A potted history of us and boats

February 10, 2021

Reading time: 11 minutes

In 22 years, we’ve gone through a lot together. Too much to say it all here, but if we want to look at how we found ourselves 6 weeks from leaving the UK to go and live on a boat we’ve never seen, we need to start somewhere around the early 2000s.

This about a girl, looking at a guy, looking to the horizon, and how we got to where we are now.

Dreaming of a warmer life

We always wanted to live abroad, and after even before Colin had visited the Caribbean that was a target. We’d actually barely travelled together. Thanks to being students, we had only had one trip to the family holiday home in Iona, a semi-working trip to the Czech Republic, and a week in Tenerife.

In 2004, when Ailsa was in her final year at uni, we went to Barbados for 2 weeks. Ailsa had already been with her mum in 1997 and 2001. We didn’t just go for a holiday, we went looking for a house. We were THAT confident. Ailsa was training in portrait photgraphy, and Colin was a web developer. We had this idea that we’d offer contemporary honeymoon and wedding photoshoots based around a British market. We had a week of fun holidaying, then a week of looking at property with our friend Johnny Cool.

Colin sits in a net hammock strung between two palm trees on a tropical beach
Colin at Bottom Bay, Barbados in 2004

In the end, we realised three things.

  • It’s not that cool to move to another country and try to take local business.
  • We realised that the practicalities of working visas and buying property abroad were just too daunting while we were in our early-20s.
  • Ailsa actually kind of hates posing people. We did a friend’s wedding soon after the trip and it turns out she’s much happier taking candids.

A dream unfulfilled

We gave up on the idea of moving abroad, and, desperate to buy property, we bought a flat in Edinburgh within 3 weeks of deciding to change tactic. We moved from Cambridge a few months later. Over the next few years our love of the Caribbean didn’t wane. We made it back to Barbados in 2007 and 2010, and to Montserrat and (briefly) Antigua in 2012. We spoke longingly of the idea of moving to Montserrat, but we still had concerns about taking employment from local people. In 2013, we combined Barbados and Montserrat in one long trip. Oh, and we eloped while we were there. Johnny gave Ailsa away.

Colin walking away from a very small plane on a runway in Montserrat
Landing in Montserrat in 2013

A spark

A year or so after we got married, we were in a funk. Ailsa had been battling depression, and we were both feeling hemmed in and unfulfilled at work. Our finances were in the toilet after we’d ended up unable to sell an old flat (cheers 2008 recession). We felt like we hadn’t got married just to sit at desks in different places, and never have the time or money for fun. We were truly sick of the Scottish weather.

Ailsa was visiting her brother in August 2014, and Colin was at home reading Dead Calm. He phoned Ailsa to say “what about a boat?”. She said “sure”.

An image of a Facebook post by Colin on 24 August 2014. It reads “So it’s totally realistic to cash in flats, buy a catamaran, and quit modern life (as we know it). Really rather tempting.
How it started…

Wait, what, a boat?

Yeah, we know! Colin had sailed as a boy, with holidays on Lake Windermere, and in Greece in his early teens (he mostly remembers only eating pizza). Ailsa had enjoyed catamaran day trips ever since her first one in Barbados aged 15, and 3 nights on an Egyptian felucca on the Nile aged 20.

Ailsa takes a selfie of herself and Colin while they are lying on the net of a catamaran in the sun
On a catamaran day trip in Barbados in 2007

But we hadn’t really sailed. Not really at all.

How it happened, a timeline

We decided almost immediately after Colin’s eureka moment that we would sell the flat we lived in. We planned to move back to the old flat that wasn’t selling, and downsize. What follows is 6.5 years of work, planning, and false starts before it all comes together.


November 2014 – sold our flat, and moved back into our old flat (which we’d rented out since 2008). The plan was to sell and downsize further, with an aim of leaving the UK in March 2016.


March 2015 – We signed up for RYA Day Skipper theory with Kipper Sailing. We also accepted an offer on our flat, and put one in on a new place which we were confident would build value. At that point we planned to live there for 1-2 years then either rent it out or sell up. We also had our first little taste of sailing, with a 2 hour dinghy lesson on Loch Tay.

July 2015– We moved to our central Edinburgh flat. We also had our first little taste of boat life, when we sailed out of Antibes (France) for 2 nights on board Aonami with Roberto Minoia.

September 2015 – we sat and passed our Day Skipper theory exams.

October 2015 – we took our RYA Competent Crew and Day Skipper practical courses back to back with Sunsail in the BVI’s over a fortnight, and loved it. We immediately signed up for our next theory test, and started to consider how we could take on crewing work. We had a notion that if one of us had RYA Yachtmaster we could run a kind of mobile AirBnB on our floating home.

Colin is sitting in the cockpit of a yacht at sea, wearing a tshirt which says “life is better sailing”
Aboard Nipolos 3, learning to sail with Sunsail BVI in 2015

March – May 2016 – we passed our Coastal Skipper exams, again with Kipper Sailing. Note that we’ve already passed our original ‘flitting’ date!

