Trip Report: Toddler-Friendly Caribbean Beach Trip

All the details from our spring break trip to Sint Maarten so you can recreate it for yourself...

Apr 25, 2025

My goal with Travel with Toddlers is to help you have more fun on vacation—so that it *actually* feels like a vacation. After we go on a toddler trip, I’ll write up all the details so you can recreate it yourself. Consider this the equivalent of me forwarding our trip planning Google Doc in newsletter form. This is super long, so consider reading it in the app or in your browser vs. your inbox.

Would you go to the airport without knowing your final destination?

I’m a Type A planner…but so is my partner. Our first trip we planned together (Iceland) we couldn’t agree on who would plan it because we *both* wanted the satisfaction of doing the itinerary. So we both planned a complete 10-day road trip around the ring road and spent weeks negotiating stops where we couldn’t spell the destinations because of all the extra consonants. (We had an incredible trip.)

Me in my Instagram travel girl era, admiring one of the many waterfalls in Iceland.

Since then, we’ve both lightened up a bit. Certainly now as parents, it’s difficult to find the mental space to even get excited about a trip, let alone manage the logistics. Since I ran point on our Disney trip this past fall, my partner handled our spring break.

But he wouldn’t tell me where we were going until the last minute.

Honestly, this kind of spontaneity is so hard to find now that we’re regularly nap trapped. I’m always playing defense against a hangry toddler schedule (who inherited that from me, poor thing) and while we fudge the timing pretty often—I’m proud of how far I’ve come from my postpartum anxiety days of obsessing over the minute it turned 1 PM and it was 2nd nap—I still cling to the schedule like a life raft during long, but fun, motherhood days. It was just what I needed to add extra excitement to our trip.

All this to say, I *did* manage to find out we were heading to Sint Maarten a few days before our flight, but only because I correctly guessed the hint my partner gave me as I finished packing the gazillion bags we needed with our toddler beach stuff and the absolutely gigantic slumberpod/blow-up bed combo.

The trip. was. amazing. Just what I needed: Sunshine, long beach mornings hunting for seaglass or digging in the sand; lazy afternoons alternating between playing mermaid or lying down; mango with breakfast and fresh fish for dinner. Below, you’ll find a full write up of our trip: What we brought, where we stayed, and what I’d recommend (or not) for you to recreate this trip for your family.

This toddler’s job is beach.

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For spring break, I want to actually relax.

Every trip I take, toddler in tow or not, I set an intention for the trip. “Goal” seems too formal here; unless it’s a bucket-list trip or a physically challenging one, it doesn’t make sense to set a goal. In this case, I wanted to relax—for us, that meant saying no to all of the wonderful, amazing things the larger island has to offer, like exploring the capital, Philipsburg, or doing a day trip to nearby Anguilla. This is my long way of saying, we didn’t leave the resort, so we didn’t really “see” Sint Maarten.

Past traveler me is cringing at this, because I usually love getting a feel for every new place, or at least hitting a local bar for real food. I realize this means we could have been anywhere, but that was kind of the point. I just needed someone else to take care of me for a week, somewhere warm, with a beach and a pool. So that’s what we did!

If you want a more detailed guide to Sint Maarten or have slightly older kiddos that want to explore, here’s a great Lonely Planet overview, or you can read Mirva’s Travel with Toddlers interview.

That’s why where you stay is everything.

We stayed at the J.W. Marriott St Maarten Resort and Spa, at Dawn Beach, on points. I asked my husband how he picked the resort: “A combination of points redemption for the property, a direct JetBlue flight from Boston, and good reviews.” A solid formula for any toddler beach trip. (And yes, this is 100% my love language.)

When I was a travel agent—one of the many perks of working for Tripadvisor at the time—I had to take an entire course on Marriott’s many, many offerings. The tiers are confusing and somewhat convoluted because of their M&A strategy, but basically a J.W. is fancier than a Westin (so, fancy) but not quite as in-your-face luxury as a Ritz-Carlton. This particular property got flipped into a J.W. after Hurricane Irma in 2017 which destroyed much of the island. It definitely had a corporate post-pandemic decor vibe (lots of impersonal abstract art and whitewashed walls) but we spent almost all of our time outside, either lounging around a gigantic two-tiered pool with multiple “baby” spots (1-2 inches deep) and a swim-up bar (my toddler would ask for pieces of pineapple, adorable) or plopping ourselves on the beach. Both were great and cleaned regularly—we would arrive at literally 7:30 AM to the beach with no seaweed in sight.

The incredible view from our room. The resort is only three floors high—this is the top floor.

Our room was spacious, an Ocean View with King Bed and Sofa Pullout. We didn’t use the pullout but had enough space with it closed to set up our toddler bed. The bathroom had a bathtub, which we always request as it’s just easier than showering with a wiggly toddler. Most of all, it was clean. Housekeeping came twice a day, which to me felt like the biggest treat because most properties make you request housekeeping these days. After I requested extra towels on the first day, they consistently brought the extra towels every time we swapped out.

