Private charters available for all trips!
Learn about St. Michaels Harbor while cruising in a historic sailing yacht along the Miles River. Sit back, relax, and enjoy the scenery!
Enjoy a breathtaking Chesapeake Bay sunset while sipping a glass of Champagne or beer or wine on this cruise!
Enjoy free Champagne while taking in the beauty of a sunset or the rising of the moon with this cruise!
Come aboard the Selina II and learn the basics of wine tasting and sample great vintages with Capt. Iris.
Looking for a Chesapeake Bay boat tour or sailing charter in St. Michaels, MD? Want to get out on the water? Unique, upscale, and exclusive, the luxury sailing yacht Selina II limits her passengers to just six guests for an intimate taste of the history of sailing.
Come join us for a relaxing two-hour sailing trip. Or your St Michaels boat ride could be a romantic sunset champagne cruise aboard the beautiful, authentic, and meticulously restored historic catboat Selina II.
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! Sail Selina II is ranked the #1 boat tour in St. Michaels and has been for 15 years running.
Sit back and relax. Want a drink? We’ve got it! Beer, wine, Champagne, and soda are available for sale on all trips and are included on our evening sails.
Sail Selina’s skippers have a combined sailing history of 90+ years, and her crew has a combined sailing history of 30+ years. We all love to sail!
And all that is in a gorgeous setting. Sail Selina was built as a gentleman’s yacht in the Gatsby era and is finished in freshly varnished mahogany and brightly polished bronze.
Our captains are known for their storytelling skills and offer a trip balanced with some touring, some sailing, and some time to simply relax and kick back.
