Every summer, for as long as I can remember, my family would spend a month on our sailboat. Me, my mom, my dad, and my little sister sailing up and down the Chesapeake Bay on our 28' Pearson, the Jenny Rebecca. I loved those summers. Playing Yahtzee. Rowing the dinghy ashore. Catching soft shell crabs off the pilings and selling them to nearby restaurants.
It was all so exciting. The waves. The people. The new adventures. I loved how happy and carefree my parents were on those trips. It's hard to be unhappy on a boat. How does that saying go? A bad day on the boat is better than a good day anywhere else. Can't say I disagree.
Once I moved away from home, I didn't get to sail much. Once in awhile we'd spent a weekend on the boat as a family again and eat cereal from tiny, perforated boxed, lined with tin foil so you could pour the milk right inside. We'd talk about our summer trips to Mears Marina in Annapolis or to Mrs. Kitching's on Smith Island.
I miss that time on the boat. Something about the water and the time away from all the hurry of our normal lives. It had been years since I had been sailing when I was offered the chance to sail with a flotilla in the British Virgin Islands. I was delighted and couldn't wait to see how similar -- and different -- my experience might be. This time I went with my girlfriend, a colleague, and a Captain named Alden.
Before we left, I spent a lot of time online at Discover Boating, a cool resource if you want to find out more about boating, including all of the options and costs.
I was really surprised to find out that 90% of Americans live an hour or less from a navigable body of water; boats larger than 26 feet are considered yachts; and 3 out of 4 American families with boats earn under $100,000 a year. It made sense. My family certainly didn't have any money when I was growing up and the boat was actually a way for us to vacation -- extensively -- in an affordable way.
Our 39i was chartered from SunSail and was docked at a marina in Wickhams Cay on Tortola. I was blown away. It might have been thousands of miles from the one in my childhood memories but it was pretty much the same in every way.
Our boat, the Pinguino, had 3 cabins, 2 heads (both with "showers"), wood detailing, a self-furling jib, and lines rigged to the cockpit. In other words, easy to sail. Way easier than the Jenny Rebecca. I was thrilled at the prospect. But compelled to reminisce about the old days as well. "Back when I sailed with my dad, it took a crew of three and a Captain with nerves of steel to navigate the bay." I had a very big imagination as a kid.
We spent the week sailing and snorkeling and visiting places like the Soggy Dollar Bar and the Bitter End Yacht Club. The latter of which I absolutely loved. We also had the chance to play around with several powerboats. A really swanky one (rumored to have been taken out just the week before by Beyonce and JayZ); a sportier one that I got to drive; and one we took deep sea fishing.
Don't tell my dad, but I really loved the power boating. I will always be a sailor at heart. But when you want to get where you're going, you can't beat it. I loved the way the boat leapt up out of the water and crashed back down again like it was showing the sea who was boss.
There were lots of proud moments on the Pinguino. When we raised the sails each day. When we beat the other boats on our flotilla to our destination. When my girlfriend learned starboard from port and walked across the deck with ease, throwing lines, setting anchor, and mooring the boat like a pro despite it being all brand-new to her.
One day on the Pinguino, I cleated a line for Captain Alden and he quickly rushed to the bow to check my work. He grinned when he saw what I had done. "It's perfect. I couldn't have done it better myself." I was so proud. I snapped a photo and sent it to my dad. "You taught me well," I wrote.
It's amazing the confidence you can gain, even as an adult, mastering a skill, especially on the water. Maybe because the sea is so vast and so strong. To learn to work with it and not against it, to learn to enjoy it and not fear it is a powerful thing. And, if you let it, the sea will happily shoulder all of your stress while you enjoy the kind of buoyancy that only being on a boat can bring.
I travel a lot, but that week sailing in the British Virgin Islands felt not only like sheer pleasure, but also like returning home. The familiarity of the water. The amazing friendships we made. The hours of sailing along the ocean, sometimes peacefully and steadily and at other times racing and tacking and heeling over so far that you have to brace yourself with your feet in the cockpit if you want to keep from sliding off the high side and onto the floor.
So much was the same. The rice in the salt shakers. The Sperry Topsiders without socks. The dinghy to go to shore. The little cereal boxes even still boast perforations, although they don't hold milk anymore. And the feeling, the peace and well-being and the sense of truly being where one belongs, that was all exactly the same. And that week, I realized how much I missed it.
When I returned home I quickly found myself back at Discover Boating. I knew I had to get back to boating. I was surprised to learn about fractional ownership and that chartering a boat, even with a Captain, was no more expensive than a nice resort. Our trip worked out to be about $1,300 a person for seven days, including provisioning.
Boats don't care who you are or how much money you make. The water doesn't care what you wear or how your hair looks. You can buy or rent or share or even simply crew for other owners or renters.
It's been a month or so now since that sad day when I had to say good-bye to Pinguino and all of my new friends at the dock, lug my sail bags into a cab, and watch out the back window as the marina faded into the distance. Since then I've bought a new set of sail bags emblazoned with my initials. I consider the act one of positive thinking. I plan on needing them soon.
And I now never leave the house without the gold Tiffany sailboat charm that my girlfriend surprised me with on my fortieth birthday just two weeks ago. Seems my reclaimed joy of boating was as obvious to her as it was to me and she wanted me to have my totem to wear with me all the time. It reminds me to breathe and trust and relax. It reminds me how strong and capable I am. And it reminds me who I really am despite all the noise. It's good to know where you most belong. And I know for sure, it's the sailor's life for me.
HuffPost Lifestyle is a daily newsletter that will make you happier and healthier — one email at a time. Learn more