How do we untie the lines that bind us? Family, jobs, homes, schools, pets, friends… our lives are built on the myriad of small connections and huge decisions that we have made over a lifetime.

Appealing though it is to dream of handing in your notice, locking up the house and sailing off into the sunset, the reality is that it can take a daunting amount of planning and organisation to disentangle our land-based routines.

There is no ‘right’ time to go – there are cruisers who have enjoyed bluewater adventuring with a newborn baby, others who’ve waited until their 70s and plenty of others who found their life circumstances changed dramatically but their sailing plans could be adapted to carry on.

We spoke to those who have made the move to liveaboard or long-haul cruising to find out why they chose to go when they did, and what lessons they’d pass on to anyone thinking of making the leap.

The boomers

When Kathleen Casey-Kirschling was born at 0001hr on 1st January 1946 in Pennsylvania, she became the USA’s very first baby boomer, the first of the generation that would redefine ‘retirement’.

It’s no surprise that when she and her husband chose to retire they did so aboard a yacht (albeit a motoryacht, their Grand Banks 42). It was named First Boomer.

The post-war generation who were born between 1946-64, are now in their mid-50s to early-70s, and statistically healthier, wealthier and more active than any previous generation, so in the best position to enjoy long-haul cruising.

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For many third age cruisers their yacht is the reward for four decades of working at a successful career or business. Final salary pension schemes – and, in the UK, tax changes which allowed lump sums to be drawn from pension funds without penalty since 2015 – have enabled many to bolster their income to contend with the costs of a bluewater trip.

It is not entirely straightforward for those in their 50s and 60s: elderly parents, ‘boomerang’ children who’ve returned to the family home, and new grandchildren are often emotive pulls back to shore. The increased expense of travel and health insurance for over-65s can be an added complication.

But there are many who have made it work, and for whom retirement afloat signals the best years of their lives. “They say that the time to reef is when you first think of it, but unless you have unlimited resources, casting off the lines is seldom that simple.

“For Terry and me, it started as an impossible dream, crashed on the rocks of various recessions and slowly morphed into a plan and then reality,” recalls Alan Ryall, who has been sailing with his wife, Terry, since 2013. Both are in their mid-60s.

Having owned boats for 25 years, the Ryalls bought their Island Packet 465, Seminole Wind, in 2011 with the specific aim of bluewater voyaging. After completing Yachtmaster, first aid and survival training, and a full year of shakedown cruising, they sailed across the Atlantic in 2013.

The couple initially tried downsizing from working full-time to part-time, “so we could try and get the best of both worlds,” recalls Alan. “It failed miserably.”

“We hauled out in Antigua where I jumped straight on to a flight to Singapore in time to run a major conference. We were constantly finding a place to leave the boat and it was just frustrating.

“We came back once to find a major lightning strike had caused over $70,000 damage because work pressure meant she had been left in Florida in the storm season, fortunately with the permission of our insurers.”

A health scare made them reassess. “We took a knife to the lines and left work behind for good,” Alan explains. “Our house in London was sold and we bought a smaller apartment to rent, so we had no emotional attachment to it.”

Possessions were dealt with ruthlessly. “They fell into two categories: a small pile of must-keeps and a large pile of dispose of (give to family, charity shop or sell). I can’t even remember what we disposed of so we didn’t need it – it was a cathartic experience.”

Other attachments were harder to break. “For a while we both had elderly and infirm mothers and so we flew home on a regular basis to share the load. We lost both of them within a year and it taught us that we always need a reserve fund to get us home in an emergency,” says Alan.

The trickiest thing for the Ryalls was finding the right moment to shift from working life to liveaboard life. “We had a clear financial plan that was originally over 10 years, but got stretched due to recessions and life getting in the way.

“We decided to wait until we were financially sound rather than going early and having to face going back to the workplace.”

Was it the right time for them? “For us the financial security and the achievement of many of our life’s goals means that this is a new phase rather than a temporary phase.

“We are very lucky. We have the health, vitality and financial resources to embrace our new life. It could so easily be different and so I’d say, when the time feels right, do it. Don’t wait for absolute certainty.”

The home schoolers

Taking your children on a family bluewater adventure is a dream for many – turning off social media and exam pressure, and exposing them to different cultures and hands-on experiences instead has huge appeal.

But picking the right moment in between critical school years can be a challenge. While some families do cruise successfully with toddlers and teenagers, for most there is a ‘sweet spot’ that makes primary school age the ideal time to go.

