Take to the Seas for a Retirement of Freedom, Adventure, and Close Community

"There’s not much in life that can match the thrill of sailing into the Guna Yala islands (off the north coast of Panama) for the first time. Anchoring in crystal-clear water behind islands with thatched huts, while molaclad Guna women paddled their ulus out to greet us and show us their handiwork.”

For Tom and Julie Bennett, experiences like this one aren’t uncommon. They have been living a cruising retirement for over two decades, exploring the world from the deck of their sailing boat Gris-Gris. They can go wherever they want, whenever they want…and they take their “home” with them everywhere they go.

“The cruising life gives us the ability to sail to exciting and exotic destinations. We love having the freedom to sail where we want, on our own schedule, and make our own adventures,” says Julie.

There’s something very appealing about the idea of living aboard a sailboat.

Cruising the world’s oceans in search of new experiences, exploring new cultures, and meeting people you might never have had the chance to meet if you traveled the world by plane. It’s the ultimate roving retirement.

Rob and Lauren Dehaan’s life on the Southern Comfort has taken them around the globe. ©ROB AND LAUREN DEHAAN
Rob and Lauren Dehaan’s life on the Southern Comfort has taken them around the globe. ©ROB AND LAUREN DEHAAN

For Rob and Lauren Dehaan, the plan wasn’t necessarily to live on a boat. “Sailing was a way for us to travel to destinations we wanted to reach and to have our things with us and be comfortable where we were,” Lauren says.

Rob adds, “While you can travel by plane, a boat gives you that independence, and you can get to places that most people can’t go to. And because the boat essentially becomes a house, with its ability to provide everything you need for day-to-day living, like water and electricity, you have that freedom.” The promise of adventure, and the nearby shore.”The freedom to make our own adventures.For Rob and Lauren, it’s not always the location that leaves a lasting impression… but the people they meet there. “For us, the place we found most fascinating was French Polynesia,” Rob says. “But not just for the blue waters, and palm trees, and the glittering white-sand beaches. It was the harmonious nature of the people that stuck with us.

“On a visit to one particular atoll, near Tahiti, we walked around a local village and after about half an hour a woman came out of her house. She approached us and put three black pearls into Lauren’s hand and said, ‘Thank you for coming to visit our island.’ It’s experiences like that one, or being able to help the locals, or have them help you fix an outboard or whatever, that makes this life so special.”

Getting Started

Before they retired in 2002, Tom and Julie both had enjoyed successful careers in New Orleans—Tom as a bar and music-club owner and Julie as a petroleum engineer/landman for a multinational oil corporation. “But for fun, we had boats and sailed and fished for years around the south eastern Louisiana area, which is known for those recreational delights,” Tom recalls.

Spending a few days on a boat and living on a boat for long periods of time are two very different things. To get a feel for what that might be like, the Bennetts took part in several sailing races across the Gulf of Mexico to Isla Mujeres and also spent some time sailing farther along the Yucatán before returning home. “That allowed us to get an idea of what living aboard and cruising was like,” says Julie, “and we were positively influenced by other sailors we met along the way who were already ‘living the dream.’ It also helped us gain confidence in our ability to handle the open-water as well as to hone our navigational, anchoring, maintenance and other skills while having fun in gorgeous places.”

As with any good retirement plan, research is essential. While Tom and Julie test-drove life on a boat with their recreational sailing, they also started working on what they called “The 5-Year Plan” to get themselves ready for a full-time life on the seas.Living on a yacht is a fraction of the cost on land.“We became armchair sailors and gobbled up everything we could read about the life and boating. We also took courses in local yacht clubs and coastguard organizations to beef up on safety and enhance our navigation and other skills. Finding and equipping the right boat occupied us while we scheduled our early retirements, set up our finances, and sold off the house and our cars.” Rob, by contrast, has been sailing for most of his life. A teacher for 20 years, he also worked as a sailor and traveled the world, mostly by boat. On a trip to the U.S., Rob met his wife, Lauren, “the Queen of Florida,” as he calls her. “I had to wait until Lauren retired before we could set sail again,” Rob says. But once she did, the couple were off. In 2009, they set sail for the Caribbean, then went onto Panama, through the South Pacific, until they arrived in Australia, where they’ve been based since 2018, living aboard Southern Comfort.

Rob says one of the most important aspects of getting ready to live on a boat is to get the right vessel. After all, it will become your home. As Rob puts it, “The boat has to be in good order because your life literally depends on it. You can buy a bad house that might fall down or get damaged in a storm, but it probably won’t hurt you. Being on the ocean (a sometimes unpredictable place), a bad boat is not what you want. It has to be fully functional. But there are so many good boats out there for sale.”

