– The one day trip every visitor should make.
I’ve watched hundreds of visitors leave on the morning boats and come back with that same look — slightly sunburned, slightly overwhelmed, already wondering when they can go back. Shoal Bay does that to people. The whole island does that to people.
Chic without being showy. Authentic without trying too hard. It attracts billionaires and celebrities every winter season, but it never lost the quiet, unhurried soul that makes it special. Less jet-set than St Barths, more real.
Shoal Bay was recently ranked among the 50 most beautiful beaches in the world by The Guardian. USA Today put two Anguilla beaches in their global top 10. These aren’t random accolades — anyone who’s stood on that sand understands immediately.
One thing I tell every visitor: don’t wait to book. The Boomerang — consistently the most in-demand tour — sells out on average 41 days in advance. December through April, the best boats are gone weeks before people even land at SXM.
If you have one day to spend on a neighboring island, make it Anguilla. None of the people I’ve sent there have ever come back disappointed.
This page covers organized boat tours only. If you’d rather go independently, here’s my guide to the Anguilla ferry from St Maarten.
Shared tours from $135. I’ve picked the ones worth your time.
Want a quick answer? These are the three tours we'd book ourselves.
Yes. And I’d say that even if I weren’t local.
Anguilla is not St Maarten. It’s quieter, slower, and somehow even more beautiful. The beaches are in a different category entirely — the sand is finer, the water clearer, the crowds thinner. Shoal Bay East is one of those places that makes you question every beach you’ve ever been to before.
The crossing takes 20 minutes. A well-organized tour handles everything — the boat, the passport check, the snorkeling gear, the rum punch, the BBQ lunch on board. You leave St Maarten in the morning and you’re back in time for dinner in Grand Case.
The only people I’ve seen regret the Anguilla day trip are the ones who didn’t book early enough and missed their preferred tour. Nobody who actually goes comes back disappointed.
Worth it? Without hesitation.
Best Boat Trips from St Maarten to Anguilla (Our Top Picks)
Two stops, one unforgettable day.
The catamaran leaves Simpson Bay in the morning and crosses to Prickly Pear first — a tiny, almost deserted island with turquoise water and coral reef you can snorkel directly from the shore. Then it heads to Meads Bay in Anguilla for a second swim stop before sailing back. The pace is unhurried. Nobody is rushing you anywhere.
What people consistently mention in their reviews: the crew, the food, and the rum punch. BBQ ribs, grilled chicken, Johnny cakes — cooked on board while you’re in the water, served with an open bar that runs all day. It’s the kind of lunch that tastes better because you’ve been swimming for two hours.
The best choice if you want a relaxed, well-organized day with no logistics to think about. Everything is included, the boat is spacious, and the stops are genuinely beautiful.
One thing to know: bring your passport — you’re crossing into Anguilla, a British territory. It will be checked at departure.
✅ Free cancellation · Open bar · BBQ lunch · Snorkel gear included
→ Book the Prickly Pear catamaran trip
This is the tour that keeps selling out — and the one people mention most when they say Anguilla was the highlight of their entire trip.
Four to five stops in one day: snorkeling with sea turtles at Little Bay, Prickly Pear Cay, Shoal Bay, Meads Bay, sometimes Maunday’s Bay. The boat covers more ground than any other tour on the island, and it does it without feeling rushed. You arrive somewhere beautiful, you stay long enough to actually be there, then you move on.
What everyone talks about after this tour — more than the beaches, more than the turtles — is the crew. Not just professional. Actually fun. The kind of people you end up exchanging numbers with at the end of the day.
The bar runs all day — hand-shaken signature cocktails, not just rum punch from a bucket. Lunch is a proper BBQ cooked fresh on board while you’re in the water. It costs a little more than the catamaran option. Everyone I know who’s done both says it’s worth it.
One thing to know: the turtle sighting isn’t guaranteed — it depends on conditions. But the beaches, the crew, and the food are consistently exceptional regardless.
✅ Free cancellation · Open bar · BBQ lunch · 4-5 stops · Snorkel gear included
→ Book the Boomerang — swim with turtles
682 reviews. 4.8 stars. Years of consistent delivery.
There’s something reassuring about a tour with that kind of track record — not because the number is impressive, but because it means hundreds of different people, on hundreds of different days, with hundreds of different expectations, all came back happy. That’s harder to fake than a handful of glowing reviews.
It’s a powerboat excursion from Simpson Bay — faster and more dynamic than a catamaran, with multiple stops around Anguilla’s most beautiful bays. Beach hopping, snorkeling, swimming, drinks flowing all day. The crew gets mentioned in almost every review: knowledgeable, fun, attentive without hovering.
