Intentional travel with balance & ease
Our Sint Maarten Family Trip: Sun, Sand & Strollers
Written By
Joba
April 20 2026
In April, I turned 30. And after being cooped up in the Canadian winter since having a baby, I knew I only wanted to celebrate somewhere warm, with turquoise water, good food, and waves crashing. Plans changed at the last minute, so I had to pivot to Sint Maarten (SXM) but as long as I got to share the adventure with my little family, all was right in my world.
This post is part itinerary, part practical guide, because travelling with a baby will absolutely change your travel style. For example, late nights out? Not so much. But more time lounging by the pool? Absolutely. And I’m not complaining. Here's how our five days in Sint Maarten went:
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What You Need to Know Before Visiting SXM
Before you start planning, here are the things that made this trip much easier and saved us time and money.
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Best Time to Visit: Mid-December to April, which is the dry season and tie in well with Christmas or March Break. Shoulder seasons like May and November can also be great.
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Getting In: Citizens of Canada, the US, UK, and EU/ Schengen countries can visit Sint Maarten visa-free for up to 90 days. Canadian permanent residents and holders of multiple-entry visas from the US, UK, and EU/ Schengen countries can also visit visa-free. Make sure to confirm exact visa policies ahead.
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Currency: USD and EUR are the official currencies, and credit cards are widely accepted on both sides of the island. Cash is still handy for smaller local spots, like souvenir shops.
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Getting Around: There are no rideshare apps and the costs of regular taxis add up fast, so your best bet is to either rent a car or book a private driver. Our driver was Marc, and he was lovely to work with: +1 (721) 553-7953
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Language: English, Dutch & French
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Connectivity: Skip the cost of roaming with your carrier by getting an eSIM.
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Country Hopping: Take a 25-minute ferry from Marigot on the French side to Anguilla for a relaxing day on the beach, or a 40-minute ferry to St Barts for a day of luxury shopping.
eSIM / Connectivity Affiliate
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Where to Stay in Sint Maarten
SXM has a Dutch side (Sint Maarten) and a French side (St Martin). Trying to figure out what side you should stay on is one of the first things you'll consider when planning your trip, and the honest answer is: it depends on what kind of trip you want. If you’re still trying to decide, check out my guide here on how to pick. The good news is that ycan easily cross between both sides freely with no border drama.
We stayed on the Dutch side, at La Vista Hotel, which is a small boutique hotel only a few steps from the beach. It was quiet enough, which is exactly what we needed with a 5-month-old in tow. I loved the scenery, the room size, and the proximity to a lot of places, especially our favourite restaurants in SXM.
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My Full 5-Day Itinerary
Day 1: Touchdown & The Best Ribs Ever
We flew in from Toronto, which was only 4h 30m, and after checking in, we just took in the island air and beauty that was our hotel poolside.
Later that evening we went to grab dinner at the famous Captain's Rib Shack, and let me tell you, the BBQ ribs, jerk wings and mac and cheese hit all the right spots. We decided to take our meals back to the hotel, and this set the tone for our whole trip, as the to-go dinner strategy was much easier with our baby’s nighttime routine.
Practical Tip: Keeping day 1 slow and activity-free meant we were able to rest and be refreshed for the rest of our trip
Day 2: Exploring the Dutch & French Sides
Our driver took us through both sides of the island, giving us a history lesson on the people of this Caribbean gem.
After, we visited Parrotville Bird Park, which is a great family-friendly hidden gem might have loved more than anything else I did on this trip. At $15 for adults, $7 for children and free for babies under 2, we got to see and feed lots of beautiful birds. The place also includes an outdoor playground for older kids who need an area to play.
Our driver recommended Cynthia's Talk of the Town for lunch, and it was chef's kiss. It is in Grand Case, which is on the French side and quite popular for its restaurant row. Dinner was another to-go situation, this time from Fritay’s. The red snapper is worth the hype. Iykyk
Day 3: Day Trip to Anguilla
If you're visiting Sint Maarten and you skip Anguilla, you're missing a big part of the experience. Anguilla is just a 25-minute ferry ride away. It is quieter, less touched, and somehow even more beautiful. Anguilla is a whole other country, so be sure to bring your passport along with you, and cash for departure tax.
We headed to Marigot (on the French side) to board one of the first ferries of the day. A one-way trip costs about $70 USD in total per adult and can only be booked in person.
