Busy Waterfront at the Inn at Perry Cabin

On any given day, the waterfront at the Inn at Perry Cabin by Belmond is a happening spot in St. Michaels. Glistening vessels line the dock, everything from a luxurious 55’ Hinckley yacht to various sized sailboats. It’s easy to spend several minutes soaking in the sights and sounds of the historic property. From one moment to the next, you can go from feeling lazy in an Adirondack chair to feeling energized by the thought of a sail along the Miles River.

Photograph courtesy of Jason Varney.

On the heels of the hotel’s bicentennial year, the Inn at Perry Cabin by Belmond is showcasing a refreshed look and rolling out new offerings that are appealing to both guests and residents. Exciting things are happening here. Remember the Gazebo Bar? It’s coming back. In addition to maintaining the exquisite 200-year-old gardens, the property has dedicated itself to the farm to table initiative and is currently planting produce for sustainability. Down the road, Harbourtowne Resort in St. Michaels is now in the fold and reopening as The Lodge at Perry Cabin with the much-anticipated PGA-recognized golf course, The Links at Perry Cabin, in 2018. But, on this warm, sunny day, we explored all that the waterfront has to offer.

Taking a sail with Captain Jason Pinter, director of waterfront activities and Sailing Academy, is part sailing lesson and part tour. He explains various nautical terms and what’s happening on board while pointing out the highlights of St. Michaels Harbor and the Miles River. Jason was hired to start the property’s charter boat operation in 2014 and opened the American Sailing Association-certified Sailing Academy a year later. This year, guests now have the option to “Skip the Bridge” and sail into St. Michaels for the weekend on board Five Star, a pristine Hinckley yacht.

Here, you can’t go wrong whether you want to learn to sail or prefer to book a two-hour charter with a U.S. Coast Guard-certified master captain. Whether you partake in the luxury accommodations of Perry Cabin or not, everyone can treat themselves to the beauty of the Miles River on board an Alerion or Tadorne yacht or French Canal Commuter. For an added bonus, partake in a bottle of wine or a picnic, ordered through the hotel, during the charter.

“Sailing is such a part of life here on the Shore and it allows people to experience and explore the area in a new way,” said Jason, who grew up on the water in Annapolis. While Jason, at 12 years old, taught himself to sail in his neighbor’s dinghy along the Severn River, he and his crew of certified instructors can now provide tailored instruction.

The Sailing Academy provides several options in a three- or five-day course: Basic Keelboat Sailing, Basic Coastal Cruising and Learn to Sail in a Weekend, as well as private instruction. The yachts range in size from 26 to 38 feet and are considered high end and high performance but are also extremely comfortable. They are perfect for both beginners and the more experienced. The program offers ASA certification programs, which sets the Sailing Academy apart from other schools.

Jason began his career teaching children at the Annapolis Sailing School 19 years ago and eventually became general manager of the school. He also served as director of the Chesapeake Boating Club. During stints with The Moorings, a boat chartering company, and Sailing magazine, he missed introducing people to sailing. “I missed ‘that’ moment when a sailor was born,” said Jason. “When you turn off the engine, get in the groove and the sail snaps in the wind; then there is just this silence except for the water splashing against the boat and you look over and you see this smile on their faces. Then you realize you just created a sailor. That’s why we do this every day.”

Of course, being out on the water all day and having a great suntan is nice, Jason admits, but seeing that smile is what makes it worth it. Jason is careful to explain that it’s not just about the boats and the beautiful Miles River, it’s all the interesting people you get to meet, too. He said, “You meet people from many different personalities from all over the world and it keeps it fresh and interesting.”

Captain Sean Dunn agrees that two days are never the same. “You’re on the same body of water every day, but it’s never the same day. You can see a pod of dolphins one day, the weather is always different and there are always great boats coming in to St. Michaels, which is such a popular spot for boaters.”

It’s clear that both Captains Jason and Sean, who met at the Annapolis Sailing School, have a great admiration for the Chesapeake Bay. They both go into teacher mode explaining the expanse and scope of the Bay and its 100,000 tributaries. “You could spend a lifetime and never see everything in the Bay,” said Sean, as he prepared for a two-hour charter with guests. But Sean and Jason do their best to show people the Miles River and beyond from their home base at the Inn at Perry Cabin by Belmond.

To learn more about chartering a cruise or enrolling in the Sailing Academy at the Inn at Perry Cabin, located at 308 Watkins Avenue in St. Michaels, visit belmond.com/inn-at-perry-cabin-st-michaels or call 410-745-2200 or email Jason.pinter@belmond.com.


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Allison Rogers



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