Things to do in St. Michaels
Discover amazing St. Michaels activities and premium in-home experiences.
St. Michaels, a charming harbor town on Maryland's Eastern Shore, offers a perfect blend of maritime history and classic coastal charm. With its captivating waterfront views, delightful seafood eateries, and bustling boutiques along Talbot Street, visitors can enjoy sailing adventures or simply unwind in this picturesque setting where the Chesapeake Bay gracefully kisses the shorelines.
Popular Activities in St. Michaels
Private Tiki Boat Cruise from Nautilus Point
BYOB private floating tiki bar for 8–16 to sip, cruise, and celebrate around Annapolis Harbor
Paddleboard & Kayak Rentals in Annapolis
Explore scenic Back Creek at your own pace with high-quality paddleboards or kayaks
Explore the Charm of St. Michaels
St. Michaels is a picturesque harbor town where history, maritime culture, and modern-day leisure blend seamlessly along the Chesapeake Bay's serene shores. Known for its rich heritage as a shipbuilding center during the 19th century, this quaint destination now invites visitors to explore its charming streets lined with boutiques, art galleries, and inviting cafes. A visit here feels like stepping into another era while enjoying all the comforts of today.
Your journey in St. Michaels could begin at the Chesapeake Bay Maritime Museum—an iconic spot that offers hands-on exhibits showcasing local nautical traditions and stunning views of nearby watercrafts gently bobbing on Miles River’s surface. As you stroll through town, don’t miss tasting freshly caught seafood at one of many dockside restaurants or sipping craft beer from Eastern Shore breweries that capture regional flavors perfectly.
The allure doesn't end there; outdoor enthusiasts will find plenty to love too! Rent a kayak for an afternoon paddle among scenic coves or cycle down tree-lined trails revealing glimpses into Maryland’s natural beauty around every bend—all just minutes away from bustling city life yet worlds apart in tranquility offered by this unique haven called St.Michaels!