When a Retirement Home Is a Boat in the Caribbean

Two years ago, Harry Weidman and his partner, Ann Stockton, were visiting the U.S. Virgin Islands, where they were thinking about buying a condo. A friend they were sailing with suggested they buy a boat instead. “He lit a dormant fuse. I couldn’t sleep that night, wondering, could I possibly pull this off?” says Weidman, 62.

For years, he had sailed on other people’s boats and dreamed of living on one. He felt happiest and most serene on the water, especially once land had disappeared from view. Neither Weidman nor Stockton had ever owned a boat, let alone a sailing vessel, but taking a leap of faith, they bought Whisper, a 40-foot catamaran.

Now, Weidman and Stockton, 60, are living the dream. Whisper is home while they spend the next three years of the five they’ve allotted for exploring the Caribbean. “We’re in different places all the time,” he says.

Along with exploring each island’s culture and meeting people from around the world, Weidman and Stockton swim and snorkel every day, marveling at beautiful sunrises and sunsets, the latter with a sundowner cocktail in hand. Stockton loves sleeping while the boat gently rocks. She has woken in the wee hours to bright moonlight streaming through an open hatch overhead.

Their nomadic lifestyle promises freedom and adventure, trades one set of costs for another, requires certain skills and temperament, and gives new meaning to downsizing. After moving out of their New Jersey apartment in early November 2020, the couple filled a 10-by-20-foot storage unit with their belongings and sold Weidman’s car and a vacation-rental home of Stockton’s in Florida. They moved aboard Whisper and its roughly 1,000 square feet of living space with three bags and two backpacks.

Compact Living

Weidman and Stockton live in one of Whisper’s two hulls, where they share a cabin and a full-size bathroom. Stockton gets the boat’s only closet, a space just 2 feet wide and 3½ feet high. The other hull has two small guest cabins and another bathroom. Their “onebutt” kitchen features a propane stove with two burners and an oven just big enough to accommodate a 9-by-13-inch pan. The small refrigerator runs off batteries, and because its freezer doesn’t really freeze, the couple stores their cheese in it. There’s no microwave, dishwasher or washing machine, and a table with bench seating usually gets passed over because Weidman and Stockton mostly eat on deck.

Every bit of space is used, and organization is key. Through one of the guest cabins there is access to the “garage,” a storage area where a chest freezer is kept. All storage bins are labeled, and Stockton keeps a list of where everything is. In one of the bench seats are canned goods with the tops labeled for easier identification.

Whisper has two sails and two 29-horsepower diesel engines. When the couple took possession, they spent 10 days getting to know the boat. Initially skittish about sailing, they motored about until they befriended a sailing instructor who taught them the basics and put them through their paces. “At first, our course looked like an echocardiogram. We went back and forth without making much forward progress,” says Weidman. One advantage of sailing in the Caribbean, he says, is having room to set various courses and play with setting and trimming the sails.

Mother Nature provides most of their energy and water free of charge. Although the boat has a generator, the couple primarily relies on solar energy and storage batteries. A reverse osmosis system desalinizes sea water to make it potable at a rate of up to 20 liters per hour, and they can store up to 550 liters. To conserve, they take “navy showers,” which consist of getting wet, turning off the water, soaping up, shampooing, and rinsing quickly. Open windows and a sea breeze substitute for air conditioning, but the humidity is their nemesis, requiring even unworn clothing to be washed periodically to stop it from mildewing. They do most of their laundry by hand but visit laundromats on land for washing sheets and towels.

An Acronym for ‘Bust Out Another Thousand’

Weidman paid $218,000 in cash from his retirement funds for Whisper. The couple couldn’t find financing because of the boat’s age (it was built in 2005) but had the boat inspected for insurance and peace of mind. They blew through at least $10,000 in the first few months for repairs and replacements. “Boat is an acronym for ‘bust out another thousand,'” says Weidman.

Their 2021 living expenses totaled $62,240, with nearly half going toward boat-related costs such as maintenance, insurance, electronic navigation, weather reports, fuel, mooring and customs fees, and their Boat U.S. membership, the seafaring equivalent of AAA’s roadside assistance. Boat insurance, alone, costs them $5,612 annually. Their policy, purchased through a yacht insurance brokerage in Florida, provides $250,000 of hull insurance and $1 million in liability, among other coverage. They’re insured in the Caribbean Sea and when they navigate in waters of the U.S. Virgin Islands and British Virgin Islands, but not Cuba, mainland Columbia, Venezuela and Haiti. The policy also excludes coverage for hurricanes north of 12 degrees latitude between July 1 and Oct. 31. During those months, the couple heads south to Grenada or Trinidad and Tobago, where their insurance will still cover them and hurricanes are less likely.

Whenever possible, they avoid docking Whisper at marinas, which charge by the foot of boat length. They typically anchor wherever they like for free, but while visiting St. John’s, much of which belongs to the Virgin Islands National Park, they must pay to tie up to mooring balls, because anchors tend to dig up the ocean bottom. Since Weidman qualified for his National Park Senior Pass and Federal Recreational Lands Pass, the cost to tie up to these buoys is half of the usual $26 per night.

