Lambada: The Catamaran Day Sail to Anguilla from St Maarten
I've been skippering catamarans out of Simpson Bay since 2014, and this is the run I never tire of. The catamaran day sail to Anguilla from St Maarten takes Lambada, our 65-foot sloop-rigged cat, across roughly twelve miles of open channel to the uninhabited Prickly Pear Cays — snorkel the reef, swim off a quiet Anguillan beach on the way home, with lunch and an open bar going the whole time. If you're still weighing your options, browse the rest of our boat trips around Sint Maarten before you commit a whole day to this one.
About the Lambada Anguilla Day Sail
Cancel up to 24 hours ahead for a full refund if the weather turns or plans change
Hold your seats today and settle up closer to sailing day
A genuine full day from dock line to dock line, not a quick coastal loop
Lambada is a wide, stable sailing cat with shade, trampolines and deck room to spare
Reef snorkeling at Prickly Pear plus a swim stop off an Anguillan beach
Lunch, snorkel gear and an open bar are all part of the fare
Check Live Availability & Prices
Live sailing dates and per-person prices for the full-day Lambada catamaran day sail to Anguilla's Prickly Pear Cays from St Maarten.
Why Book the Lambada Day Sail
Most days on Lambada we cast off from Simpson Bay around mid-morning, sheet in the main once we clear the channel buoys, and ride the prevailing easterly trade winds north toward Anguilla. On a sailing catamaran that crossing feels alive — you get the heel, the hiss of the hulls cutting water, and that long flat horizon of Caribbean blue with Anguilla's low green ridge slowly rising ahead. It's about twelve miles of open water, and I'd rather make it under canvas than motor it, because half the joy of this trip is the sail itself.
What sets the catamaran day sail to Anguilla from St Maarten apart is the destination. Prickly Pear is uninhabited — two scrubby cays with a reef I've been anchoring off for years, and water so clear you can read the depth gauge by eye. Add the lunch, the open bar, and a swim stop off a soft Anguillan beach on the run home, and you've got a full 7.5-hour day rated 4.6 stars. If you only want a couple of hours afloat, our half-day catamaran snorkel cruise with open bar and lunch is the gentler pick.
What You'll See and Do
From the moment we drop the dock lines this is a sailing day first, a beach day second. Across the seven and a half hours you'll:
- Sail the open trade-wind channel between St Maarten and Anguilla on a 65-foot cat
- Anchor off the Prickly Pear Cays and snorkel a healthy fringing reef
- Drift over coral heads spotting parrotfish, sergeant majors, rays and the odd green turtle
- Swim and wade off a quiet Anguillan beach on the return leg
- Take a turn helping trim a sheet or steer if you fancy a hand on the wheel
- Refuel between stops with lunch and a bar that stays open all day
What's Included (and What Isn't)
What's Included
- A full day's sailing aboard Lambada, a 65-foot catamaran with crew
- Snorkel mask, fins and vest for the Prickly Pear reef stop
- Lunch served on board between the stops
- An open bar running all day — rum punch, beer, soft drinks and water
- A snorkel and swim stop plus a beach pause off Anguilla
Not Included
- Anguilla arrival or marine-park fees, if they apply on your date (confirm at booking)
- Crew gratuities, which are optional but always appreciated by the deckhands
- Your own beach towel and reef-safe sunscreen
How the Sailing Day Unfolds
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Morning
Cast off from Simpson Bay
We board in Simpson Bay, run through the safety brief, motor out of the lagoon and raise the main once we're in clear water.
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Late morning
The crossing
Lambada settles onto a beam reach in the trades and makes the twelve-mile run north toward Anguilla under sail.
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Midday
Prickly Pear Cays
We drop anchor over the reef, hand out snorkel gear, and you're in the water exploring the coral and serving up lunch back on deck.
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Afternoon
Anguillan beach stop
On the way home we pause off a soft Anguillan beach for a swim, a wade ashore and a last round from the bar.
