Toronto-born Jamie Ingall just goes for it. No holding back, no second-guessing, and maybe not that much planning, either. 

I first met Jamie in the summer of 2011. She was a tanned and barefoot sailing instructor, living in a sail locker at a yacht club on Toronto Island, working on boats by day and and drinking Kraken Black Spiced by night. She’s the fly-by-the-seat-of-your-pants type with an appetite for adventure like no other. I remember a few years later calling her from Jamaica and asking if she wanted to join me for a sailing regatta. She landed the next morning. 

Eventually Jamie became a commercial airline pilot, but in 2017 she and her then-boyfriend, Trevor, decided to quit their jobs, buy a boat, and sail to the Bahamas.  

Hey Jamie. Congrats on getting married! Don’t take it the wrong way but I find it crazy that you’re married. 

I find it crazy and I’m pretty sure my husband does too! We just celebrated one year in September. It’s actually nice given how much time we spend apart to have the extra sense of commitment and teamwork. Having a life partner is rad!


So, summer ’11 and ’12 we worked together at Queen City Yacht Club. Those were fun summers. Although I recall having the flu every Thursday for some reason. 

Was a great lifestyle. We barely left Toronto Island, unless we needed food or beer. I often look back fondly on those years. I get the flu a lot worse these days – another thing I miss about back then!


So, enough nostalgia. The latest on your Insta feed is you and your husband winning a fishing tournament. Congrats! I didn’t know you were into fishing.

We dabbled in fishing while we were on our sailing trip but really had no idea what we were doing. There’s my first cruising tip: learn a little bit about fishing before you go! 

Now that Trevor’s landed a job Captaining a sportfishing boat, we’ve found ourselves fishing competitively! I’m learning a lot. I won the award in the Montauk Canyon Challenge for Best Female Angler for my albacore tuna weighing in at 38 lbs! But to be honest I think I may have been the only female in the tournament so perhaps I won by default.


Did you eat it? 

We sure did! We fed our neighbors’ neighbors with that trip. Poke bowls for days.

Cool. So you’re hanging out in New York? Give us an update as to what’s going on. 

I had been working for a United regional carrier based in Milwaukee, Wisconsin. But after the pandemic hit, the flying pretty much stopped at the airlines. Luckily Trevor works for incredible people so I was able to move onto the boat with him and enjoy summer in the Hamptons. 

And Trevor is a boat captain?

Well, he works on a 76’ sportfishing vessel. He’s responsible for repositioning the yacht up and down the east coast of the US and throughout the Caribbean, maintaining it, etc. It's a great gig. 

So, the point here is to learn a bit more about the time you guys took a winter off and sailed your boat from Toronto to the Bahamas. Let’s talk about that. Tell us how that all started. 

Well, Trevor and I had been dating a while - we’re talking early 2017 and he was working in New Zealand - and on one of our regular Facetime calls in February he said something along the lines of, “Let's quit our jobs, buy a boat, and sail to the Bahamas for the winter." So, he was home by the end of March, and we had our boat by mid-April and we left on our trip that fall!

I couldn't imagine it any other way. What kind of boat did you buy for this trip? 

The plan was to buy something in the forty-foot range but we quickly realized it wasn’t in the budget. We knew if we wanted to just pick-up and do this on such short notice and without going into debt, we had to scale back our hopes and dreams a little bit. 

So we settled on a 1978 twenty-nine foot Bayfield named ‘Frannie C’. We kept the name. Not sure who Frannie was, but we like her!



How much did you pay?

We paid $13,000 CAD. The listing price was $15,000 but we found enough wrong with it to knock off a few grand.

How much did you have to put into it? 

I would say about $5,000. But some of that was aesthetic (e.g. we did the floors because I didn’t like them, and to this day Trevor will say was a waste of money). Biggest ticket items were an inflatable dinghy and life raft. And maybe some other safety equipment. 

