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2 Hour Relaxing Chesapeake Day Sail

Join a Sail Selina cruise as a crew member or just sit back and unwind while taking in unforgettable Chesapeake sailing in St Michaels, MD!

Quick Details

⏰   Check-in: 15 minutes prior to departure

📍   Location: Harbour Inn, 101 N Harbor Road, St Michaels MD

icon, arrow Free Cancellation: 72 hours before departure for private charters, 24 hrs for per person bookings

⛈️  Weather:  Full refund for cruises cancelled due to weather

icon Trip Advisor’s #1 Boat Tour in St Michaels

⭐⭐⭐⭐⭐ Google Reviews: Over 1,040 5 star reviews!


Private Charter

Enjoy 2-Hours of Sailing on the Chesapeake Bay

(Available on a per person basis or as a private charter)

Ready to embark on an unforgettable adventure? Step aboard and become a valued member of our crew on this 2-hour Chesapeake boat cruise, where you’ll experience the thrill of sailing firsthand.

Or if you’re seeking tranquility and awe-inspiring vistas, settle into your seat, breathe in the salty sea air, and lose yourself in the captivating beauty of the Eastern Shore during this fantastic 2-hour Maryland sailboat cruise.

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.

Indulge in the sensory feast of freshly varnished mahogany and brightly polished brass aboard the premier charter boat in St. Michaels, MD. As you journey through maritime history, your captain will reveal the secret behind why yachts opt for varnish instead of paint, all the while treating you to exclusive behind-the-scenes insights into the operation of classic sailing vessel. Allow yourself to be transported to another era, where timeless elegance and maritime splendor await your discovery.

Sail Selina II, St Michaels MD - Discover the great Chesapeake Bay and enjoy a unique sailing experience aboard our classic sailboat

You will depart from the dock at the Harbour Inn and Marina in St. Michaels, MD and Captain Iris (or her first class relief captain and crew) provides a personalized harbor tour. You learn about the picturesque waterfront, the history of St. Michaels, MD and the story of her grandfather’s boat, the Selina II, on this amazing Chesapeake sailing tour. We pass right by the Chesapeake Bay Maritime Museum where you discover why the first screwpile lighthouse was dragged down the Bay by the ice a full mile. Then we depart the harbor and go out into the Miles River, put up sails, and follow the wind.

Available on a per person basis or as a private boat cruise.

You are welcome to participate as a working crew member or simply sit back and relax; we’re here to help you complete your historic yacht experience!

Raising Sails on Selina II, St Michaels MD. Discover the joy of raising a sail and enjoy a unique sailing experience aboard our classic sailboat


  1. James V, Trip Advisor: “My wife and I took a ride on the Selina II in late September. We had a fantastic time. The captain regaled us with stories of how she restored the boat and other interesting historical tidbits about St. Michaels/the Chesapeake. Her first mate served us some small snacks and they had a wonderful selection of beer and wine. We caught a beautiful sunset in front of us and a rainbow behind us. Overall, it was just a delightful experience. Highly recommend!” – Sept 2023

  2. Thomas S, Trip Advisor: “Captain Iris and her first mate were very pleasant, engaging, and extremely knowledgeable about the history and ecosystem of the St. Michaels area. We would definitely recommend, and will look forward to going again.” – October 2022

  3. Jenny W, Trip Advisor: “We’ve sailed on the Selina II numerous times, and it never fails to be magical. Beautiful boat, beautiful people and lovely views of St. Michaels.” – October 2022

What to expect:

Immaculate Sailboat: Our beautifully kept sailing boat offers a luxurious and comfortable sailing experience. Guests have consistently praised the impeccable condition of the sailboat, making it the perfect setting for a memorable trip on the water.

Friendly and Experienced Crew: Our knowledgeable and engaging crew will enhance your sailing experience by providing valuable insights about the area and sailing. Guests have raved about the crew’s friendliness and expertise, making them feel welcome and comfortable throughout the trip.

Tranquil Sailing Trip: Take a break from the hustle and bustle of daily life with our peaceful and serene sailing experience. Guests have consistently praised the calming and rejuvenating experience of being on the water, creating the perfect escape from the stresses of everyday life.

