This article is from the summer 2025 edition of Mobile Baykeeper’s print quarterly, CURRENTS. The magazine is mailed to active members who have given more than $50 in the past year. To get on the magazine’s mailing list, donate here.
By Hanlon Walsh
For many, the idea of leaving behind the daily grind to set sail on a spontaneous open-water adventure remains just that — a dream. A can to kick down the road when the time is right. Something to push off until retirement. An outlandish idea that never leaves the shoreline.
But for my close friends and Mobile residents, Robert Willett and Isabel Goodwin, that dream became a reality last summer when they embarked on a sailing sabbatical along the rugged coasts of New England and Maine. What might sound spontaneous, however, had been years in the making.
Robert, 34, grew up sailing on Dog River, where his dad Bob taught him the ropes at an early age. From solo outings on the Sunfish to cruises on the family Hobie Cat and 32-foot sailboat, he developed a knack and passion for sailing that stuck with him, even during years spent living far from the coast in Colorado after he graduated college.
“From second grade on, I can remember going to the BVIs with another family friend of ours on a Catamaran,” Robert says. “We also went to Vancouver and spent many summer sailing trips in Michigan. I enjoyed it more than my mom and sisters, so when I got older, it was just my dad and I who went.”
That father-son bond, forged through summers of sailing in Traverse City, Michigan, never left him. And it sparked an idea to one day take the helm of a bigger sailing adventure himself. Isabel, 30, grew up in Maine and moved to Mobile in 2018 for a nursing job and to be closer to extended family living on the Gulf Coast. As Mobile’s resident “Mainer,” she’s often asked how she ended up in the Port City. Though it wasn’t the easiest transition at first, Isabel met Robert in 2019, and the two hit it off instantly.
While she didn’t have Robert’s lifelong sailing background, her New England connections and nostalgia for Maine summers led the charge in bringing their summer sabbatical to life. Escaping the Gulf Coast hurricane season and unforgiving summer humidity were also added incentives. Despite being raised on different coasts, both Robert and Isabel shared a love for the water and longed for a break from routine. I’ve been fortunate to join them on many outdoor adventures myself, but I can’t say I would have signed up for this one.
“We started talking about this five years ago,” Isabel says. “I had always been interested in doing some big adventure while we’re still young and have the flexibility to do it. Sailing came about because it felt like more of a challenge. Anyone can rent an RV or build out a van and road trip through the parks, but not everyone lives on a sailboat for a few months.”
Robert had sailing experience and the lingering itch to do something bigger. Isabel brought the vision to reality with local knowledge and a nudge in the right direction from her mom, Susannah. Together, with their trusted Golden retriever, Gus, and family support along the way, they would make a small but mighty sailing crew.
Testing the Waters: 2019-2024
Before their sailing sabbatical came to fruition, Robert and Isabel spent years honing their craft. They went out for occasional afternoon jaunts on his family’s 22-foot sailboat directly from their Dog River pier. They raced in the Dauphin Island Regatta for a few years. They even took short overnight trips around Dog River and the Bay. But sailing the jagged coastline of Maine for 10 weeks would require a deeper level of knowledge and hands-on experience. And, most importantly, a bigger boat. Originally, they envisioned sailing from Mobile to Maine, but quickly realized that dream wasn’t practical — or affordable. That’s where Susannah came into the fold.
“Luckily, my mom encouraged us take the leap and connected us with her friend Lance, who owns a sailboat in Rhode Island,” Isabel says. “Once that happened, everything fell into place.”
“Next, we trained in Gulfport on a 40-foot sailboat,” Robert says. “Our instructor made us do everything — he really threw us into the deep end. It was exactly what we needed.”
“I didn’t grow up sailing,” Isabel adds. “I didn’t even know which way to face into the wind, so I took a beginner course with Robert through the American Sailing Association. That gave me a great foundation, but the real learning happened once we were out there.”
After a four-day sailing boot camp in Gulfport, the two were ready for the next phase: training on the very boat they would be sailing in. To kickstart their journey, Robert and Isabel traveled to Rhode Island for a week-long crash course with Lance himself on his 38-foot Beneteau, sailing during the day and learning every inch of the boat.
“It was the perfect size boat for the two of us and Gus,” Isabel says. “Not too big, not too cramped.” By mid-July, the couple was ready to set off. They had saved money, made respective work arrangements, and carefully mapped out their course.
