Crown the King of the Fall Martini

Stay Your Way: Dreamy Stays in St. Michaels & Beyond

Whether you’re planning a romantic retreat, a girls’ getaway, or a solo escape, St. Michaels, Tilghman, and the Bay Hundred area offer a chic and cozy mix of lodging options for every style and budget.

From boutique inns and charming B&Bs to waterfront resorts and private cottage rentals, you’ll find the perfect place to relax, recharge, and wake up to stunning Chesapeake Bay views.

Your dream getaway starts here—book your perfect stay today!

Find the perfect place to fit your needs here.

Savor the Flavors of St. Michaels: A Foodie’s Paradise

Nothing says Chesapeake Bay vibes like cracking into a steaming pile of locally caught Maryland blue crabs, but that’s just the beginning! St. Michaels is home to an incredible culinary scene that goes beyond seafood—offering something delicious for every craving.

Seafood & Chesapeake Classics
From perfectly seasoned steamed crabs and golden, lump-filled crab cakes to sweet soft-shell clams and fresh rockfish, our waterfront town is a seafood lover’s dream.

A World of Flavor
Craving something else? We’ve got it! St. Michaels serves up an eclectic mix of dining options, including:
Steakhouses for the ultimate indulgence
Authentic Mexican bursting with bold flavors
Classic Italian with homemade pasta & rich sauces
Greek & Mediterranean favorites like gyros, fresh seafood, and vibrant mezze plates

Find Your Perfect Spot
Whether you’re looking for a romantic waterfront dinner, a lively crab feast, or a cozy spot for cocktails & small plates, St. Michaels has a table waiting for you. Explore our incredible restaurants here! 

Find the perfect restaurant here.

Shop, Sip & Stroll: A Boutique Lover’s Dream in St. Michaels

Calling all trendsetters, treasure hunters, and boutique lovers—St. Michaels is your ultimate shopping destination! Wander through our charming, walkable streets and explore a carefully curated mix of stylish fashion, artisan jewelry, home décor, and unique finds you won’t see anywhere else.

Chic Boutiques & One-of-a-Kind Finds
From boho-inspired clothing and handcrafted accessories to coastal home décor and locally made art, our shops are full of pieces that tell a story—just like your next adventure.

Sip While You Shop
Take a break at one of our local tasting rooms, where you can indulge in small-batch wines, craft cocktails, and gourmet bites—the perfect pairing for a girls’ getaway or a solo shopping spree.

Ready to Discover Your Next Favorite Spot?
Explore our unique shops and boutiques right here in St. Michaels—where every corner holds something special. Come shop, sip, and stay a while! 

 Find our unique shops here.

Whether you're an experienced kayaker, a day-tripping boater, a sailing novice, a history buff, an avid fisherman, or anyone else who yearns to spend some time on the water, you will find something to do in St. Michaels and Tilghman Island. It's time to get out on the water and enjoy the outdoors!  Find your boating options here.