Your boat will also be your biggest outlay when starting out. Rob says this can often put people off the idea of living on a sailboat. And there is a common misconception that life on a yacht is prohibitively expensive. But these sailing retirees don’t think that’s the case…

The Cost of Living on a Boat

Even after 20 years living on their sailboat, life is still an adventure for Tom and Julie Bennett. ©Tom and Julie Bennett
Even after 20 years living on their sailboat, life is still an adventure for Tom and Julie Bennett. ©Tom and Julie Bennett

Like with any retirement, your cost of living will depend on a lot of different, and personal, factors. “It’s difficult to pin down a consistent budget for someone to follow because not only does every cruiser have different lifestyle priorities and needs, but where you are cruising and what kind of boat you’re on has a huge impact on your budget,” says Julie. “You have maintenance and marina costs and health and boat insurance are big factors that everyone has to consider too. And it’s important to include allowances for airfares and travel expenses depending on how much time you will spend away from the boat. All that being said, cruising can be as expensive or inexpensive as you want, and we see plenty of folks out here doing it on both ends of the spectrum.”

“Living on a yacht is a fraction of what it would cost us to live on land,” says Rob of his and Lauren’s lifestyle. “For us, that’s probably because you have less choice on a boat. If everything is functioning, you have virtually no overheads. Food and fuel costs are our main expenses when we’re living on the boat. We make our own water and have solar panels for power—so in essence we are living entirely off the grid. Obviously, you’ll spend on whatever you’ve got to have, but when it comes to actually living on the boat, we spend about $800 to $1,000 a month.

Rob says that there are other costs outside of day-to-day living expenses that you have to consider—like maintenance—and they recently bought the Starlink satellite system, which costs $120 a month. “It’ll give us unlimited internet when we need it,” Rob explains, “but we can also stall it, when we don’t need it.”

Sophie Darsy, who sails the world with her partner Ryan Ellison, says that your location has a huge impact on your budget. “Our monthly expenses vary wildly based on where we sail,” she says. “On average, we live on about $3,500 month, which is less than we spent when we had an apartment on land.”

Sailing Practicalities…Your Questions Answered

Kathleen Evans

After a recent stop in Burmuda, Sophie and Ryan are continuing their sailing adventures and heading north, to Canada. ©KENWIEDEMANN/iStock
After a recent stop in Burmuda, Sophie and Ryan are continuing their sailing adventures and heading north, to Canada. ©KENWIEDEMANN/iStock

What does it take to prepare for a life sailing the high seas? Even if you don’t have experience, your dream can become a reality. Ryan Ellison and Sophie Darsy share their story of how to prepare for such a lifestyle. “In 2015, Ryan randomly came up with the idea of quitting our corporate jobs, buying a boat and leaving our hometown of Stockholm to travel the world by sea after he read an article about a couple who had done the same thing,” says Sophie. “We were not sailors and were not in the financial position to buy a yacht. The idea that we could make it work felt nearly impossible, as neither of our jobs translated to remote work, and we had no idea how to sail a boat.” In the seven years since, Sophie and Ryan have become sailing experts. They’ve sailed the world, and they are creating an extensive online course with video lessons to help people do what they did (see: ryanandsophie.com). Here, they answer some of the common questions they get about living on a sailboat.

Do I need a license to sail a boat?

“Technically, no one needs a license or accreditations to sail the world. But you will most likely need it for insurance or to register your boat. The two internationally recognized standards are the ICC (International Certificate of Competency), which is distributed by the Royal Yachting Association (see: rya.org.uk) upon completion of the Day Skipper course, and the IPC (International Proficiency Certificate), which is delivered by the American Sailing Association (see: asa. com).

“For the RYA Skipper course, you learn not only how to handle a boat, but also how to budget, how to downsize efficiently, how to cook in a galley, not to mention all the mechanical skills that need to be mastered in order to maintain and repair the boat when it breaks and you are at sea.”

How much will a boat cost?

“On average, you can purchase a seaworthy, mid-range, 45-foot monohull for $100,000 to $150,000 and a catamaran of the same size for around $250,000 to $500,000. Add to that the $1,000 cost of having the boat surveyed and the cost of transporting. Insurance costs between 1.5% and 3.5% of the hull value annually.

What insurance will I need?

“As a sailboat owner, you need at least to have liability and salvage insurance. We have insurance that covers our boat and our belongings based on where we sail. And we have healthcare insurance and travel insurance, too.”

What resource would you recommend for getting started?

“Our favorite book to get started was Beth Leonard’s The Voyager’s Handbook, which covers most aspects of getting ready for a sailing voyage.” (You’ll find it on Amazon. com)

Ryan and Sophie say that this sort of lifestyle takes an abundance of due diligence, research, and some perseverance. But they both agree, “Don’t give up when it’s hard. We are so incredibly grateful about how much of the world we have gotten to experience with memories we will forever treasure.”

