Written by Karen Kennedy
July 2018

Why would a single female set off with her dog down the East Coast, all the way from Manhattan N.Y. to Vero Beach Fla.? Simply put: a passion for sailing, a sense of adventure and a disdain for cold New York winters.

I started boating by crewing on race boats in New York and the Caribbean. I finally bit the bullet in 2013 and bought a fixer-upper of my own.

Too Many Toads, my 35-foot Hinter-hoeller Niagara, named after my father, is a sailboat that I “rescued” after Hurricanen Sandy. After watching a plethora of videos online and reading several books, I started the restoration process and spent four months working on her before launch.

After the boat rescue, came the dog rescue. Sailor, a Texas Heeler, was just 9 weeks when I adopted her, and she adapted to the boat with great enthusiasm. As an exceptional guard dog, Sailor alerts me when another boat, kayak or even a marker nears the boat.

My usual cruising ground is the Long Island Sound, and we often visit Block Island and Newport, R.I. along with Cape Cod, Mass. I was both excited and nervous to venture down the East Coast and the Intracoastal Waterway (ICW) this past winter to escape the chill of New York. I expected to experience some judgment as a solo woman cruising and to be lonely at times, but I was unsure how I would handle it.

I left Manhattan at the end of September on a beautiful sunny day, cruising down the East River with the current behind me. The waves calmed as I approached New Jersey. My energy was high and the sun was shining, so I decided against stopping in Cape May and turned into the Delaware Bay. That night, I anchored at Delaware City Marina and planned to fuel up first thing in the morning to begin the next leg.

Departing the next day with the current to our backs, Sailor and I experienced heavy winds that picked up on the nose. Water crashed over the bow the entire way, but Sailor managed to hide behind me to keep dry. We transited through the C&D Canal and eventually anchored in Rock Hall, Md., for the night. The next day, we cruised to Annapolis City Dock on Spa Creek.

We stayed in Annapolis for three weeks, and I spent my time working at the United States Powerboat and Sailboat Shows, where I participated in a diesel class. After the boat shows, I tried to leave Annapolis twice to continue my trip. On the first attempt, I only reached the mooring field near the Naval Academy when I had to set anchor due to smoke billowing from my engine. After I changed the engine filters, I waited for conditions to improve and set off again. Unfortunately, during the second attempt, a strong current dragged me toward a rocky shore, even with the anchor down. I was towed to Whitehall Marina in Annapolis where my engine was repaired. I could finally make my way down the Chesapeake Bay! Next stop was Zahniser’s Yachting Center in Solomons Island, Md.

After a few days exploring Solomons Island, I was ready to head down the Bay to my the next location. However, my boat had other ideas and I faced another setback as my boat refused to start. Since the temperature had gotten much colder at this point, I suspected that my boat’s glow plugs were the root of the problem. Fortunately, the service team at Zahniser’s Yachting Center quickly obtained a set of new plugs needed for me to get underway the following day.

The coldest part of my transit was south from Solomons to Hampton, Va., where I docked at Downtown Hampton Public Piers. I especially enjoyed the marina’s on-site garden and used hand-picked herbs to make fresh salads.

The next leg of my trip was Portsmouth, Va. where I planned to spend just one night. However, the staff at the local tourism office had other plans for me. They mapped out where to locate museums and the Lightship Portsmouth, along with directions to take the ferry over to Norfolk for the annual Grand Illumination Parade. This turned my stay into several days.

After leaving Portsmouth, Va., I set out to begin the ICW. I spent Thanksgiving anchored in Belhaven, N.C., and reunited with two boaters I met at Zahniser’s Yachting Center.

Continuing down the ICW, I headed for Charleston City Marina in Charleston, S.C., and did more sightseeing. Sailor was thrilled at her first dolphin sighting. The marina offered a courtesy shuttle to downtown, which made it easy to explore the city, particularly the French Quarter and Battery Promenade.

Moving south on the next leg, I landed at Downtown Marina in Beaufort, S.C. The marina staff was extremely helpful, and I enjoyed walking through the historic district and visiting antebellum mansions.

While in Beaufort, I walked Sailor to the park near the marina, where I met a gentleman who asked me about my travels and what I did on the boat. I replied, “Everything.” He was shocked to learn that I was a solo traveler without a man on board.

Next up, Savannah, Ga., which quickly turned into one of my favorite stops. While in Savannah, I docked at Thunderbolt Marine and ventured into the city with the marina’s courtesy car. The large oak and Spanish moss trees were abundant, and the historic district was filled with beautiful cobblestone streets.

The Municipal Marina in St. Augustine, Fla., was my next destination. Due to high winds, cold and rain, I unfortunately ended up docked for three weeks longer than I anticipated. However, this allowed me to explore the beautiful historic city at my leisure.

After St. Augustine, I tied up in Vero Beach Fla. at Vero Beach City Marina. I connected with several other cruisers during the marina’s weekly potluck — a nice hiatus from the solitary life that had become familiar by this point. Sailor especially enjoyed this leg of the journey, because an impressive dog park was near the marina along with dolphin sightings several times a day.

Besides visiting some of the most breathtaking cities along the East Coast, my favorite part of the trip was realizing that I could do it. And do it alone. One of the most challenging parts about single-handed sailing is the lack of time to accomplish the jobs that two people can easily manage together.

Solo cruisers work twice as hard, so instead of not believing that we are doing it on our own, buy us a drink at the bar. Chances are we’ve had a rough day.

To learn more about Karen’s journey, search for “Women Who Own Boats” on Facebook, where Karen and other female captains discuss their trials and tribulations in an environment with other female boat owners who are doing it on their own.