Looking for a relaxing waterfront escape with that cozy, small-town feel? I say, head to St. Michaels, Maryland! When I first strolled its charming harbor along the Chesapeake Bay, I knew you'd love it too. You can hop on a scenic cruise, savor fresh-caught seafood, browse adorable shops, or dive into the town’s maritime history. Whether you're planning a romantic weekend or a family getaway, I truly believe this place delivers.
Best Time to Visit
In my experience, late spring through early fall (May to October) is when St. Michaels shines. You’ll enjoy warm weather and blue skies—perfect for boating, al fresco meals, or just wandering the waterfront. I’ve gone in July and spent an entire afternoon watching the sailboats glide by. You might never want to leave.
How to Get There
- By Car: I usually drive in from D.C. or Baltimore—it's an easy 1.5-hour trip via Route 50 and MD-33. You’ll pass by beautiful countryside on the way.
- By Boat: If you’re like me and love arriving in style, come by boat! The Miles River welcomes you with open arms. There are marinas and transient slips waiting for you.
- By Air: I’ve flown into BWI and Reagan National before—they’re both about 90 minutes out. Once you land, the scenic drive makes the last leg feel like part of the getaway.
Where to Stay
- Inn at Perry Cabin – I splurged here once and it was unforgettable. If you’re looking for spa days, fine dining, and peaceful river views, you’ll love it.
- St. Michaels Harbour Inn, Marina & Spa – You’ll appreciate the easy marina access and spa perks. I liked how close it was to everything in town—no need to drive once you’re settled in.
- The Wildset Hotel – When I stayed here, I fell in love with the stylish rooms and restored historic charm. If you enjoy a modern coastal vibe, you should absolutely check it out.
Top Attractions in St. Michaels, MD
Climb the 1879 Hooper Strait Lighthouse and Light Your Imagination with Nautical History -
Set Sail Through Time at the Chesapeake Bay Maritime Museum and Trace the Bay’s Story -
Wander the Past at St. Michaels Museum and Meet the Heart of a Seaside Town -
Shop and Savor at 208 Talbot Where Local Luxury Meets Eastern Shore Flavor -
Dine with Charm at Bistro St. Michaels and Enjoy Culinary Craft in a Cozy Setting -
Feast Fresh at Chesapeake Landing and Taste the Bay in Every Bite -
Crack Crab and Raise a Toast at St. Michaels Crab and Steak House -
Cruise the Miles River on the Patriot and Drift Through History in Style -
In Summary...
(and if you want to revisit my photo journey)- • Climb the 1879 Hooper Strait Lighthouse and Light Your Imagination with Nautical History
- • Set Sail Through Time at the Chesapeake Bay Maritime Museum and Trace the Bay’s Story
- • Wander the Past at St. Michaels Museum and Meet the Heart of a Seaside Town
- • Shop and Savor at 208 Talbot Where Local Luxury Meets Eastern Shore Flavor
- • Dine with Charm at Bistro St. Michaels and Enjoy Culinary Craft in a Cozy Setting
- • Feast Fresh at Chesapeake Landing and Taste the Bay in Every Bite
- • Crack Crab and Raise a Toast at St. Michaels Crab and Steak House
- • Cruise the Miles River on the Patriot and Drift Through History in Style