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Duration: 2 hours


Sail along the scenic Chesapeake Bay for a two-hour journey through Saint Michaelss, Maryland. Take in the beauty of the water and coastline while enjoying the relaxing ambiance of a sailboat ride guided by knowledgeable crew members.

🌊 Sail the Chesapeake Bay on this 2-hour cruise as part of the crew or a relaxing passenger

🚣‍♀️ Take the helm and steer the boat or help raise the sail and feel the wind in your hair

🌅 Sit back and soak in the breathtaking views of the Eastern Shore scenery while enjoying the luxury of Selina II's mahogany and brass interior

⛵️ Experience the intimate history of sailing on this premier charter boat with a maximum capacity of just 6 guests


When do I choose a date?

After purchase, you can request your preferred dates and times by following the instructions in the email you receive. If it's a gift, the recipient will also get an email with booking instructions.

Monday - Friday (except holidays)

Practical information

Any restrictions to participate?

  • Age: All ages are welcomed.

Who can you accommodate for?

  • Children: All participants must have a paid ticket to participate, children included.
  • Individuals with disabilities: While the ship does not have a ramp for wheelchair access, the captain and crew have been able to get everyone on and off regardless of capability!
  • Pets: Canine guests are allowed! Dogs must be in a carrier — like a bag or basket — or wearing booties so they do not scratch the varnished surfaces of the boat.


What to expect on the day of the experience?

  • Duration: 2 Hours cruising on the water
  • What’s included: Bottled water, binoculars, sunscreen, sunglasses, Free parking, Rain jackets, hats, wind-gear, blankets. 
  • There are beverages (beer, wine, and sodas) for purchase on the ship. You are welcome to bring your own beverages for an additional fee.
  • Who will be present: Your captain, crew and other guests (up to 6 people)
  • Spectators: No spectators are allowed, everyone must have a ticket
  • Photo/ video: Photos are allowed and encouraged.

How to prepare?

  • Weather dependency: It is at the captain’s discretion to cancel due to weather. This decision is made 15 minutes prior to departure.
  • Arrival: 15 minutes prior to departure
  • Parking: Free parking at the Harbour Inn
  • What to wear: Dress is casual. The temperature can be cooler out on the water, please dress accordingly. Passengers should wear only soft soled shoes such as sneakers, deck shoes, flip-flops or sandals. Heels and boots can scuff the deck.
  • What to bring: You are welcome to bring your own food aboard. 
  • Restrooms/ lockers/ changing rooms: There is a restroom on board; however, it is limited and is down 4 steps, so it is recommended guests take advantage of the shore-side facilities inside the Harbour Inn before embarking.

Full description

On this 2-hour Chesapeake sailing tour, Sail Selina II offers you the opportunity to become part of the crew and learn the ropes of sailing, from raising the sail to steering the boat. Or, if you prefer a more laid-back experience, simply sit back, relax, and soak in the breathtaking Eastern Shore scenery while listening to the sound of the wind and water. Either way, this 2-hour Maryland sailboat cruise promises a fantastic, relaxing experience.
This unique, upscale, and exclusive luxury sailing yacht that accommodates just six guests, creating an intimate ambiance that immerses you in the history of sailing. The yacht is freshly varnished with mahogany and brightly polished brass, making it a premier charter boat in St Michaels, MD. It's a great opportunity to sail into another time and place, learning more about the history and craft of sailing.
Overall, this 2-hour Chesapeake sailing tour is an excellent way to relax and unwind while learning about the art of sailing. Whether you choose to participate as a crew member or simply sit back and enjoy the ride, you'll surely have an unforgettable experience aboard Selina II.

Returns, exchanges and cancellation

Unused Experience Vouchers can be returned within 30 days for a full refund to the original purchaser, no questions asked.

If you have any unused Experience Vouchers, you can exchange them for anything else in our marketplace, no matter when. If you choose an experience that's more expensive, you'll need to pay the difference, but if you choose one that costs less, you'll receive a credit towards your next booking.

No refunds are allowed once the experience is booked, but you can reschedule up to 24 hours before your experience, for a date within a year of the original booking. To reschedule, contact the experience provider directly. No-shows or rescheduling less than 24 hours in advance means losing the value of your experience.

Duration: 2 hours
Regular price $123
$123 Regular price Sale price
You save $-123

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Here's what others have to say!



Based on 0 reviews

Vivian E

I recently took my friends on a 2 hour Chesapeake sail and it was one of the most memorable experiences we've ever had. The captain was fantastic and gave us an incredible tour of the bay, pointing out different landmarks and wildlife along the way. The boat was spacious and comfortable, and we even got to enjoy some snacks and drinks while taking in the scenery. It was a perfect afternoon and we can't wait to do it again.

Victoria H

If you're looking for a unique and exciting way to explore the Chesapeake, I highly recommend a 2 hour Chesapeake sail. The boat was well-equipped and the captain was friendly and professional. We got to learn about sailing and even got to try our hand at navigating the boat. It was a fun and educational experience that I would recommend to anyone.

Emily U

I recently went on a 2 hour Chesapeake sail and it was an absolutely breathtaking experience. The captain was knowledgeable and skilled, and the boat was well-maintained and comfortable. We got to see some stunning scenery and wildlife, and it was the perfect way to unwind and enjoy the beauty of the Chesapeake. I would highly recommend this sail to anyone looking for a peaceful and serene experience on the water.