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Sail Selina II

Relaxing Chesapeake Bay Sailing Tours, Sailboat Rides & Sightseeing Boat Trips in St. Michaels, MD

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Our Popular St Michaels Maryland Sailing Charters and Relaxing Chesapeake Sailboat Cruises

Best Relaxing Luxury Sail Boat Tours on Chesapeake Bay

Looking for a relaxing Saint Michaels, Chesapeake Bay boat tour? Want to get out on the water, unwind and spend some time in nature? If you’re wondering about things to do in St. Michaels MD or seeking top attractions in St. Michaels Maryland, look no further than the luxury sailing yacht Selina II. Unique, upscale, and exclusive, she limits her passengers to just 6 guests for an intimate taste of the history of sailing.

With freshly varnished mahogany, brightly polished brass, and comfortable seating, let Sail Selina II, the premier sailboat in St Michaels, MD, be your sightseeing charter boat. Hop aboard 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 knowledgeable 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 tours in St. Michaels MD, beer tasting cruises, moonlight sails 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 day trips to 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. This year there have even been porpoise sightings.

Looking to relax? We are the St Michaels MD harbor cruises to choose!

Learn more about the history of our sailboat and all the fun outdoor activities in St. Michaels, MD here:

 

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

Sail Selina II Saint Michaels Maryland Chesapeake Sailing tours boat trips Lyon Rum
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
Sail Selina II Saint Michaels Maryland Chesapeake Sailing tours boat trips raising the sail
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 II Saint Michaels Maryland Chesapeake Sailing tours boat trips
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
Sail Selina II Saint Michaels Maryland Chesapeake Sailing tours boat trips guests taking a turn at the wheel
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
Sail Selina II Saint Michaels Maryland Chesapeake Sailing tours boat trips Lyon Rum
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
Sail Selina II Saint Michaels Maryland Chesapeake Sailing tours boat trips sailing excursions romantic date night
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
Sail Selina II Saint Michaels Maryland Chesapeake Sailing tours boat trips sailing excursions people having fun
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 II Saint Michaels Maryland Chesapeake Sailing tours boat trips
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

Experience the ultimate sailing adventure on the Chesapeake Bay with Sail Selina, a true symbol of excellence and commitment to providing the best sailing and boating services - Our passion for sailing has led us to achieve the highest standards and earn a Gold Medal award, representing our unwavering dedication to exceeding our guests' expectations - With a full range of sailing and boating services, including private charters, sunset sails, family-friendly adventures, and wine tastings, Sail Selina offers the highest quality and personalized experiences on the Chesapeake Bay - Fall in love with the stunning natural surroundings, charming towns, and rich history of the Chesapeake Bay, as you sail aboard our well-appointed and comfortable yacht - Book now and discover the unparalleled quality and dedication of Sail Selina, the premier sailing adventure on the Chesapeake Bay!

When 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.

Everything Is Included

Savor the taste of luxury of hand picked wines available on all our St Michaels boat rides. Sail Selina offers both reds and whites, providing the ultimate sailing and wine tasting experience on the Chesapeake Bay - This stunning image showcases the elegant and refined design of Sail Selina's etched wine glasses, a perfect complement to our premium wine tastings and luxurious sailing adventures - With a variety of wine tasting packages to choose from, Sail Selina offers a unique and personalized experience for wine enthusiasts and sailing aficionados alike - Fall in love with the rich flavors and aromas of the finest local and international wines, as you sail in style aboard our comfortable and well-equipped boats - Book now and discover the unrivaled taste of luxury and elegance with Sail Selina, the premier wine tasting and sailing adventure on the Chesapeake Bay

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.

Over 96 Years of Experience

Experience the ultimate sailing adventure on the Chesapeake Bay with Sail Selina. Our quality has achieved the highest standards and has been rewarded with a quality ribbon, representing our commitment to excellence and dedication to providing the best sailing and boating services – It is a symbol of our passion for sailing and our mission to exceed our guests' expectations - With a full range of sailing and boating services, including private charters, sunset sails, family-friendly adventures, and wine tastings, Sail Selina offers the highest quality and personalized experiences on the Chesapeake Bay - Fall in love with the stunning natural surroundings, charming towns, and rich history of the Chesapeake Bay, as you sail aboard our well-appointed and comfortable yacht - Book now and discover the unrivaled quality and dedication of Sail Selina, the premier sailing adventure on the Chesapeake Bay!

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!

Spacious & Beautiful Boat

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.

The Best Captains

Experience the thrill of the journey with Sail Selina's ship's wheel, the ultimate symbol of adventure and maritime history - This stunning image captures the timeless elegance and authenticity of Sail Selina's ship's wheel, a testament to the classic and refined design of the sailing vessel - With our skilled and experienced crew at the helm, enjoy the excitement and thrill of sailing on the Chesapeake Bay, as you witness the power and precision of the ship's wheel in motion - Fall in love with the rich and storied history of the high seas, and experience the magic of sailing aboard an iconic and timeless wooden sailboat - Book now and discover the wonder of the ship's wheel of Sail Selina, an experience that will transport you to another time and place!

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.