Day-to-Day Life on a Sailboat

While life on a boat can be full of adventure and fun, it can also be surprisingly “normal.” As Rob points out, about 95% of your time is spent “on anchor” (that is, docked somewhere) and the rest of the time is spent getting to your next destination. “Once the anchor is set, and the sails are put away, we lead a relatively normal life,” he says. “Our morning begins with coffee when the sun is rising and then we set off and walk or take the local bus into the nearest town and go to the grocery store, do laundry, find a hardware store, that kind of thing. You kind of become integrated into local life very quickly.” Tom and Julie have a similar routine. “We wake up in the morning in time to get our coffee and tune in to local SSB (Single Sideband) radio that people take turns hosting,” says Tom. “It allows cruisers to check-in and tell each other where they are and what’s happening and to offer assistance or stuff for trading or to ask for help. It also gives us a chance to share weather forecasts and report any emergencies. This information often helps us to plan passages to other places and maybe even hook up with a buddy boat for longer sails.

“After that, we usually spend the morning doing chores or maintenance, including making fresh water to fill the tank, or doing laundry or replacing/ repairing faulty equipment, scrubbing the waterline. After lunch and maybe a nap, we spend the afternoon fishing or snorkeling. Often we’ll get together on each other’s boats for dinner or happy hour or maybe a game of bocce ball on a nearby island.”

Julie does concede, though, that what seems routine for them is quite different than for those with more “conventional” lifestyles. “Like at night, one of us always sleeps with one eye/ear open because at anchor on the water, things can change in a flash,” she explains. “The heaviest squalls seem to come through in the dark and it gets exciting when the wind switches suddenly in an anchorage and boats start to drag! And there have been plenty of times we’re up at 4 a.m. getting drenched in the cockpit, standing at the helm making sure we stay safe.

“But the other side of that is we often take showers off the back of our boat after our afternoon snorkel while watching the ospreys return from their hunting and seeing giant sea turtles who surface nearby. Not your normal grooming routine if you’re a landlubber.” good for the soul!”

But no matter how healthy you are, there will be times when you’ll need the services of a doctor or dentist or other healthcare professional. Rob says, “In all my years of sailing, I have always found that if you need medical care, you’ll find it…especially outside of the U.S. Thankfully we haven’t had any major medical incidents while sailing but for any minor issues, we have paid out of pocket. In lots of places we’ve been to, health clinics have been free for minor ailments.”

Lauren adds, “When we were in Panama, we had some medical issues that needed to be dealt with and we were able to get what we needed and we just paid for it ourselves…but it came at a very reasonable cost.”

Tom and Julie, too, pay for any medical expenses out of pocket. “Before our Medicare coverage kicked in, we paid high premiums for policies that had international clauses,” Julie explains. “Over time, we realized we were paying less out of pocket for healthcare wherever we happened to be, so that’s the way we went and just kept a catastrophic policy.”

A Tight-Knit Cruising Community

Your sailing adventures can start close to home...Mexico’s Isla Mujeres is a popular spot for sailors. © THIAGO SANTOS/iStock
Your sailing adventures can start close to home...Mexico’s Isla Mujeres is a popular spot for sailors. © THIAGO SANTOS/iStock

Talking with the Bennetts and the Dehaans about their sailing retirements, one thing jumps out: the strong sense of community and camaraderie that exists among those who live on the world’s oceans. They all agree: a big part of the fun and adventure of this kind of life is because of the like-minded folks you meet along the way.

“There’s no denying that, in spite of the exotic and wonderful places, the best part is really the other cruisers and locals we’ve met and continue to call our friends,” says Julie. By all accounts, fellow cruisers are always ready and willing to help each other out, and there’s a generosity within this global community, with everyone sharing spare parts and supplies when others need them. “The fact that we depend on one another builds a comforting camaraderie within our cruising community that we really like,” Julie adds. “Working together makes it even more fun in those times when we can play together. And our life provides lots of opportunity for that.”

On a much more personal level, Rob points out that if you’re taking your significant other with you on a sailing adventure, it’s important that you’re both “on board” with this way of life. Life on a sailboat is very much a team effort. “When you’re with your partner on a boat, you are with that person, literally, 24/7,” Rob says. “There is not a moment when you’re not both an integral part of this experience. You have to be so attuned to each other in every way in order to make it work. But it’s the making of an incredible bond, because you share such amazing experiences.”

Proven Resources To Jump-StartYour Sailing Adventure

The internet is full of websites that will help you plan your sailing retirement. But with so much out there, we asked our sailing retirees what they’d suggest. They seconded , which Ryan and Sophie mentioned, and, in addition, share these five recommendations: Noonsite: noonsite.com. Rob Dehaan says this is the ultimate resource for anyone interested in a sailing retirement. It’s got tons of information from cruising resources to ports of entry in countries around the world, routing info and lots more. There’s a section of recommended books, broken down by topic, and their section on visas is also useful as entering a country by sailboat can come with different requirements than if you enter by plane.

