• St Michaels from the Water Itinerary

  • St Michaels on the Water Itinerary


    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.  They 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 in the US.  Bike and Kayak rentals are available.


    Day 1




    • In the afternoon, ensconce your self in the beautiful history of St Michaels by taking a Narrated Historical Cruise aboard The Patriot (cruising weekdays at 12:30 and 2:30pm and weekends at 11am, 12:30, 2:30 & 4pm) in St Michaels or enjoy an environmental cruise provided by Dockside Express out of Tilghman Island.  You may also want to rent a jet ski or skiff for your own personal tour provided by Tilghman Island Marina & Rentals.



    • Spend the late afternoon browsing the wonderful shops, stop at the St Michaels Winery or Brewery to imbibe in some wonderful libations and prepare for an enjoyable dinner at one of St Michaels fine eating establishments.



    Day 2


    ·         Kick your morning off with a quick fishing, crabbing or oystering excursion aboard one of the charter boats out of St Michaels or Tilghman Island.  We have many great trips to offer including: Screaming Eagle Charters, Let’s Go Crabbing, Huntress Charters and Chesapeake Bay Fly Fishing.  Another option would be a light house tour out of Tilghman Island provided by Chesapeake Bay Lighthouse Tours.


    ·         After this on the water morning, you are going to need to eat.  You could have picked up a box lunch from one of our restaurants or markets or traveled the short walk to many of our great Talbot Street restaurants like the Big Pickle, Ava’s Pizza & Wine Bar, Akai Sushi, Theo’s Steak Sides & Spirits, Marco’s, Carpenter Street Saloon, Characters Cafe or stayed on the harbor once again for a great lunch.




    ·         After lunch is a great time for a sailing trip, relaxing afternoon on the beach or a little sea glass hunting on the shore line.   St Michaels is the home to many historical sail boats including the 42’ Cat Boat, The Selina II built in 1928, docked in St Michaels harbor,  The Rebecca T. Ruark, the  oldest working Skipjack located in Tilghman Island, The Skipjack H. M. Krenz docked at the Maritime Museum and the Lady Patty, a  canoe stern Ketch built in 1931 which leaves from Tilghman Island also.  If you are in need of a little relation, we have a few beaches that you may enjoy.  The first is in Claiborne at the old ferry terminal.  This beach is also a great place to enjoy some sea glass hunting.  Another great location is Lowes Wharf Marina, located in Sherwood where you will have a nice beach, bar, food and even possibly a beach volleyball game.


    ·         After this wonderful day on the water, enjoy a stroll down the quant streets of St Michaels and take in the historic homes before your evening begins.  Live music is played many week nights and weekends at Carpenter Street Saloon and Characters.



    If you have limited time in St Michaels, here are the must see attractions to maximize your time.

    View St Michaels Highlights Itenerary


  • History and Heritage Itinerary

    As an Historic City, St Michaels has much to offer.  Learn the history of Boat building, our revolutionary adctions druing the war of 1812 and 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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  • St Michaels From The Water Itinerary

    If you think St Michaels is a beautiful town, wait until you see it from the water.  Learn the history of the area, see the amazing 300 year old mansions owned by Union and Confederate Generals or enjoy the flora an fauna up close.  This is an itinerary not to miss!

    View St Michaels From the Water Itinerary 

  • Arts & Culture Itinerary

    Arts & Culture fans rejoice!  St Mcihaels has arts and culture in abundance for you to enjoy.  This itinerary will help you find our favorite treasures.

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  • Food, Wine & Shopping Itinerary

    St Michaels is renowned for it's restaurants and shopping.  This itenary will highlight the many earing and shopping establishments that will be the highlight of your trip.

    View the Food, Wine and Shopping Itinerary 

  • Family Fun Itinerary

    From Encounters with Crabs and Oysters to sitting on the cannons in our many parks, St Michaels has a plethroa of activities to keep the kids educated and entertained.  This itinerary captures the best of our family fun.

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  • Adventure and Sports Itinerary

    Nestled on the beautiful St Michaels horbour and surrounded by serene landscape, St Michaels offers many adventurous activities, from biking and hiking the many trails of the bay hundred area to kayaking, canoeing or sailing on the highly ranked waterfront.  St Michaels has much to offer the outdoor adventurer.

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