City Guides: Things to do While Boating in St Michaels, Maryland

Jonathan Timianko

May 9, 2023 — 3 min read

Located along the Chesapeake Bay and the Miles River, St. Michaels sits south of Kent Island and southeast of Annapolis. The charming Eastern Shore town is known for its historic charm, coastal scenery, boating and sailing and abundance of outdoor and water-related activities. Let’s check out a few things to do from private boat docks for rent in Maryland.

Chesapeake Bay Maritime Museum

Photo: Wikimedia/Public Domain

The Chesapeake Bay Maritime Museum is dedicated to preserving and celebrating the Chesapeake Bay's rich maritime heritage. Explore a variety of exhibits, including displays on the Bay's watermen, lighthouses and boats. The 1879 Hooper Strait Lighthouse, once used to guide ships in the Chesapeake, is located at the museum.

Take a scenic cruise aboard the museum's historic boats and enjoy stunning views of the river and its surroundings. Kayak and paddleboard rentals are also available for those who want to explore the waterways on their own. The museum also offers boatbuilding workshops and various educational programs for visitors of all ages.

St. Michaels Winery

Photo: St. Michaels Winery (Facebook)

The St. Michaels Winery is a fun spot to visit from a private boat slip rental. This winery offers tastings of their award-winning wines and a beautiful setting to relax and enjoy a glass of wine. Take a tour to learn about the winemaking process and see the vineyards. The winery also offers a variety of events, including live music and food pairings.

Shopping

Photo: Visit St. Michaels, Maryland (Facebook)

Looking for a little retail therapy from a private boat lift for rent? St. Michaels is home to many charming boutiques and shops. From clothing and jewelry to home decor and antiques. The town also hosts several craft fairs and farmers' markets throughout the year. Visitors can find handmade crafts, local produce and other goods.

After all that shopping, check out the area’s delicious seafood. The town is home to many excellent restaurants that serve fresh seafood dishes, including crab cakes, oysters and rockfish. Many of these restaurants offer outdoor dining and dock and dine options with beautiful views of the water.

St. Michaels Museum

Photo: St. Michaels Museum (Facebook)

Explore regional history at the St. Michaels Museum from a private boat lift for rent. Located in a 19th-century home, exhibits include the area’s early settlers, the War of 1812 and the town's role in the oyster industry.

St. Michaels Nature Trail

The St. Michaels Nature Trail is a peaceful and popular spot for hiking and birdwatching. The 1.3-mile trail winds through woods, wetlands and fields. It offers beautiful views of the Miles River.

We hope you’ve found some ideas for your next trip to the Eastern Shore. Have fun exploring St. Michaels from a private boat lift rental.

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