Top Things to Do in St. Michaels, MD —
A Local’s Guide from St. Michaels Sailing Charters
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 St. Michaels Sailing Charters, 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 1935 Historic Yacht Lady Patty
Step aboard Lady Patty, our beautifully restored 1935 yacht and experience St. Michaels from the water. Lady Patty carries a rich maritime legacy when she was first built in Solomons Island, Maryland. Originally designed as an offshore racing yacht, she was later restored as a charter sailboat while retaining her original wooden cockpit, wheel, and mast. This historic yacht accommodates up to 13 passengers and is maintained for both safety and comfort, offering modern-day sailors a unique chance to experience the Chesapeake Bay aboard a true piece of maritime history. Choose from day sails, romantic sunset cruises, wine and beer tastings, 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. Sail the Chesapeake Bay on Spacious Catamaran Epiphany
Step aboard Epiphany, our modern luxury catamaran, the ideal setting for a relaxing day on the water with up to 13 of your family members and friends. Designed for comfort, she features both forward and aft cockpit areas covered by a continuous hardtop, offering excellent protection from the elements. The aft cockpit’s spacious dining table is the perfect spot to enjoy a charcuterie board along with a selection of wine, beer, and soft drinks available for purchase. We offer small-group sailing cruises for up to 13 guests for an intimate and unforgettable experience. Choose from day sails, romantic sunset cruises, wine and beer tastings, 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.
3. 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.
4. 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.
5. 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.
6. Savor Local Flavors
St. Michaels boasts an impressive food scene. Favorites include:
- Ruse at Wildset Hotel for upscale and creative food
- 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
7. 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!
8. 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.
9. 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 St. Michaels Sailing Charters.
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 Lady Patty or Epiphany is at the top of your list. There’s truly no better way to experience the Chesapeake Bay than with the wind in your hair, a drink in your hand, and the unmatched freedom that comes with sailing.
📍 Location: Harbour Inn, 101 N Harbor Rd, St. Michaels, MD 21663. Free parking available.
📞 Call: 410-849-9864📧
Email: [email protected]
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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! St. Michaels Sailing Charters is one of the top-rated things to do in St. Michaels, MD, offering historic sailing tours, modern luxury catamaran sailing experiences, romantic sunset cruises, and private charters on the Chesapeake Bay.