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A Serenade for Lady Liberty

Guest on the deck of America 2.0 in NY Harbor for Jazz Cruise

“Classic Harbor Sunset Jazz Cruise new way to enjoy isle & waters of Manhattan”

– The Komisar Scoop

Statue of Liberty and Schooner America 2.0

At Classic Harbor Line, we pride ourselves on offering unique and unforgettable experiences on the water like our America 2.0 Jazz cruise. Recently featured in The Komisar Scoop, our Jazz Sail from Lower Manhattan to New York Harbor aboard the 105-foot sailing yacht, Schooner America 2.0, provided an evening to remember.

The Magic of the America 2.0 Jazz Cruise with Classic Harbor Line

As America 2.0 sailed close to the Statue of Liberty, our passengers were treated to an impromptu performance by a dozen members of the Paris-American Club. All of a sudden the group broke into “La Marseillaise” in honor of the French gift to America. This unexpected serenade added a charming and patriotic touch to the cruise, especially with Bastille Day just around the corner.

The main musical entertainment for the evening was a delightful mix of jazz tunes performed by the Boatband. Led by fan favorites Michael McGarril on saxophone, Christian Nourijanian on keyboard and Dustin Kaufman on drums. Undoubtedly, the band’s soft melodies provided the perfect backdrop for conversation and relaxation. Classics like “Blue Skies” were beautifully paired with modern favorites such as Otis Redding’s “The Dock of the Bay.”

Before the serenade, the journey began at Pier 62 at Chelsea Piers. Firstly following the stunning shoreline of the Financial District to New York Harbor and the iconic Statue of Liberty. Passengers were comfortably seated on benches along the port and starboard sides of the schooner. Those on board enjoyed a breathtaking sunset on the return trip.

The crew of America 2.0 added to the experience by hoisting sails and adjusting ropes. The crew also served complimentary beverages, including wine, beer, champagne, and soft drinks. Guests were welcome to bring their own snacks, making the evening both elegant and moreover, personal.

The Schooner America 2.0 is a modern homage to the original Schooner America, which won the first America’s Cup in 1851. America 2.0 operates in New York City from June through October and in Key West from November through May. Emphatically, this schooner combines historical elegance with contemporary comfort.


Join us every Tuesday from 6:45 pm to 8:45 pm for our Jazz Cruise, departing from Pier 62 at Chelsea Piers. We look forward to welcoming you aboard for an evening of music, sailing, and spectacular views.

For more information and to book your unforgettable evening on the water, click here!

CBS New York!

the Yacht Mariner Three sailing down a river full of boats and fireworks going off in the distance

“You get the sunset and the fireworks which is a great show!”

– Rossilynne Culgan (Timeout New York)

Fireworks light up the sky in NY Harbor on 4th of July

A huge thank you to Timeout New York for the shoutout on CBS New York!

As the 4th of July approaches, there’s no better way to celebrate America’s Independence Day than by experiencing the iconic New York City fireworks from the water. Classic Harbor Line invites you to join us for an unforgettable evening aboard our elegant yachts and schooners, offering you the best seats in the city for this dazzling display.

At Classic Harbor Line, we pride ourselves on providing a fun and luxurious experience on the water. Our fleet combines elegance with modern comfort, ensuring a memorable night for all our guests. Like Rossilynne mentioned on CBS New York, the cruise included watching the sunset over the New York City skyline. Once the sky darkens a spectacular fireworks display will light up the night sky.


From our yachts and schooners, you’ll have a front-row seat to the fireworks. Panoramic views of iconic landmarks such as the Statue of Liberty, Ellis Island, and One World Trade Center will make it a night to remember.

Choose from our meticulously maintained vessels. Our yachts Manhattan and Manhattan II offer climate-controlled observatories and open-air decks. With large windows and spacious seating, you won’t miss a moment of the action. For those who love the romance of sailing, the Schooner Adirondack and schooner America 2.0 provide a classic maritime experience. Sail through the Hudson River and feel the excitement build as you approach the fireworks display.


Our 4th of July cruises are designed to make your evening special. Enjoy an open bar and light hors d’oeuvres as you relax and take in the scenery. Our professional and friendly crew will ensure you have everything you need for a perfect night. The cruises depart from Chelsea Pier 62 and last approximately 2-3 hours, including the fireworks display.

