How to Sail Off into the Sunset
Escaping the 9-to-5 world and cruising to paradise is possible. Here's the way to do it.
Years ago, I was researching a piece on the Orange Coast College School of Sailing & Seamanship and visited one of its beginning sailing classes. I met Brian, a guy whose plan was to sell everything he owned, buy a boat and sail around the world. Brian told me this as he mis-tied a bowline and failed to properly fold a sail. Brian said he planned to leave in the spring. I labeled him as completely bonkers, really naive and an awesome interview.
Brian also turned out to be infectious. After a few weeks of secretly studying the School of Sailing’s catalog offerings, I sat in a taco stand and told my wife I thought we should sell our house, quit our jobs and sail to Tahiti. “Terry, we don’t even know how to sail,” she said. I pulled out the catalog. “I have a plan,” I said. Then I ordered more beer.
It took more than a few drinks but somehow I convinced Gayl, and three years later, after taking everything from basic sailing to advanced anchoring, we quit our jobs, sold our house, bought an old, leaky boat, and set sail on a two-year, 6,000-mile journey to the Sea of Cortez, mainland Mexico and the South Pacific.
But as much as it felt like we were alone in our adventure, doing something no one else does, we knew we were wrong. There’s a strong and large cruising community out there. And, as I learned from all the questions friends hit me with when we returned, most people dream of cutting all the strangling ties to life on land and sailing over that horizon. But what usually stops them is the logistics of simplifying, the fear of the unknown, and, well, OK, sanity.
“There’s a lot of anxiety and trepidation built into cruising. The what-ifs can drive you crazy,” says Andy Turpin, managing editor of Latitude 38, which holds the Baja Ha-Ha cruising rally from San Diego to Cabo San Lucas every fall. Founded in 1994, the rally serves as a first step to cruising for up to 400 boats. “It serves as the initial step for would-be cruisers to quit procrastinating, throw off the dock lines and go cruising. It’s the entry point for a lot of people who might not go if they weren’t going with a group, because of all the anxiety,” he says.
I asked Turpin, along with a few other seasoned cruisers, to help answer questions about the not-so-crazy-after-all idea of leaving your Starbucks-fueled, climate-controlled existence for a life at sea.
Do I have to sell everything and quit my job?
Not necessarily. Most do. We did. But there are also “commuter cruisers,” Turpin says. These are people who spend part of the year cruising and part of the year at home. They may rent out their home or even work while they cruise. Newport Beach’s Craig Chamberlain, who owns yacht insurance company Novamar, did this with his wife and son. They set sail in 2006, cruising Mexico for six months at a time, with Chamberlain working remotely.
“These days, you don’t have to check out of life for three years, especially in Mexico,” he says. “With cell service, email, maybe an Iridium phone, a lot of people really can go for six months, leave the boat for the offseason, and return,” he says.
It worked out so well for the Chamberlains that they started another business in Mexico and have been splitting their time between Puerto Vallarta and Newport Beach ever since.
What about pirates?
“When people hear you didn’t run into pirates or storms, they suddenly don’t want to hear about your trip anymore,” says Suzanne Fults with a laugh. She and her husband, Greg, and children Kyle (14 at the time), Cory (10) and Heidi (7), cruised Mexico for a year in 2003. They ran into no pirates. They didn’t hear of anyone running into pirates. And in fact, unless you’re planning to sail through the dark back alleys of a border town, you have a better chance of running into a whale than a pirate.
Even with the recent years of violence south of the border, Chamberlain says he can’t think of a time when the mayhem has directly affected the cruising community.
“We did have an incident a few months ago where some narco guys burned the outside of a bank, a truck and a gas station,” Chamberlain says. “But they told people what they were going to do and to get out of the way. And pirates? Nah. My wife says she feels safer here than in California.”
Is it hard to find a good cruising boat?
Anyone who’s ever shopped for used cruising boats will tell you that the sailboat classifieds make real estate ads seem like humble understatements. That was verified for us with the very first boat we looked at. It sounded great in the ad: one owner, many upgrades, GPS, radar, new rigging and sails. I called the number and made an appointment. The next day at the dock we stared in disbelief.
“I must have gotten the slip number wrong,” I said.
The listing guano-covered wreck in front of us could not be the boat described in the ad. Then all hope was dashed as Bill, the owner, walked up. “A spray with the hose and she’s ready to go, eh?” he said.
“The ad said new rigging and sails,” I said.
“That’s right. Brand spanking new in ’85.”