July 2016 – debt was holding us back, so Ailsa got a promotion at work. We flew to Grenada to take our Coastal Skipper practical aboard Chao Lay with Grenada Bluewater Sailing.

Colin is standing on the coach roof of a yacht at anchor, wearing swimming trunks. The boom of the yach has “Bluewater sailing” written on it
Coastal Skipper with Grenada Bluewater Sailing in 2016


August 2017 – yep, still in debt. We didn’t want to loose our skills, so we took a cabin on a Seafarer traing yacht, Vestavagoy, out of Sibenik in Croatia.

Colin and Ailsa sit on a harbour bench by streetlight, holding up cans of beer and smiling
In Sibenik after a long night sail in 2017. The boat was dry so we had to find a midnight beer on land

September 2017 – by this point we’d learned a lot more about the realities of taking on charter work, and it seems less realistic for us. We consider the idea of buying a cheap boat and keeping it in Edinburgh. The idea seems less appealing as we head in to winter, and Ailsa waits for an MRI for chronic hip pain.

July 2018 – our finances are finally healthy enough for us to try a bareboat charter, albeit on the smallest, cheapest yacht in Barefoot’s fleet out of Blue Lagoon in St Vincent. It’s a disastrous 10 days thanks to the boat, but we take it well, and we decide that once our debt is clear we’re ready to buy our own boat.

Ailsa and Colin sit on opposing benches of a small cockpit under way. They are smiling but nervously.
A welcome moment of the autopilot working in SVG in 2018 on our first bareboat


December 2018 – the world falls apart for us. One of our best friends dies suddenly, having previously been in remission for breast cancer. Ailsa’s mum is also diagnosed with cancer at stage 4, this time melanoma. We have to slow down our planning. We do, at least, come up with a plan, to move to Florida to stay with friends when we’re ready to buy a boat.

July 2019 – we have our second bareboat, a week out of Guadeloupe after a week on land. Ailsa’s mum passed a few days after we flew out. We didn’t know her cancer had become so imminently terminal, and Ailsa’s parents avoided telling us until there was no other choice while we were on our way there. She asked that we stay and send home stories from a place she’d always wanted to see. We had some smooth sailing on a 42′ Dufour with Dream Yacht Charters, but the week was tinged with sadness.

Ailsa takes a selfie while sitting beside Colin at the helm of a large monohull yacht. Both are smiling and relaxed.
Getting comfortable sailing from Guadeloupe to Dominica in 2019

It’s on

December 2019 – we visit our friends in Florida, and whilst they decide not to stay there long-term we decide that we’ll sell our flat, get visas and move to Florida in July 2020 regardless.

February 2020 – we get our US B1/B2 visas, which even if we don’t go to Florida to buy a boat will be useful for sailing the USVI.

Er, pause again

March 2020 – Do we even need to say it? You know the drill.

This part will make your head spin

July 2020 – suddenly flats in our area are selling, fast, so we make the snap decision to go on the market. We’ll find temporary accommodation and fly to wherever a good boat is, cash in hand.

August 2020 – We go on the market on 12 August. Two days later, Colin sees a post about a 1997 Prout 45′ for sale in Bequia. We have a couple of chats with the owner, and by 20 August we’ve decided that (survey dependent), we’ll buy her.

September 2020 – on the 3 September we get confirmation of selling our flat, and we pay our first deposit on Mirounga. By mid-September we’ve started to renovate part of Ailsa’s dad’s house, his old office wing, so we can live in it.

Colin and Ailsa are sitting on rocks at a Scottish beach, at different heights. The image is close cropped so that Colin is leaning against Ailsa’s torso. Both are smiling and wearing sunglasses. Behind them is a clear blue sky
At the beach in Iona, the day we paid our first deposit on Mirounga

November 2020 – we say goodbye to Edinburgh and move back to Ailsa’s hometown, Kelso, into a building site.

January 2020 – we book our flights to Bequia for late-March. We finish our DIY renovation, and list the flat on AirBnB for after we leave. Ailsa hands in her notice at work. We’re optimistic, but the UK is back in lockdown and Mirounga is on the hard in St Lucia – her owner hasn’t been able to get back to the Caribbean to splash and move her.

And here we are

It’s now February 2020. We’re still in lockdown. Mirounga is still in Saint Lucia. We have two weeks of quarantine accommodation booked for our arrival, and back up accommodation should Mirounga’s current owner have any delays. We have agreement from our employers that we can work remotely during April, but nothing lined up beyond that. The little AirBnB we’ve lovingly created already has a few bookings, an income source for Ailsa’s dad. We leave in 6 weeks, but we haven’t started to pack. We’re too young to hope we can get a Covid vaccination any time soon. We have a home lined up for our beloved cat.

If we’ve learned one thing in the last 6.5 years, it’s that the best laid plans don’t always unfold as you’d expect. It’s taken us three times as long as we thought it would to get to this place. But at the same time we’re more experienced. We’re older. We’ve faced greater challenges. We’re debt free and have savings. We’ve had time in the UK, and time with friends and family, that we wouldn’t trade. Fingers crossed that we don’t have more delays, but we know if we do we’ll take it in our stride.

C & A.