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            • St Michaels Maryland

            • Tilghman Island Itinerary

            • Tilghman Island Tilghman Island offers gracious hospitality, fresh seafood, natural beauty and is a refreshingly relaxing vacation destination. She is spirit of the Eastern Shore of Maryland on the Chesapeake Bay.


              If you like to spend time in the great outdoors and on the water, while learning about the Chesapeake Bay, Tilghman Island is a wonderful place to explore.


              Whether you're an experienced kayaker, a day-tripping motor boater, a sailing novice, or anyone else who yearns to spend some time on the Chesapeake Bay or the scenic streams, creeks, and rivers that flow to and from each day, we can provide the information you need to get your day started.  Check out theTilghman Island Itinerary to get you started.

              Tilghman Island is home to many unique water based activities ranging from narrated historical cruises on a national historical landmark aboard the oldest working skipjack on the Chesapeake Bay.  
              Enjoy kayak, canoe and paddleboard tours along the quiet creeks, or rent a jet ski or boat for a fun day of exploration. 

               

              The fun doesn't stop on the water, you can find wonderful restaurants on the island, all specializing in Chesapeake Bay cuisine, to fulfill your Chesapeake Bay experience.

              There is so much to see and do, you'll want to extend your stay so you can enjoy even more the next day or two! 
               Tilghman Island has wonderful Inns or Bed and Breakfasts to enjoy your relaxing and peaceful home away from home. 

            • Let's Get Your Day Started! 

              First Stop:
              Visit Phillips Wharf Environmental Center, an interactive educational complex, offering visitors a peek into the aquatic wonders of the Chesapeake Bay. Immerse yourself in the rich history of the ecology and fisheries of the Chesapeake Bay. 
               
              Second Stop:
              Hop on one of the areas boating excursions, from educational skipjack voyages on an historical landmark, fishing on a charterboat, or a relaxing on a romantic sailing cruise, you're sure to enjoy your time on the water, whatever your choice.   


              Third Stop:
              Enjoy lunch at a restaurant of your choice, either along the water, or one of the cafes in town offering delightful fare. There are many outstanding places to choose, featuring local regional seafood dishes and of course, Maryland Blue Crabs!


              Fourth Stop:
              Rent a kayak or a canoe and follow the shorelines along the creeks to catch glimpes of waterfowl, fish and maybe even a dolphin! 


              Fifth Stop: 
              Rent a bike, and meander around the island, with little vehicle traffic to worry about, biking along Tilghman Island is a wonderful chance to get out on the road,  be sure to check out our water and bike trails. 


              Sixth Stop:
              Enjoy dinner at a restaurant of your choice, with so many top rated restaurants to choose from, you'll want to stay another day....or two, to try them all!

            • Upcoming Events

            • Find Accommodations Find Accommodations

              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.

            • Local Eats & Drinks Local Eats & Drinks

              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.

            • Shopping in Town Shopping in Town

              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.

            • On the Water On the Water

              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.

            • Special thanks to William Wilhelm Photography, the Town of St. Michaels and the Chesapeake Bay Maritime Museum for the use of their photos.

            St. Michaels Maryland Business Association
             PO Box 1221, St. Michaels, MD 21663

             smbamd@gmail.com

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