Annapolis 2025 - Where Dreams Set Sail

Day 1 - October 11, 2025

The pattern on vacation is always the same: I stay up way too late trying to chronicle our adventures, and then the kids wake up before the crack of dawn. I like to chalk it up to vacations being their absolute favourite thing, they get uninterrupted time with the three people they love most… now plus one more.

And honestly? From our side, we’re just as obsessed. We’ll happily trade sleep for a few extra hours with our little duo. Every bit of time together feels like a bonus round we never want to end.

Seems like our “hotels with breakfast included” journey started strong and has been on a steady downward spiral ever since.

This morning’s setup was… creative. In the lobby, there’s a tiny nook with a toaster and a coffee machine, think small walk-in-closet and you'll get the idea. Near the elevator sits a table full of “grab-and-go” breakfast boxes. Inside each box: one bagel, a square of cream cheese, shitty “juice,” a yogurt, and a bag of tiny muffins. Sometimes. The “sometimes” is important because on day two, the muffins just straight up ghosted us.

Clearly, the hotel’s plan is to prevent breakfast abuse by handing out identical boxes. Not a terrible idea, except no one’s actually watching the boxes. I saw a couple of guests pull off what can only be described as a full-blown muffin heist.

And while I respect the hustle, the system still falls apart when you consider someone like me. Out of the five items, there are three I’m not touching: the yogurt, the muffins, and the shitty “juice.” The kids are even worse.

So there we were, Sophie and I making do with our toasted bagel and cream cheese, while the kids stared into their boxes like prisoners in a minimum-security breakfast facility.

Adding insult to injury, the internet was spotty at best, making my travel chronicling a frustrating, soul-testing experience. Which, of course, meant I went to bed far later than any reasonable person should after a day of “vacation.”

The hotel sits right next to the local airport, which means most guests are just passing through, one-night stands with the complimentary breakfast. Not us though. We booked for a two-night stand, how romantic of us.

We were placed on the second floor, the proud “non-smoking” floor. You couldn’t miss it. Every door had a “No Smoking” sign, every hallway had a “$100 penalty for smoking” poster. It was a full anti-smoking campaign… it smelled EXACTLY like a smoking floor. Go figure.

We’re about 30 minutes out from the boat show because everything closer was priced for people with fancier blood than ours. Still, we made the best of it. Sophie and I both come from hostel-travel roots, and we consider that a vital life skill to pass on to the kids, how to find adventure even when your room smells faintly of cigarettes and despair.

At the end of the day, we’re here to sleep and recharge. The real money and energy should go into the experiences we’ll actually remember… not the thread count on the sheets.

An early wake-up call has one undeniable perk: you’re guaranteed to be early for whatever you’re doing that day. The boat show didn’t start until 10 a.m., which gave us plenty of time to get lost, find parking, and still look like we totally meant to be that punctual.

That’s exactly what happened. We found a city-run parking garage with tons of space, $23 for the day, which was by far the cheapest option and only a short walk from the docks. Win. We spent the extra time getting our bearings.

The town itself had strong Charlottetown, PEI meets Portland, Maine vibes, cute, coastal, and just the right amount of quaint. As we made our way toward the water, we passed rows of old homes fully decked out in Halloween decorations, which kept the kids entertained and mildly spooked the entire walk.

First order of business at the docks: locating a free public washroom, an absolute must for any family traveling with a pregnant wife. Once found, we ran a series of rigorous tests to confirm long-term viability. I’m pleased to report we successfully established our forward operating loo.

With that critical mission accomplished, we strolled around to take in the sights and sounds before making our way to the entrance, where a line had already started to form.

While we waited, Wesley spent a good chunk of time staring through the fence at the boats like a tiny prisoner dreaming of freedom, his little hands gripping the chain links, eyes full of longing. I get it, kid. We all want out sometimes.