The Steventon family set off from the Isle of Wight last July. Tom and Philippa are sailing with their sons Stan and Ted, aged eight and six, aboard their Bowman 40, Bella.

“We had actually attempted to leave once before when Stan was 11 weeks old,” recalls Philippa. “We did a ‘gentle’ shakedown cruise to the Outer Hebrides and back, and then thought better of the whole idea. For us, it was just too hard work with a newborn.

“After Ted arrived we moved ashore for a few years. We did quite a bit of research into when would be the best time for us to take the boys out of school without disturbing their education too much – although we do believe the whole experience will enhance their education rather than disrupt it.

“The salient points for us were that the boys were able to read, write and swim before we left. We also wanted them to be old enough to remember this experience when they are older and be part of it as much as possible.”

The family have planned to cruise for two years initially, spending the first year in Europe before crossing the Atlantic to the Caribbean. “From there we will make a decision as a family as to what we do after that,” Philippa explains. They have timed their trip so they can return before their eldest enrols in secondary school, or continue to home educate.

After a summer off, Tom and Philippa started ‘boat school’ in September so the boys began lessons at the same time as their friends back home. “We try and do four 45-minute lessons a day and split them between us,” explains Philippa.

“We are trying to make school as related to what we are doing as possible. We are also trying to follow the boys’ interests, and map the UK national curriculum to them.

“Before we left, boat school was the bit that I was most daunted about. But, dare I say it, it’s actually been quite fun. Not least because, by splitting the teaching between Tom and me, we are both guaranteed a bit of child-free time each day. That’s important for everyone’s sanity!”

Keeping the family home is an additional complication for those wanting to retain a base. “Fortunately, we managed to rent our house out to good friends which meant that we could leave quite a bit of furniture in the house. The rest of our possessions we either gave away, sold or put in storage.”

Without the cash injection of a house sale, family cruising can depend on rental income and what Philippa describes as “some serious belt tightening.”

One of the most positive surprises the Steventons have found is that, although they have sailed as a family since the boys were babies, liveaboard life is a different rhythm to enjoy.

“We’ve actually learned to cruise. In recent years summer holidays have been hammering it to either France, the Channel Islands or Devon, where we collapse in a heap for a week or two before hammering back home again.

“This summer we did the odd longer passage but we finally seem to have learned how to do smaller coastal hops of a few hours every day or two, drop the hook, have a swim and a look around and move on again.”

The solo skipper

Donald Begg had always dreamed of sailing around the world on his Bowman 48 Lydia: “My problem is that my wife doesn’t like long-distance sailing,” he explains.

Nevertheless, Begg completed his circumnavigation by breaking the world tour down into sections and using a variety of approaches over three years. He joined the 2016-17 World ARC and sailed Lydia with friends from St Lucia to Tahiti, where he laid the boat up and went back home.

Later that year he returned to sail single-handedly from Tahiti to New Zealand. He and his wife spent some time in New Zealand, before he single-handed on to Australia, where the couple spent a month exploring.

Then in 2018 he rejoined the World ARC in Queensland, and completed his circumnavigation with the rally, using a mix of crew he had recruited from crew sites, and ‘floating’ crew who had been with the World ARC for previous stages on other boats.

“I started off sailing with friends, but I ran out of friends – not in a pejorative sense but there’s only a limited number of people who could get away for long periods of time. That floating pool of manpower on the World ARC has been quite handy for someone like me who hasn’t got a natural crew.”

Although Begg is confident in single-handing long passages, he admits: “It is a great challenge, and it’s a terrific thing to have done, but you’re also very glad to arrive. “You get bored in your own company, you get lonely. In my case you get very fed up with your own cooking! And it’s nice to share it with people.”

Practically speaking, solo skippers are not allowed on the World ARC, and while Begg was insured to sail solo prior to 2017, he has found it more difficult and expensive since.

Spending long periods away from home is not for everyone. “It’s been tough, but we’ve found a compromise,” he comments. “I’d always said when I had the time I wanted to sail around the world, but when reality comes it’s not that simple.”

The grown-up gap year

For older families who don’t want to disrupt the key school and exam years, one option is to go as a ‘gap year’. The Chatfield family from Gloucestershire chose to time their World ARC two-year voyage around their son Josh’s education, setting off after he left school on their Grand Soleil 56 Mad Monkey.

The trip was a long time in the planning. “About six years before we left mum and dad spoke to my head teacher at school and said, we’d like to do this trip with Josh, when’s the best time to do it?” recalls Josh.

The family decided that after A-levels but before university would be ideal, but an early hurdle was that many universities Josh approached would not defer a place for two years. Thankfully, Lancaster University, one of his preferred choices, was willing to guarantee a place on his return.