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Late afternoon
Sail back to base
We point the bows south and ride the wind back across the channel to Simpson Bay to wrap the day.
Important Things to Know Before You Go
A long day at sea rewards a little preparation. From the helm, here's what I tell every group at the dock:
- This is a true open-water crossing — if you know you're sensitive, take a motion-sickness tablet 30 to 60 minutes before we board, not after
- Anguilla is a separate British territory, so carry a passport and confirm any arrival or marine-park fees that may apply for your date
- Bring a card or small cash for fees and crew tips, since there's no cashpoint mid-channel
- Sun is relentless across 7.5 hours on the water, so reapply reef-safe sunscreen through the day rather than just once at the dock
What to pack
- Swimwear worn under your clothes and a towel for the beach stop
- Reef-safe sunscreen, a brimmed hat and a cord for your sunglasses
- A dry bag or waterproof case for your phone and camera
- Cash or a card for fees and gratuities
What to leave behind
- Anything that can't take salt spray or sand
- A packed afternoon schedule — Lambada has you out until late afternoon
Where It Departs — Simpson Bay, Sint Maarten
Who This Tour Is For
Lambada's Anguilla run is built for travelers who want to give the sea a full day rather than a quick taste:
- Sailing fans who'd rather feel a catamaran heel than ride a motorboat across
- Visitors keen to step onto a second island and count Anguilla among their stamps
- Easygoing groups who like an all-inclusive lunch-and-bar day afloat
- Casual snorkelers chasing the clearest reef water on this stretch of coast
Not ideal for
- Anyone tight on time, since this trip eats the whole day
- Travelers who get badly seasick on open-water passages
- Visitors who'd rather sightsee on land than spend hours under sail
Lambada Anguilla Day Sail — FAQ
Will the channel crossing make me seasick?
It can be livelier than a coastal cruise — we cross about twelve miles of open trade-wind water, so there's a real swell out there. From years on this run my advice is simple: take a motion-sickness tablet 30 to 60 minutes before boarding, sit aft near the centerline where Lambada moves least, and keep your eyes on Anguilla's ridge ahead. If the forecast looks rough we'll tell you, and you can shift to our calmer luxury catamaran day sail with lunch and drinks instead.
Do I need my passport for Anguilla?
Yes — Anguilla is a separate British territory from St Maarten, so bring your passport and check current entry rules and any fees for your travel date. If you'd like a hand confirming the paperwork before you sail, just reach out to us through the contact page and we'll talk it through.
What's included in the fare?
The day covers your full sail on Lambada, snorkel gear for the Prickly Pear reef, lunch on board and an open bar that runs all day. Anguilla arrival or marine-park fees, crew tips and your own towel and sunscreen sit outside the price. You can compare what's bundled against our other Sint Maarten catamaran trips above.
How much does the Anguilla day sail cost?
It starts at $135 per person for the whole all-inclusive day. That's a fair price for 7.5 hours under sail with lunch and an open bar thrown in — weigh it against the shorter half-day option on our catamaran snorkel cruise with open bar and lunch if you'd rather not give up a full day.
Where exactly does Lambada sail, and where does it leave from?
We depart Simpson Bay on the Dutch side of Sint Maarten, cross the channel to Anguilla's uninhabited Prickly Pear Cays for the snorkel stop, then pause off a quiet Anguillan beach on the return before sailing back to Simpson Bay.
What Travelers Say About the Lambada Sail
Captain Dwayne and the crew made this. We sailed almost the whole way over, which I wasn't expecting, and the reef at Prickly Pear was bursting with fish. Lunch was generous and the rum punch never ran dry. A full day well spent.
The crossing was a touch bumpy but the tablet I took at the dock sorted me out, and once we anchored it was paradise. Loved that Lambada actually sailed instead of just motoring. The beach stop on the way back was the perfect wind-down.
Best day of our trip. Two islands, clear water, an open bar and a crew who clearly love what they do. The trampolines up front were the best seat on the boat for the sail across.