What could be more “St. Michaels” than a sunset sail on a beautifully restored wooden yacht? A tour with Sail Selina II is one of the quintessential experiences for visitors to St. Michaels, right up there with the Chesapeake Bay Maritime Museum and ice cream at Justine’s. Over the past 25 years, visitors and locals alike have sailed aboard the 1926 catboat Selina II with Captain Iris Robertson, the granddaughter of the boat’s original owner.
Robertson has announced that this season will be the last for her company, Sail Selina II, on the Chesapeake Bay. The captain is retiring, and Selina II will start a new adventure in New York. The 2025 season will be a Bay farewell tour, of sorts, with special events planned throughout the spring and summer.
The boat has had a remarkable journey thus far. Built at Sweets Shipyard in Greenport, New York, she was designed after the classic New England Crosby Cat Boats. Catboats, typically defined by their single large sail on a mast close to the bow, are usually beamy and stable, and Selina II is no different. She has a 16-foot beam and is 41’6″ long overall, making her the largest surviving vintage catboat.
Selina II was built for the Hird family on Shelter Island, New York. She passed to the Hirds’ daughter, Esther, who, with her husband, kept the boat on Shelter Island until 2001. That’s when their daughter, Iris Robertson, brought the yacht to the Chesapeake Bay. Robertson had been living in Somerset County, but moved up to St. Michaels where she felt there was a market for cruises. She knew she couldn’t maintain her grandfather’s boat as a private vessel, so she opened Selina II for charters.
Both in 1980 and again in 2001, the wooden boat underwent extensive restorations to keep her in sailing condition. She has been kept as true to her original design as possible, except for a few modifications to make her charter-ready.
Before arriving on the Chesapeake to stay, Selina II traveled the East Coast to take part in patriotic celebrations, from the 1976 U.S. Bicentennial celebration in New York Harbor to Boston’s 250th anniversary in 1980 and Norfolk, Virginia’s Portfest, among others.
Since 2001, Robertson and her crew have made Sail Selina II part of the Talbot County, Maryland, experience. “We’re incredibly grateful to have had the privilege of sharing the magic of the Chesapeake Bay with so many people over the years,” says Robertson. “From family outings to romantic sunset sails, each journey has been a testament to the enduring charm of this incredible region.”
With her polished brass and mahogany, the boat has been an irresistible backdrop for photo shoots and reality TV shows over the years. The onboard experiences include sunset champagne cruises, educational tours, and there is even a special package for marriage proposals.
To send Selina II out in style this season, the charter business is planning farewell voyages, themed cruises, and a 1920s-themed Flapper Gala on May 3, 2025. It is planned as a “glamorous evening of dancing, dining, and live entertainment under the stars” at St. Michaels Harbour Inn. The 2025 season runs April through October, and bookings are open now.
“Our community has supported us throughout these years, and we want to honor them with an unforgettable final season,” says Robertson.
Robertson herself is looking forward to retirement, though she doubts she’ll sit still for long. She lists gardening, spending time with her husband, and maybe driving somebody else’s boat as aspirations. “Know anyone who needs an experienced Chesapeake Bay captain?”
In 2026 (Selina II‘s 100th birthday!), she will pass to the family’s fourth generation, as Robertson’s niece and nephew-in-law become the yacht’s next stewards. They will operate small, intimate cruises like the ones Sail Selina II is known for on the Bay… only she’ll sail in the town where she was built, Greenport, New York. The niece’s first name happens to be Selina. Her daughter carries on that name, too. Their two children will be 10 and 6 when the boat arrives. As Robertson explains it, “They are still young enough to get a really deep-seated connection to the boat so then it when it gets to be their turn in another 30 years, they’ll be excited to be the fifth generation. Succession planning at its finest!”
