• St Michaels Maryland
  • Suggested Itineraries

  • Traveling along Talbot County's rivers, streams and coves, you will journey over 600 miles of shoreline, a treasure of Maryland's Eastern Shore. The Chesapeake Bay, the nation's largest estuary, is our crown jewel. 

    Learn about our Chesapeake Bay maritime history or how we fooled the British in 1813, a fun filled day is ahead. 

    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. 

    While you visit St. Michaels, Tilghman Island and our beautiful Bay Hundred area, you'll enjoy regional fare along our picturesque harbor.  Or you can taste your way through town in our specialty shops and enjoy fine hand crafted spirits.

    Choose your itinerary or do all of them while you're here or come back soon...we're a great place to visit, again and again. 

    Browse through our many lodging options, like award winning inns and quiant bed-and-breaksfasts here


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    Nature and Maritime History Itinerary


    If you think St Michaels is a beautiful town, wait until you see it from the water.  Learn the maritime history of the area, while learning how to help to preserve the Chesapeake Bay's future. Hop on a charter or narrated cruise to learn about St. Michaels from the water and catch glimpes of waterfront mansions while you history about our area.
    This is an itinerary not to miss!



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    St. Michaels History and Heritage Itinerary

    As an historic city, St Michaels has much to offer it's visitors and residents, alike.  In 1677 an Episcopal Parish was established on the banks of the Miles River and named after Saint Michael the Archangel. From its early days as a shipbuilding town, its growth as a center for the oystering and crabbing trades and through its late twentieth century transformation into a tourist and sailing haven, St. Michaels and its citizens have forged a way of life that is renowned for its beauty, tranquility and craftsmanship. Learn the history of boat building, our revolutionary actions during the War of 1812, and learn about the history of the Chesapeake Bay while you take in the beautiful sights of St Michaels from land and the water.


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    Foodie and Shopping Itinerary

    Whatever you're in the mood for, St. Michaels can satisfy. Discover the diverse dining experiences and the mouth-watering dishes along athe way, and see why St. Michaels is changing the Eastern Shore's culinary scene.  We'll steer you on an exploration of Chesapeake Bay regional tastes, as well as offer glimpses of world wide cuisine.  Between tasting stops, you'll stroll our streets to enjoy our historic charm and entice you with our trendy unique boutiques and specialty shops along the way. 



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    Tilghman Island Itinerary

    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.

  • Before You Visit:

  • St. Michaels, Tilghman and the Bay Hundred area have a wide range of lodging options to suit every taste and budget. Find the perfect place to fit your needs here.

  • Nothing says Chesapeake Bay like a steaming pile of locally caught Maryland blue crabs, and our restaurants are serving the Chesapeake Bay's bounty, from steamed crabs and crab cakes to sweet soft shell clams and fresh rockfish.  Find the perfect restaurant here.

  • St. Michaels offers shopping galore, with an eclectic range of shops, including jewelry, clothing and home decor, galleries and more!   Stop by one of the many tasting rooms, offering specialty foods and locally made libations. 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.

  • 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


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