He had me there.
When Bill opened the hatch to the main cabin, the pungent odor of a neglected holding tank and un-pumped bilge blew us back. Nostalgia for the guano smell set in. Bill flipped on the cabin lights and I instantly yearned for them to go out again. Darkness was much kinder to my cruising dream. The GPS looked as old and worthless as the rusting stove, and the radar resembled something off the “Sea Hunt” set.
“Yeah, she’s a beauty,” said Bill, eyeing the stained salon settee with affection. “Hate to give her up.” Then, without a hint of irony, he added, “But the upkeep is killing me.”
In time, we learned how to decode ads and noticed they ranged from obviously deceptive to brutally honest.
“Sleeps eight” meant only if five of them enjoy sleeping in the fetal position out in the rain. “Ready to go cruising tomorrow” meant on the condition that your first landfall was a full-service shipyard on the near side of the bay.
Then there were the misguided souls who seemed reluctant to join the deceptions. “Loaded with equipment,” they’d start hopefully, then list: “ham radio (needs wiring); professional sextant (no mirrors); electric windlass (none working).” It seemed a form of public confessional.
My favorite, though, was when the advertiser listed additional equipment for sale outside the purchase of the yacht. They read something like: “Sold separately: numerous hats; dock plant; complete set ‘Hardy Boys’ mysteries; eight-inch black and white TV (not working).”
In the end, we found a 1976 Westsail 32-foot cutter for $47,000 that had been around the world before. It was solid, half the price of most boats and seemed “ready to go cruising tomorrow.” We spent another $30,000 getting it ready to go cruising a year later.
I’m a lawyer. Now I have to fix toilets?
Yep. Here’s the bad news: If it’s on a boat, it will break and at the worst possible time. Here’s the worse news: All those years of law or med school or running a corporation? Not gonna help you when it does. And unless you’re planning your cruising route based on West Marine locations, you’re likely not going to find supplies or servicemen. Fixing everything from the windlass to the watermaker – and the head – is up to you.
Some people love that – Newport Beach’s Richard Straman, the well-known car restorer, for instance. With his wife, Lani, Straman shuttered his business, sold his house and sailed away in his 86-foot all-wood 1923 schooner Astor in 2000. Despite the maintenance a nearly century-old wooden boat demands, they’re still out there. “My dad absolutely loves working on Astor,” says daughter Mariah, who cruised with her parents through the South Pacific right out of high school. “He thinks of cruising as working on your boat in foreign ports with minimal supplies.” When that’s your idea of fun, cruising is a breeze.
For the rest of us, when things break, panic sets in. That’s about the time I would recall what my OCC sailing center diesel mechanic instructor said: “When something breaks, don’t get your tools out. Because if you get your tools out, you’re likely to use them.” Thankfully, this advice usually worked thanks to the tight bond the cruising community shares. Instead of my tools, I would reach for the radio and within minutes I would have someone as handy as Straman walking me through a repair or rushing over in a dinghy with a part and his own tools.
Do I need a shakedown cruise?
You probably need several. In a shakedown cruise, you sail your boat offshore and spend a few nights at sea to test the boat. A common route is around one or more of the Channel Islands, spending one to three nights at sea. If anything on the boat isn’t seaworthy, that’s when you’ll discover it.
Here’s the thing: More often than not the shakedown cruise uncovers weaknesses in you as well as your boat. But it’s better to discover these now rather than after you’re “all in.” Remember, every year, a new batch of “lightly used” cruising boats ends up for sail in Cabo San Lucas.
“We get a lot of people who’ve sailed all their lives in 25 knots of wind every weekend, but they’ve never spent a night at sea,” says Turpin. “Stay out there and stand watch, and see how you feel after doing three hours on, three hours off for 24 hours.”
Speaking from personal experience, the answer is: like a zombie. A wet, cold, hungry one convinced his wife will call a divorce attorney the moment landfall is made.
On an extended crossing it takes about five days before you come out of the zombie mode and approach anything like enjoyment.
That’s about the time something breaks.
How much equipment do I need?
Suddenly becoming a plumber, carpenter, electrician and mechanic, in addition to skipper, navigator and head dishwasher, can sound like a jail sentence. The trick is to have enough to be comfortable but not so much that you become a slave.
