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Family Vacation Packages

Family Friendly, bring the whole tribe aboard Sail Selina II in St. Michaels MD during your family vacation

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

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

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

Fun Family Vacation Packages

When planning your next family trip let it be Sailing St Michaels MD. Looking for an unforgettable and extra special family outing? We love welcoming families aboard! The Selina II can accommodate all ages, from toddlers to grandma and grandpa. In fact, the kids can have run of the kid-friendly cockpit. Talk about fun!

Reserve Selina II for a private charter and bring up to six of your family members out for a wonderful one-on-one experience (sailing participation optional). Our yacht is the perfect back drop for a family portrait so be sure to bring your good camera along. Or we can refer you to a local photographer for a professional shoot.

Explore the great out of doors with your kids! We have infant, toddler, and youth life jackets to fit all sizes and ages.

Please contact us directly for more information, including ages appropriate for lessons.

Set sail with your family on Sail Selina's kid-friendly St Michaels boat tour and enjoy unforgettable moments on the beautiful Chesapeake Bay

Trip Advisor Testimonials:

  • “The Perfect Stable Family Outing” by Emily G. – “We had an amazing time sailing with Sail Selina. The crew was wonderful, accommodating and so engaging with our children. It was the perfect stable family outing and I will definitely be recommending this for other families.”

  • “Family-Friendly Sailing Experience” by Linda C. – “We had a fantastic family sailing experience with Sail Selina. The crew was exceptional in making everyone feel comfortable and safe, including our little ones. Highly recommend this family-friendly experience.”

  • “Memorable Family Sail Experience” by Harry S. – “We had such a memorable time sailing with Sail Selina. The captain and crew were accommodating and informative, and made sure my family felt welcome and had a great time. We would definitely do it again next season.”

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.

Stable Sailing Platform: Selina II’s stability, ensures a relaxing sailing experience. Guests with young children have appreciated the stable sailing platform, allowing for a safe, comfortable, and worry-free enjoyable trip on the water.

Ideal Sailing Conditions: Guests praise Chesapeake Bay’s perfect weather for sailing which provides optimal sailing conditions, enhancing the overall experience and creating the perfect environment for a memorable trip.

sail Selina St Michaels Maryland family fun private charter. explore Chesapeake Bay on a historic sailing vessel on your private tour


  • 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.
  • 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 72 hrs:  Private Charters can be cancelled outside of 72 hours of departure time. Please email cancellations to
  • 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