Cool. So when did you leave? What route did you take? 

We left Toronto on September 27th and went across Lake Ontario, through the Oswego/Erie barge canals, and then down the Hudson River to NYC. This is kind of “the way out” of the Great Lakes and to the ocean.


One issue we had was our timing, which was autumn. The locks close for the winter, but if you want to know when the locks will close on a particular year, you'll just get a typical sailor-vague, weather-dependent non-answer. So here’s my cruising tip #2 – don’t bother! Just get out as early as you can! Knowing this, and since I was working still, Trevor got our friend Dave to help him with this first part.


Once they got to the Hudson River, they went about halfway down and left the boat in Poughkeepsie, upstate New York. Toronto to Poughkeepsie took them 8 days. Dave wrote a rather amusing blog post about the journey on our website.

Ok and then what?

Once we were both back on the boat we went down the Hudson River and out into the ocean from New York City. From there we did a combination of offshore sailing and motoring the Intracoastal Waterway (ICW). It really went NOTHING like what we’d planned (at one point we were thinking we’d just jet right out into the ocean and go straight down to the Caribbean.) But yeah, in the end it went a little something like this:

Offshore sail NYC -> Norfolk, Virginia

Intracoastal Waterway Norfolk -> Beaufort, North Carolina

Offshore sail Beaufort -> Southport, North Carolina

Intracoastal Waterway Southport -> Charleston, South Carolina

Offshore sail Charleston -> Brunswick, Georgia

Intracoastal Waterway Brunswick -> West Palm Beach, Florida

Offshore sail West Palm Beach -> Miami, Florida


We wanted to sail more, but didn’t always have the weather for it. Our engine wasn’t the most reliable and it wasn’t a very stable boat in greater than five-foot seas. So we were always hopping into the ocean when we could, but motoring/sailing down the ICW the rest of the time. I wrote a post about some of the offshore sailing and Intracoastal waterway experiences we had on our way south.

How long did the entire trip to Florida take? 

The Toronto-Poughkeepsie leg through all the locks and canals was one week. Then it was about six weeks before we arrived in Miami on December first. But there were ten days or so in North Carolina when we were rebuilding our engine which obviously we didn’t plan for.  So I’d say about four-and-a-half weeks from New York to Miami.

What was the best/worst part?

I’d say the best part is a tie between the wildlife and the awesome people we met.  Like, in North Carolina we met this guy Chris who lent us his car to go get engine parts and groceries – that made our week! And we met some cool folks while waiting for weather in Beaufort – there are a lot of fun bars there. It’s this cute little coastal town that we’d probably never have explored if it weren’t for those circumstances. 

The worst part was not getting to sail as much as we wanted. A good chunk of the ICW is so narrow you have to motor it. So you’re putting in eight to ten-hour days motoring along at five knots, listening to the loud engine and smelling the Co2 fumes.




And then once you were in Florida you sailed across to the Bahamas? 

We spent the entire month of December in Miami, enjoyed Christmas with friends, and left for the Bahamas on New Years Eve, arriving in Bimini on the first morning of 2018!

How was that ride? I’d image pretty rough in such a small boat?

We accidentally chose the calmest weather window you could imagine and it was a beautiful crossing! There was a lot less wind than forecasted so we ended up having to motor the entire way across! I wrote about the Gulfstream crossing too if anyone is interested in learning more about the infamous Gulfstream or entering a new country by boat.

If you want to hear about rough in a small boat I should tell you about our trip from Chub Cay in the Berry Islands to Nassau. Through the tongue of the ocean things can get nasty, and it was a night sail. Gusting to forty knots and six-foot swell. That’s the day we found out just how NOT waterproof our hatches and companionway were. We took waves over the ENTIRE boat and had a few inches of water on the floor down below. 

And so other than that gnarly sail, you just hung out down there all winter? 