The 10 a.m. opening came quicker than expected, thankfully, because our little zombie crew wasn’t built for long waits. As we scanned our tickets and shuffled in, we were told we’d need to park our Cadillac stroller. Honestly, I saw that coming. Rolling that thing around on the docks sounded like an insurance claim waiting to happen, and I like to think of myself as danger-aware.

So, we parked the Cadillac stroller and grabbed only the essentials, the kids and their life vests. Our beloved Nap Wagon 4000 was left behind, surely relieved to no longer be a glorified pack mule for half our worldly possessions.

That’s right, we brought life vests for the kids. Some might call that overkill; we call it “parental realism.” Sophie and I weren’t about to take any chances around water, because when you’ve got small humans, you learn fast how quickly “we’re just looking” can turn into “oh no.”

To our surprise, a lot of the event organizers and exhibitors actually thanked us for bringing life vests for the kids. Then they followed it up by saying how many parents didn’t bother, which completely boggled our minds.

Sure enough, as we made our way around, we saw kids running along the docks, jumping on and off boats, and skipping around near open water without a vest in sight. On the second day, we even heard about an incident where a child around Wesley’s age, a year and a half, accidentally fell in. Thankfully, thanks to quick reactions from the people nearby, everything turned out fine. But still… why even take that chance?

I get that everyone parents differently, but for us, the rule is simple: the kids come home safe. Always.

Most people probably don’t know this about Sophie and I, but long before we ever stumbled onto YouTube sailing families, I’d dreamed of sailing around the world. It was one of those big, wild ideas that I filed under “Yeah right.” I shared this dream with Sophie just as a way to share deeper things about me and to my surprise she was really into this idea.

Then, years ago, we discovered Sailing Zatara, a family who sold everything, packed their four kids onto a boat, and set off to explore the world with almost no sailing experience. Watching them do what we’d only imagined made the dream feel a little more real… and maybe even doable.

Up until then, I hadn’t done much to chase it besides learning how to sail. Since then, it’s become our shared dream: to buy a big sailing boat, ideally a catamaran, load up the kids, and head off to see the world. It’s very on-brand for Sophie, given her love of travel and general fearlessness about life. But she’s also the planner in this relationship, the one who takes my “yeah right” and starts researching prices, routes, and school options at sea.

During one of those daydreaming sessions, we found the boat we both fell in love with: the Leopard 50.

So, naturally, Sophie being Sophie, she reached out directly to the manufacturer in South Africa to find out where we might actually see one in real life. Lo and behold, they told us the Leopard 50 would be on display at the Annapolis Sailboat Show.

And that’s all it took for a plan to start hatching in Sophie’s mind: a family road trip. Sure, it would be a vacation for the parents, but more importantly, it would be an adventure for all of us, a chance to feed the dream a little.

Fast-forward to now, and here we were, about to step aboard that boat, the one we’ve imagined ourselves living on, the one that’s fueled countless “what if” conversations after bedtime.

I don’t know if this dream of ours will ever fully materialize, but man, I’d love nothing more than to chart the world with the people I love most by my side. My heaven would be seeing the wonders of the world through the eyes of my children, with Sophie, the love of my life, right there beside me.

We started with the Leopard 42 since it was the first one at the entrance. As we made our way through, from the cabins to the cockpit, the kitchen, and every little nook, I couldn’t help but watch the kids. Their excitement was contagious. To them, this wasn’t a boat; it was a floating playground, a house that just happened to move.

Lola climbed up behind the wheel and, with all the confidence of a seasoned captain, asked, “Where do you want to go, Dad?”

“France,” I said.

She spun the wheel dramatically. A few seconds later, she turned back with a grin and declared, “We’re here.”

Then again, “Turkey!” “Australia!” “Greece!” Each time, she steered, paused, and proudly announced our arrival.

Standing there, watching her, I couldn’t help but think: I want this for her. For me. For us.

To my amazement, Wesley was just as excited, though I’m pretty sure most of it came from following his big sister around in total adoration. He’s growing so fond of her lately, and honestly, it’s one of the most heartwarming things to witness.