 Captivating Narratives: Our interesting stories and information about the area and sailing will provide an educational and engaging experience that enhances the trip. Guests have appreciated the captivating narratives shared by the crew, providing a deeper understanding of the area and sailing.

 Historic Sailboat: Sailing with us is a unique opportunity to help preserve a historical treasure. We appreciate your support!. Guests have raved about the unforgettable experience of sailing with us, recommending it to friends and family as a must-do activity.

Sail Selina II - Discover the great Chesapeake Bay aboard a St Michaels MD boat tour and enjoy a unique sailing experience aboard our classic sailboat.


•Weather: We want to ensure your safety and comfort, hence the captain may decide to cancel due to bad weather, and this decision is made 15 minutes prior to departure. Rest assured there is no charge if the sail gets cancelled. We’re often asked whether we sail in rainy weather. We do sail even if it’s lightly misting, but not in heavy rain as we want you to have the best experience possible. Its no fun sitting on the pouring rain!

•Beverages: **Beer/wine tasting add-on is only an additional $20 per person (21 and older). The beer tasting is an unlimited sampling of 6 Maryland craft beers, the wine tasting is a flight of 3 whites & 3 reds plus a glass of your favorite wine. Or you can simply buy by the glass: Icy Cold Beer $6, Wine $9.50. Coke, Diet Coke, Sprite are also available for sale, and bottled water is complimentary. BYOB $25.**

Sail Selina II - Participate in a sailing excursion on the great Chesapeake Bay aboard a St Michaels MD sail boat charter and enjoy a unique boating experience aboard our classic sailboat.

•Swag: Our ships store includes custom Selina II embroidered polo shirts, baseball caps, zip hoodies and can coozies.  You can pre-order at checkout or let our crew know you are interested in shopping for a souvenir.

•Comfortable Seating: Sturdy Double Settees on either side of the ship’s wheel offer seating on cushions for 2 big people. Or sit in our vintage captains chairs with cloth seats located on the cockpit sole for seats that offer back support.  All seating offers good visibility from the cockpit area where you will be sitting.  Occasionally guests ask to go forward and sit on the hard cabin top. You are welcome to do so if you have good balance, are sure footed, and can hold a hand rail.

Attire: Be sure to bring comfortable shoes, cameras, and a light jacket in spring and fall.

Sail Selina II - Discover the joy of steering a classic yacht on Chesapeake Bay aboard a St Michaels MD. Our boat rides offer a unique sailing experience aboard a beautifully restored historic sailing vessel

•Max 6 passengers: Children of all ages are welcome aboard the Selina II. We love kids! We have infant, toddler, and youth life jackets to fit all sizes and ages. The U.S. Coast Guard considers all children (regardless of how small they are or what age they are) to be passengers, and as such, you need to count them in, too. For example, mom, dad, and their six-month-old are three guests, not two.

•Safety: Sail Selina II is exceptionally clean and well-maintained, with all modern safety features (life jackets, VHF etc) tastefully concealed to honor her historic legacy. Foul weather gear is available in the event of unexpected bad weather.

•Cancellation 24/72 hrs: Reservations made on a per person basis can be cancelled up to 24 hrs before departure for a full refund.  72 cancellation for Private charters.

•Toilet: Yes, we have a very clean marine head onboard for your convenience; however, it is limited and located down four steps. To ensure your maximum comfort during your journey, we recommend you make use of the shore-side facilities inside the Harbour Inn before embarking.

•Accessibility: Getting aboard is easy most of the time unless we have an extremely high or extremely low tide in which case there is a step up or a step down to get aboard. Most of the time the deck is just about the same height as the dock so its a simple to walk aboard.  Once on deck there are 2 steps down into the cockpit.  Our Captain and first mate are there to assist any one who needs a hand while on the stairs.  So far we’ve been able to get everyone on and off regardless of capability, yea!

•Parking: Free parking where we are parked at the Harbour Inn, 101 N Harbor Road, St Michaels MD 21663.  If there are no spaces available, then there is parking on the side streets and along the waterfront down past where the work boat tie up.

Please note: If you are not booking a private charter, this sail requires two or more people. Amusement tax and crew gratuity added on.

Still have questions? ☎ 410-726-9400


Sail Selina II - Unwind and relax on the Chesapeake Bay aboard a St Michaels MD boat trip with a glass of wine in your hand and feel the sun on your face