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Number of People: 6
Duration: 4 hours
Package: Up to 6 people


Charter a private sailboat and enjoy a personalized half-day cruise exploring the Chesapeake Bay in Saint Michaels, Maryland. Bask in the tranquility of the open water while taking in the picturesque scenery and savoring the company of your chosen guests.

🌊 Set sail on the Chesapeake Bay for a private 4-hour half-day sail around the St. Michaels area.

🚢 Depart from the dock and start with a mini-tour of the picturesque harbor before heading out into the Miles River, where we'll hoist the sails and let the wind guide us.

🧺 Choose from a simple picnic lunch or savor a taste of the Eastern Shore with a delicious crab cake lunch while enjoying the serene beauty of the bay.

😃 Get ready to have an unforgettable day on the water and make memories that will last a lifetime!


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: Four hours sailing on the water.
  • What’s included: Exclusive use of the boat for up to six guests, Bottled water, binoculars, sunscreen, sunglasses, Free parking, Rain jackets, hats, blankets. There are beverages (beer, wine, and sodas) for purchase on the ship. You are also 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

Join us for a private 4-hour half-day sail and explore the beautiful St. Michaels area of Chesapeake Bay. We'll depart from the dock and start with a mini-tour of the harbor, where you can enjoy the picturesque views of St. Michaels Maryland from the waterfront. Then, we'll venture out into the Miles River, hoist the sails, and let the wind guide us. During the sail, we can provide a simple picnic lunch or a delicious Eastern Shore crab cake lunch, making it the perfect day out on the water. So, come aboard and get ready to experience the charm and beauty of Chesapeake Bay.

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 hours in advance means losing the value of your experience.

Number of People: 6
Duration: 4 hours
Package: Up to 6 people
Regular price $1,235
$1,235 Regular price Sale price
You save $-1,235

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Here's what others have to say!



Based on 0 reviews

Monica H

If you're looking for a fun and unique way to spend a day on the Chesapeake, I highly recommend a 1/2 day private charter. The boat was well-equipped and comfortable, and the captain was excellent. We got to see some amazing sights. It was an unforgettable experience that I would recommend to anyone.

Carla J

I recently went on a 1/2 day private charter and it was an amazing experience. The boat was spacious and comfortable, and the captain was knowledgeable and friendly. We got to explore some of the most beautiful parts of the Chesapeake and even got to try our hand at fishing. It was the perfect way to spend a relaxing day on the water.

Pauline K

We recently took our family on a 1/2 day private charter on the Chesapeake and it turned out to be one of the best family outings we've ever had. The boat was spacious and comfortable, and the captain was fantastic with kids. It was a perfect day on the water, exploring the beauty of the Chesapeake, and we can't wait to do it again.