Special Wine Tasting Cruises
Learn about St. Michaels Harbor while cruising in a historic sailing yacht along the Miles River on the Eastern Shore of Chesapeake Bay. Sit back, relax, and enjoy the outdoor scenery on your personalized boat tour!
Enjoy a breathtaking Chesapeake Bay sunset while sipping a glass of Champagne or handcrafted beer or wine on this romantic St Michaels, MD sunset cruise near me!
Enjoy free Champagne while taking in the beauty of a sunset or the rising of the moon aboard this romantic Moonlight Cruise!
Come aboard Sail Selina II in St Michaels MD and learn the basics of wine tasting and sample great vintages with Capt. Iris and her crew during this 2hr outdoor excursion. Our wine cruise is just an hour from Annapolis, making it the perfect day trip.
Looking for a relaxing Saint Michaels, Chesapeake Bay boat tour? Want to get out on the water, unwind and spend some time in nature? Unique, upscale, and exclusive, the luxury sailing yacht Selina II limits her passengers to just 6 guests for an intimate taste of the history of sailing.
With freshly varnished mahogany and brightly polished brass, let Sail Selina II, the premier sailboat in St Michaels, MD be your sightseeing charter boat. Hop aboard Sail Selina II and experience another time and place.
Come join us outdoors on the water for a relaxing 2-hour sailing trip on this nostalgic river boat cruise. Your St Michaels, Maryland sailboat ride includes a personalized informative tour with our 1st-class captains and friendly crew. We know you’ll love all the boating trips aboard our meticulously-restored historic 1926 sailboat Selina II, including romantic sunset cruises, our super popular day sails, and our specialty outings like sailing lessons, wine tasting cruises, beer tasting cruises, and more.
For private sailing tours, the Sail Selina II is docked at the Harbour Inn & Marina in the heart of St Michaels, MD, a charming eastern shore town known for its wonderful seafood restaurants and quaint small-town feel.
If you are looking for things to do in St Michaels Maryland or if you want a sailing charter on the Eastern Shore of the Chesapeake Bay, Sail Selina II’s relaxing sailboat trips are just 90 minutes from Philadelphia, Baltimore and Washington D.C. and just 60 minutes from Annapolis.
Outdoors in nature, our sailing boat offers your choice of a public or a private boat ride in one of the best places to sail. Chesapeake sailing is known for its beauty and gorgeous sunsets. Your sailboat charter includes a boat sail through the harbor and then out into the Miles River for spectacular views and sometimes even wildlife viewing like Osprey & Bald Eagles.
We are the St Michaels boat ride to choose!
Learn more about the history of our sailboat and all the fun things to do in St Michaels, MD here:
A friend was visiting from Baltimore and we went sailing last night for the sunset cruise. It was amazing, the sailboat was gorgeous, the Captain and her first mate were exceptional, and the beauty of the river was breath taking. I am so glad I discovered Sail Selina II, I will be taking many friends and family members on this beautiful adventure when they come to visit me in Easton. Thank you for a remarkable memory and such a beautiful experience.
– Sharon G., TripAdvisorA golden opportunity to sail on a captain owned historic wood yacht! It was a dog day of August with precious little wind, yet we enjoyed every minute of our trip. Captain Iris was a gracious host, passionate generational owner, not only captain but articulate professor of both sailing and ship building. We highly recommend sailing aboard the Selina ll. The crew is fabulous as well.
– Anne T., TripAdvisorHubby and I spent a sunset afternoon on Selina 2 with Captain Iris and first mate Jesus. We had a lovely cruise drinking champagne and listening to Captain Iris talk about St Michael and the history of her family sail boat. What I loved was she was mentoring a future captain in the making - a twelve year old from the area who wanted to learn more about sailing. This is so worth it and I very much encourage you to go!
– Amy G., TripAdvisorMy wife and I had a great time on this vintage sail boat. The Captain and First Mate were great hosts teaching us a lot about sailing and the history of the bay at the same time. Loved that the boat holds only six guests at a time, only four aboard for our trip, making it a very intimate experience!
– Richard G., TripAdvisorThe two hour cruise In the company of Captain Iris, Crewman Chris, and four other guests provided the best evening of our August vacation. The generous hospitality (nice selection of wine and beer if champagne was not your preference) was supplemented by the unexpected and pleasant opportunity to observe several races and Captain Iris was generous with her knowledge of sailing the Tred Avon areas of the Chesapeake. The Salina II will see us again when we return.
– Dave C., TripAdvisorTook a moonlight cruise on the Sail Selena II. Had a lovely evening star gazing, sipping wine, chatting with the other couple aboard. Cap’t Iris and her ever so sweet (and personable) first mate were both kind and knowledgeable. We enjoyed the evening immensely. We would recommend this outing without hesitation. Such a great experience!
– Nicole H., TripAdvisorBeing a motor-head all of my life never really let me get the deep appreciation of the sea as I experienced when I sailed on the Selina II. To cruise along with nothing but the sound of the waves, wind and seagulls was a truly eye opening experience for me. Captain Iris was absolutely enchanting with the stories of Saint Michaels and her beloved Selina II. The cruise was intimate with only 2 other couples and was an experience I will long remember.
– Ray D., TripAdvisorCaptain Iris runs a fabulous operation out of St. Michaels. This was our first time visiting the town and this was such a great way to experience St. Michaels and the Chesapeake. The Sunset Champagne cruise was fun and intimate as only 6 people maximum. The two other couples we met were so sweet. Sail Selina II is a must do in St. Michaels!
– Jenny T., TripAdvisorWhen looking for things to do in St Michaels MD, our reviews tell the story! Limited to just six guests, Sail Selina II is ranked the #1 Maryland sail boat tour in St. Michaels and has been for 18 years running.
Sit back and relax. Want a drink? We’ve got it! Cold beer, red & white wines, Champagne, and soda are available for sale on all our Maryland sailboat rides and are included on our evening charters.
Sail Selina’s top-notch skippers have a combined sailing history of 90+ years, and her friendly crew has a combined sailing history of 30+ years. We all love to sail and we love taking people for sailboat rides!
All our relaxing sailing boat charters are in a gorgeous setting. Sail Selina II was built as a gentleman’s yacht in the Gatsby era and is finished in freshly varnished mahogany and brightly polished bronze. Her spacious cockpit is the perfect setting for a Maryland sail on the ultimate charter boat in St Michaels, MD. Join us for a sailing charter boat tour and unwind with an authentic taste of the history of sail.
Our St Michels boat tour captains are known for their storytelling skills and offer a boat trip balanced with some touring, some sailing, and some time to simply relax, unwind and kick back. When sailing on the Chesapeake in St Michaels, choose from a basic sailboat ride, or opt for a specialty outing like a local craft brew beer tasting cruise or a sunset champagne charter.
