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Full-Day Private Sail

Enjoy a full 8 hour day of sailing in the beautiful waters of the Miles River on Chesapeake Bay.

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

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

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

Private Charter

A Full-Day Private Sail on the Miles River

Join us on the Selina II for a private 8 hour full-day sail that is bound to have everyone smiling ear to ear. We depart the dock and do a mini-tour of the harbor (St. Michaels is very pretty to see from the waterfront), and then we go out into the Miles River, put up sails, and follow the wind.

Sit back and relax, or if you prefer to participate you can help raise sails and steer the boat. If you are interested we can share the story of the historic yacht Selina II, the history of the St Michaels Island area, learn about the Chesapeake Bay environment, and take in the beautiful scenery along the banks and hidden creeks and coves of the Miles River. This wonderful, relaxing and intimate experience is one to remember!

Trip Advisor Testimonials

  1. “Amazing Full Day Private Charter” by Ryan B. – “We had an amazing full day private charter with Sail Selina. The captain and crew were extremely knowledgeable, accommodating and professional. We had a great day on the water and would highly recommend Sail Selina for a private charter.”

  2. “The Best Day on the Water!” by Nicole S. – “Our full day private charter with Sail Selina was the highlight of our vacation. The captain and crew were friendly and knowledgeable, the boat was comfortable and clean, and the views were unbeatable. Highly recommend!”

  3. “Incredible Private Charter Experience” by Jill P. – “We had an incredible private charter experience with Sail Selina. The captain and crew were excellent and provided a personalized, informative and fun experience for our group. We would highly recommend Sail Selina for a unique and unforgettable experience.”

a group of people sitting at a table eating food

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.

•Food Options: On your full-day private sail, we can cater a simple picnic lunch or an Eastern Shore favorite: a crab cake lunch catered from the Harrison Harbour Lights traditional family restaurant.

Beverages: Beer/Wine tasting add-on is a fun and refreshing way to quench your thirst while exploring the shores of the Chesapeake Bay. At only an additional $20 per person (21 and older) this is a great value.  The frosty cold 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.

•Swag: Our ships store includes 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.

•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.

•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.

• Cancellation 72 hrs: Full refunds on cancellations up to 1 week before departure. 50% refund up to 72 hrs. No refund within 72 hours. Please email

•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 boat tie up.

Still have Questions? ☎  410-726-9400

Amusement tax and crew gratuity added on.