After years of dreaming, saving, and planning, it was finally time to set sail.
Sailing Away: July 15, 2024
Robert and Isabel cast off from Lance’s house near Newport, Rhode Island, on the morning of July 15. Their end goal? Sailing to Mount Desert Island near Acadia National Park in Maine, where they would meet family to celebrate Susannah’s birthday during Labor Day weekend.
But it didn’t take long for reality to sink in soon after the couple set sail.
“We were so excited — I had just taken my first Polaroid shot of Robert,” Isabel says. “About an hour in, the engine overheated. We had just left the mooring and were headed to Martha’s Vineyard. Robert noticed something wasn’t right, and Lance had to come meet us in his boat to help fix it.”
“It was a rough start,” Robert adds. “But we got it fixed and still made it to Martha’s Vineyard that night.”
From there, they sailed through Cape Cod, Provincetown, and Salem. In Portsmouth, near Isabel’s hometown, they docked for a week, letting the pace slow. But everything changed once they reached Portland, Maine.
“That’s when we really hit our stride,” Isabel says. “The scenery ramped up with endless islands and quiet coves. We were island hopping without any expectations, and they were constantly exceeded with each new island we discovered.”
Robert agrees: “Someone recommended this old book called A Cruising Guide to the Maine Coast and it became our Bible for the trip.”
A Day in the Life on Deck
As they headed down east toward Acadia National Park, their daily rhythms shifted. Mornings often came early, thanks to the wake of lobster boats and being exposed on a mooring. Anchoring decisions factored in not just tides and wind — but Gus.
“Gus refused to pee on the boat, so we always had to anchor within dinghy distance of shore,” Isabel says. “He held it up to 12 hours sometimes.”
They ate well, navigated constantly, and shared responsibilities. “Isabel was the helmswoman a lot,” Robert says. “I did most of the cooking and navigating.”
The tides, too, were a major adjustment. “In Alabama, we barely think about tides,” Isabel says. “In Maine, we were dealing with 13-foot swings. That made both of us nervous.”
Friends and family joined different legs. Robert’s dad sailed with them for a week in Portland, cruising around different islands in Casco Bay. Robert’s cousin Hendy, who had raced with them in the Dauphin Island Regatta, also spent a few nights aboard.
“We were glad to welcome a rotating cast of visitors,” Robert says.
Isabel and Gus on Mistake Island in Maine
Gus and Robert cruising through Cape Cod Canal
“After learning how to sail from my dad as a kid, it was a special full-circle moment to have him with us on our boat for the week.”
While the trip was smooth sailing overall, they encountered their fair share of challenging weather conditions along the way. At first, wind was scarce, so they motored more than expected early on. The New England fog also rolled in thick on multiple days, and their radar stopped working early in the trip.
“For the first month, I was using just one weather model, and it was always wrong,” Robert says. “Then I realized there were eight different models in the app. It was a game-changer.”
A Shift in Perspective
After weeks away from phones, emails, and meetings, both Isabel and Robert noticed a deeper change taking place. “My thoughts and inner dialogue slowed down a lot,” Robert says. “I was thinking more clearly, reconnecting with nature and the water. It took a few weeks to sink in, but I definitely noticed a big mental change.”
“I was feeling really stuck — just going to work, coming home, taking little trips here and there,” Isabel says. “I needed something to shake things up. This changed my whole perspective.”
“I know it’s hard to tell the average person, ‘Just quit your job for three months,’” Robert says. “But we planned and saved for a while. And fortunately our employers were supportive. It was worth it.”
Now back home in Mobile, the couple encourages others to pursue their own version of a sabbatical — whether on the water or somewhere else entirely.
“If you can swing it, you should do it,” Isabel says. “Even if it’s not sailing, there’s something really powerful about stepping away from routine. You come back different — more relaxed, more grateful.”
“We were lucky to have Lance’s help, and we started planning nearly a year out,” Robert says. “If you’re in Mobile or Baldwin County and want to learn how to sail, there are yacht clubs and forums where you can crew on someone else’s boat. That’s how a lot of people get started.”
With detailed planning, supportive families, and a little luck along the way, Robert and Isabel turned what was once a sailing daydream into a 10-week sailing sabbatical — one tide, island, and harbor at a time.
