America 2.0 Archives - Classic Harbor Line
Check Availability Buy Tickets Now

Sarah Pennington Managing Director of Classic Harbor Line

by
Mother and daughter waves to neighboring sailboat in the harbor

“The first time I went sailing, I was two or three years old. I really encourage families and kids to come sail!”

– Sarah Pennington

Portrait of Managing Director Sarah Pennington on aboard boat in Classic Harbor Line fleet

Read the full article here!

We at Classic Harbor Line are thrilled to see our Managing Director, Sarah Pennington, celebrated in Westchester Women Magazine! Sarah’s journey is a testament to her dedication to the waters of New York City and her unwavering passion for sailing.

Sarah’s maritime adventure began in her 20s when she chose sailing over grad school after teaching at an all-girls camp.

Once she had made this decision, it led her to a job in Maine. There she developed a love for schooners and tall ships, ultimately inspiring her move to New York City. In 2002, Sarah joined Classic Harbor Line as a crew member, quickly rising to Manager by the end of her first season. She easily was able to obtain her Captain’s license and begin driving in New York Harbor. Undeniably, Sarah has since transformed our operation. Under Sarah’s care Classic Harbor Line changed from a single sailboat to a fleet of 13, including both sail and motor yachts. Locations for Classic Harbor Line are also in Boston, Newport, and Key West.

One of Sarah’s favorite times to sail is in June, particularly during the Sail GP event on June 22-23. This exciting spectacle, similar to the America’s Cup, can be enjoyed from our Statue of Liberty cruises. Sarah’s enthusiasm for these events is contagious, and she reminds everyone to bring sunscreen, hats, sunglasses, and an extra layer, as it’s always brighter and cooler on the water.

Classic Harbor Line offers a variety of tours from Chelsea Piers. Sarah encourages families to experience the joy of sailing on our performance schooners, offering a unique and non-touristy view of the harbor, Ellis Island, and the Statue of Liberty.

Book your unforgettable adventure with us today. Join us and experience the passion and expertise that Sarah Pennington brings to Classic Harbor Line!

Classic Harbor Line Pride

by
Between the sails of Classic Harbor Line's schooner the Pride flag waves in the sun.

“We’ve got all of our picks of the best parties, events, performances and more LGBTQ+ things to do in NYC to celebrate Pride Month.” -Timeout

Classic Harbor Line's Schooner Adirondack sails in the Hudson with 400 sqft Pride Flag in tow

Read the timeout article here!

Classic Harbor Line Pride sails are back, and they’re better than ever! Picture this: a two-hour cruise on a majestic classic Schooner, where you’ll soak in jaw-dropping views of the city’s landmarks.

Mark your calendars for Saturday, June 29, and Sunday, June 30. We’re setting sail from Pier 62 at Chelsea Piers. As we glide past One World Trade Center, Ellis Island, and the iconic Statue of Liberty, a vibrant 400-square-foot Pride flag will be fluttering above us, celebrating love and pride.

Saturday tickets are priced at $125/adult, and Sunday tickets for $150/adult. Our Sunday sail will have the best seat in the house for the Pride fireworks show. Each ticket comes with your choice of drink—beer, wine, champagne, or soda—and you’re welcome to pack a picnic for the ride.

Purchase your tickets here!

Every cent of the net ticket sales goes straight to the Hetrick-Martin Institute. HMI is the nation’s oldest and largest nonprofit supporting LGBTQIA+ youth. This year, as we celebrate our fifth anniversary of this fabulous partnership, we’re aiming to raise a whopping $15,000 for HMI. Come a help us do it!

Come for one of Classic Harbor Line Pride Sails, bring your pride, and let’s make some waves for a fantastic cause. See you on the water!

From part time to management at Classic Harbor Line

by
Captain Cait Field at the helm of one of our schooners

NY POST:

“Seasonal gigs can bring extra cash, career changes — and job offers” – Vicki Salemi

Read the full NY Post article here!

Our own Captain Cait Field was interviewed about her story of going from part time to management at Classic Harbor Line.

Captain Cait Field, our general manager at Classic Harbor Line grew up sailing small boats in Long Island. Field transitioned to working full-time for the company two years ago after an extensive background in both sailing and science. The Brooklyn resident initially joined Classic Harbor Line while pursuing her Ph.D. in biopsychology. All while working as the Freshkills Park manager at the NYC Department of Parks & Recreation.

Despite her extensive career in the sciences, her passion for the maritime world led her to embrace a full-time role with Classic Harbor Line. Additionally, as a captain, Field often officiates weddings, having taken up the role after numerous requests. She emphasizes the importance of staying open to evolving career paths and the joy she finds in being on boats. From part time to management at Classic Harbor Line is no small feat and we are all so happy that Capt Cait is part of our team!

Come from a cruise with us and meet Captain Cait Field in person! Though, Capt. Field has a mountain of responsibilities, she still finds time to captain a tour now and again. Click here to see what cruises we have in our schedule!

We have daily public trips year round, from our summer sunset sails to our holiday Cocoa and Carols Cruises. We offer special events for every holiday. What’s one of our favorite examples? Watching the 4th of July fireworks from one of our beautiful schooners! Additionally, we offer private charters. Guests who are interested in anything from a special proposal, to a company team building day on the water, to a relaxing family outing can find the perfect package for them. We can’t wait to see you out on the water!

A unique sailing experience aboard Schooner America 2.0 and Light Bites with Marea

by
classic harbor line

Forbes LogoLook no further for NYC unique experiences! New York City offers a variety of unique sailing experiences that allow you to explore the city from the water and enjoy breathtaking views of the skyline. We partnered with Marea to create a memorable experience in NY Harbor. See what Forbes has to say about the experience! Click here to read the article. 

Solar Eclipse Day Cruise viewing on Yacht Manhattan II in NY HarborWe offer a range of sailing trips, including an evening on the water with Marea aboard the Schooner America 2.0 at sunset. So, set sail with us and enjoy some fine dining! You can enjoy this relaxing cruise while taking in iconic sights. Sights like the Statue of Liberty, Ellis Island, and the Manhattan skyline while enjoying some some light bites from Marea.  At Marea, the authentic, seasonal flavors of coastal Italy meet the style and swagger of New York to form a new kind of gusto. Marea floats to the top for restaurant culture, with exquisite food and unmatched service that set the stage for an experience like no other.  

These sailing experiences offer a unique perspective on New York City. They provide a relaxing and picturesque way to enjoy some sightseeing and see the city’s iconic landmarks from the water. Make your sailing adventure in NYC memorable and join us for this unique adventure in NY Harbor.