Summer 2024

The Water Edition

By Lauren Hurwitz

Sunny days are here to stay – at least for the next few months – and what does that mean for you? Time to get out and enjoy the water surrounding New York City, and no one does that better than Sarah Pennington, Managing Director of Classic Harbor Line, who has dedicated her life to the local waters. Sarah’s dedication to the water started when she walked through a career fair in her 20s and someone asked if she knew how to sail. Pennington had taught sailing at an all-girls camp at the University of Iowa for two years and says she, “really loved being outside instead of going to grad school.” She decided that one day, she was going to sail around the world. She took a job in Maine, and while up north, she learned all about schooners and tall ships and developed a major inclination to move to New York City. 

“I always thought there would be nowhere else in the world that was more exciting than NYC and decided I must go live there,” Pennington says. In 2002, she took a crew position with Classic Harbor Line in NYC, becoming Manager at the end of her first season. From there, she earned her Captain’s license and grew the one-vessel, single-location operation into a fleet of 13 vessels including sail and power boats built locally up in Albany with four locations (adding Boston, Newport, and Key West) and featuring dynamic public programming and top-notch private charters. 

One of Pennington’s favorite times to sail in New York is June as the city is host to Sail GP from June 22-23. “It’s like the America’s Cup Series – it’s even the same boats that they use to compete in the Cup. It’s a huge spectator event so we are really excited for that,” she says. Any Classic Harbor Line sails and cruises to the Statue of Liberty that overlap with Sail GP racing times will capture views of the race. But regardless of when or how you choose to hit the water, there are a few things to keep in mind that will make life on the blues a bit easier. According to Pennington, “It’s always brighter and cooler on the water, so depending on the time of day and year, you and your guests should consider bringing sunscreen, hats, sunglasses, and an extra layer.” 

When you head to Chelsea Piers and visit one of Pennington’s Gilded Age-inspired boats, know there are a variety of tours in store for those who love nature and the outdoors. Friday tours are a collaboration with the American Institution of Architects and focus on climate change where they discuss environmental factors you can see such as rising sea levels and sustainable buildings. “About 25% of our visitors are there for architecture tours of New York City. They want to see hi-rise residential projects, municipal projects, and touristy things too. There is so much to see like Hudson Yards, Frank Gehry projects, and “Star-citecture.” Incredible gems have come up in the past few years that you can see from the water like the triangle-shaped VIA 57 West residential building by renowned Danish architect firm BIG-Bjarke Ingels Group, a unique view of the iconic Empire State Building lined up behind the modern architecture of the Vessel and Hudson Yards, and Little Island which is a fantastical-redesign of Pier 55 converted to a public park and amphitheater, or the Brooklyn’s shores which is the adaptive reuse architecture project of a former Domino Sugar refinery and grounds which have become big deals for our guests,” Pennington says. In the summer, the company offers tours with urban naturalists where they go to abandoned islands and structures and discuss wildlife and migratory birds.

Most of the company’s visitors are actually locals from right here in the tri-state who are hoping to enjoy the wine-tasting or champagne and cheese tours. The latter takes place on Fridays, Saturdays, and Sundays and features a rotation of different bottles and cheeses with self-guided tastings aboard and is a great choice for those who prefer an unnarrated experience and want to socialize with family or friends who are also aboard the ship.

Pennington says sailing can also be a wonderful family affair. “We are renowned for sailing, even though we operate schooners, we have performance schooners – the Ferraris of sailboats. We turn off the engines and it’s great for families and kids. Moving by wind power and at the same time seeing the harbor, Ellis Island, and the Statue of Liberty in a non-touristy way can be great. If a kid has never sailed before, this is a great way to introduce them to the art and beauty of sailing. “The first time I went sailing, I was two or three years old. I really encourage families and kids to come sail,” Pennington adds. 

Direct bookings can be made by visiting or by calling the Classic Harbor Line NYC at (212) 627-1825.