Seats are limited, so don’t miss out on this extraordinary opportunity to celebrate Independence Day in style. Whether you’re a local or visiting from out of town, Classic Harbor Line’s 4th of July cruises promise an evening of elegance, excitement, and unparalleled views.

Book your cruise today!

Join us for an evening of fireworks, festivities, and unforgettable moments on the water.

4th of July Firework Magic

Fireworks light up the sky in NY Harbor on 4th of July

“Where to Watch 4th of July Fireworks in NYC 2024”

Condé Nast Traveler

Guests on the deck of schooner America 2.0 in NY Harbor

When it comes to experiencing the magic of the 4th of July fireworks in New York City, there’s no better way than being right on the Hudson River. We at Classic Harbor Line are thrilled to be recommended by Condé Nast Traveler as the river cruise to take for this spectacular holiday! Here’s what Juliet Izon had to say about our offerings:


“There may be no way to get closer to the fireworks action than by being on the Hudson River itself. And many of the city’s famed cruising companies will be offering special trips just for the 4th of July holiday. Much of Classic Harbor Line’s fleet will be running that night, from cruises with Yacht Manhattan and Manhattan II, along with a Fourth of July sail aboard the Schooner Adirondack.”

Imagine yourself aboard one of our elegant yachts or schooners. You take in the vibrant city skyline as it comes alive with fireworks. Our fleet will be out in full force, offering various unique and unforgettable experiences:

  • Yacht Manhattan and Manhattan II: These classic 1920s-style yachts offer a luxurious and intimate setting. With climate-controlled observatories and open-air decks. Enjoy panoramic views of the fireworks while sipping on your favorite drink from our full-service bar.
  • Schooner Adirondack: For those who prefer the charm and romance of sailing, our Schooner Adirondack provides a classic sailing experience. Feel the wind in your hair and the excitement in the air as you glide through the water. Be perfectly positioned to watch the dazzling fireworks display.

Schooner America 2.0, and Yacht Kingston will also be taking to the waters for the spectacle.

Book Your Spot Straightaway!

Undeniably, spaces are limited! Our 4th of July cruises are always in high demand. Don’t miss your chance to celebrate America’s birthday with style and class aboard Classic Harbor Line.

Visit our website or call us at (212) 627-1825.

Abandoned Islands Sunset Cruise

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!

Fireworks with Classic Harbor Line

Guests sit aboard America 2.0 during the 4th of July Fireworks cruise, sailing down the Hudson

“Here are the top 4th of July events in NYC for making the most of America’s Independence this year.”

– Timeout

Fireworks light up the sky in NY Harbor on 4th of July

We are thrilled to share that Timeout has recommended Classic Harbor Line as a top way to experience the 4th of July fireworks in New York City! See the fireworks with Classic Harbor Line!

At Classic Harbor Line, there’s no better way to celebrate Independence Day than being on the water. Especially when you’re perfectly surrounded by breathtaking views of the city skyline and an unforgettable fireworks display.

Our 4th of July cruises depart from Chelsea Pier 62 and offer a VIP-level experience, complete with an open standard bar and ample light hors d’oeuvres.

Imagine watching the brilliant fireworks display reflected on the water. Your backdrop consists of the Statue of Liberty and One World Trade Center. Meanwhile, you sip on something deliciously bubbly and take a bite of something tasty. The combination of the vibrant colors, the stunning skyline, and the festive atmosphere creates a truly unparalleled experience. It’s not just a cruise! This is a celebration of our nation’s independence in one of the most iconic cities in the world. With this in mind….

Don’t miss your chance to celebrate the 4th of July in style with Classic Harbor Line. Book your seats now and get ready for an evening of breathtaking views, delicious refreshments, and unforgettable fireworks.

Visit our website or call us at (212) 627-1825 to secure your tickets today!

We can’t wait to welcome you aboard for a night to remember!

NYC’s Abandoned Islands

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!

Classic Harbor Line’s Urban Naturalist Tour

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.

Classic Harbor Line Pride

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

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!

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


“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!