Architecture Archives - Classic Harbor Line
Check Availability Buy Tickets Now

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!

Arquitectura de NYC

Passing by the Cooper Building and the Empire State building on a Arquitectura de NYC

“Nueva York desde el agua: otra perspectiva”

– Esquire

Classic Harbor Line está encantada de aparecer en el artículo ” Qué ver en Nueva York: 6 planes originales que (quizás) nadie te ha contado” de Esquire managzine.

Nos emociona compartir que Classic Harbor Line ha sido destacado en la revista Esquire por nuestra experiencia única: el “Paseo en Barco por la Arquitectura de NYC con narración en español”. Este recorrido de dos horas y media ofrece una perspectiva impresionante de la ciudad de Nueva York, vista desde los ríos Hudson y East River.

Best NYC Architecture Boat Tour | Classic Harbor Line

Si eres amante de la arquitectura, este crucero es una oportunidad imperdible. Durante el paseo, podrás admirar y aprender sobre los secretos de algunos de los edificios más emblemáticos de la ciudad. Desde la comodidad de nuestro barco, disfrutarás de vistas del skyline de Nueva York, incluyendo un paso cercano a la icónica Estatua de la Libertad, conocida cariñosamente como Lady Liberty por los neoyorquinos.

Nuestro recorrido no solo se centra en la observación, pero también en la educación. A través de una narración detallada en español, descubrirás curiosidades fascinantes sobre el urbanismo de Nueva York, como el hecho de que los constructores deben comprar el “espacio aéreo” para seguir construyendo hacia el cielo. Además, conocerás a los arquitectos, incluyendo varios de origen español, que han dejado su huella en la metrópoli.

Únete a nosotros en Classic Harbor Line y vive una experiencia inolvidable descubriendo la arquitectura de Nueva York desde sus ríos. ¡Te esperamos a bordo!

Te recomendamos organizar tu visita con tiempo, ya que nuestras salidas son limitadas. ¡Compra tus entradas aquí!

AIANY Architecture Tour

classic harbor line

NYC Architecture Boat Tour

AIANY Architecture Tour

Highrises, Skycrapers, and Supertalls

In New York in the early 20th century, well-known highrise buildings like the Woolworth Tower, the Chrysler Building, and the Empire State Building reached for the sky and were dubbed “skyscrapers”. Today, the iconic New York City skyline is marked by a recent proliferation of much taller, super-slim, ultra-luxury residential towers. These pencil-thin buildings constitute a new type of skyscraper, made possible by remarkable feats of engineering, advances in material strengths, and a real estate market that drives building heights—and prices—ever skyward. The AIA Around Manhattan Architecture tour highlights the architects and engineers composing a new vision of the NYC skyline with these height-shattering new buildings. We’ll will shed light on the engineering marvels and zoning requirements that allow these heights, as well as the range of architectural styles across the city: super-stretched art deco, purist 3-dimensional grid, and the sloping, chiseled or crystalline forms that visibly break from the traditional NYC skyscraper.

As of January 1, 2019, New York City has 8 officially completed Supertall buildings, and that number could be doubled by January of next year.  So, what’s the difference between a regular highrise building and a “Supertall” skyscraper? 

Highrise refers to any building in New York That is over 75 feet tall (or the limit of how high a FDNY ladder truck can reach).


Skyscraper is a more metaphorical definition.  The term is borrowed from sailing and it describes the highest most point on the tallest mast on a sailboat.


Supertall, however, is a relatively new term by comparison, and is an official designation awarded by the organization called Council on Tall Buildings and Urban Habitats to any building over 984 feet. The measurement marks the height of a building to the “top of the architectural expression” – not counting flagpoles, chimneys or antennae. However, “masts” are fair game—hence why we see such a proliferation of tall masts on top of recent supertall skyscrapers.


It has been several decades now since New York held the record for the tallest building in the world (with the Empire State building and World Trade Center North both holding that title at different points). Today, the distinction goes to Burj Khalifa in Dubai at a whopping 2,723 feet.  Still, New York is experiencing a new bumper crop of “Supertall” buildings.  So, here they are – THE SUPERTALLS OF NEW YORK, many of which you’ll see on our AIANY Around Manhattan tour:


  1. One World Trade Center: 1,776 FT


Skidmore Owings & Merrill, Architect


  1. 432 Park Avenue: 1,397 FT


Rafael Viñoly Architects


  1. The Empire State Building: 1,250 FT


Shreve Lamb and Harmon, Architects


  1. Bank of America Tower: 1,200 FT


Cook + Fox Architects


  1. 3 World Trade Center: 1,079 FT


Rogers Stirk Harbour + Partners


  1. New York Times Tower: 1,046 FT


Renzo Piano Building Workshop with FXFOWLE Architects


  1. Chrysler Building: 1,046 FT


William van Alen, Architect


  1. One57: 1,004 FT


Atelier Christian de Portzamparc