Our boat was built in 1976; it had a tiller, a tiny cockpit and a lot of nostalgia. We added refrigeration (which broke), GPS and autopilot (which broke), but not much else. During our almost month-long crossing to the South Pacific, one of us was always up top, in the weather, keeping watch, since we couldn’t afford the battery power it took to run the radar more than an hour a day. We were usually wet, cold and tired, forcing ourselves awake with a two-dollar egg timer that went off every seven minutes.
Friends John and Sarah, a few hundred miles ahead, had a wind generator, diesel generator, autopilot and multiple flatscreens throughout the boat showing radar, positioning – and movies. Their watches consisted of reclining on their main cabin settee watching Hollywood blockbusters and eating popcorn. Needless to say, we were jealous.
Until one day in Tahanea, a remote, uninhabited atoll in the Tuamotu Archipelago. Crystal water, gentle breezes, some of the most abundant sea life in the South Pacific. In short, the payoff for all the blood, sweat and money it took to get there.
One morning we planned a dive. We loaded the gear in the dinghy and went to get John and Sarah, but only she came to the rail. “John can’t go,” Sarah said. “He’s on the satellite phone with our freezer maker. They’re walking him through fixing it.”
John’s freezer was $25,000 – more than half the cost of our boat – and it had hundreds of dollars worth of steaks inside (John hated fish). The satellite phone bill? Who knows? What I do know is that while we swam with sharks and manta rays, John was with Hal from customer service. It reminded me of why most people go cruising in the first place: to simplify their lives.
What about our kids’ school?
Oh, yeah, you’re also a teacher now. The upside? Amazing field trips every day. That’s one reason virtually every cruiser we met who had kids said they believed their children were getting more out of traveling than they were missing at home.
“I wanted to expose my kids to cruising and seeing things outside the Orange Curtain,” says Chamberlain. “There’s a great big world out there. People live in lots of different ways, and I wanted them to experience a simpler life.”
For the Fultses, it was a similar story: School was a few hours every morning, then it was adventure time. Kyle Fults, who was 14 at the time, says it was a life-altering experience.
“When I came back, things other kids worried about seemed unimportant,” he says. “Seeing other cultures, being responsible for fixing things ourselves – that gave me a lot of confidence, appreciation for what I had and perspective about what’s really valuable.”
Living in such tight quarters also brought the family closer together. “It forced us to respect each other’s privacy and rely on one another,” Kyle says. So don’t worry; the kids are all right.
When do I know I’m ready?
That’s easy. You will never feel ready. Ever. That’s one reason the annual Baja Ha-Ha is heralded by so many; it provides a much-needed deadline (this year: October 25). “At the end of the event the one thing people say more than anything else is that if it wasn’t for the event’s concrete starting date I never would have gone,” Turpin says.
What about storms?
If you get caught in a bona fide storm, you probably screwed up by being in the wrong hemisphere in the wrong season. But you’ll likely experience some big wind and waves. Gayl and I got absolutely pelted off Ensenada with 35 knots of wind and 14-foot seas. Being day sailors from Newport, we felt like we were riding out a hurricane. But we made it. And it made for a great story in Cabo.
Turpin says that for the Baja Ha-Ha fleet, wind is usually not an issue because many of the sailors are from the Bay Area, where 25 knots is normal.
“If you’re from Orange County or San Diego, 20 knots is sort of a big event,” he says. “But generally people acclimate when the wind gets up and hang in there because they figure, ‘Hey, everybody else is doing it, so it’s probably not that threatening.’ ”
Probably the worst weather we experienced was in the notorious ITCZ, a zone of inclement weather near the equator on the crossing to the South Pacific. For four long, long, long nights, we watched lightning crack all around us. But we made it, and probably only stressed out a few years of life. After sailing through paradise, I called that a bargain.
How Expensive is Cruising?
If cruising was a mutual fund, it would be obnoxiously front-end loaded. The buy-in cost can be extreme, especially if you don’t own your boat. That and the equipment required for an extended cruise will easily top $100,000 and can go much higher.
But once you land in paradise, the cost of cruising becomes much more reasonable. Depending on your idea of a good time, it can seem downright cheap, even in expensive places.
Tahiti, for example. Plan a normal 10-day vacation to Bora Bora and you’re staring at five figures. But when Gayl and I cruised through the Society Islands, we spent $600 to $1,000 per month. That’s everything, from baguettes to biodiesel. We anchored in front of $1,200 a night resort bungalows for free, enjoyed the biggest pool the world has to offer, and ate fresh sashimi from the fishing we did. Our income was exactly zero, but I can’t remember feeling more wealthy.
Because sometimes, crazy pays off.