Anguilla: Prickly Pear Cays Sailing & Beach BBQ Day Trip

Summary

Historic sailing to Prickly Pear Cays with snorkeling and Caribbean barbecue

You’ll step aboard Tradition in Anguilla for a slow sail to Prickly Pear Cays—with mimosas in hand and stories from your local crew echoing over the waves. Snorkel quiet reefs, feast on a Caribbean barbecue lunch right on the sand, and sip rum punch under sharp blue skies before heading home salty and happy.

Step-by-step itinerary

Day 1 — Sail to Prickly Pear Cays and relax

• Board the traditional Caribbean sloop
• Enjoy morning mimosas or orange juice
• Listen to captain's safety briefing and history
• Help raise sails or watch marine life
• Throw out fishing line
• Snorkel the Prickly Pear reef
• Swim, float, and search for shells
• Sip rum punch on beach chair
• Enjoy Caribbean lobster lunch on beach
• Explore beaches and feed bananaquit birds
• Depart Prickly Pear by 2 PM
• Sail back with rum punch and snacks

Top questions

How long is the sailing trip from Anguilla to Prickly Pear Cays?

The entire day trip lasts about 6 hours including sailing time and time spent on Prickly Pear Cays.

Is lunch included during the Prickly Pear Cays sailing tour?

Yes, a Caribbean barbecue lunch featuring lobster is included on the beach at Prickly Pear Cays.

Are drinks provided on board during the day trip?

Unlimited drinks are included—mimosas or fresh juice in the morning, plus rum punch, wine or beer later.

Do they provide snorkel equipment?

Yes, use of snorkel equipment and swim aids is included in your booking.

What wildlife might you see during this sailing tour?

You might spot turtles, flying fish, dolphins, sea birds nesting on Prickly Pear Cays, and colorful reef fish while snorkeling.

How many guests are allowed on each sailing trip?

The Tradition hosts up to 12 guests per day trip for an intimate experience.

Is hotel pickup included for this Anguilla sailing tour?

No hotel pickup is mentioned; guests meet at Sandy Ground/Road Bay to board Tradition.

What happens if there aren’t enough passengers booked?

If fewer than 6 people book for your date, you’ll be offered an alternative date or a full refund.

What’s included

Your day includes sailing aboard Tradition with her local crew from Sandy Ground in Anguilla to Prickly Pear Cays and back again; unlimited drinks from morning mimosas through afternoon rum punch; all snorkel gear; beach chairs; a full Caribbean barbecue lunch (with lobster); plus homemade chocolate chip cookies and fresh watermelon before returning mid-afternoon.

What’s the experience like?

Someone hands me a mimosa before I’ve even found my sea legs. The deck of the Tradition creaks under bare feet—she’s older than I am, and you can feel it in the wood, in the way Captain John tells stories about smuggling rum (he swears it was legal, mostly). There’s this salty morning air and the kind of breeze that makes you squint at the horizon. We’re barely out of Sandy Ground when Li laughs at my attempt to help hoist the sail—turns out it’s heavier than it looks. I just let the crew do their thing after that and watch for flying fish instead.

The sail to Prickly Pear Cays isn’t fast, but nobody seems in a hurry. At some point, someone points out a turtle surfacing near the bow—just for a second—and then we’re drifting closer to these pale beaches that look almost fake. The sand is so white it hurts your eyes. Lunch smells like charcoal and lobster; I’m still picking bits of grilled pineapple out of my teeth when our guide nudges us toward the water with snorkels. I’m not much of a swimmer but floating above that reef is…well, quieter than I expected. Fish dart everywhere and there’s this weird silence except for your own breathing through the tube.

After lunch, there are bananaquit birds swooping down for crumbs (they’re bolder than you’d think), and someone tries to teach me how to say “Prickly Pear” in Creole—I butcher it completely. Rum punch appears when you least expect it. The sun feels different here, sharper maybe? Anyway, by 1:30 we’re back on board for the upwind ride home. It gets choppy enough that I nearly lose my hat—Li just grins at me over her watermelon slice like she’s done this a hundred times.

I didn’t expect to care about an old boat or chocolate chip cookies at sea, but honestly? I still think about that view off the stern as we sailed back toward Anguilla. Not sure if it was the rum or just something about being out there with strangers who don’t feel like strangers anymore.