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Wine Cruises: Looking to get away? Connect with others? Want unique experiences?


Treat yourself and a friend! What better way to sample wine without worrying about driving. Book a personal wine tour during your alternative vacation in St Michaels. The wine selection: We bring wine country to you.  We purchase all of our wine from our Maryland Distributor who personally picks these great vineyard offerings. You won’t find these labels at the grocery store or your big box liquor store.
Let our captain be your tour guide with meaningful travel and enjoy a day of sailing as one of the things to do in St. Michaels, MD.  We’ll introduce you to the varietals that made California wines famous – Pinots, Cabs, Zins and Chardonnay. And we also bring a few unique hidden gems to our International wine list to share with you. And if you are interested in St Michaels Winery wine we can arrange that too although we don’t normally stock it as they are right up the street and give you another thing to do during your visit to St Michaels.


a bottle of wine and a glass of beer on a table


Escape from the crowd. A private yacht charters on the Chesapeake Bay experience rivals the wine tours at the vineyard and are a getaway from crowds and big groups.  Located in Talbot County on Maryland’s Eastern Shore, St Michaels is only a short drive from Annapolis, Baltimore, Philadelphia, Wilmington, Washington D.C., and worth the drive from New York City and other points North, West and South.
What got us started offering sail charter wine tasting tours was when a guest asked “do you offer a ‘Mom’s Time Out’ Wine Tour?” The answer?  Sure! You deserve it. Sail Selina II’s Wine tasting cruises are available all week long and can be booked per person, or as a private Sailing tour. Sit back and relax, soak in the sights, and enjoy your flight of 3 white wines and 3 red wines. Once you figure out your favorite then enjoy a full glass of it too. And since we don’t run a winery, there’s no sales pitch or pressure to join a wine club or buy a case of wine after your tasting.
Is there someone in your group that really would just rather have beer?  We can accommodate that request too. Sail Selina II has a selection of Maryland craft beers to choose from, no problem.


a large ship in a body of water


Sail Selina II is located on the waterfront docked at the Harbour Inn in St Michaels on the Eastern Shore in Talbot County. We are so close to all the hotels and Inns there’s no need to drive.  You can walk just about anywhere, and for guests at The Inn at Perry Cabin they have a shuttle van, or if you want to zip around town in an electric buggy called a Gem Car they are available for rent at the St Michaels Marina. Plus there are bikes for rent at Shore Pedal & Paddle.
And although our Captain & crew would love to join you in your tasting, trust that they are there to make your experience safe and memorable. Our Captains are USCG licensed with over 100+ years of combined sailing experience.  They strive to provide you, your friends, and your family with a personalized experience that will be remembered for years to come.


a man and a woman holding a bottle of water


Sail Selina II in St Michaels, MD is ranked as Trip Advisor  #1 Sailing boat tours and is considered by many to offer some of the best Chesapeake Boating on the Eastern Shore. If you are looking for boat tours near me for a unique and memorable family vacation activity, or simply a day off for a specialty wine tour or beer tour, look no further.
Exclusive people seek exclusive experiences. Visiting a winery is a distinctive and remarkable experience and that’s great, but to do a wine tasting in the great outdoors on a Chesapeake Bay sailing charters is unique and exclusive attraction indeed.
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