Although diesel fuel spiked to $8 per gallon at the beginning of the Russia-Ukraine war, the price has since fallen to about $6 per gallon as of this writing. The couple typically fills up every six months at a cost of about $650.

The rest of their annual living expenses are mostly for groceries, Wi-Fi and phone service, dining out and activities, including excursions and Stockton’s certification in scuba diving. They manage their finances remotely and use stateside addresses (a sister’s in his case, a friend’s in hers) for conducting their personal business. He takes Social Security and draws income from retirement accounts he accumulated during his career as an information technology professional. Stockton, who sold her personal-training business, still teaches a few clients via Google Meet three days a week. The couple primarily use their credit cards but sometimes withdraw local currency from ATMs to pay local vendors who accept cash only.

For now, neither one of them has health insurance. Stockton says they couldn’t find an affordable plan that would cover them wherever they might be. If they have a health emergency, they will pay out of pocket for care, and if the situation is serious, they will fly to the States for treatment.

Challenges, Ahoy!

Living in the Caribbean isn’t all rainbows and unicorns, says Weidman. Everything is more expensive because it’s imported. “It would be cheaper for you to put rum on your Cheerios than milk,” says Stockton. When friends and family visit and ask what they can bring along, she asks for coffee.

Stores have limited inventory and run out of certain items, like peanut butter and Diet Coke. The couple sometimes visit three stores to get everything they need. Produce often isn’t high quality and needs to be cooked or frozen quickly. “You can’t say, ‘I’ll make this tonight.’ Instead, you go to the store, see what they have and make that tonight,” says Stockton.

Whenever they visit a Cost-U-Less, a chain of local warehouse stores, they stock up on meat and dairy, for which they pay a premium, and load up the freezer. Rather than risk ice cream melting when they carry it back to the boat in an insulated backpack, they splurge and eat it at ice cream shops. To avoid bringing cockroaches on board, they remove all their supplies from packaging before loading them onto a tender and then aboard Whisper.

When they initially explored the boat’s storage lockers, they wondered why the previous owners had kept so much junk. But the couple quickly realized that when they needed something, they couldn’t just run to Home Depot. Marine stores near the water charge three times the price for the convenience of a walkable location. So they keep anything that might prove useful in a pinch — a strip of Velcro, a length of rope, an old valve, even glass jars.

“Island time” is real. Businesses and government offices may close unexpectedly. And, at first, finding a reliable technician — one who completed the job when promised and didn’t overcharge — was challenging. The couple eventually met other boaters who have “walked in our flip-flops” and could provide trustworthy referrals, says Weidman, whose many do-it-yourself skills have paid off in spades.

The lifestyle is transient. While spending hurricane season in Grenada in 2021, the couple made good friends. “We hung out with them nearly every day for three months, and then — they’re gone!” Stockton says. “It’s hard to get used to that.” Coordinating visits from stateside friends and family is difficult, because the couple often doesn’t know where they will be from one day to the next, and meanwhile, their guests need to make reservations.

Weidman and Stockton also can’t go home on a whim together. Even if they could afford to leave Whisper in a marina, they would need to reserve a spot well in advance. It would be risky to leave the boat unattended on anchor or a mooring ball.

Living together in such close quarters, sometimes under trying conditions, can test any relationship. Early on, the couple sailed in 8-to-12-foot seas between St. Martin and St. John. The trip should have taken 24 hours but lasted more than 40. “They were hard hours, and it was hell,” says Weidman. “I thought Ann was going to leave me.” He doesn’t take it personally if she wants to walk on the beach alone without him. “When you’re living on a 40-foot catamaran with the same person 24/7, it gets a bit tough to find private space,” he says. They’ve known boat owners who quickly sold their boats or put them out for charter because one partner was miserable.

Experienced boaters are more likely to succeed at this way of life, Weidman and Stockton say. “Being new, we learned a lot the hard way,” says Weidman. The couple suggests renting a boat for a month before taking the plunge, but they have no regrets. In fact, they’re considering extending their five-year Caribbean adventure to sail around the world. “Twenty years from now, you regret the things you didn’t do more than the things you did. I would have regretted it the rest of my life if I didn’t take the chance to buy this boat,” says Weidman.

Getting Started

The boating life comes in many forms. Besides sailboats, many retirees live on power boats and cruise inland, intercoastal and coastal waterways in the U.S. Anyone considering a partial or long-term retirement on a boat can find out more information from boat owner associations such as the America’s Great Loop Cruisers’ Association  and the Marine Trawler Owners Association.

To find boats for sale by owners or brokers, check association websites as well as other sites, such as boattraderboatquest and yachtworld, that feature classified ads.

To find financing, ask a boat broker or dealer for a referral or check the member directory of the National Association of Marine Lenders.

The U.S. Coast Guard Auxiliary offers a variety of courses, from fundamentals to advanced skills, for power boaters and sailors. Courses can be virtual or in the classroom. Many are offered for less than $100. The American Sailing Association has classes online, ranging in price from $15 to $160, and at more than 300 affiliated sailing schools across the U.S. and popular sailing locales internationally. In the U.S., ASA classes in person may run several hundred dollars.


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