Yeah, we had zero plans. At that point we sort of knew we wanted to spend the rest of the trip in the Bahamas. There’s so much to see there and we both had to be back to work by April-ish. We ended up doing a lot of island hopping. We did the Berry Islands, Nassau, the whole Exuma chain (a few times), and then also Long Island and Conception Island.

Top three things about Bahamas boat living:

Definitely number one is being able to jump off your back deck into crystal clear water, the diving is just INCREDIBLE. And delicious if you spearfish.





 Also, the feeling of freedom. Sometimes we’d wake up and just decide to move to a different island. Or we’d have planned to sail somewhere and just decided to stay another day. Having ZERO commitments and only the weather to dictate your schedule is something else. 

Time moves SO slowly because you’re not busy. It’s such a strange but delightful feeling to get up and just have no obligations whatsoever and getting to just say, well, should we go exploring with the dinghy? Sail somewhere? Spearfish a new reef? Cook something cool? Sit our butts on a beach? Get randomly day drunk? I don’t know the options were just endless yet at the same time there was nothing to do. 

I’d pick the randomly day drunk. 

So a lot of people are reading this because they’ve always thought about taking off and living on a boat for a year. And then COVID hits and all-of-a-sudden normal freedoms are taken away, and a lot of people realize the scarcity of time and are like, ‘shit, we need to make these things happen!’ And now many people are in this new kind of work-from-home existence and living on a boat while working is actually feasible. What advice would you give to anyone who might want to do what you did? 

My advice would be to not worry so much about the “perfect timing” or the “perfect boat” or even being “fully ready”. There’s never going to be a perfect time. And no boat is perfect. In fact ours was such a bad choice! Too small and not great in any kind of adverse weather. 

Sure, we both had experience backing us (me being a sailing instructor previously and Trevor being a motor yacht Captain), but there are plenty of people with FAR less experience than us doing it. I guess what I’m trying to say is, don’t overthink it. If it’s something you want to do then JUST DO IT. You’ll be fine. Don’t make any risky decisions and you’ll get down there eventually. 




 Any other resources for people considering this trip?

Well, here’s what we’ve got from sailing Frannie:

I’ll also note that it doesn’t have to be just a trip like in our case. There are a lot of people who are literally leaving life behind to sail. Using various methods of supporting themselves. Some do it in phases, coming home to work during hurricane season for example. Others have remote jobs where they can work from anywhere. Some make their living by YouTube even. Checking out their YouTube, blogs, or social media can be really helpful if you want to learn more about cruising. I’ll link my top 5 favourites below:

Sailing Uma 

A rad couple making videos that are super informative (talking about how they afford it, how they refit their boat, etc.) And now they are in Europe and doing some realllllly incredible exploring. Also, Kika speaks out about the racism she has experienced in her life, and the inequality she has experienced as a Haitian woman. She’s really just a beautiful badass that is doing great things!  

Four Sheets to the Wind

A hilarious couple from Wisconsin, Missy and Kyle. An example of people who just went for it with little experience! They’ve made it all the way to Grenada from Wisconsin and Missy is such a laugh! Kyle really just goes for it and figures things out along the way.

Sailing La Vagabonde 

They started on a monohull and now are sailing on a catamaran. Their early videos back when they had no idea what they were doing are especially funny/helpful, they’ve been sailing around the world for about five years now. They have a baby now, and they’ve really refined their videos. They’re very well done and it’s just so calming to watch. And they are both rather funny so it’s always a good laugh. 

Sailing Soulianis 

Their videos have been TOP NOTCH since the beginning because it’s what they do for a living (production), and their channel follows them from complete newbies who don’t even own a boat, to doing a refit, to actually making it down to the Caribbean!

Parlay Revival

My husband especially likes these guys. They bought a hurricane damaged catamaran and refit it in the Caribbean – now the channel follows his journey to try to sail it back to New Zealand! 

Thanks Jamie, hope we can grab a beer soon!

Or twelve!

Interview: Mike