– 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.
Shared tours from $135. I’ve picked the ones worth your time.
Note: This page covers organized boat tours only. If you’d rather go independently, here’s my guide to the Anguilla ferry from St Maarten.
Want a quick answer? These are the three tours I'd book myself
Yes — and I’d say that even if I didn’t live here.
Anguilla is not St Maarten. It’s quieter, slower, and somehow even more beautiful. The beaches are in a different category entirely — finer sand, clearer water, fewer crowds. Shoal Bay East is one of those places that makes you question every beach you’ve ever been to before.
The crossing takes about 20 minutes. A well-organized catamaran trip handles everything — from the sailing to the snorkeling stops, lunch on board, and the easy rhythm of the day. 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 it are the ones who waited too long and missed out on their preferred tour. Nobody who actually goes comes back disappointed.
Worth it? Without hesitation.
Best boat trips from St Maarten to Anguilla (my top picks)
There are hundreds of catamaran trips to Anguilla listed online, and very little to tell them apart at first glance — same itineraries, same promises, same turquoise-water photos.
After two decades living here, you start to see which operators truly stand out — the ones visitors come back raving about, and the ones we choose ourselves for a proper day out on the water with friends or family.
These are the ones I’ve selected here.
Because I know plans can change when you’re on holiday, all links go through trusted booking platforms — with instant confirmation and the flexibility to cancel if your plans change.
This is the one that sells out first — and the one people remember most.
Four to five stops in a single day: snorkeling with sea turtles at Little Bay, Prickly Pear Cay, Shoal Bay, Meads Bay — sometimes even Maunday’s Bay.
The boat covers more ground than any other tour, yet the pace never feels rushed. You arrive somewhere beautiful, stay long enough to enjoy it, then move on.
What people talk about afterwards — more than the beaches or even the turtles — is the crew. Not just professional, but genuinely fun. The kind of atmosphere that turns a day trip into something you actually remember.
The bar runs all day — proper cocktails, not just rum punch — and lunch is a fresh BBQ prepared on board while you’re in the water.
If you’re hesitating between the different catamaran options, this is the more active, more varied experience — and the one people choose when they want to see as much as possible in a single day.
One thing to know: turtle sightings aren’t guaranteed — it depends on conditions. The rest of the experience, however, is consistently strong.
This is the one that sells out first — and the one people choose when they want a more active, full day on the water. If you see your dates available, it’s worth securing your spot — departures can fill up quickly, especially during busy periods.
→ Book the Boomerang — swim with turtles
Two stops, one effortless day on the water.
Your catamaran leaves Simpson Bay in the morning and heads first to Prickly Pear — a small, almost untouched island with clear turquoise water and a reef you can snorkel straight from the beach.
Later, you’ll stop at Meads Bay in Anguilla for a second swim before the sail back. The pace stays relaxed throughout — no rushing, no strict timing, just a smooth flow from one stop to the next.
What people consistently mention in their reviews: the crew, the food, and the rum punch. BBQ ribs, grilled chicken, Johnny cakes — prepared on board while you’re in the water, then served with an open bar that runs all day. It’s the kind of lunch that simply feels better after a long swim.
Perfect if you want a carefree, well-organized day without having to think about anything. The boat is spacious, the atmosphere easygoing, and the stops genuinely beautiful.
One thing to know: bring your passport — you’ll be crossing into Anguilla, a British territory. It’s checked before departure.
This is one of the easiest ways to experience Anguilla without overthinking the day — everything is handled for you, from the sailing to lunch and swim stops.
→ Check availability for your dates & secure your spot
682 reviews, 4.8 stars — and 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 reflects hundreds of different days, different crews, and different travelers… all coming back satisfied. That kind of consistency is hard to fake.
This is 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 throughout the day.
The crew is mentioned in almost every review: knowledgeable, fun, and attentive without ever feeling over the top.
A solid choice if you’re looking for something reliable, slightly faster-paced, and easy to book with confidence.
One thing to know: you’ll need your passport — you’re crossing into Anguilla.
At this point, it’s really about choosing something you can rely on — this is one of those options that simply works, day after day.
→ Book the Anguilla Getaway cruise
One of the highest-rated tours on this list — at a lower price point.
The name can be a bit misleading — “In Style” might sound formal. It’s not. What people consistently describe is a day that feels more relaxed, more natural, almost like being out on the water with a crew that genuinely enjoys what they do.
Four stops — Shoal Bay, Little Bay, Meads Bay, Maunday’s Bay. The best of Anguilla in a single day, at a pace that lets you actually enjoy each stop rather than just moving through it.
Smaller group, open bar, lunch included — and an overall atmosphere that feels more personal than most.
A smart choice if you’re looking for something high-quality, a bit more intimate, and priced just below most similar options.
At this price point, it’s one of the smartest choices on the list — especially if you prefer something a bit more personal and less crowded.
→ Book Anguilla in Style
47 reviews — every single one 5 stars.
That kind of consistency doesn’t happen by accident. It happens when a captain understands that a private charter isn’t just a tour — it’s someone’s anniversary, someone’s birthday, or simply their one perfect day before flying home. And he treats it that way.
Just you and your group. No strangers, no fixed schedule, no compromises. You tell the captain where you’d like to go — he takes care of the rest.
Conditions right for Little Bay? You go. Want to stay longer at Shoal Bay? You stay. That flexibility is the whole point — and something no shared tour can really offer.
It’s a different kind of experience — one that’s less about ticking off stops, and more about creating a day that feels entirely your own.
It costs more than the group options. But the people who’ve done it don’t describe it as an excursion — they describe it as the highlight of their trip.
This is the kind of experience you choose when the day matters — when you want complete freedom, privacy, and something that feels entirely your own.
→ Book the private speedboat charter to Anguilla
The crossing takes around 20 to 30 minutes, depending on the boat. Some days the channel is glassy flat and you barely feel it. Other days it’s a bit choppy — if you’re prone to seasickness, sit towards 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 three to five stops throughout 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 checking the time. That’s usually the best sign.
You’ll be back at the marina by late afternoon — just enough time to shower and make it to dinner in Grand Case.
One thing I always tell people: bring your passport, reef-safe sunscreen, and a dry bag for your phone.
(If you’re unsure what to pack, I’ve put together a simple guide here.)
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 lively.
Lined with beachfront restaurants and that effortless Anguilla feel — relaxed but refined.
If your tour stops here for lunch, you’re exactly where you want to be.
The quietest of the three. Long, soft, almost empty.
On a clear day, you can see St Maarten from the shore — close enough to feel familiar, far enough to feel like a proper escape. 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.
🌊 Looking for more adventures on the water?
→ See all things to do in St Maarten
→ Best catamaran tours in St Maarten
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!
→ Vacation Rentals : Start with our own curated selection of villas and rentals — some owners accept direct bookings. If you don’t find what you’re looking for, VRBO and Booking.com have a wide selection.
→ Hotels : TripAdvisor and Booking.com are our go-to for the best rates.
→ Car Rental : Renting a car is essential in St Martin. DiscoverCars searches all local companies for the lowest rates.
→ Tours & Excursions : I book through Viator and GetYourGuide — both offer free cancellation on most tours.
→ Flights : I search Expedia for the best deals to SXM Airport.
→ eSIM : Skip the roaming fees. Airalo works perfectly in St Martin.
→ Follow me on Facebook here
*Transparency note
Some links on this page are affiliate links. If you choose to book through them, I may earn a small commission — at no extra cost to you.
It helps support the time and care that goes into creating these guides, so thank you.
