Meet Karen Kennedy, a “50ish female” who single-hands her sailboat. Leaving a “rat race job” at Morgan Stanley, Karen now moves at a slower pace on board her Niagara 35-foot sloop, Too Many Toads, named for her father.
Karen restored the boat herself, after Hurricane Sandy hit New York in 2012. Six years ago she started a Facebook group, Women Who Own Boats (Solely Without Men). “It offers a great support community for women who own their own boats and are doing it alone,” she says.

How did you first get involved in boating?
After leaving Manhattan for the Bronx, I knew none of my friends would take the uptown train to visit me, so I went to a local yacht club and started racing. This soon turned into racing on larger sailboats in the Caribbean. I credit my racing career for having the knowledge and experience to single-hand my boat.

Where do you travel with your boat?
My cruising ground is the East Coast from Maine to Florida, the Bahamas and Caribbean. While I single-hand my sailboat, I’m not alone as my rescue dog, Sailor, is always on watch to talk to dolphins and chase the pirates and jet skis away.

Which destination do you most enjoy?
My favorite cruising ground is the Bahamas because Sailor gets to run on the beaches and swim almost every day. We spend a good amount of time in Florida, but it is not Sailor’s favorite. Sailor wishes Florida had more off-leash dog friendly beaches.

What are your must-have items on board?
A good wireless speaker to keep me from getting bored while transiting single-handed. Dinghy davits are also a must for me while cruising to get the motor and dinghy up.
In the galley, a flame tamer keeps food from burning. Also, a pressure cooker cuts down on propane usage. I even use it for baking.
Sailor’s AstroTurf to go potty is a must on board. She also needs a lot of peanut butter for inside her bones.

Describe your greatest challenge on the water:
Solo sailing is a big challenge, but being a female adds a whole other dimension to the mix. Sexism in sailing is still very prevalent. In the Bahamas, several males who were single-handed sailing told me I had no business being there and that I wouldn’t make it back. One guy went all out to attempt to prevent me from going to the Bahamas. Hopefully, seeing and reading about this issue will bring more awareness to it.

What would be your dream boat?
While a Swan 60 has always been my dream boat, I believe ‘love the one that you are on and truly enjoy her.’ Larger boats can be a lot more work, so I’m happy with a 35-footer for now. If I win the lottery, I might change my mind.

Any advice to new boaters?
Get out on as many boats as possible. Go on your dock mate’s boat, race at a local yacht club, or join a club with a boat that you can take out. I always say you learn something on every boat. Sometimes it’s what to do and sometimes it’s what not to do.

Anything you would like to add?
Don’t be afraid to buy a boat that needs work if that’s what you can afford. I spent months grinding, repairing fiberglass, fairing and sanding my boat. There are so many books and videos out there that anyone can do it.