St. Michaels blends maritime history, vibrant dining, and waterfront beauty into one unforgettable getaway.
This itinerary, designed for two nights and three days, offers a perfect balance between relaxation and activity, with plenty of opportunities to savor the flavors and stories of the Eastern Shore.
Day 1:
Settle In
Arrive in St. Michaels on Friday afternoon and check into the Wildset. Situated on Talbot Street, St. Michaels’ main thoroughfare, the Wildset has been named one of the 25 Best Boutique Hotels in the World by Hotels Above Par.
Take time to settle in before venturing out to acquaint yourself with St. Michaels. Stop into Book Hounds pick-up a weekend read before toasting over margaritas at San Miguels Mexican Restaurant. Stay for an authentic Mexican dinner or make your way to Foxy’s Harbor Grille to dine by the water. Follow it up with a sweet treat from Justine’s Ice Cream Parlour.
Day 2:
Explore the Area
Enjoy a relaxing morning at the hotel before hitting St. Michaels trending brunch spot, The Galley, for a delicious breakfast (which you can pair with mimosas). Afterwards, stretch your legs with a walk to the Chesapeake Bay Maritime Museum, and spend your morning exploring their 18-acre waterfront campus and learning about the Eastern Shore’s maritime heritage.
Upon leaving the museum, grab a custom sandwich and drinks from the Village Shoppe before meeting your captain to board the St. Michaels Sailing Charter. Enjoy the sunshine and views from the Epiphany, a Leopard 44 catamaran while catching the breeze along the Miles River.
Head back to the hotel to refresh. Once you’re ready to emerge, take a leisurely stroll along Talbot Street, allowing time to pop into the variety of shops waiting to welcome you. End at Lyon Rum’s Golden Hour for a pre-dinner cocktail before returning to the Wildset to dine onsite at Ruse. Enjoy the creations of James Beard-nominated Executive Chef Michael Correll, whose relationship with local farmers, watermen, and purveyors allows him to create an unrivaled dining experience. Post dinner, wander outside to make smores at the Wildset’s fire pit, where you can enjoy a cocktail and conversation with other guests before turning in for the night.
Day 3:
A Final Hoorah
On Sunday morning, borrow a bicycle from the hotel and follow the St. Michaels Museum’s self-guided tour to explore the town and learn its history. After returning your bikes, linger over breakfast and coffee at Carpenter Street Saloon (locally known as C-Street), where their homemade pancakes will fill your belly after the morning’s ride. Afterwards, pop into a gallery, pick up a keepsake from a local boutique, or simply sit by the harbor watching the boats pass before heading home.
Tips for a Memorable Weekend:
Make Reservations: While walk-in guests are always welcome, availability may be limited at times, so a reservation will guarantee your space and eliminate undue stress.
Check our Calendar of Events: Explore our calendar of events to help plan your weekend getaway to coincide with festivals and special events.