Top Things to Do in St. Michaels, MD —
A Local’s Guide from Sail Selina II
Planning a visit to Maryland’s Eastern Shore? Welcome to St. Michaels—one of the most charming waterfront towns on the Chesapeake Bay! Whether you’re here for a romantic weekend, a family adventure, or just a relaxing day by the water, this little town is packed with character, culture, and unique coastal experiences. As the crew of Sail Selina II, we’ve spent over two decades sailing out of this harbor, and we’re excited to share our favorite things to do in St. Michaels, MD.
1. Sail the Chesapeake Bay on a Historic Yacht
Step aboard Sail Selina II, our beautifully restored 1926 yacht, and experience St. Michaels from the water. We offer small-group sailing cruises limited to just six guests for an intimate and unforgettable experience. Choose from day sails, romantic sunset cruises, wine and beer tastings, moonlight sails, and even weddings onboard or wharfside. Whether you’re joining the crew or relaxing with a glass of bubbly, it’s one of the most unique things to do in St. Michaels.
2. Visit the Chesapeake Bay Maritime Museum
This is a must-see for maritime lovers! The Chesapeake Bay Maritime Museum features exhibits on oystering, boatbuilding, and regional history. Climb the Hooper Strait Lighthouse for amazing harbor views and get up close with traditional boats. A perfect activity before or after your cruise.
3. Shop and Stroll Along Talbot Street
Downtown St. Michaels is full of charming boutiques, art galleries, and coastal-themed shops. From nautical home décor to local handmade jewelry, you’ll find something special to take home.
4. Tour and Taste at Lyon Rum Distillery
Just steps from the harbor, Lyon Rum offers small-batch rum crafted on-site. Stop in for a tasting flight or grab a bottle of your favorite to take back. Bonus: Sail Selina II features Lyon Rum in its onboard speakeasy-style bar by request.
5. Savor Local Flavors
St. Michaels boasts an impressive food scene. Favorites include:
- Ava’s Pizzeria & Wine Bar for upscale comfort food
- The Crab Claw for classic Maryland seafood
- Bistro St. Michaels for a refined dinner with locally sourced ingredients
6. Explore by Kayak or Paddleboard
For the active traveler, rent a kayak or paddleboard and explore the Miles River at your own pace. You’ll often see herons, osprey, and sometimes even dolphins!
7. Catch Live Music or a Festival
Check the town calendar—there’s often live music on weekends, farmer’s markets, or special events like WineFest, Antique & Classic Boat Festival, and Fall into St. Michaels.
8. Stay in a Historic Inn or Waterfront B&B
Extend your stay at one of St. Michaels’ charming inns like The Old Brick Inn, Wild Set, Wades Point Inn or the waterfront Harbour Inn—home port of Sail Selina II.
Plan Your Visit
No matter what brings you to St. Michaels, you’ll find plenty to fall in love with. For an unforgettable experience, make sure a sailing trip aboard Sail Selina II is at the top of your list. After all, there’s no better way to experience the Chesapeake Bay than with the wind in your hair, a drink in your hand, and the timeless beauty of a classic wooden sailboat beneath your feet.
📍 Location: Harbour Inn, 101 N Harbor Rd, St. Michaels, MD 21663. Free parking available.
📞 Call: 410-726-9400📧
Email: [email protected]
🧭 Directions: https://tinyurl.com/SelinaMap
Looking for more ideas? Don’t hesitate to ask our crew for personalized recommendations when you sail with us.
We hope you liked this info! Sail Selina II is one of the top-rated things to do in St. Michaels, MD, offering historic sailing tours, romantic sunset cruises, and private charters on the Chesapeake Bay.