Why would boat owners on the Chesapeake, who already spend half the year enjoying their boats and the other half taking care of them, want to get on a plane just to go boating in the off-season?
It’s a fair question, but our time speaking with charter captains and bar owners in the Caribbean reveal that Chesapeake Bay boaters make up a noticeable chunk of boating tourists in the islands. We asked Bob Lipkin, the founder of cruising magazine Latitudes and Attitudes known for decades by his alterego, “Bob Bitchin”, what’s so appealing about a charter—even if you’re a seasoned boater. For him, it starts with seeing the world.
I didn’t get into boating until pretty late in life. I was about 30 years old the first time I set foot on a sailboat, and that experience was a life-changer.
My first sailing experience was aboard Stone Witch, a 74’ Barque that was the flagship for the environmental group Greenpeace. It was the 1970s, and the Stone Witch would arm itself with protesters so that we could blockade the entrance to Diablo Canyon’s construction of a nuclear power plant off the coast of San Obispo. With no motor, and just four 21-foot oars, we drank tepid Kool-Aid and loved every minute of it.
After returning from adventures around Central America in 1979, I immediately bought the first boat I could afford. She was a Cal 28 I named Rogue, and I moved aboard. Over the next 50 years of boat ownership, as I went from a 28-footer to a 30 footer, then to a 51-footer, and finally Lost Soul, a 68-foot Formosa Ketch, I realized that life just got better and better.
I lived aboard and cruised all over the world. From Southern California to Tahiti, Samoa, Tonga, and then Hawaii. I kidnapped the bartender of the Portofino Marina and later married her. Together, we’d bring young people aboard to learn the cruising lifestyle, enlisting them for major crossings and minor boatwork. We sailed back to the mainland, then down to Central America and through the Panama Canal. We explored the Caribbean, the Atlantic and the Mediterranean.
I soon realized that chartering opened up my world to faster, more fun trips. To prepare for my first ocean crossing back in 1983 (to the South Pacific), I worked for months and read everything I could get my hands on. It was an entirely different way of living: we used to varnish our eggs so as not to have to refrigerate them (later finding out that if you buy unrefrigerated eggs they will last for months without refrigeration), and we’d tear the paper labels off canned goods and write on the can with a magic marker so when they’d get wet we could see what was in them. There were endless chores to ready a boat for such a trip.
But I soon realized that for less than one-third the cost of prepping my boat and stocking it, I could hop on a big silver bird and be anywhere in the world in less than a day.
There was still a part of me that wanted to prove to myself that I could make those crossings, but once I did, It was no longer a challenge. I could have a near-new boat just about anywhere in the world, and spend a week exploring before returning home. That was more attractive to me instead of the months at sea spent just to get to paradise.
Now, I admit that getting there is half the fun on a sailboat, and I do enjoy long crossings. But my adventuresome spirit wants me out there more than I could afford. Not so much the money, as the time. Life can get in the way of living.
Over the years, my charter adventures took me all over the world. From Tahiti and the islands of Ta’aha, to Bora Bora and Huahini. It took days to get there, where I boarded a nice boat from Sunsail and enjoyed a great week sailing in paradise; then later a few days to get back to the office where I started working for (and on) my next vacation.
And I think that’s the difference: chartering is a vacation, while sailing your own boat is a way of life. You can (and should) embrace both.
In 1999, while I was working at the magazine I owned at the time, Latitudes and Attitudes, I came up with the idea for a flotilla charter. The idea for “Share the Sail” was to get together with a bunch of people who wanted to go to Bora Bora, line up a few boats from the local charter companies, and show people what it was like to live the cruising lifestyle.
Over the next 25 years we enjoyed flotilla charters in the BVI’s, Greece, Samoa, New Zealand, Thailand, Croatia, and many other exciting locations.
There are many good charter companies out there, offering all levels of comfort. Over the years I’ve chartered with Sunsail, The Moorings, Tahiti Yacht Charters, Dream Yachts, BVI Yacht Charters, and many more. It’s helpful to know which are luxury charters, with skippers and cooks, and which are bareboat charters, where you pick up the boat at the docks and sail it yourself. That’s the most fun in my opinion, but once in a while it’s nice to have a local skipper to show you around.
The real advantage to chartering is that your friends get to join you and share the costs. To sail from the East Coast to the Med, you’ll need thousands of dollars in supplies, a few months (or more) off from work, and a friend or paid crew to help you. But there is nothing stopping you from calling your favorite chartering company, lining up a boat and some friends, and taking a week or two to explore paradise.
I lived aboard for over 40 years and have sailed the world. Wherever I wanted to go, I did. First with Lost Soul, and then, after I proved to myself that I could do it, I chartered. The two types of cruising cannot be compared. On your own boat you feel the pride of making a crossing, on a charter boat you have the option to sail anywhere in the world in a week or so.
As a former liveaboard, I can honestly tell you that after a while you find that chartering can be a great way of experiencing what it’s like to sail anywhere in the world, with as little as a couple weeks’ notice. I can highly recommend it.
Bob “Bitchin” Lipkin is the publisher behind Biker Magazine, Tattoo Magazine, and Latitudes and Attitudes. He’s traveled all over the world by both motorcycle and sailboat, and today calls the Sierra Nevada Mountains his home. Sign up for his newsletter at www.bitchinattitude.com
