The Catamaran Day Sail to Anguilla from St Maarten
For a full day on the water, this is the big one. The catamaran day sail crosses from St Maarten to the Anguillan cays on a 65-foot sailing catamaran, with a snorkel and swim stop at Prickly Pear and a beach pause on the way back — all food and drinks included. It's seven and a half hours of open-water island-hopping, rated 4.6 stars. Here's what to expect, plus how it compares with the other Sint Maarten island tours.
About the Anguilla Catamaran Day Sail
Cancel up to 24 hours before for a full refund
Hold your spot and pay closer to the day
A full all-inclusive day on the water
A spacious sailing catamaran with room to spread out
Stops at Prickly Pear and an Anguillan beach
Food and an open bar included all day
Check Live Availability & Prices
Real-time dates and prices for the full-day catamaran sail to Anguilla's Prickly Pear Cays from St Maarten.
Why Book the Anguilla Day Sail
This is island-hopping at its best. You board a 65-foot sailing catamaran in Simpson Bay and cross the turquoise channel to Anguilla — a quieter, lower-key island famous for its clear water and white sand. The day includes a snorkel and swim at the Prickly Pear Cays and a beach stop off an Anguillan shore, with food and an open bar flowing the whole time.
At seven and a half hours it's the longest trip on this site and the one to pick when you want a proper full day at sea rather than a quick cruise. It's rated 4.6 stars. Compare it with the rest of our island tours in St Maarten.
What You'll See and Do
A full day that mixes sailing, snorkeling and beach time. Expect to:
- Sail the open channel between St Maarten and Anguilla
- Snorkel the clear water at the Prickly Pear Cays
- Swim and relax at a beach stop on the way back
- Spot reef fish, rays and the occasional turtle at the snorkel stop
- Enjoy food and an open bar between the stops
What's Included (and What Isn't)
What's Included
- A full-day sail on a 65-foot catamaran
- Snorkel gear for the Prickly Pear stop
- Food and an open bar all day
- A snorkel/swim stop and a beach stop
- A friendly sailing crew
Not Included
- Any Anguilla arrival or marine-park fees (confirm at booking)
- Gratuities for the crew (optional but appreciated)
- Your own towel and reef-safe sunscreen
How the Day Flows
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Morning
Depart Simpson Bay
Board the catamaran in Simpson Bay and set sail across the channel toward Anguilla.
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Late morning
Prickly Pear Cays
Anchor at the cays to snorkel and swim in the clear water.
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Midday
Lunch & open bar
Enjoy food and drinks on board as you relax between stops.
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Afternoon
Beach stop
Pause at an Anguillan beach for a swim and some sand time.
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Late afternoon
Sail home
Cruise back across the channel to Simpson Bay to finish the day.
Important Things to Know Before You Go
A long, rewarding day at sea — pace yourself with the open bar and plan for sun.
- It's a full open-water crossing, so take a seasickness tablet beforehand if you're prone to it
- Anguilla can charge arrival or marine-park fees — confirm whether they're included
- Bring a card or cash for any fees and crew tips
- There's a lot of sun across 7.5 hours — reapply sunscreen through the day
What to pack
- Swimwear under your clothes and a towel
- Reef-safe sunscreen, a hat and sunglasses
- A waterproof phone case for the snorkel and beach stops
- Cash or a card for fees and tips
What to leave behind
- Anything that can't get wet or sandy
- A packed afternoon schedule — this trip takes the whole day
Insider Tips for the Anguilla Sail
What experienced day-sailers suggest:
- Ask whether Anguilla fees are included before you go so there are no surprises
- The open channel can be bumpy — take motion-sickness tablets 30–60 minutes before boarding
- Stake out a shaded spot on the catamaran early; the sun is relentless mid-channel
- Pace the open bar — it's a long day and the snorkel stop is better enjoyed sober
- Bring a dry bag for phones and cameras for the tender and beach stops
- This is a full day, so don't book anything else for the afternoon
Where It Departs — Simpson Bay, St Maarten
Who This Tour Is For
The pick for travelers who want a full, all-inclusive day island-hopping at sea.
- Sailing and beach lovers who want a proper full day on the water
- Travelers keen to add a second island, Anguilla, to their trip
- Groups happy with an all-inclusive food-and-drinks day
- Casual snorkelers who want clear water and a relaxed pace
Not ideal for
- Anyone short on time — it takes the whole day
- Travelers prone to seasickness on open-water crossings
- Visitors who want island sightseeing on land instead of a sail
St Maarten to Anguilla Catamaran Sail — FAQ
Where does the catamaran sail to?
It crosses from Simpson Bay in St Maarten to Anguilla, with a snorkel and swim stop at the Prickly Pear Cays and a beach stop off an Anguillan shore. Compare it with the other island tours in St Maarten.
How long is the day and what's included?
It's a full 7.5-hour day with snorkel gear, food and an open bar included. Any Anguilla arrival or marine-park fees may be extra — confirm at booking. You can check live availability for your date above.
Will I get seasick on the crossing?
It's an open-water channel crossing, so it can be bumpier than a coastal cruise. If you're prone to motion sickness, take a tablet 30–60 minutes before boarding and keep your eyes on the horizon during the crossing.
Do I need my passport for Anguilla?
Anguilla is a separate territory, so carry your passport and check current entry requirements and any fees when you book. Contact us if you'd like help confirming the details before your trip.
How much does the Anguilla day sail cost?
It starts at $135 per person for the full all-inclusive day. Compare it with the rest of our Sint Maarten island tours to weigh it against the shorter coastal cruises.
What Travelers Say About the Anguilla Sail
An incredible full day. The crossing to Anguilla was beautiful, the water at Prickly Pear was the clearest I've ever snorkeled, and the food and drinks kept coming. Worth giving up a whole day for.
The catamaran was spacious and the crew were brilliant. Two great stops, a proper beach pause and an open bar all day. Take a seasickness tablet for the channel and you'll have a perfect day.
Loved adding Anguilla to our trip. Sailing, snorkeling and a beach all in one day, all-inclusive. The clear water alone was worth it.