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Sarah Pennington Managing Director of Classic Harbor Line

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

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!

From part time to management at Classic Harbor Line

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!

The Ultimate Fireworks Cruise

Macy's 4th of July fireworks display from a Classic Harbor Line Cruise

New York Daily News – “Where and when to watch 2023 Macy’s July 4th fireworks in NYC

the yacht manhattan sailing down a river full of boats and fireworks shooting in the distance

Classic Harbor Line is excited to be featured in the New York Daily News article “Where and when to watch 2023 Macy’s July 4th Fireworks in NYC”.

Get ready for an unforgettable Independence Day celebration with Classic Harbor Line’s spectacular Macy’s 4th of July Fireworks Cruise. As New York City lights up in patriotic splendor, there’s no better place to be than aboard one of our elegant yachts. Sail the Hudson River for front-row views of the dazzling fireworks display.

Celebrate the 4th of July with Classic Harbor Line: The Ultimate Fireworks Cruise

Our cruises offer the ultimate way to experience the America’s birthday. Firstly, step aboard the beautifully crafted Yacht Manhattan or Manhattan II. Once aboard you’ll be greeted with a complimentary drink and light hors d’oeuvres. As we set sail from Chelsea Piers, you will enjoy panoramic views of the iconic NYC skyline. Thereafter coming upon views of the Statue of Liberty, and the Brooklyn Bridge. All beautifully illuminated against the twilight sky.

As the evening progresses, settle into your comfortable seating and prepare to be awed as the sky bursts into a kaleidoscope of colors. The Macy’s fireworks show, renowned as one of the largest and most impressive in the country, is perfectly viewed from your front row seat on the water. With an open bar and ample space to relax and take in the sights, our cruise ensures a memorable 4th of July for all.

Whether you’re celebrating with family, friends, or that special someone, Classic Harbor Line’s 4th of July Fireworks Cruise promises an exceptional experience. Our attentive crew is dedicated to making your night enjoyable and stress-free. We give you the ability to focus on the beauty of the fireworks and the joy of being on the water.

Book your seats now to secure your spot on the most exciting cruise of the summer. Join us for a night of celebration, stunning views, and undeniably unforgettable memories with Classic Harbor Line.