi service to get into town and explore.

There are great restaurants on the main street (Talbot street) including crab and seafood specialties. Mixed in between the restaurants are plenty of retail shops and galleries. While you are off the boat, we recommend a visit to the Chesapeake Bay Maritime Museum, which has its own list of fun activities for the whole family in the summer. Walk around town and take note of the historic buildings, some dating back to the late 1600s. If you did not bring your own toys on the boat, stop by Shore Pedal & Paddle for bike, e-bike, kayak, or stand-up paddleboard rentals. There will be no lack of places to explore in the area by bike or kayak.

Want to stay a bit longer?  Make your venture to the Eastern Shore a 2 – 3 day excursion by exploring some of the great rivers and creeks around St. Michaels. The Wye River is a nice place to check out, offering a number of coves which surround Wye Island, a park with over 2,000 acres of nature to explore. If you are looking to get away from the hustle and bustle of downtown, check out Leeds Creek, right across the Miles River from St. Michaels. Head in and drop your hook, and enjoy this peaceful retreat.  Let Annapolis Bay Charters help you get the most out of your charter on the Chesapeake Bay. Our staff has over 30 years of experience. Contact us today.

For help planning your trip visit the St. Michaels town website.