“Resort” is a generous term as the property isn’t very large at all and doesn’t have many amenities you see in sprawling all-inclusives. Besides the pool and beach, they have a small garden, a gym, two restaurants that are actually the same restaurant right next to each other, but one is really expensive/fancy and the other is a normal restaurant, a pickleball court, and a spa. They advertised water sports and we saw a bunch of kayaks chained up at the beach, but never saw the shack open, even when we went at the hours concierge told us to.

The waves weren’t super calm, though, so it didn’t bother us since our toddler just wanted to dig all day—I wished I had packed our snorkel gear though, as I just assumed we could rent it when we wanted to tag in and out parenting. (I mean, assumed based on the information on their website…)

Beach, all day.

Dawn Beach may not have the Instagram cred of Maho Beach or the calm waters of Mead’s Bay in Anguilla but I loved this beach because we were one of two resorts on it, and never saw a single vendor. Because neither resort was very large, there was plenty of space to find your own spot on the beach. We always got chairs and umbrellas as there’s no natural shade (to be fair, we got to the beach ridiculously early.) I’d call the waves moderate, but with a toddler we’re not swimming in them anyway. Tons of flotsam and jetsam washed up on the beach every day, though, with more seaglass than I’ve ever seen. We had so much fun hunting for shells and seaglass all week. I was glad I packed my own toys, though, as the resort didn’t have any lying around.

The pool got a lot busier than the beach during the day. If you have Super Mega Awesome Marriott status, you got to sit in comfier beach chairs or could rent a cabana for $$ each day. We didn’t rent one but most of the families with babies we saw did, which I thought was very smart. Otherwise, the chairs filled up quickly, which wasn’t a big deal as LOL to sitting with a busy toddler anyway. (And also, I believe in getting in the water and playing! We had so much fun.)

Gorgeous, groomed beach!

I like to establish a vacation “routine” for these kinds of trips. My toddler (and let’s be real, me) thrives on this, and it’s so nice not to have to think about every detail. For this trip, we:

Woke up 7:00 AM
7:30 AM Breakfast Buffet at Carambola
8:30 AM Beach!
10:00 AM Snack (brought from home)
11:30 AM Lunch either at Carambola or the pool bar. The pool bar was just what you’d expect, and the service was much, much slower, so we usually went back to the main restaurant.
12:30 PM Pool time wiggles
1:30 PM Shower and naptime back in our room. Our toddler has been on-and-off dropping their nap but WOO we slept every day this trip.
3:00 PM Snack on the deck listening to the day’s live music by the pool; tag-in and out with one parent using the spa facilities and the other doing crafts in the room—even if you don’t have a massage scheduled, you can use the steam room and sauna, which was soooooo nice.
5:00 PM Dinner at Carambola
6:30 PM Beach playtime for moonrise
7:30 PM Bathtime and bedtime.

The kid’s menu really worked.

The major disadvantage of this resort is that you couldn’t walk to another restaurant—and the idea of hauling the car seat, booking a car, and then hoping our toddler would eat just felt like too much for two very, very tired parents after a long winter.

But we never got tired of this restaurant’s food—it was always prepared well, came out quickly, and had variety throughout the week with different specials. Every single server would come check in with our toddler and say hello, high five, or just chat, and THAT is why we kept coming back again and again. They knew how to make a meal go smoothly with a kid, including getting the food out early. I appreciated that so much more than a well-prepared red snapper dish.

The morning Breakfast Buffet was a huge highlight, actually. Because we’re Super Elite Platinum Amazing Vibranium members at Marriott, the buffet was included. 10/10 would recommend, made-to-order eggs, smoothies, fruit, french toast, granola, pastries…everything was kid-friendly. Our toddler ate SO MUCH. Weeks later, they’re still talking about that buffet. (Sometimes creating your clone is SO weird.)

We kept meaning to book a dinner at Liguria, the fancy Italian restaurant, but inertia kind of took over by day three (that, and our toddler started requesting specific menu items at dinnertime after memorizing the kids menu.)

Final take: A great plop vacation spot.

I wanted a place to relax in the sunshine and the J.W. delivered! We tried a busy all-inclusive resort last year at Beaches Turks and Caicos and while I loved that resort and totally recommend it, I wanted something more low-key this year. I say this every year but winter is HARD here in New England, especially for this outside mama. I’m not hardcore enough to force my toddler outside when it’s 10 degrees out, even if we’re bouncing off the walls.

This vacation was just what I needed. Not much to do except the beach and the pool, and that’s just the way I liked it. We were one of many families with young kids at the resort, and even though there wasn’t a kids-only pool, I never felt like we were taking up space. And the toddler giggles running headlong across the beach at sunset? I wanted to bottle it up and keep it forever.

Good night giggles on the beach after a wonderful day.

Let me know if you have any questions about this trip! Or if there’s anything else I can answer about planning a spring break with a toddler in general.

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