The Blessing of the Fleet, usually held at the start of a new season on the water, is a tradition that goes back centuries, to Catholic fishing villages on Europe’s Mediterranean coast. Catholic immigrants eventually brought it to the United States, and it has been a practice in water communities ever since, from the bayou to Cape Cod and here on the Chesapeake Bay.
Typically a Blessing of the Fleet entails a local clergyperson giving a blessing to the working watermen that will venture out on their boats, asking God to protect them from harm and praying for a bountiful season. On the Chesapeake Bay, it often marks the arrival of spring. The Blessing of the Fleet is usually held between March and May in Bay towns where people earn their livelihoods on the water: Tangier, Smith Island, Chincoteague, Cape Charles, Reedville, Rock Hall, Kent Island… you get the idea. St. Mary’s County, Maryland, holds its own Blessing of the Fleet event in October, at the start of oyster season.
On April 11, Chesapeake Bay Magazine experienced a very different Blessing of the Fleet in St. Michaels. It involved a bagpiper, French caviar, and bountiful champagne—all to welcome back The Inn at Perry Cabin’s fleet of pleasure boats and the seven Helly Hansen-clad captains that serve as skippers, tour guides, and caretakers all at once.
Because the fleet spends winter at Haven Harbour South in Rock Hall, the boats must be brought back down the Bay to St. Michaels in the spring. Over the past few years, this “Return of the Fleet” has evolved a full Inn experience. Guests watch as a parade of boats glide up the Miles and into their slips for the charter season. The Blessing of the Fleet follows. This year, we rode along to fetch the fleet from Rock Hall and back, spending time with the boats and the captains who drive them.
The Inn at Perry Cabin, a high-end historic resort next door to the Chesapeake Bay Maritime Museum on the Miles River, has quietly built an impressive fleet of its own boats—each one as high-maintenance as it is beautiful. We can’t think of another privately owned and operated charter fleet on the Bay as well-curated as Perry Cabin’s beautifully varnished vessels. (The teak budget is $30,000!)
Maintaining a fleet of boats at the Inn is a way to connect guests with the Chesapeake Bay and the Inn’s own maritime heritage. (The original owner so admired Commodore Oliver Hazard Perry during the War of 1812 that he designed part of the estate to resemble Perry’s cabin on the USS Niagra… hence the name Inn at Perry Cabin).
The Inn has only been offering charters for the last dozen years. Captain Jason Pinter, Director of the Waterfront and Sailing School, started with one sailboat and a clipboard at the front desk for any interested guests to sign up for a sail. It quickly became clear that there was strong demand, and now the waterfront program includes a wide array of boats and on-water experiences. Tip: You don’t have to be a guest at the Inn at Perry Cabin to book a charter Call 443.258.2228 or email guestservices@perrycabinresorts.com.
Under Pinter’s leadership, the waterfront program has gone above and beyond expectations, investing in a fleet of graceful teak-trimmed sailboats, a charming French canal boat, a rigid-bottom Zodiak, a roughly $2 million Hinckley Talaria 55′ Flybridge, and even its very own historic skipjack, the Stanley Norman, built in Salisbury in 1902. All but the Zodiak and the skipjack are painted in the Inn at Perry Cabin’s signature “Stars and Stripes” blue.
It seems that the Inn’s captains are living the dream, spending their days cruising around the Bay on elegant boats. Some are semi-retired, living in St. Michaels only during the season. Some have grown children. One young captain started at Perry Cabin as a dockhand and is now a trusted skipper, when he’s not working in boat restoration in nearby Easton. The captains are personable and take a genuine interest in their passengers. They are also tough when they need to be. During our Return of the Fleet on a rainy and cold April day, they gamely layered up with foul-weather gear and sailed the open-cockpit boats home. (We were snug and dry in the Hinckley, feeling just a tiny bit guilty about it.)
The fleet’s four sailboats, named Stargazer, Starlight, Starbright, and Midnight Star, range from 26-40′. They are used for charcuterie-and-champagne cruises or sailing lessons from captains who are ASA-certified sailing instructors. The shallow-draft canal boat Harbor Star is good for short, scenic jaunts in the Miles River.
