• St Michaels Maryland what to do
  • Nature & Maritime History Itinerary

  • Sailing on the Miles Rriver
    If your idea of a fun vacation is time spent in the great outdoors while learning about the Chesapeake Bay, you've come to the right place!

    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. 

    The St Michaels area is home to many unique water based activities ranging from narrated historical cruises, ecological kayak tours, sailing cruises and jet ski rentals. Adults can learn the history of St Michaels while enjoying the beautiful old mansions and wildlife that make our area so special. The kids can visit the hands on area of the Chesapeake Bay Maritime Museum or ride on the back of a Jet ski with Mom or Dad. Our bike riding trails are second to none providing fantastic scenery, great bike trails and a ride on the oldest continually operating ferry to Oxford in the US. 

    With so many sites and attractions within 15 miles of each other, it's easy to sample a variety of activities in a single day. Better yet, why not extend your stay so you can enjoy even more the next day!

  • Let's Get Your Day Started! 

    First Stop: 
    Visit the Chesapeake Bay Maritime Museum, situated on 18 waterfront acres, featuring the Hooper's Strait Lighthouse at the heart of the complex, the museum offers exhibits, demonstrations, boat rides on the Miles River, and annual festivals that celebrate Chesapeake Bay culture, boats, seafood, and history.

    Second Stop:
    Hop on one of the areas boating excursions, from narrated river boat tours, to educational skipjack voyage to a relaxing and 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, in town, or along the water, there are many outstanding places to choose, featuring local regional seafood dishes, Italian, Irish, you name it!

    Fourth Stop: 
    Hop in the car and travel to Tilghman Island to visit Phillips Wharf Environmental Center, an interactive educational complex, offering visitors a peek into the aquatic wonders of the Chesapeake Bay. The Phillips Wharf Environmental Center is open to the public Thursday-Monday from April to November, 10:00am – 4:00pm. While visiting the center, adults and children will have the opportunity to see, touch and learn about some of the inhabitants that live in the Chesapeake Bay waters.

    Fifth Stop:
     If you have hiking or biking on your mind, be sure to check out our water and bike trails. Situated throughout the Bay hundred Area, it offers miles of trails designed with the nature lover in mind.  Want to get out on the water? There are several places to rent paddleboards, canoes and kayak to make it easy to sample the best of land and bay in a single afternoon. 

    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!

  • 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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