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Number of People: 6
Duration: 2 hours
Package: Up to 6 people


Experience the beauty of the Chesapeake Bay on a relaxing day sail cruise in Saint Michaelss, Maryland. Set sail for two hours on this private charter and enjoy the stunning scenery, fresh air, and perhaps even catch a glimpse of local wildlife while learning about the area's rich history from knowledgeable guides.

🌊 Join our crew on a 2-hour Chesapeake sailing tour and become part of the team, helping raise the sail or even steer the boat, or simply relax and enjoy the Eastern Shore scenery.

⛵ Sail into another time and place with freshly varnished mahogany and brightly polished brass.

🏰 Learn about the history of St. Michaels, MD and Captain Iris's grandfather's boat.

💫 Create unforgettable memories on the beautiful Chesapeake Bay!


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 pay 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 additional 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

This experience offers a unique and exclusive 2-hour Chesapeake sailing tour where you can become a crew member and help raise the sail or steer the boat. If you prefer a more relaxing experience, you can sit back and enjoy the Eastern Shore scenery while listening to the sound of the wind and water. This luxury sailing yacht limits her passengers to just 6 guests for an intimate taste of the history of sailing.
The yacht departs from the dock at the Harbor Inn and Marina in St. Michaels, MD, and Captain Iris or her first-class relief captain and crew provides an informative personalized harbor tour. During the tour, you can learn about the picturesque waterfront, the history of St. Michaels, MD, and the story of her grandfather's boat, the Selina II. You will also pass by the Hoopers Strait Lighthouse at the Chesapeake Bay Maritime Museum.
After the tour, the yacht departs the harbor and goes out into the Miles River, putting up sails and following the wind. As a guest, you are welcome to participate as a working crew member or simply sit back and relax. The yacht is here to help you complete your historic sailing experience. This unforgettable Chesapeake sailing tour is perfect for creating unforgettable memories on the beautiful Chesapeake Bay. Book your next sailing experience today!

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.

Number of People: 6
Duration: 2 hours
Package: Up to 6 people
Regular price $715
$715 Regular price Sale price
You save $-715

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Here's what others have to say!



Based on 0 reviews

Phillip A

I recently went on a 2 hour private Chesapeake sailing charter and it was an absolutely incredible experience. The captain was knowledgeable and experienced, and he made us feel completely safe and comfortable. The scenery was stunning and we even got to see some wildlife. I would highly recommend this charter to anyone looking for a unique and memorable adventure.

Carlos S

I recently surprised my family with a private Chesapeake sailing charter and it was the highlight of our vacation. The captain was great with kids and made the experience fun and educational. We all learned a lot about sailing and got to see some amazing sights along the way. It was a truly unforgettable experience that we'll never forget. I would highly recommend this charter to anyone looking for a unique and memorable adventure with their family.

Samantha L

If you're looking for a fun and relaxing way to spend an afternoon, I highly recommend a private Chesapeake sailing charter. The boat was spacious and comfortable, and the captain was friendly and professional. We got to see some beautiful scenery and even learned a few things about sailing. It was the perfect way to unwind and enjoy the beauty of the Chesapeake.