Confessions of a DIY Charter Skipper

My wife, Kati, and I had built a small and profitable business in Nottingham, England. We decided to take a well-earned six-week vacation in Greece during our two young daughters’ school holidays. We ­rented an RV to travel at our own pace, stopping wherever and ­whenever we wanted. When we arrived in Athens, we chartered a Coronado 35 ketch for a week and sailed around the stunning Peloponnese, crewed by two American lads because we had never sailed before.

Inspired by this experience, we sold our business, house and furniture, and bought a 40-foot Endurance ketch, which we named Tranquility Base in honor of the first American moon landing. With our children aboard, we set sail for the Mediterranean on what was meant to be a two-year ­sabbatical—and we ended up staying for seven. 

After the first year, we ­realized that we needed to start earning again to sustain our nomadic lifestyle. What better way than to use our beautiful boat to charter?

Charter sailing was in its infancy in the Mediterranean back then, and I signed on with a British charter agency targeting novice sailors who were looking to learn in the sun with a captain and cook. That’s when things started to get interesting.

Bookings Begin

Our first guests were an American couple traveling through Europe who ­wanted to see if they liked sailing. Our boat was perfect for them: ­comfortable, manageable and well-equipped for short coastal trips.

One afternoon while we were anchored in a quiet bay, the wife decided to go for a swim. For reasons of modesty, she wore a wool poncho over her swimsuit. It quickly became waterlogged. The weight of the soaked fabric dragged her down. She managed to shed the poncho and grab hold of a floating line we had over the side, but she didn’t have the strength to climb back aboard.

I couldn’t lift her out of the water, so I rigged the main boom with a snatch block and passed a line beneath her arms to form a sling. Kati lowered the lifelines between two stanchions as I hoisted the guest up and over the rail. She came aboard safely—albeit ­awkwardly—landing on deck like a beached fish.

It was an unglamorous start to our chartering career, but it taught us an early and valuable lesson: Be ready for anything.

The One-Armed Sailor

On another charter, we hosted a couple whose husband had only one arm. He was considering buying a sailboat and wanted to find out if he could handle things on his own. Since we’d advertised that our ketch was rigged for shorthanded sailing, he saw it as a good test platform.

Our self-tailing electric winches were key to making sailhandling manageable for him. But at the time, portable electric winch handles—now common and helpful—weren’t yet available. He managed admirably under calm conditions and found ways to adapt, but it was clear that sailing solo or in rough weather would present serious challenges.

In the end, he chose to buy a powerboat—probably the wisest and safest option for his needs. I’ve often thought about that experience and whether someone with a similar limitation could truly handle a sailboat safely without a capable crew, ­especially in an emergency.

The Drunks

While in Gibraltar, I accepted a charter from five men who, coincidentally, were also from our hometown of Nottingham. From the outset, they were more interested in partying than sailing. Sensing how the week might unfold, Kati made the smart decision to stay ashore with our daughters in a rented chalet. I stayed aboard to skipper the boat and quickly came to regret it.

The group’s main goal was drinking and meeting women. They also wanted to sail to Tangier, Morocco, about 40 miles across the Strait of Gibraltar. I warned them that the Strait was busy with commercial traffic and that Morocco had a different cultural attitude toward gender and public behavior, especially where Western tourists were concerned. They didn’t care.

Once in Tangier, they met three local sisters who invited them back to their apartment. What the men didn’t realize was that the women still lived at home. The evening ended not with a party, but instead with tea served under the strict supervision of their father, who told them that any infidel who laid a hand on one of his daughters would lose his head. The scimitar mounted above the fireplace suggested that he meant it.

On the sail back to Gibraltar, one of the men wore a kandura​—a long, traditional robe—that got caught in the sheet winch while we were tacking. He was yanked to his knees and tangled in the lines while his friends laughed. I had to reroute another line carefully to free him, a process that took a good amount of time and effort.

It was a charter I was glad to see end, and a firm reminder that good seamanship sometimes includes managing difficult personalities as much as handling sails.

Some Caught the Sailing Bug

Not all guests were challenging. In fact, some became longtime friends, and a few bought their own boats. One family with two young daughters chartered with us near Saint-Tropez in the South of France. We spent several days sailing around Île de Porquerolles until, unexpectedly, I was told we needed to return immediately to Port Grimaud. The wife feared she was having a miscarriage. I hadn’t even known she was pregnant. Thankfully, they had good insurance and were flown back to England on a medical flight. She received prompt care.