After exploring the Leopard 42, we made our way to the farthest dock, where all the catamarans were hanging out. The Leopard 52, the newer replacement for the 50, was waiting for us.

Once aboard, it felt like stepping into a supersized version of the 42. Everything was bigger, sleeker, and more customizable, especially when it came to the number of rooms and how they were laid out.

We learned pretty quickly that owning one of these floating mansions is a lot more feasible when you partner with a charter company. It reminded me a bit of our condo in Tremblant: we wanted a place there, but not the full-time financial responsibility. Chartering a boat works the same way, you buy it, let others rent it out for ridiculous fees, and in doing so, they help pay it off.

I remember Sophie saying she expected to feel something when she finally stepped onto the boat, some big, emotional wave of certainty or excitement. But to her disappointment, it didn’t quite happen that way. No lightning bolt, no cinematic moment of euphoria.

And honestly, I get it. These boats are expensive. That kind of price tag tends to keep your feet pretty firmly planted on the deck.

Unless, of course, you’re four or almost two years old. Then you get swept up in the magic just fine.

At one point, Lola was walking through the cabins, confidently picking her room and announcing to anyone within earshot that this was her boat. She’s the cutest, and maybe, just maybe, she’s the one who gets it right.

On my end, I was genuinely impressed by the ingenuity of it all. These are literal floating houses, packed with technology, clever design, and a level of comfort that still feels almost impossible for something that sails. Having followed a family who’s actually grown up on one of these, I’ve seen what that life looks like… what it promises.

Still, it doesn’t feel anywhere near attainable at these prices… not unless we sold our house and maybe a few vital organs.

One key thing about choosing this kind of life, though, is knowing how you handle the sea. From the docks, it’s hard to tell for sure, but the waves were enough to give us a small preview. I already knew I was fine, I found that out the best possible way, during an epic sailing trip in Croatia back in 2015. The kids seemed fine too.

Sophie, however, wasn’t. She started feeling really nauseous, so we decided to head back to land just as the rain began to fall and find some lunch. Once we were on solid ground, she slowly started to feel better.

Of course, nausea also happens to be a side effect of pregnancy, so she wasn’t quite sure which culprit to blame: the baby or the boat. Either way, it was time for a break and a much-needed meal.

Near the show, we spotted a poke bowl place, not the most obvious choice for picky eaters, but when you break it down to the basics, you realize it’s mostly white rice… and white rice is a certified kiddie favorite. Add a “kids eat free” sign to the mix, and suddenly it was a risk-free proposition. In we went.

We ordered four bowls, with only one containing raw fish. Sophie had to skip that one, given the little dumpling growing in her tummy, much to her disappointment.

Lola, as expected, resisted at first. The sight of all those ingredients mixed together was clearly an act of culinary chaos in her eyes. But once she started eating the parts separately, she did surprisingly well.

Wesley, on the other hand, required a bit of tactical intervention. I had to dig past the veggies and chicken to uncover the rice before he’d agree to take a bite. Once I did, we were in business.

After lunch, Sophie was feeling a bit better, still not 100%, but at least no longer looking like she’d lost a round to food poisoning. So, we decided to walk it off and explore the immediate area a bit.

This was when the PEI-meets-Portland vibes really started to kick in. The main strip, with its rows of shops, restaurants, and expertly curated tourist traps, looked exactly like Queen Street in Charlottetown. You know that stretch where you can buy anything from an artisanal candle to a lobster-shaped bottle opener for $29.99? Yeah, that vibe.

We wandered a bit further into the local neighbourhoods and found ourselves surrounded by these beautifully kept, cozy little homes, quaint in that “I bake sourdough and compost religiously” kind of way. Well, except for the sidewalks. The tree roots there have gone full Godzilla, tearing through concrete like it’s papier mâché. Navigating that mess with a stroller felt like competing in some kind of municipal obstacle course.

But hey, maybe that says something about the community, right? Choosing nature over convenience. Or maybe the city just ran out of tax dollars. Either way, it’s a vibe.

