Dan Levine learned early that particular pleasure that comes with the snap of a sail as it unfurls to catch a big gust of air – and feel the power of a boat that is riding the wind…

As a child, he grew up sailing on the Chesapeake Bay, a 200-mile by 30-mile pelagic enclave tucked between Maryland and Virginia. He and his father would hop aboard their dinghy every weekend and head out toward open water, 

By the time he was a high school junior in 1986, he was ready for a bigger adventure. So the father-son duo, this time along with Levine’s brother and two friends, sailed to Bermuda – a trip that would last 10 days. None of them had sailed that far before, and in the days before GPS, this also meant using a sextant to navigate the sea. Throughout the trip, the weather would nearly get the best of the five-man crew.

“We had a situation where the wind was against the current which makes for steep sharp waves,” Levine said. “We got clobbered.”

The boat suffered some modest damage.

“I’ve never been in a situation where I thought ‘this is it’ and I was out of options,” Levine said. “But it was uncomfortable.”

Eventually, the trips would get even longer. Levine and his dad went on to traverse the entire Atlantic Ocean to the United Kingdom, and then on through the English Channel that connects the country to France.

For Levine, sailing had become a passion. He saw himself living his dream on the water, or as much of it as he possibly could, anyway. But life had other plans. He eventually got married – and while his newfound beloved appreciated his sailing hobby, she didn’t love it the way he did. And had no desire to accompany him on every trip. 

“I had ambitions to sail away with a young family,” he said. “What I discovered was that it wasn't in the cards.”

It was more than 40 years ago that he realized he’d need other people to go sailing with. He would find them in the back room of Radnor Valley Country Club, where the Philadelphia Sailing Club (PSC) now meets on the third Wednesday of every month. Launched as a club in 1980, the group – which is open to anyone who wants to join – has now organized trips all over the globe to faraway destinations like Greece, Sweden, Croatia, Australia, Tahiti and Thailand. With these trips, members get to indulge their shared love of the open sea – where daily routine is determined by the arc of the sun, the lift of the water, and the power of the wind. 

“What I found was a number of people in my situation who had spouses and families who supported their sailing but didn’t necessarily want to go,” he said. “It gave me the social life and the companionship of other sailors, and I was able to also scratch the itch to go on longer and more adventurous trips.”

Most trips tend to be close to home. Approximately six times a year the club organizes trips to a marina in Rock Hall, Md., where it charters boats to explore the Chesapeake Bay. In fact, most members don’t own their own boats; the group charters them for every trip.

But the international trips, pitched and organized by members, are where they get to really test themselves. 

The most recent big trip, a week-long expedition to St. Martin in the Caribbean that they took in March, was organized by PSC member Ray Enger. He happened to be chatting with one of the skippers on a previous trip and asked when a foray to the Caribbean – somewhere he’d been dying to go – would be in the cards.

“He said ‘as soon as you set it up,’” Enger said. The reward for planning a trip is that you don’t have to pay for the cost to charter the boats. 

The trip eventually came to pass, and everything ran smoothly – even if the wind didn’t cooperate as much as the club’s sailors would have liked. One day, the plan was to make the roughly 32-mile sail (that’s about 28 nautical miles) from St. Barts to St. Kitts, but the winds weren’t strong enough to get there by dark, and charter companies want the boats moored or anchored by the time the sun goes down to keep the vessels safe. But that’s the nature of sailing, Enger said. You have to go where the wind takes you. Literally.

“We always have a plan A and a Plan B in mind,” he said. “And a Plan C depending on what we found when we got there.”

For many members, that’s the fun part.

“It’s part of the adventure," said Angela Rowland, a PSC member for five years. “You have to be flexible and think on your feet a little bit because you’re at the whim of the wind.”

Enger and the rest of the club members who managed to make it on the trip slept on the boat each night, in between visits to various islands in the vicinity. Typically, the boats the club charters have enough space to sleep six or seven people. That means there usually are two or three cabins (that’s sailor speak for bedrooms), a salon (living room), a galley (kitchen) and a head (bathroom). 

“We call it camping on the water,” said Greg Cream, who’s been a PSC member for more than 35 years. But that might be a tad bit misleading since almost all the boats do have heating, air conditioning and electrical outlets. 

“They’re not stripped-down items,” Cream said. “They’re made for people who want to buy them and be comfortable.”

The smaller, 38-foot boats the club charters are typically worth about $350,000, Cream said. For international trips, the club will sometimes rent larger, 45-foot to 60-foot vessels worth anywhere between $800,000 and $1 million. 

For that reason, charter companies don’t let just anybody captain them. Typically, each boat will require a skipper, which the club refers to as an “experienced crew member” – or ECM – to captain the boat. Depending on the country you’re in, that could mean a skipper needs to show a resume, or some other kind of certification, to take the boat out on the water. 

In Europe, charter companies typically will need to see a captain’s license to take a boat out on the river, Cream said. In the United States, skippers can have licenses to boat in the state they’re chartering, or they can have a federal license, which supersedes the state license. If none of the trip’s attendees meet the local requirements for captaining a chartered boat, charter companies will typically make captains available for hire.

And that’s another reason many members, including Rowland, join the club. She’d been sailing on lakes, but didn’t have access to bigger boats and other resources enjoyed by more experienced sailors.

“I was looking to increase my sailing adventures,” Rowland said. “I researched opportunities in the area and came across the PSC.”

The club’s annual “skills weekend,” held in the Chesapeake Bay, was particularly appealing to her. It’s where the club’s more experienced sailors will spend a weekend on a boat mentoring the newcomers.

“It’s perfect if you’re a sailor who wants to work on your docking, tacking or anchoring,” she said. That experience also comes in handy in potentially dangerous situations, like when the boat gets caught in a thunderstorm out at sea. 

They do check weather forecasts before taking out a boat, and sometimes charter companies will prevent the boats from going when there’s a possibility of inclement weather. But – as all sailors know – storms do happen. Typically, Kraemer said, they come and go rather quickly.

“I don’t know anybody who hasn’t been caught in one sooner or later,” said Harry Kraemer, PSC’s treasurer. “They seem like moments of terror, but we usually survive it alright.”

It’s a small price to pay for the feeling Kraemer gets when out at sea. It’s what keeps him going.

“It’s amazing to me that a 20-ton vessel can move along in relative silence without the sound of an engine consuming fuel,” he said. “I’m awed by the power of the wind.”