For father Mark the trip was a chance to reconnect with his son before he left home: “I had spent a lot of time away from home with my job, so I had missed a lot of time with Josh.”

However, maintaining an 18-year-old’s social life while sailing around the world with his parents was a challenge. Fortuitously, and unusually, there were a handful of other ‘youngsters’ on the 2017-19 World ARC, who formed a tight-knit group.

“For me, it was very important to have other young people there,” recalls Josh. “You’re away for two years and I think the average age of a World ARC cruiser must be about 55 going on 60.”

Not all had such a successful trip – another father and son started the World ARC, only for family relations to break down and their trip to end in the Indian Ocean. It highlighted that cruising with family can intensify any tensions in the relationship.

“The first four months were very challenging,” Mark admits, “We were sailing in the Med with our friends, who were all around our age in their 50s, and Josh found that very difficult. He had left school, where he was with his peers every day, and then suddenly he was with adult company every day.”

To redress the balance, the family invited some of Josh’s friends to join them on the boat, but the timings didn’t work – something Mark says he would have planned differently with hindsight. “However, as soon as we got to Las Palmas to meet the ARC, the young adults group formed and he was just away!”

“I’d be lying if I said it was all plain sailing,” agrees Josh. “There were arguments, of course there were. My Dad is very regimental. Everything has a plan and so for me, as a 20-year-old living on the boat, it did cause some tensions. But we overcame them.

“In fact my dad and I got on best when the conditions were bad. I remember when we were crossing the North Atlantic, going from Bermuda to the Azores; that was possibly the best time I had with him.

“We went through 48 hours of about 50 knots. Dad and I just alternated one hour on, one hour off, which is obviously mentally and physically tough. But those are the times that I think will stay with us because we had to rely on each other.”

From the outset, Mark had also designated Josh as first mate, giving him the same level of responsibility as any other adult.

There were unexpected benefits: Josh found that other World ARC participants had had successful careers in the field he wants to work in, and was able to glean life and career advice from them.

For Mark, the trip achieved his goal of real father-son bonding time: “The one to one time that we had was absolutely perfect. You really do get to know somebody inside out.”

The novice adventurers

For most bluewater sailors the big trip has been years, if not decades, in the making, a dream of far horizons formed during days and cold night watches spent sailing familiar waters.

Not so the Eccles family. Formerly a motoryacht owner, Leo Eccles says he and his wife, Kate, had dreamt of cruising around the world, but always envisaged going after they retired and their daughters, currently ten and eight, had left home.

However, a few serendipitous events planted a different seed in his mind. When their motoryacht was out of service for six months after a lightning strike, a friend let them use their sailing yacht (with skipper) instead. The family instantly fell in love with sailing and decided to sell the motorboat.

Then hearing a talk about the Oyster World Rally one evening opened their eyes to the possibility of completing a circumnavigation.

“We realised that there were ways of doing it as amateurs that would give us a security blanket. Getting parts sent out, having visas taken care of – things that would take a lot of the stress away. So we decided, why don’t we just do it now?” said Leo.

“Our eldest daughter was turning nine,” recalled Kate, “And I realised they’re half way to adulthood already. In a few years time they’re not going to want to be with us – so why are we waiting?”

The family bought the Oyster 655 Man of War at the start of the summer in 2019 ahead of the 2022-23 Oyster World Rally.

“We wanted to have a couple of summers to check we were happy on board for an extended period of time,” says Leo. They spent their first eight weeks living aboard this summer, “And we loved it.”

Aware of their own inexperience, the Eccles family are going to be completing their rally with two full-time paid crew, and may take a third for the longer passages. However, Leo and Kate plan to get as hands-on as they can.

They have been learning from their skipper aboard Man of War and will take RYA qualifications, as well as attending courses for the world rally participants on topics like navigation and first aid.

“As a family it has been lovely learning something that’s new to all of us together,” says Leo, “and the girls have been putting us to shame on some of it already.”

The Eccles have wholly committed to their 18-month life changing adventure. They are selling their Monaco home and spending the weekends selling belongings at a French brocante. Kate will home school her daughters, planning to use the Laurel Springs online tuition programme.

A commodities trader, Leo will continue working throughout the trip. “I have got to slightly modify how I trade, so it will be more longer-term positions.” But otherwise, he says, “We made a conscious decision to really sever as many ties as we can for these 15 months and just really enjoy the time on the boat.”

First published in the December 2019 edition of Yachting World.