By the time we looped back, Sophie was feeling much better, and the kids were due to wake up soon, so we parked the stroller in our usual “you can’t bring that in here” spot. The kids, in a shocking twist, decided to sleep a little longer. So we did what any responsible parents would do, sat down right there on the pavement beside them and chatted. Hard-core parenting at its finest.

Once the kids woke up, we did what every responsible parent does in a new town, got ice cream. It’s basically a travel law at this point. You can’t claim to have explored a place until you’ve dripped something sugary onto its sidewalks.

We strolled up the strip, cones in hand, taking pictures along the way, just your standard “we’re totally nailing this parenting thing” shots: kids grinning, us pretending not to be happy, Sophie pretending she's in China again and skipping line ups for photo ops. Classic family travel content.

We started exploring the other exhibitors’ models, and when we stepped onto the Majestic 530, Sophie immediately noticed something different. The aft, the back of the boat, had an actual separation between the outdoor living area and the water. Most of the other models had these wide-open layouts, like “here’s your cocktail, try not to trip into the ocean.” But this one? It felt secure. The kind of design that lets you take a deep breath as a parent.

Inside, the kitchen instantly gave off “come hang out here” vibes, warmer, more inviting, less “display model” and more “actual home.” Even the bedrooms felt designed for living, not just looking.

That same thoughtful design carried through to the front of the boat, too. Normally, catamarans have those two trampoline-like nets up front, great for sunbathing, not so great for adding usable space. This one skipped the nets entirely, going all in on livable area.

And then, right there on the bow, was a single-person hot tub and a cold plunge. Not that I cared. I mean, maybe the hot tub…sure . but sacrificing precious storage space for buckets of pool chemicals? Not this guy.

This boat gave Sophie that feeling she was expecting to have on the Leopard 52. It was around this point that it hit me: this whole boat-buying adventure was starting to feel a lot like when we were house hunting. And Sophie's feeling was kind of an intuitive approach to this whole notion.

When Sophie first convinced us to buy a house, we went in full of confidence and absolutely no clue. We had all these preconceived ideas about what we wanted, like we were some kind of house whisperers dream team. But it wasn’t until we actually started touring homes that reality kicked in. Every visit chipped away at our “must-have” list and added something new we hadn’t even considered. By the end, we were basically redrawing our entire wish list in crayon.

Each showing taught us something, what we truly valued, what we could live without, and what absolutely drove us nuts. Slowly, visit by visit, we narrowed in on what felt right.

That same process seems to be unfolding here. This boat show has made it clear that our house-hunting lessons are going to come in handy for boat shopping, too.

Now we know a few things for sure:

We like a closed-off back, no toddler cliff diving, thank you very much.

A shielded cockpit for the captain, this we learned from YouTube vids. In rainy weather if you don't have a windshield it makes keeping an eye out and steering very difficult.

Livable space up at the bow.

Comfy, spacious rooms that don’t feel like fancy closets.

A big, covered main area in the back, because us redheads don’t do well under direct sunlight. We’re not quite vampires, but we definitely burn in the sun if left out too long.

A functional kitchen that feels like a real one, not a camping experiment.

And of course, plenty of space for board games. That last one’s mine, but it’s going on the list anyway.

We hit one last boat before calling it a day. It was nice, but it just didn’t hit quite like the Majestic 570. Kind of like when you finish a meal with a salad… fine, but the magic’s already happened.

By then, the show was winding down anyway, so we took that as our cue to pack it in. We walked back to the car, the kids half-awake and sticky from who-knows-what, and made the 30-minute drive back toward the hotel.

Right near our hotel was a Chick-fil-A, and let’s be honest, resistance was futile. Parents, tired kids, fried chicken, it’s science.

The second we pulled into the lot, the kids spotted the park beside it and lost their minds. Perfect. We wanted them to burn off whatever sugar-fueled energy they had left. And burn they did. They pecked at their food between runs, then played like absolute demons set loose on a jungle gym.

