June 2024 - Classic Harbor Line
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Sarah Pennington Managing Director of Classic Harbor Line

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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

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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

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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!

Classic Harbor Line’s Urban Naturalist Tour

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Schooner Adirondack sailing on the Hudson River with a rainbow over the NYC Skyline

Classic Harbor Line’s Urban Naturalist Tour

“Discovering New York’s Forgotten Isles:

A Unique Cruise Experience” – Hal C Clarke

Couple gazes out the windows of interior cabin at abandoned island across the water

TJV News reports on our exciting new cruise! Read the article here.

Experience New York City like never before with Classic Harbor Line’s Urban Naturalist Tour, offering an up-close look at the forgotten islands along the East River. These islands are teeming with history, having hosted baseball stars, maritime disasters, wildlife sanctuaries, and deadly diseases.

Our tour begins at the tiny Belmont Island. Then navigates past Roosevelt and Randall’s Islands before reaching Mill Rock at the Harlem River’s mouth. Next, we venture through Hell Gate to North and South Brother Islands; home to idyllic serene shorebird sanctuaries with a storied past.

Guided by naturalist Gabriel Willow, you’ll hear captivating tales of these islands’ inhabitants, including Typhoid Mary and former Yankees owner Jacob Ruppert. Following Ruppert, he owned a summer home on South Brother Island, where Babe Ruth often practiced batting. Ruppert is known for transforming the Yankees by bringing Babe Ruth to the team and building Yankee Stadium. The mansion burned down in 1909, and the island remained largely abandoned until it was transformed into a bird sanctuary in 2007.

You’ll also learn about the eerie remains of the quarantine hospital on North Brother Island, where Typhoid Mary spent her final years. Both islands now thrive as seabird sanctuaries, however they are now untouched by human activity.

The tour continues past Mill Rock, a fortified position during the War of 1812, now a nature educational center, and Belmont Island, created during tunnel construction beneath the river. Finally, the tour coincides with the sunset. The cruise offers stunning views of the city illuminated by night, providing a beautiful contrast to the natural stillness of the river islands.

Don’t miss this unique journey through New York’s hidden historical gems.

A $124 ticket includes a glass of champagne and a sandwich, making for a perfect evening on the water. Running every Sunday through July, this three-hour cruise aboard a 1920s-style yacht promises an adventure through time.

Book your ticket today and bring binoculars to enhance your experience.

Abandoned Islands Sunset Cruise

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Cruising past Abandoned Islands off the right bow.

Abandoned Islands Sunset Cruise

untapped New York’s Things to do this week in NYC : June 26th- July 3rd

Guests take photos of the abandoned islands and landscape port side

untapped New York named Classic Harbor Line‘s Abandoned Islands Sunset Cruise one of the top things to do this week in NYC!

Join Classic Harbor Line for a remarkable sunset cruise exploring the hidden gems of New York City’s North and South Brother Islands. Our expert urban naturalist will guide you through the particularly fascinating history of these islands. Many now reclaimed by nature and serving as sanctuaries for shorebirds.

Indeed! Bring your binoculars for viewing stunning wildlife!

Discover the captivating stories behind the 19th-century quarantine hospital, the former summer estate of a Yankees owner, and other intriguing mysteries of the East River islands. Sip on a glass of something bubbly while enjoying this unique blend of history and natural beauty.

Hot Tip! Keep an eye out for Black Crowned Night Herons among the ruins!

The tour, priced at $124, includes a glass of champagne and a sandwich. The cruise is timed correspondingly with sunset, providing stunning views of the city illuminated at night. This tour is offered aboard either our yacht Manhattan or Manhattan II. The Abandoned Islands Sunset Cruise is a limited engagement for the months of June, July, and August.

Read untapped new york‘s article about the Abandoned Island’s Sunset Cruise here! Looking for tickets? Book tickets here!

NYC’s Abandoned Islands

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Off bow of Manhattan, guests see an Abandoned Island in the distance

“The Forgotten History of NYC’s Abandoned Islands – and how you can see them up close”

Comprehensive map of NYC with dots indicating; N.Brother Island, Mill Rock, S. brother Island, Roosevelt Island, Belmont Island, and Chelsea Pier 62

This story by Alex Oliveira highlights our unique new cruise. The Urban Naturalist Tour: Abandoned Islands. Classic Harbor Line‘s tour explores the abandoned islands along New York City’s East River, overflowing with history and natural beauty.

The cruise runs three-hours on our beautiful 1920s-style yacht. The tour reviewed was narrated by naturalist Gabriel Willow.

During the tour, guests visit several islands including; Belmont, Roosevelt, Randall’s, Mill Rock, North, and South Brother Islands. Each of these islands have diverse histories, from being homes to baseball stars like Babe Ruth to sites of historic maritime disasters and quarantine hospitals. Therefore, this cruise offers insights into these diverse histories and highlights the wildlife sanctuaries that have now become part of the island’s new life.

The tour, priced at $124, includes a glass of champagne as well as a sandwich. The cruise is correspondingly timed to allow you and your loved ones to enjoy all there is to see at sunset. This tour provides stunning views of the city illuminated at night. Additionally, passengers are encouraged to bring binoculars for unforgettable wildlife viewing aboard our boating adventure!

Read about NYC’s Abandoned Islands in the article here!