Anguilla: Classic Sailing & Snorkel Tour with Open Bar

Summary

Experience Anguilla’s coast by sail then snorkel Little Bay reef

You’ll sail Anguilla’s coast on a classic sloop with a local crew, then snorkel Little Bay’s reefs where turtles and pelicans drift by. Drinks flow freely and there’s time to swim or just watch sunlight flicker off the water. It all feels easy—like you belong here for a while.

What’s the experience like?

Someone hands me a cold drink before I’ve even found my balance on the deck—rum punch, sweet and sharp, sweating in the morning sun. The boat is called Tradition, and she creaks in a way that feels old but safe. Our captain, who everyone just calls “Boss,” grins as he tells us about smuggling rum up these same waters back in the day. I’m not sure if he’s joking or not. The sails go up with a snap and suddenly we’re moving, wind in our faces, salt spray on my lips. There’s this moment when you realize you can’t hear anything but water and canvas—no engines, no traffic, just the sound of the Caribbean doing its thing.

We drift for maybe an hour (I lose track), watching pelicans dive-bomb for fish near the cliffs. Boss points out Little Bay ahead—a slice of turquoise tucked under these wild rocks. He says turtles like to hang around here, and sure enough, someone spots one poking its head up before disappearing again. The crew jokes about jumping off “the rock” but I’m already thinking about how cold the water will feel. Turns out it’s warm—almost too warm—and floating above the reef feels like flying over a garden you’re not supposed to touch.

I try snorkeling for longer than I thought I would—stingrays gliding past, tiny fish darting everywhere. At some point Li from the crew laughs when I try to say “thank you” in Creole (definitely butchered it). Back on deck there’s more rum punch and someone passes me a towel that smells faintly of coconut sunscreen. We sit in the shade swapping stories with strangers who don’t feel like strangers anymore. It’s funny—I didn’t expect to care so much about an old boat or a hidden cove, but now I keep thinking about that quiet blue water under the cliffs.

Step-by-step itinerary

Day 1 — Sail and snorkel at Little Bay

• Sail onboard classic West Indian Sloop
• Snorkel and relax at Little Bay

Top questions

How long is the sailing & snorkeling tour from Anguilla?

The half-day tour lasts approximately 3-4 hours including sailing to Little Bay and time for snorkeling or relaxing.

Is snorkeling equipment provided on this Anguilla tour?

Yes, all snorkeling gear and swim aids are included at no extra cost.

Where does the sailing trip depart from?

The captain picks you up at the small wooden dock in Sandy Ground village.

Are drinks included during the sail?

Yes, unlimited alcoholic and non-alcoholic drinks are available throughout the tour.

Can beginners join this sailing & snorkel adventure?

The tour is suitable for all physical fitness levels; no experience needed.

What’s included

Your day includes pickup at Sandy Ground dock by your captain, unlimited drinks from an open bar (alcoholic and non-alcoholic), use of towels and all snorkel equipment, plus guidance from a friendly local crew throughout your authentic sailing adventure.