Sail Selina II

Chesapeake Bay Sailing Charters in St. Michaels, MD

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Best in Luxury, Best in Boat Tours, Best in Service

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 boat ride or romantic sunset champagne cruise aboard the beautiful, authentic, and meticulously restored historic catboat Selina II.

The #1 Boat Tour in St. Michaels on TripAdvisor!

chesapeake bay cruises Sunset Cruise in September

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., TripAdvisor
chesapeake bay sailboat tours Wonderful Sail

A 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., TripAdvisor
sail selina st michaels charters Went twice and coming again soon!

Hubby 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., TripAdvisor
sailboat charter chesapeake bay Two hour cruise out of St Michaels

My 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., TripAdvisor
chesapeake bay cruises Sunset cruise with champagne and wine

The 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., TripAdvisor
chesapeake bay sailboat tours Wonderful anniversary evening!

Took 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., TripAdvisor
Sounds of the Sea

Being 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., TripAdvisor
sail selina st michaels charters Great Sailing

Captain 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., TripAdvisor

Why Sail Selina II?


Rated #1 on TripAdvisor

chesapeake bay sailboat tours

Our reviews tell the story! Sail Selina II is ranked the #1 boat tour in St. Michaels and has been for 15 years running.

Everything Is Included

sail selina st michaels charters

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.

Over 92 Years of Experience

sailboat charter chesapeake bay

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!

Spacious & Beautiful Boat

chesapeake bay cruises

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.

The Best Captains

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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.