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5 Things You Need to Do for the Ultimate St Michaels Boating Vacation


  • Escape to another universe just a short drive away in St Michaels, where your boating vacation becomes a sensory adventure. Experience the charm of this Chesapeake Bay gem with activities like spa treatments, shopping, and dining at top restaurants. Explore Eastern Shore Brewery & Lyons Distillery, kayak along serene waters, and embark on historic cruises. Don’t miss the highlight of your trip: a Chesapeake Bay sailing charter aboard the historic 1926 family yacht, Sail Selina II. Step back in time and create unforgettable memories.


  • Sail Selina II’s current Coast Guard licensed Captains Iris Robertson and Tim Dunlap are so inspired by St Michaels & the Miles river allure that they both are excited to offer both 2 hour Day Sails, as well as half day (4hrs) a full Day Sail (8hrs includes a picnic lunch), sailing lessons, and wine tasting cruises. Chartering a yacht in St Michaels and sailing the Miles River, a bay off the mighty Chesapeake, is a relaxed, upscale experience, with friendly conversations about area history, our maritime past, and chats about conservation & environmental challenges facing the Bay if you are so inclined.  Every outing is different and tailored to your interests. We love guests who ask lots of questions!

There are a ton of things to do in St Michaels:

  1. Get to know this historic little town
    St Michaels, Maryland gets it start very early in American history, we call the years from 1640-1840 the colonial era. The main economic engines were boat building & agriculture. From 1840-1930 we had the oyster years, with over 6000 boats like Skipjacks, Bugeyes and Buy boats harvesting so many oysters they built a railroad from St Michaels to New York City just to move the heavy freight.  The Depression decade from 1930-40 saw St Michaels, MD fall into obscurity, and the remote location had the economic revival of the war effort of the 1940s and Eisenhowers Interstate programs in the 1950s pass us by. By 1960 you could have bought any property here for back taxes. By then a few fore thinking well heeled locals came up with the idea to start a regional museum to create tourism, and in 1965 the Chesapeake Bay Maritime Museum opened its doors.
  2. Immerse yourself in St Michaels today

Known for our culinary prowess, our quaint little “foodies town” boasts a lively main street.  Starting at the Maritime Museum and walking south takes you to Olivins, where you can sample all sorts of exotic olive oils and vinegars, and then on to Symaptico with hand selected Italian food stuffs (don’t miss the gelato straight off the boat from Italy).  The shopping is anything but tee shirts and flip flops with great clothiers and jewelry stores along the way that will impress as you wander down to the Brewery, Distillery, & Winery.  Teetotalers?  We have 4 world class Spas to completely pamper yourself.  Some folks like to relax simply strolling the streets soaking up the late 20th century architecture with immaculately maintained gardens in the historic district.  Others take advantage of the 4 golf courses within 30 minutes drive of St Michaels.  Bottom line this town has something for everyone.

  1. Food Food & More Food
    Did we mention St Michaels is a “foodie town?”. Boasting a disproportionately large number of great restaurants for the size of the town you have your choice of classic seafood joints which you can get to by boat! Or use the water taxi , casual pizza bars & nouvelle Mex  & oh so scrumptious gourmet dining at 208 Talbot The list goes on, and on, and on . . .
  2. Festivals parades

If you don’t already feel like St Michaels is different, it is known for its seriously friendly people and endless parades and fun odd-ball events like the Jack Russel Terrier races (in the fall). In order to get in with the locals, show up at open mike night, Thursdays every week, at the Carpenter St Saloon.  Too much to list here, go to to find out what’s going on.

  1. Out on the water –

And absolutely plan on enjoying a day of sailing with and then add to the experience with a try at stand up paddleboards (SUPs) and/or kayaking followed by a tour on the Buy Boat Winnie Estelle.  The Patriot offers a tape recorded tour of the Miles river, and Sail Selina offers star gazing, sunset champagne sails, sailing lessons, wine tasting cruises, beer tastings, and oh so romantic engagements & elopements.

Find out more
The best times to visit are from the beginning of May through the end of Oct.  These months are comfortable temperatures with May, September & Oct being the most manageable without tourist crowds.

For more information about Sail Selina in St Michaels, email us at or give us a call at 410-726-9400

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