I’m about to escape again—this time to Sicily where I’ve never set foot. And by escape, I mean charter for a week on a sailboat that I’ll never have to varnish, wash, or fix anything on outside of paying for running into a quay or dinging the prop on a rock. It sounds too good to be true.
When I had my own boat, Indigo, I loved her fiercely and readied her for far flung adventures with a mad dedication. I sanded, polished, refitted, outfitted, and generally donated sweat and lots of blood to the dream. Right after buying her, a dock neighbor quipped, “Between all that work, don’t forget to go sailing and enjoy yourself.”
What did he know? I was making her perfect and that was all that mattered. She had to be pristine even at the expense of long sailing weekends and lazy afternoons at anchor. My floating to-do list was long, but I could swagger down the dock knowing that people stopped to notice her gleaming hull and new canvas.
A few years on, life changed and Indigo didn’t go cruising on the colorful waters for which she was named. A friend tried to console me by saying, “Just charter. You can go anywhere in the world faster, cheaper, and without ever having to do anything but sail.”
It’s true that cruising for a week or two on someone else’s boat doesn’t elicit the same emotions and won’t form the same heartfelt connection to the yacht. But it sure can be easier. Broken heads, fried electronics, and bilge pump anxiety still happen, but they’re blissfully temporary. As captain, my primary job is to ensure a safe platform, to keep the crew entertained, to pack in as much fun as possible, and maybe to figure out how to switch water tank manifolds and find the wine opener. At the end of the trip, I step off onto the dock, “hand off the keys,” and head for the airport.
Don’t get me wrong. I miss Indigo with every fiber. For years, she was my purpose and my big fiberglass baby, which is why I sent out birth announcements when I first purchased her. My grandchild-less mother didn’t find the humor in it. There’s no replacement for cherishing your own boat or living the cruising dream, but there is the next best thing of “owning” a recent model yacht for a week that has more amenities than your banker in good conscience would allow you to add to your own boat. And there are no yard bills.
Chartering opens up the world without long ocean passages, hundreds of dollars in diesel or winterizing. Chartering is a drop-in lifestyle where you jump aboard a boat that’s already in Tahiti, Greece, or Sicily, take your Instagram shots, and disembark before your teenagers revolt for lack of WiFi. Chartering is a way to knock out line items on the bucket without selling the house or getting lost in the Bermuda Triangle. And boat bucks aren’t spent on invisible jobs in the engine room but rather on exotic excursions and decadent dinners. It’s the difference between ordering dessert and growing your own sugarcane. Both work, but one is easier and faster.
Chartering also keeps you on your toes. Not only do you need to continually learn new cruising grounds, you get to test different boats. I’ve learned a lot via charter including the word for beer in a dozen languages and how much I love to drive cats. The complacency of the familiar is replaced with a steep learning curve on every single trip and that makes you a better sailor. And I’ve found myself to be much more bold with charter boats because I’ve already paid for the insurance and I don’t have to fix the results of any adventurous docking, so Med mooring in a Meltemi be damned.
Look, this isn’t a love letter to borrowed boats that bring sticker shock when booking a weeklong vacation. But it is a reminder to pull up from the three-foot level perspective when pricing a charter, and to remind yourself of all the things you won’t be paying for while sailing someone else’s boat.
Do I still want to come home to Indigo? Absolutely. But if that’s not possible, I’m embracing Plan B and opting for the escape hatch of chartering rather than missing seeing and sailing the world.
October 2025
