Modern Sailing member Jonathan Arena’s love for sailing started in an unlikely place: a quiet lake in the suburbs of Philadelphia. With no easy access to the ocean, he first discovered the thrill of sailing on a Hobie Cat at Marsh Creek Lake, a spark that stayed with him and eventually grew into a lifelong passion. Today, Jonathan is an accomplished sailor who has completed nearly every ASA course and gained invaluable experience from tackling challenges from short-handed sailing on the Bay to leading his own crew on charters in Belize and the British Virgin Islands. Read in Jonathan's own words about how he has discovered sailing as both a personal adventure and a way of connecting to nature, history, family, and the broader world.
Jonathan Gets Hooked on Sailing
Growing up in the suburbs of Philadelphia, I didn't have easy access to the ocean, but there were lakes nearby. At Marsh Creek Lake, a rental stand offered kayaks, paddleboards, and a few Hobie Cats. The Getaway — a 17-foot catamaran with bright neon sails — immediately caught my eye. At 14, renting one was exhilarating, and I returned every summer, learning to sail (and capsize) until college took me to Rhode Island.
While studying design at RISD, I took a class called "Sea, Ships, and Society." It was an incredible class that covered the arc of sailing’s impact in the world — how sailing influenced globalization, trade, and the development of port cities. It connected the dots from traditional sailmaking techniques to the historic impact of places like Nantucket. Proximity to Newport, RI fueled my interest further. I was fascinated by the summer cruising crowd that turned Newport Harbor into a seasonal destination, and by the legendary craftsmanship of local boatyards like Herreshoff, Hinckley, J/Boats, and Sparkman & Stephens. The history of the America's Cup added to the allure.
After college, I moved to the Bay Area in 2010 and was immediately struck by how integral sailing is to San Francisco's identity. You can't picture the Golden Gate Bridge without imagining sailboats heeled over in the foreground. This iconic scene became an ideal to me. In 2011, I took a job in Sausalito, working across the parking lot from Le Garage Bistro. I began seeking out the local sailing community and connected with a skipper named Walter, who owned a J/105 and needed crew for Friday night beer can races.
At 24, it was surreal to spend Friday evenings racing on the Bay during golden hour, with the fog pouring down the Sausalito hills like a slow-motion avalanche. The boats tacking for position in tight quarters before the starting line and ripping upwind against the backdrop of the setting sun.
Completely captivated by sailing, I signed up for my first course at Modern Sailing, taking the 5-day ASA 101/103, Basic Keelboat/Basic Coastal Cruising combination course. That was over ten years ago, and since then, I've completed nearly every course available, having just completed ASA 108, Offshore Passagemaking in late September.
Challenges Lead to Growth
One aspect I love about sailing is the feeling of taming nature, using only your sails, the boat, and a bit of strategy. After my initial courses, I started chartering boats from Modern Sailing to get more practice.
Often, I brought along friends and family who had no sailing experience. This meant I had to manage almost everything myself, especially when sailing in strong wind. Out on the Bay, I was essentially single-handing, which was invaluable for building my skills and confidence.
My first major test came when I decided to skipper a charter in Belize with friends from grad school. Belize is a challenging place to sail for for a first international charter — it is full of shallow shoal waters and coral heads, with extremely outdated charts and isolated anchorages. Managing the boat and an inexperienced crew in unfamiliar conditions was exhilarating but very difficult and mostly characterized by a lack of sleep for fear of dragging anchor at night. I was overly cautious, constantly checking an unreliable anchor alarm that kept going off every 30 minutes due to poor GPS connection. That trip taught me a lot about seamanship, delegation, and trusting both my skills and my crew.
In the winter of 2022, I chartered a 50-foot catamaran in the British Virgin Islands for my extended family. By then, after over 60 charters with Modern and much experience sailing solo or with minimal crew, I felt comfortable handling the larger vessel.
My younger brother and I had developed a good rhythm from sailing together in the Bay Area, often double-handing. We had a shorthand that made managing the boat seamless, allowing the rest of the family to relax and enjoy their vacation.
The Heart of the Matter
I love the romance of sailing. It's an endless journey — the more you learn, the more you realize there's still so much to discover. Sailing is pure in the sense that it's about harnessing nature with a machine honed and refined over hundreds of years. It has given humanity incredible opportunities for discovery and knowledge, serving as the backbone of commerce, cultural exchange, and development for centuries. Innovations like the chronograph, GPS, and celestial navigation all have roots in sailing.
I’m also obsessed with the design of sailboats. As a designer and furniture maker, it is easy to get caught up in the details of boats and their aesthetics. There’s something timeless about a cutter-rigged ketch with long shearlines and extended overhangs that catches your eye.
The week I spent sailing in Belize stands out in memory. We dove in crystal-clear waters, witnessed incredible sunsets, and caught fish that we speared ourselves for dinner. Anchoring in secluded spots off the beaten path added to the adventure. It was a perfect blend of exploration, nature, and the simple joys of life at sea.
Lessons Learned with Modern Sailing
I've taken every ASA class from ASA 101, Basic Keelboat Sailing to ASA 108, Offshore Passagemaking at Modern Sailing. The instructors are exceptional — not only skilled and experienced but also welcoming and passionate. Sailing in San Francisco presents unique challenges: fog, heavy winds, and crowded marinas. Their guidance has been invaluable in preparing me to handle these conditions confidently.
The longer courses, like the ASA 105/106, California Coastal Combination Course and the ASA 108, Offshore Passagemaking, were particularly impactful.
Spending extended time on the water allowed me to observe the instructors' tendencies and behaviors in dynamic conditions. This immersive experience was the best teaching environment, offering insights that go beyond standard coursework.
Future Sailing Dreams and Plans
I have a deep love for the ocean and the natural world. One of my greatest ambitions is to experience as much of the world as possible, and traveling by sea feels like one of the most incredible ways to do that. With this in mind, my sailing aspirations are:
- Own a sailboat: I want my children to experience and appreciate the ocean and the natural world firsthand and would love to spend a chapter of our lives cruising with them. They’re a bit young now (1 and 4), but in time I’m sure they will make great crew.
- Sail to Hawai'i: Inspired by my favorite sailing book of all time, Hawaiki Rising, I aim to undertake this significant voyage, both for the challenge and the experience, on my own boat – perhaps I’ll do the Pac Cup as crew first before I skipper my own race.