If you want a well-organized, reliable day in Anguilla without overthinking the choice — this is it.
✅ Free cancellation · Open bar · Lunch included · Snorkel gear · Passport required
→ Book the Anguilla Getaway cruise
Same price as the Getaway Cruise. Higher rating. And a completely different atmosphere.
The name is a little misleading — “in Style” sounds like it might be stiff or formal. It’s the opposite. What people describe consistently is a day that felt personal. Not a group of strangers herded from beach to beach, but something closer to a day out with a crew that genuinely enjoys what they do and shows it.
Four stops — Shoal Bay, Little Bay, Meads Bay, Maunday’s Bay. The best of Anguilla in one day, at a pace that lets you actually be somewhere rather than just tick it off. Open bar, lunch included, small group.
At $149 with a 4.9, it’s quietly one of the best options on this list.
✅ Free cancellation · Open bar · Lunch included · 4 stops · Passport required
→ Book Anguilla in Style
47 reviews. Every single one gives it 5 stars.
That kind of consistency doesn’t happen by accident. It happens when a captain understands that a private charter isn’t a tour — it’s someone’s anniversary, someone’s birthday, someone’s one perfect day before they fly home. And he treats it accordingly.
Just you and your group. No strangers, no fixed schedule, no compromises. You tell the captain where you want to go — he makes it happen. Conditions good enough for Little Bay? You go to Little Bay. Someone wants to stay longer at Shoal Bay? You stay. That flexibility is the whole point, and it’s what no shared tour can give you.
It costs significantly more than the group options. But the people who’ve done it don’t describe it as an excursion. They describe it as the best day of their trip.
✅ Free cancellation · Drinks included · Snorkel gear · Private group only · Passport required
→ Book the private speedboat charter to Anguilla
The crossing takes 20 to 30 minutes depending on the boat. Some days the channel is glassy flat and you barely feel it. Some days it’s choppy — if you’re prone to seasickness, sit at the back and keep your eyes on the horizon. It passes quickly either way.
The moment the water shifts from deep blue to that impossible turquoise, you understand why people come back.
Most tours make 3 to 5 stops across the day. You snorkel, you swim, you eat a proper BBQ lunch cooked fresh on board — not packed sandwiches. The open bar runs all day. At some point you stop noticing the time. That’s always the best sign.
You’re back at the marina by 4-5pm — enough time to shower and make your dinner reservation in Grand Case.
One thing I always tell people: bring your passport, reef-safe sunscreen, and a dry bag for your phone. Everything else is provided.
The beaches are the reason people come back. Not the restaurants, not the hotels — the beaches. Here’s what you’ll actually see on most boat tours.
The one everyone talks about — and it lives up to it. Two miles of white sand, turquoise water so clear you can see the bottom from the boat, and somehow never crowded. The Guardian ranked it among the 50 most beautiful beaches in the world. I’ve been there more times than I can count. It still stops me every time.
If you end up at Shoal Bay — and you will — don’t leave without stopping at Madeariman Restaurant. It’s right there on the sand, feet-in-the-water lunch, Caribbean food, the kind of place where you order one more thing because you’re not ready to leave yet.
I filmed this a long time ago. The beach hasn’t changed. Time flies…
More elegant, more alive. Lined with beachfront restaurants and the kind of effortless luxury Anguilla does better than anywhere else in the region. If your tour stops here for lunch — you’re in the right place.
The quietest of the three. Long, soft, almost empty. On a clear day you can see St Maarten from the sand — close enough to feel familiar, far enough to feel like you’ve escaped. That contrast is very Anguilla.
With a few good options on the table, here’s how to think about it in 30 seconds.
You want the best value shared tour → Prickly Pear Catamaran. Open bar, BBQ lunch, Shoal Bay — everything included from $135.
You want the most stops and the best crew → Boomerang. 4-5 beaches, hand-shaken cocktails, consistently the most talked-about tour on the island. Book early — it sells out 41 days in advance.
You’re traveling as a group or family → Private Speedboat Charter. Your boat, your schedule, your beaches. No strangers, no fixed itinerary.
You’re on a cruise ship → Boomerang — cruise ship friendly, guaranteed return time.
Your budget is tight → Prickly Pear at $135 is the best entry point without compromising on quality.
Fallen in love with Anguilla?
If your schedule allows an extra night — or you’re already planning a longer stay — Anguilla has some of the most beautiful boutique hotels and private villas in the Caribbean.
I've lived in St Martin for 25 years — and I'm an epicurean at heart, in love with my island. I've been giving out insider tips for almost 15 years.
Let me help you plan your perfect vacation in St Martin / St Maarten!