YouTube: youtube.com. It seems like an obvious one, but Tom Bennett says videos he has found on here have helped them out when they have found themselves with a maintenance issue but not near an expert repair service.

American Sailing Association: asa.com. This website is cleverly organized by skill level: Beginner, Intermediate, and Advanced. Each section has info and resources, like online webinars and courses, each geared for different stages.

America’s Boating Club: americasboatingclub. org. With clubs all around the U.S., America’s Boating Club also offers sailing lessons and courses to help you prepare for life on a sailboat. They also have a lot of free information about getting started on the website.

Royal Yachting Association: rya.org. uk. A U.K.-based organization, the RYA website has a lot of useful information if you’ll be spending some time around the U.K., but it also has more general tips and advice, as well as offering captain’s courses and courses in navigation and seamanship.

The Rewards Outweigh the Challenges

As with any retirement, anywhere in the world, there are challenges that come with living on a boat. Tom says, “Certainly, dealing with mechanical, electrical and other boat repairs and issues that crop up all the time in remote places where there are no parts stores or expert repair services has taught us how to troubleshoot and fix things on the fly. Lately, we can be thankful for YouTube and the ability to tap into the wealth of advice and information that’s available on the internet.”

For Rob and Lauren, there are times when the inclement weather can take its toll. “For the most part, we love living on our boat,” says Rob, “but I do hate when we run into bad weather, particularly when you’ve done your best to find a suitable bay to shelter and ride it out, and it goes on for days. It can get weary…but then, nothing lasts forever.”

But both couples agree that deciding to spend their retirement sailing around the world has been the best decision they have ever made. “We can truly say that we’re extremely satisfied to have chosen to retire and live and cruise aboard our sailboat,” says Julie. “If you’re thinking about giving this lifestyle a try, we would encourage you not to wait.”

The Dehaans agree. “Do it now. Don’t wait,” advises Lauren. “When we can do things like visit Easter Island for a week on a whim (we flew there while on anchor in Tahiti) and learn all about those amazing statues, talk to the locals about the incredible archaeology their home is so famous for, and experience the history of such a fascinating place, why would we want to live any other way?” Rob adds.

Test Drive Life On Board: Sail Panama's Pacific CoastWith An Expat Captain

Peaceful, beautiful, and not a hotel chain in sight on Panama’s Guna Yala islands. © DIEGOCARDINI/iStock
Peaceful, beautiful, and not a hotel chain in sight on Panama’s Guna Yala islands. © DIEGOCARDINI/iStock

Fred Ebers says the sea has always been in his blood. He first started sailing in high school when he helped his uncle on a U.S. Power Squadron cruise from New York City, up the Hudson River and canals, into Lake Champlain in upstate New York. As a former Merchant Marine ships’ officer, a marine surveyor, and a maritime industry executive, Fred has lived all over the world: the Middle East, Italy, Korea, Japan. Today, he calls Panama home. And it’s from here that Fred has taken his love of all things sailing to another level.

“Sailboats have always been recreational for me,’ says Fred, “although down through the years I did live aboard for months at a time while sailing in different parts of the world.” These days, Fred has a 48-foot sailing catamaran, Zenith, which he keeps in the Linton Bay Marina, near Portobelo, on Panama’s Pacific Coast.

From his home in Anton, in the district of Cocle, about two hours west of Panama City, Fred operates his charter sailing business (see: cruisesanblas.com). This gives him the opportunity to spend time on the water—you can book a three- to seven-day trip with him on the Zenith—and then he returns home for his creature comforts. “Living on a boat full-time is not for everyone,” Fred says. “Space is tight, possessions are few, and you risk boredom if you stay in one place for too long. I choose to live both ashore and aboard my boat—it’s the perfect combination for me.” Fred offers tours around Guna Yala (formerly the San Blas islands) on the Zenith. This archipelago of over 300 islands (only about 40 are inhabited) is an indigenous reserve governed by the Guna tribespeople. “I first discovered the islands when sailing from Colombia to Panama,” says Fred. “I passed through San Blas and was amazed by the natural state of this archipelago. I found hundreds of islands with palm trees, white sand, coral reefs, shells, starfish, and crystalclear water. Development is prohibited, so there are no concrete hotels or tiled swimming pools.” It’s the perfect place for a laidback sailing adventure.

Fred offers a 5-star experience. His boat has air conditioning, a state-of-the art sound system, kayaks, paddleboards, snorkeling gear, fishing equipment, yoga mats, a hammock, beach mats, a barbecue and a large adult beverage selection for extra fun. “San Blas is a fun vacation spot,” says Fred. “It combines absolutely undeveloped, idyllic islands with adventure and relaxation.”

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