At the Helm – Captain Sarah Pennington

by | Aug 10, 2020 | Featured, Featured, Power Women


She Captain, Sarah Pennington She’s all That!

The Old Man and the Sea is a short novel written by the American author, Ernest Hemingway. It takes place in 1951 Cuba and was published in 1952, long before females took the helm. One could argue that yes, in fact, there were female Captains back as far as 231 B.C. The Norwegian Princess Sela, considered a pirate, sailed in 420 A.D.

Fast forward to the 1970s and there was Krystyna Chojnowska- Liskiewicz of Poland, Naomi James of New Zeland, Kay Cottee of Australia. Today, we see female captains in the recreational cruise industry and the US Navy, like Admiral Michelle J. Howard, the first female four-star admiral.

Today we have captains, right now in our time and right here in New York City.

Being a female entrepreneur, I am extremely proud whenever I meet females in the role of power. If there’s a female in charge of the plane or a sailing large vessel I’m on, it makes me smile from ear to ear, a sense of female pride.

I just love being that “fly on the wall” only to hear men say, it’s a woman? She’s not the one in charge? I just chuckle to myself biting my tongue and watch in amazement when they quickly eat their words. This recently happened onboard Captain Sarah’s vessel.

I’ve not only had the pleasure of being a guest on her ship but also recently the extreme pleasure of interviewing, her.

A She Captain

Captain Sarah Pennington Sailing America 2.0 Photo by Nick Appice


DTM: How did you get started in this line of work and where are you from?
Capt Sarah: I am originally from Ohio. I grew up sailing with my family on a large lake in Kentucky and then in the Houston area.  I really learned to sail when I learned how to teach sailing at a girls’ camp in northern Minnesota while in college.  I took a tall ship job on a coastal schooner right after I finished college in Maine. That’s when I got hooked on schooners. 

DTM: What brought you to Classic HarborLine (CHL)?
Capt Sarah: I came to New York in 2002. I saw an advertisement in TimeOut New York magazine for the schooner Adirondack. I called them to see if they needed a crew. The ticket agent said, “Yes, please come over as soon as possible.” I came down that day to introduce myself. The rest is history. 

DTM: What type of education or updated education are you given with CHL?
Capt Sarah: I certainly have learned so much through working with CHL.  The most industry-specific education would be that of the regulatory requirements of the field. Tangentially, since I’m involved with the business side of the company, I’ve learned so much on the marketing, tourism, PR, finance, and online sales side of the business as well.  CHL also helped me get an MBA a few years back and that really helped me put a business strategy in focus and gave me a vernacular for business. 

DTM: What is your favorite thing about working for CHL in New York?
Capt Sarah: My favorite thing about working for CHL in New York is that anybody can be on our team if you just have the right attitude. 


A She Captain

America 2.0 Classic Harborline

DTM: Share one of your most memorable/rewarding moments?
Capt Sarah: The most rewarding part of work is seeing our crew develop and take on more responsibility within the company. Some become managers, some become captains. I love to see people grow in our company.  We have a roster of mostly homegrown captains, many of whom had no marine experience when they started. A captain who drives half of our fleet now started as a part-time salesperson in our office.  She just had the right attitude, kept learning, put one foot in front of the other, and now she’s running our boats.

DTM: What is the most common misconception people have about being a Captain of a vessel in New York vs sailing the ocean?
Capt Sarah: I think the biggest misconception is that guests think we have nothing to do in the winter. We operate year-round with part of our fleet. 

DTM: Have you ever raced or sailed the ocean?
Capt Sarah: I’ve done very little offshore work and very little racing. It is not something we get much time, since we run full time with our tours in NYC.

DTM: Do you ever get bored with sailing the same route?
Capt Sarah: I’d say I’m glad we have such a magnificent skyline that is always changing.  I’m also thrilled that we have such an active harbor. That keeps us on our toes for sure. The only thing that may make for a long, dull day is a day with no wind!  

DTM: What makes a good captain?
Capt Sarah: A good captain in our industry is one who communicates and connects with the crew and their guests regularly.  Regular communication throughout the trip amongst the crew and checking in with guests periodically make such a huge difference in how everyone perceives the experience.


A She Captain

Captian Sarah Pennington Jazz Cruise America 2.0 (interacting with her guests) Photo by Grace A. Capobianco


DTM: Is there a difference between being a captain for sailing vessels vs motor yachts?
Capt Sarah: The only difference in licensing is that a skipper needs a sailing endorsement on their license to run a commercial sailing vessel.

DTM: What’s the last thing you do on your ship before you depart for the day?
Capt Sarah: We have a long list of shut down “to-do’s” for each boat, but typically, the VERY last item is to lock up and ease our dock lines a bit so the boat is not pulled hard against the dock all night.


At the Helm - Captain Sarah Pennington

Captain Sarah Pennington


DTM: Because we are Downtown Magazine, what is your favorite place in Lower Manhattan Chelsea, to the Battery to just get away and relax?
Capt Sarah: I like to bike or take a run down the Westside of Hudson River Park.  One special spot for me to grab a coffee or nice breakfast is the cafe in the lobby of the Jane Street Hotel (also right on the west side highway)…when indoor dining was permitted.

DTM: Tips, I’m all about tips for the crew. It’s very important to show your gratitude, they work so hard in such a short time, why is it important to tip?
Capt Sarah: Making a living in NYC means being able to live in NYC.  Sailing is weather dependent, seasonal, and requires some very skilled labor. Certainly, good tips help us keep doing what we love and pay the bills while doing it.


A She Captain

View onboard America 2.0 with Captain Sarah Pennington at the helm Photo by Grace A. Capobianco

DTM: What’s the best advice you can give to new captains when working with the public?
Capt Sarah: I like to remind folks I work with, “It’s just a boat ride.” We are just taking people out to have fun, so let’s not stress out too much.  Let the brain surgeons stress out.  Our job is to make fun.  Keep them safe and have fun. 

Take my advice, go online, and book anyone of Classic Harbor Line’s vessels, you just may get lucky enough to be a guest on Captain Sarah Pennington’s ship!


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