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Private Sailing Lessons

Head out on the water on our historic yacht Sail Selina II and learn to sail with the best team in St. Michaels!

Quick Details

Occupancy: Groups of 1 to 6 guests

⏰  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

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

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

Private Sailing Lesson

Take a Private Sailing Lesson in St. Michaels

We’re excited about your interest in learning to sail — or for the experienced sailor, learning the art of the gaff rig!

Because Selina II is a historic vessel, we offer a very different approach to learning to sail. In the two hours we spend together, you can expect to learn the basics: line handling, how to raise the sail, steering the boat, reading the wind, and the physics behind what makes the boat go towards the wind. We cover simple boat handling, parts of a boat, a few basic knots, touch on weather, talk about rules of the road, the simple four points of sailing, and determining proper sail set and practice tacking.

You come away realizing you’ve only scratched the surface! Lessons can be for groups of one to six guests.

Take your family on the adventure of a lifetime with our kid-friendly siling lesson boat tour - a perfect way to unwind and enjoy the simple pleasures of life.


“Incredible Sailing Lesson” by toniaross5 – “The sailing lesson with Sail Selina was incredible. The captain and crew did an amazing job teaching us everything we needed to know about sailing. It was a hands-on experience that left us feeling confident and knowledgeable. Highly recommend for anyone looking to learn how to sail!”

“Wonderful Sailing Lesson” by Lis B – “My husband and I took a wonderful sailing lesson with Sail Selina. The captain provided a great course that was tailored to our level of expertise, and the crew was patient and knowledgeable. We felt confident sailing on our own by the end of the lesson. It was an amazing experience!”

What else 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.


  • Swag: Don’t forget to visit our ship’s store and grab some awesome swag! Exclusive Selina II embroidered polo shirts, stylish baseball caps, cozy zip hoodies, and can coozies – all yours to pre-order or purchase onboard. Shop now and take home the perfect souvenir from your unforgettable sailing adventure!
  • 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.
  • Max 6 passengers: Must be 21 or older to participate in the beer tasting portion of this trip.
  • Children: 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 cancellation is 24 hrs. Private Charters are 72hrs.
  • 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!
  • 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.
  • 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 boats tie up.

Amusement tax and crew gratuity are added on.