• 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!

  • 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.

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