A few years later, that same family reappeared in Gibraltar, this time arriving in an old motorboat after navigating the European canal system. They had become skilled sailors, owning a fine boat and even undertaking deliveries across Europe.

Their journey was a rewarding reminder that some charter guests truly embrace the lifestyle, growing from nervous beginners into confident boat owners and sailors.

The Rum Deal

When we were based in Gibraltar, the British Admiralty finally ended the centuries-old practice of issuing a daily rum ration to sailors—a tradition dating to 1740. This change became a windfall for Tranquility Base. Surplus rum was sold ­locally in Gibraltar for about 10 GIP per gallon (about $13.58 US), still bottled in the original pot demijohns.

I always stocked up with a couple of gallons before heading to the Mediterranean. At dinner, we served guests neat rum and grog—the classic British naval mix of rum diluted with water—keeping alive a bit of maritime heritage.

We realized that we needed to start ­earning again to sustain our nomadic ­lifestyle. What better way than to use our beautiful boat to charter?

The raw rum was a strong, warming drink that few could handle in quantity. While the traditional naval “tot” was half a pint twice daily, most guests barely managed a couple of neat servings before feeling the effects. It was also a reliable way to encourage early bedtimes in the afternoon, which, for a skipper, was often just as ­welcome as the drink itself.

Heads and ­Headaches

Our boat had just one Baby Blake marine toilet, and it required precise instructions to operate correctly. Guests had to open the valves and pump the lever in the right sequence to avoid unpleasant consequences.

I often ended up emptying the toilet after someone got it wrong, and it wasn’t uncommon to hear a startled shriek from the head when a guest struggled. On rare occasions, I even had to put on rubber gloves to retrieve items that had fallen into the bowl.

A single toilet is far from ideal for a charter boat, especially with multiple guests. That’s why on our current boat, we upgraded to two electric toilets. They are much easier to use and far less likely to cause trouble.

Seasickness: An Inevitable ­Challenge

Mal de mer was a common issue among guests who had never been on a small boat before. We always advised them to take motion sickness tablets before boarding, just in case, but sometimes even that wasn’t enough.

When nausea hit, the best we could do was provide a bucket and discreetly dispose of the contents later. Most guests got their sea legs within a day or two, but occasionally we had to remain tied up in a marina for several days while some guests adjusted to life aboard.

Patience and preparation were key, for the guests and crew alike.

Hot-Water Hustle

Keeping enough hot water for daily showers by four or five people was always a challenge aboard our boat. When we docked in port, we could plug into shore power and easily heat the water. But anchored in secluded coves, we had to rely on the engine’s heat or our portable Honda generator to warm about 15 gallons of water. Our options were noisy and annoying for a peaceful anchorage.

On sunny days, I sometimes hung a plastic bag from the mast, fitted with a shower head. The sun would heat the water inside, providing a ­simple solar shower. The catch? After ­rinsing off, guests needed to jump into the sea to wash away the soap and cool down. Children enjoyed this, but ­many adults were less enthusiastic about the swim.

Balearic Bliss

Some of our most enjoyable charters took place in Spain’s Balearic Islands, particularly Ibiza and Mallorca, where we ran day charters for groups of young vacationers. We’d pick them up from a beach near their hotel and sail to a nearby island or sandy cove.

The days were filled with swimming, snorkeling and relaxing drinks at a local bar. Many guests would nap on deck during the leisurely return sail, soaking up the sun and sea breeze.

We repeated this routine for several days each summer. It not only brought us great memories, but it also made a valuable ­contribution to our boat fund.

From Buckets to Bathtubs

All of this happened in the ­early days of sailboat chartering, when the sea felt wide open and the rules were few. Anchoring was easy, paperwork was ­minimal, and most of us were figuring things out as we went. It was a simpler time: rugged, rewarding, and full of surprises.

Today, chartering looks ­different. You can hire a ­skipper for just a few days, or even for a single afternoon, to sail, cook dinner and head home before sunset. Boats have become floating homes with every ­comfort imaginable.

Our current 50-foot ­schooner has twin air conditioners, a washer/dryer, a deep freezer, two heads with electric toilets and showers, and a full-size bathtub with jets. It’s a far cry from our early setup with one hand-pump head and a bucket on deck.

And yet, no matter how far the gear and the business have come, some things haven’t changed at all. The sea still finds ways to keep us humble. 

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