A Perfect Week in St. Maarten with Island Hopping

After landing a new job, I took a week to celebrate in the Caribbean—easily one of the most beautiful places on earth. It was my friend’s birthday, and she invited us on a one-week trip through Saint Martin, Saint Barth's, and Anguilla. Three islands I had never been to, so the answer was obvious.

We were a group of four flying in from different parts of the country, all meeting in Saint Martin, where we were staying.

I flew American Airlines from EWR to Princess Juliana Airport for just under $1,000 in basic economy—and I have thoughts. Not all good. No miles earned, and with rising jet fuel costs, you’re definitely seeing it reflected on the consumer side. Still, we landed April 2 and met our pre-booked driver.

There was a slight hiccup. Our original driver had a fender bender the night before and reassigned us to a colleague. Nice enough, but once we paid in full early, timelines became… flexible. A note: never pay in full before the end of your stay.

If you’ve read my blog before, you already know—I’m a hotel resort person, through and through. This was my first time staying in an Airbnb. I was impressed: spotless, beautifully kept, and hosted by genuinely kind people. But for me, vacation means full service—daily housekeeping, towel refreshes, concierge, drivers on-site. That level of attention is hard to replicate. I’d do it again in theory, but it’s not my preference.

Day 1 — A Strong Start

We settled in before heading to Tortuga on the French side, right by Maho Beach, for a late lunch. We had a reservation, but it’s not essential.

We arrived during happy hour—which, in Saint Martin, is non-negotiable. Positioned directly under the flight path, planes descending overhead, the setting alone carries the experience. The food delivered. The drinks, less so—the frozen options didn’t quite land for us.

After, we walked down to Maho Beach for sunset. Watching planes land, feet in the sand—it’s one of those moments that feels very specific to this island. Locals recommend going early in the morning if you want photos with the planes.

We went back, reset, and headed out again. Dinner wasn’t planned, but our driver suggested Boca Boca—a local favorite—and it ended up being one of the better meals of the night. Casual, but done right. They even offered a complimentary rum tasting to close. No complaints there!

From there, we went to Nowhere Special—an open-air bar with live music, real energy, and exactly the kind of unpolished fun you want on your first night. We stayed until close.

Day 2 — Babacool

I started my morning early— a walk along Mullet Bay, quiet, empty, exactly how I like it. About ten minutes out, I found Da Sweet Tooth, a café with surprisingly good matcha and coffee. I went back later in the trip, which says enough.

The day was centered around Babacool Beach Club—and it was everything! Easily one of the chicest beach setups I’ve experienced. Pink everywhere, strong service, turquoise water, soft sand. It’s curated but not forced.

We stayed all day—swimming, drinking spritzes, doing very little in the best way.

Dinner that night was Jax Steakhouse, which had been heavily recommended. It lived up to it. I always lean seafood on islands, and the snapper was one of the best meals of the trip. Fresh, simple, exactly what it should be.

We kept it low-key after—Mimosa Lounge, next door. Easy, not overcrowded, but you can tell it picks up on the right night.

Day 3 — St. Barths

We took the 9:30 AM ferry from Marigot to St. Barths—tickets booked a week in advance (do this). The ferry itself was rough. Very rough. If you’re prone to seasickness, plan accordingly—or skip it entirely and book a flight or helicopter. I would next time.

St. Barths feels different immediately. More polished, more intentional. We spent the morning shopping—every major luxury house is there—and then headed to Nao Beach Club.

Nao is chic without trying too hard. The food was excellent, but the drinks stood out more. By mid-afternoon, the energy shifted into more of a party atmosphere—something between curated and exclusive.

From there, we walked to Nikki Beach. Completely different energy—loud, social, people on tables, champagne everywhere. One of the better Nikki Beach locations I’ve been to, and visually one of the most beautiful.

We ended the day there before heading back to Saint Martin.

Dinner that night was Fritay’s—my favorite meal of the entire trip. No question. The red snapper alone is worth going out of your way for. This is the kind of place you hear about repeatedly before arriving—and it still exceeds expectations.

We stopped by Captain Rib Shack for drinks, then went to Lotus Night Club. Classic nightclub setup, good music, plenty of space. If you’re planning anything more structured like bottle service, book ahead.

Day 4 — French Side

We started slow with brunch at Baratie—a bit of a drive, but worth it. Cozy, local, effortless. I had a fried lobster and waffle, which I wasn’t expecting to love as much as I did.

From there, we went to Rainbow Café. This is one you plan ahead. Beach chairs come with a steep minimum, but the atmosphere is very much the draw—celebratory, busy, high-energy. The piña colada and truffle pizza stood out. Service could have been smoother, but the setting carries.

Dinner was at Bamboo House, which might be the most visually striking restaurant of the trip. Elevated, open-air, layered with water features throughout. The sushi and cocktails were excellent, though they were sold out of several menu items—earlier reservations would help here.

We skipped going out that night—Anguilla was next.

Day 5 — Anguilla

Anguilla ended up being the highlight.

We took a later ferry, which I wouldn’t recommend—go as early as possible. The ride itself is quick and easy.

We went straight to Savi Beach, and it’s one of the most beautiful beaches I’ve seen. Clear, bright turquoise water, soft white sand, and noticeably less crowded than anywhere else we’d been.

Service here stood out immediately. We booked a cabana (beach chairs were gone), and it ended up being the better option—more space, more privacy, full setup included.

If I could change anything about this trip, I would have spent multiple days in Anguilla.

Dinner was at Palapas. A good middle ground between casual and upscale after a day like that.

Saint Martin gives you range—beach clubs, nightlife, quiet mornings, and access to two completely different islands within an hour.

It’s the kind of trip that doesn’t need to be over-explained. I’ll be back.

As always, thanks for reading.

Xoxo,

Feline Shores