Lola made instant friends, because of course she did, and at one point, Sophie went in to stay closer to Wesley. She came out looking like she’d just survived a rock concert. Apparently, the noise level in that play area could’ve powered a small city. Even Lola complained later in the car about how loud it was, which tells you everything.

Back at the hotel, it was the usual bedtime routine. We also packed as best we could and prepare things for loading into Van Diesel as it was our last night here. Once the “goodnights” were finally said and the kids were out, Sophie crashed instantly. Me? I stayed up a bit longer, tapping away at my notes, eyelids getting heavier with every line, until I finally gave in and called it a night. I didn't want to be wrecked for day 2 of the show.

Day 2 - October 12, 2025

Woke up early, surprise! In addition to our usual song-and-dance routine to get everyone ready, we also had to pack since we were leaving town today.

I tetrised our belongings into the van.

We grabbed our to-go breakfast boxes, sans muffins, and the kids enjoyed their “juice.” Nutrition is thriving in our household.

We drove to the exact same parking garage as yesterday, except this time there were no locals advertising their driveways for $30. That was the first sign traffic would be lighter, fewer cars, fewer people, fewer opportunities to regret this decision.

We waited near the front of the line with only a few people behind us. Once inside, we were told to park our stroller approximately 30 times as we were parking it.

Life vests went on, and we headed straight back to the Majestic. We just wanted to confirm it wasn’t love at first sight.

It wasn’t.

We kept exploring, this time focusing on boats that checked our newly refined criteria, mainly the “closed aft” feature. (We’ve learned some things.)

By this point, Wesley was obsessed. Every time we got off a boat, he’d immediately start chanting, “Bateau! Encore bateau! Bateau!” like a tiny French pirate with a single goal in life.

Lola, on the other hand, was showing off her sea legs. She was navigating decks and interiors like she’d been doing it her whole life.

Hitting another catamaran was easy since they were all grouped together. The docks near the Majestic and the Leopard seemed reserved for the more luxurious models. These required reservations, we had none, but thankfully, Sunday was dead. (Kid-hour bonus.)

We managed to board the Bali 5.2, and wow. Luxury has its perks. This was hands down the nicest boat we saw. It had everything we wanted, and, naturally, it was almost double the price. Cue sad music.

If money weren’t a factor, this would absolutely be our boat. It had every safety feature we cared about, plus a design that went even further. The main floor was massive and fully covered, and there was a whole second level where the cockpit sat, surrounded by extra seating for whoever wanted to keep the captain company. The view from up there was unbeatable. The bow was also fully livable, like the Majestic. In short, it had space, the most precious resource for a family of six.

We came here to dream, and to experience a little piece of that dream. For now, we won’t let finances interrupt what can only be described as a cool feeling. We’ll cross that “reality bridge” in many, many conversations over the years ahead.

We hopped onto a few more catamarans to satisfy Wesley’s never-ending boat hunger, but nothing else hit quite like our top three.

We planned to leave around lunchtime to line up the kids’ nap time with our drive to New York City, well, New Jersey technically. (We’re dreamers, not millionaires.)

The kids polished off the leftover poke bowls from the day before while we planned to eat on the road. Shockingly, the plan actually worked. For a drive that stretched past four hours, the kids slept through a solid chunk of it, which, in parenting math, basically counts as a luxury vacation.

We rolled in around five-ish, unpacked, and ordered Mediterranean food on Uber Eats. While we waited, we got the kids bathed and ready for bed, the kind of bedtime efficiency that only happens when there’s falafel on the way.

The food took over an hour to show up, and one of the plates looked like it had gone through the garbage compactor from Star Wars. The delay made sense once we realized our order was delivered by a guy on an electric bike, which is perfect for short city runs, but maybe not for cross-state missions involving hummus. Apparently, the “biker food delivery” thing is a whole movement here. We saw tons of them zipping around like a swarm of hungry bees. We were… not impressed. Mostly just hungry.

Eventually, everyone settled in for the night, bellies half full and expectations adjusted. Tomorrow would be our first full day in New York City.