Retirement on the road: Meet the couples who ditched comfy homes to sail the Caribbean – and former female sheriff’s deputy who traverses US in her RV ALONE

Some Americans dream of a quiet life in retirement, a chance to put their feet up after years of work and raising families.

But others instead take to the road and seas for a long-awaited adventure. 

Harry Weidman and Ann Stockton are one such couple who shared a nomadic dream – and who swapped bricks and mortar for a yacht to fulfil their fantasy. 

‘I knew this opportunity would be something I’d look back on and regret not seizing,’ Weidman, 63, told the Wall Street Journal. 

The former IT manager decided to buy a boat  after a day of deep-fishing at Somers Point in New Jersey. 

‘I noticed I felt most calm and serene when the shoreline drifted into the distance’ he recalled. 

Stockton, 60, sold her Florida condo in 2020 and Weidman liquidated $100,000 from an IRA to buy Whisper, a 40-foot catamaran, in the U.S. Virgin Islands. 

A friend gave the pair sailing lessons and they eventually set sail around the Mediterranean, snorkeling, eating out and hiking when in port. 

Harry Weidman and Ann Stockton. 63, and 60, are spending retirement sailing around the Mediterranean

The couple’s annual expenditure is $72,000, a large proportion of which is dedicated to maintenance of the three-bedroom two-bathroom vessel. 

‘Something is always breaking,’ Weidman told the Journal. 

Together, they earn about $6,800 a month, including $3,300 in monthly pension income and $2,000 from Weidman’s Social Security. The couple also has $730,000 in savings.

Stockton earns about $1,500 from personal training, website maintenance and bookkeeping.

They spend about $6,000 a month, paying around $540 for boat insurance and roughly $600 for groceries. 

Satellite internet and cellular-phone service cost $300; diesel, $100. Repairs average about $1,500 a month.

The couple also pays out-of-pocket for medical care, which they have found to be significantly less expensive in the Caribbean than in the U.S. 

Their favorite islands include Bequia in St. Vincent and the Grenadines, and Martinique. 

They have no plans to settle back down any time soon either, with Stockton suggesting they get an RV next. 

‘After this experience, buying a place in the U.S. doesn’t appeal to me,’ said Weidman. 

Years of retirement planning have allowed the Middletons to travel with their RV when they wish, they said. 

They have about $2 million in retirement savings, half of which is managed by John and the rest by an investment firm. About 95% of their savings is in stocks.

 Their home is paid off and they pay monthly credit-card bills in full. About half of their $10,000 monthly spending goes to expenses related to their 40-acre property, which they have no plans to sell. 

They receive about $4,500 a month in total from Social Security. 

Jenell Jones, 63, undertakes her adventures across the US solo.

Jenell Jones, 63, undertakes her adventures across the US solo

Jenell Jones, 63, undertakes her adventures across the US solo

retired sheriff's deputy, Jones explained that she sold her home in Texas and bought an RV 'because I wanted to get off the couch and have an adventure.'

retired sheriff’s deputy, Jones explained that she sold her home in Texas and bought an RV ‘because I wanted to get off the couch and have an adventure.’

Jones has become so passionate about life on the road that she now runs a club called the Wandering Individuals Network for 300 like-minded others

Jones has become so passionate about life on the road that she now runs a club called the Wandering Individuals Network for 300 like-minded others

She has forged friendships from the group, travelling to Canada, Arizona and California with members

She has forged friendships from the group, travelling to Canada, Arizona and California with members

Jones gets a roughly $7,000 monthly pension and has about $180,000 in savings

Jones gets a roughly $7,000 monthly pension and has about $180,000 in savings

Like Stockton and Weidman, Jones also plans to keep going for some years yet

Like Stockton and Weidman, Jones also plans to keep going for some years yet

A retired sheriff’s deputy, Jones explained that she sold her home in Texas and bought an RV ‘because I wanted to get off the couch and have an adventure.’

Jones has become so passionate about life on the road that she now runs a club called the Wandering Individuals Network for 300 like-minded others. 

She has forged friendships from the group, travelling to Canada, Arizona and California with members. 

Jones gets a roughly $7,000 monthly pension and has about $180,000 in savings. 

She spends close to $2,500 a month, almost half of which goes toward fuel for her 36-foot Tiffin Open Road RV and the Nissan compact car she tows behind it.

Like Stockton and Weidman, Jones also plans to keep going for some years yet. 

‘I’m just getting started,’  she told the journal. 

Norma and Mike Schufler, 73, and 75, are currently enjoying life sailing around the US Virgin Islands on their 35-foot boat, Minor Indulgence.

The boat, bought for $139,000 in 2006, sleeps six and has a shower with hot water that works when the engine is running. 

Norma, 73, who retired from full-time teaching in 2007, said it is ‘like a floating RV’.

The saying goes: ‘Buy a boat and spend the rest of your life fixing it in exotic locales,’ said Mike, 75, who is a retired horse-racing trainer from Chicago.   

The couple, who has owned boats since the 1980s now spend their time in and around the Virgin Islands and Puerto Rico from December to late May, often visiting remote spots.

On board, Norma reads and cooks. Mike, a certified scuba diver, often uses those skills to clean the bottom of the boat. 

The couple’s annual income is close to $125,000, a combination of Norma’s pension, Mike’s Social Security check, and mandatory distributions from their IRAs. 

They have about $500,000 in retirement accounts, and their home in New Lenox, Ill., is worth about $360,000. 

Norma and Mike Schufler, 73, and 75, are currently enjoying life sailing around the US Virgin Islands on their 35-foot boat, Minor Indulgence

Norma and Mike Schufler, 73, and 75, are currently enjoying life sailing around the US Virgin Islands on their 35-foot boat, Minor Indulgence

The Schulfers are scheduled to pay off their 2.75% mortgage, which costs $900 a month, in five years.

They pay nearly $8,000 in yearly property taxes, and home and car insurance total $2,600. The annual cost to insure the boat, which was severely damaged by Hurricane Irma in 2017, is $2,000. Maintenance, fuel and a spot at a marina run about $13,000 a year.

Medicare covers them in the U.S. Virgin Islands and Puerto Rico.

The couple, who has also chartered sailboats on vacations in Greece, Croatia and Tahiti, plans to keep exploring.

‘I’m not ready to swallow the anchor yet,’ said Mike.

Another couple who have opted to hit the road in retirement are Peggy and John Middleton, 68, and 70 respectively.

Around 20 years ago Peggy’s parents offered her their 1968 Airstream Globetrotter, which the pair happily accepted. 

‘We took one big trip through Nova Scotia and Prince Edward Island in 2004 and then it gathered dust in the backyard for many years,’ John said.

The couple, both retired nurses, began a a three-month, 14,000-mile journey through Canada and Alaska in May. 

The trip has cost about $15,000 in fuel, campgrounds, groceries and sightseeing excursions.

The pair mostly doesn’t plan too far in advance, enjoying the spontaneity of life on the road. 

‘That’s the beauty of being retired and traveling around in an RV. If you find a place you like, you can just stay a few more days,’ said Peggy.

The couple’s next adventure will be to tour Western Europe in a rented RV and spend time with their daughter and son-in-law who live in Munich.

‘To paraphrase Neil Young, we’d rather burn out than rust,’ said Peggy.

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