You can rent a car or get a taxi at the arrival port, but we booked a driver (Tricia: +1 (264) 729-8428) for the day to make things easier. Note: Driving in Anguilla is on the right-hand side.
Our first stop was the Anguilla sign overlooking the water, then the Anguilla Arch. The Arch is a beautiful photo spot, but feel free to skip it as it can be a little underwhelming. Next, we headed to Ocean Echo, where we had scrumptious meals and just lounged by the beach. Right by Ocean Echo was the infamous Savi Beach Club, so we decided to stop by for a few drinks. The staff was lovely and brought me a little birthday surprise that made my heart full.
This Anguilla day trip was exactly the kind of slow beach day a Caribbean trip is supposed to have.
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Day 4: Plane Spotting & Parasailing
We started the day at the legendary Maho Beach, where planes land so close overhead that it almost feels like you can touch it. This is one of Sint Maarten’s major highlights and is a must do activity. It's loud and busy but absolutely worth it.
Then, for my "turning 30" moment, I decided to go parasailing at Orient Bay beach. I’d been building up to this, and it completely delivered. Being up in the air was freeing in a way that's hard to describe, and the views? Nothing comes close tbh. I highly recommend doing something that scares you a little, especially on vacation. I also tried tubing for the first time, and it was absolute chaos in the best way. I seriously couldn’t stop laughing (and screaming).
After such a busy day, we picked up spicy jerk chicken wings, plantains and BBQ ribs from Boca Seafood Restaurant, another solid meal spot.
Day 5: Sunrise & Sunsets
I woke up early for a swim and to try to catch the sunrise in the hotel pool and it was genuinely stunning. The first half of the day was perfectly unscheduled, with us prioritizing rest.
Then, we headed to Baie Rouge for a photoshoot in the golden hour light. A perfect ending to a perfect trip. While taking professional pictures is a luxury, I like to add them to special trips as a great way to immortalize those moments in color.
Where to Eat in Saint Martin: My Recommendations
For me, food is a big part of any trip and St Martin delivered in every way. Here are some spots we tried and would genuinely recommend:
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Captain's Rib Shack: the ribs are as good as everyone says (make sure to ask for extra sauce) and it's perfect to eat there or grab your food to-go. There can sometimes be a bit of a wait because of how busy it gets, but it’s totally worth it.
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Cynthia's Talk of the Town: two words - red snapper. You have to try it. Pretty popular and busy too but had much faster service in my opinion.
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Fritay’s: This place does fish like nowhere else. The red snapper is their most popular item.
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La Dolce Vita: who doesn’t love a sweet treat?
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Boca Seafood Restaurant: Alexa play “so delicious”. This was our fav spot, and we went back a few times.
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Ocean Echo (Anguilla): I had the best burger here. It was a solid 10/10.
Joba's Pick
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My favourite meal of this trip was the spicey jerk wings at Boca. The spice and taste hit all the right spots, and you can tell because we went back a few times and made sure it was our last meal of the trip.
What to Pack for St Martin
Packing for a beach trip in the Caribbean from Canada means accounting for the flight time, the unforgiving sun, and any specific activities you've planned. My free packing checklist has practically all you need, but here is a list of specific things I'd recommend:
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Motion sickness tablets because the ferry to Anguilla can be choppy, and you'll thank yourself.
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Sun protection. I’m talking sunscreen, a hat, and sunglasses. Trust me, you don’t want to risk sunburn.
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An eSIM as you’ll be Island hopping and need to stay connected.
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An insect repellent net that can be used on a travel stroller or crib if you’ll be traveling with an infant/toddler.
Final Thoughts on St Martin
My trip to Sint Maarten was everything, and then some. One of my favorite things was the chance to island hop and get more passport stamps in the process. Aside from Anguilla, St Barths is another island that you can easily take a day trip to from Sint Maarten, as it is only a 40-min ferry ride.
This was my first trip with my daughter, and I think it makes for a lovely Canadian family vacation. It’s a direct flight out of Toronto, the flight time is short enough, and you get value for your Canadian Dollar. I shared some family-friendly activities we enjoyed in SXM here. I would definitely revisit.
Let’s connect on Instagram, where you can follow along to see more realistic travel content for families and all types of travelers.
Safe travels,
Joba.
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Written By
Joba
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