The impressive Hinckley Five Star, which comfortably entertains 8-12 guests in its spacious enclosed salon and on its decks, is for corporate groups and excursions to Annapolis or Kent Island. Pinter calls the yacht a labor of love. At 20 years old, she recently underwent an engine rebuild that required the entire pilothouse and all its furnishings to be removed. The 2700-hp Mann diesel engines had to be hoisted out and shipped to Texas. All told, the rebuilt engines cost $350,000. Equipped with only one stateroom, the Hinckley is designed, essentially, as a 55-foot dayboat—perfect for entertaining, and pretty much only for entertaining. She also burns about $400 per hour in fuel.
What Five Star lacks in practicality, she makes up for in a smooth ride, good looks, and showstopping special occasion charters. She has been used for proposals and even small “microweddings”. Almost all the boats in Perry Cabin’s fleet have been backdrops for proposals, keeping the captains on their toes as they’re recruited as accomplices in the surprise. Captain Buddy, who has been with the inn for 11 years, recalls a touching proposal that made him cry right along with the couple. Captain Mark recounts how he helped orchestrate a proposal aboard Five Star for a local woman who admired the boat every morning from her window at home. Her dog was even named Hinckley. Needless to say, when her boyfriend popped the question on the yacht, she said yes.
The Inn’s Zodiak provides a healthy contrast to the Hinckley experience. On it, a captain zips passengers up to Wye Island, a popular paddling spot just north of the Miles. It puts guests right into the Chesapeake Bay’s rich landscape, full native wildlife and secret coves. The 28-foot rigid hull inflatable boat (RHIB) is loaded with kayaks or standup paddleboards. Upon arrival, the passengers can disembark for their own paddling journey in and around Wye Island. Instead of champagne, guests are supplied with Gatorade and protein bars. Afterwards, the RHIB captain picks them up and stows the paddlecraft for the leg home to St. Michaels.
Aboard the skipjack Stanley Norman, which is listed on the National Historic Register, visitors get a close look at Chesapeake Bay heritage. The boat is an emblem of all that skipjacks once did on the Bay. During her 123 years, she has been used for oyster dredging, skipjack racing, and even as a floating classroom for the Chesapeake Bay Foundation before the Inn at Perry Cabin bought her a few years ago.
The Inn’s team of captains tell us that despite their many combined years of sailing experience, there was a steep learning curve in operating the Stanley Norman. They feared ridicule from the Talbot County watermen. But Pinter wasn’t daunted. “How hard can it be?” he said.
In the spring and summer, Stanley Norman is used for history tours, and in October and November, the Inn offers a unique charter called Experience on the Half Shell. Guests can come along to see oyster dredging in action, collecting oysters in the same way the Stanley Norman would have done in the early-to-mid 20th century. The Inn points out that any oysters they dredge up are “catch and release”, per their arrangement with the Maryland Department of Natural Resources. Even so, the Inn makes sure there are pre-sourced fresh oysters and beverages for guests to enjoy as they sail back to port.
Stanley Norman has never been outfitted with an engine, and still relies on her push boat for propulsion along with her sails. “That alone is worth the price of a charter,” Pinter quips, “watching us try to dock the skipjack with the push boat.”
The Stanley Norman wasn’t quite ready in time for the 2025 Return of the Fleet. She was busy getting a refit at the Chesapeake Bay Maritime Museum, where expert shipwrights are conveniently located next door to the Inn. The rest of the fleet, however, arrived soggy but triumphant into St. Michaels Harbor to the sounds of an awaiting bagpiper. Guests at the inn waited inside with their champagne as the rain came down.
At the dock, the captains got the fleet settled and ducked into the Hinckley to change out of their wet foulies. The bagpiper escorted the captains to the ceremony, where the pastor of the Episcopal Church in town gave a blessing and a toast. It was the old Irish proverb many of us know well:
There are good ships and wood ships, ships that sail the sea, but the best ships are friendships, may they always be!
We’ll drink (champagne) to that.
If you go: A particularly enticing offering from the Inn’s fleet is the “Skip the Bridge” package. Recognizing that unpleasant summer Bay Bridge traffic is an obstacle to bringing guests to St. Michaels, the inn offers shuttle rides across the Bay from Pier Seven Resort Marina in Edgewater aboard the Hinckley. During the 1.5-hour ride to Perry Cabin, guests are served wine and hors d’oeuvres. They are also checked into their rooms and given the keys before they even step off the boat. The best part, says Pinter, is seeing vehicle traffic inching along the Bay Bridge as Five Star goes by. It’s a satisfying splurge for a weekend away.
