The Hunt for Lost Years

The plan is simple; buy the boat, move aboard full time, sail to French Polynesia, and live happily ever after. The in between is where things get complicated. Over five years ago we dreamt up that plan having no idea what it would really take to even just get things moving forward an inch. Money, insurance, the right boat, and external commitments all prevented us from chasing the dream full force. Just over a year ago we found ourselves completely burnt out and miserable, despite having so many other incredible blessings in our lives at that time. Delaying our true dream was starting to destroy us.

We looked at our first sailboat in person in July 2024 but we were extremely limited by the singular option we had in Grand Cayman, where Theo is from and where we had been living for the past five years. Travelling off the island was always very expensive and time consuming, considering there’s only one runway on the island you can start to understand how limited we really were there. We knew we needed to travel eventually, but until then our online search was neverending. We would spend day after day scouring every corner of the internet looking for boats we thought were seaworthy and comfortable enough to live and work on. We had several requirements; we wanted a boat that would be as safe as possible offshore (keel stepped mast, full skeg, lead keel, cutter rig, just to name a few technical requirements), was around 40ft long with enough headroom for Theo who is 6’3”, and had space for friends, family or crew to stay with us.

We also needed the opposite of a project boat. Preferably we would find a boat with new standing rigging, new navigation equipment, lithium ion batteries, solar, etc. The idea was to limit the amount of time we would need to be in the dry and to ensure we could move aboard and be self-sufficient from the start. This requirement was not because we didn’t want to put in the work ourselves, but because we simply don’t have enough time for a major refit. Theo already works full time running an e-commerce business (8am-5pm EST, Monday through Friday) which is how we will fund this dream and our eventual retirement. And my time is consumed with caring for him and handling everything outside of the business, so of course I would have more time to work on the boat, but even then it would probably take us years to do a complete refit of a project boat. And if we couldn’t live and work on the boat at the same time, we would be stuck paying rent for an apartment which is exactly what we were trying to escape in the first place.

So where did we look online for this dreamy boat? The real question is where didn’t we look. We would scroll between YachtWorld, YachtR, Facebook marketplace, sailboatlistings, Instagram, various brokers websites for exclusive listings and other websites like our lives depended on it. We would watch hours of YouTube videos from Sailing Zingaro, Lady K Sailing, and other sailing influencers to learn about different boats, the lifestyle and the boat buying process. We read forum after forum of thousands of comments from real cruisers and we even read a few books, like John Kretschmer's Sailing a Serious Ocean and Don Casey’s Inspecting the Aging Sailboat. We would get so burnt out from looking for days on end that we would have to force ourselves to take a break and do something fun. Finally, in August 2025 we started to narrow down a few serious options and began flying around the world to view them in person.

Our first stop was Colon, Panama to look at a Najad 390 CC. Too small, not enough headroom, but a beautiful boat. While we were there we stayed on a Sun Odyssey 52.2 and it was like spending the weekend at the spa for us. We’ve never felt so rejuvenated and secure in our decision that we HAD to try the cruiser lifestyle or we would live to regret it for the rest of our lives. We discovered 50ft was too big for us though, considering this is our first sailboat, we want to make sure everything is a more manageable size both work wise but also cost wise. Our next stop was the dream destination: Tahiti. There was a very unique boat there, a Fair Weather Mariner 39 (if you know, you know). We almost bought this boat without seeing her in person because she seemed so perfect online, but after combing through the boat in person for a few hours we found endless rot. The chainplates were completely surrounded by rotten wood, and that boat will probably never leave Tahiti unless a brave soul is willing to take on a complete deck rebuild. Heartbroken.

While visiting my family in Massachusetts, we decided to look at a Passport 40 in Maine. Similar to the Fair Weather Mariner 39, but bigger and more commonly known. I loved it, but there were just too many projects that needed to be tackled on that boat. It just wasn’t the one for us, and there weren’t any others on the market that seemed promising. Feeling defeated, we dreaded flying back to Cayman. But we decided to take our first big leap of faith and move off the island to full time travel in search of our boat. We were determined to make this happen by Q1 of 2026.

We saw a few more boats while dropping off our belongings for storage with my family. One was a Pacific Seacraft 40 in Rhode Island, and the other was actually a catamaran, a Mahe 36 Evolution in Massachusetts. Five years ago when this dream of living on a sailboat began, we were convinced we needed a catamaran. They’re faster, more stable at anchor, and have a lot more living space. But they’re much, much more expensive. And if you want a ‘bluewater’ safe catamaran, which of course we did, you’re looking at a serious chunk more money upfront. So if we had any hopes of getting on the water soon, we had to accept that a monohull would be our first boat. During our research phase we also discovered that monohulls can be a lot better for ocean passages (apparently, this is all still quite foreign to us).

So when we found the Mahe 36 Evolution for sale nearby, it was in our pricepoint and it was somewhat of a bluewater capable catamaran, we knew we had to take a look. We were so optimistic about this boat, but when we got onboard it immediately didn’t feel right. We were shocked. It probably didn’t help that we had viewed a beautiful Pacific Seacraft 40 right beforehand just for fun (since it was quite over budget) but even so the catamaran did not feel like it was the right fit for us. I left the PSC40 viewing elated because I knew we were either about to buy a catamaran OR we were going to make the budget work for the PSC40, so either way I thought to myself ‘we finally found our boat’. And I was right. The PSC40 checked off all our boxes, the only problem was this specific boat did not have an upgraded power system or really any refit done since it was the youngest boat we had looked at by far.

So we returned to the internet to see what other PSC40’s were on the market and who has actually owned these boats. Thankfully there were several others on the market, but most of them were even more out of budget. We found a few sailing influencers online who had PSC40s so we binged all of their content and fell even more in love with the boat. I even found myself on a blog from an owner describing how amazing his boat was, and that it was currently FOR SALE! I couldn’t believe my eyes. This boat had gone through a major refit, new rigging, new electronics, self-sufficient on power and water, and even a brand new engine! Jackpot. She was located in Virginia so we booked a trip the next weekend to view her and the rest is history.

Now, it’s been one month since we moved aboard our first sailboat and we are still in Virginia getting everything ready to go. We have been loving every second of our new lives, and it feels like the wait was truly worth it for such an epic vessel we get to call our home. We are faced with a huge dilemma now of where to sail first. The cool spring weather here is slowly draining the life from us and if we didn’t have a diesel heater I think we would actually have frozen to death one of these nights. We desperately want to get back to the caribbean, to our freediving, underwater photography, coconuts, and sunshine. But hurricane season is just a month away and we might be a bit too inexperienced to face those challenges this early on in our journey.

So, do we head further south taking our time and hopefully finding warmer weather? Or do we stay where we are to refine our skills and make an offshore passage to the Bahamas in the fall? Or do we sail north like most of the other cruisers we have spoken to, explore New England and stay safe from storms? I guess you will just have to subscribe to our newsletter or follow our socials to find out what we choose to do next!

— Jordan Farrow

The Meaning Behind The Name

@SAILINGLOSTYEARS