Little Bay Sail & Snorkel in Anguilla: Classic Rum Runner

The boat you're sailing on smuggled rum through the Lesser Antilles.

A half-day sailing and snorkeling tour from Anguilla that takes you aboard Tradition, a classic West Indian sloop built in 1978 to trade cargo—and contraband—through the Caribbean. The captain picks you up at Sandy Ground, raises the sails while you help if you want, and sails 1 to 1.5 hours to Little Bay, where you snorkel for an hour among turtles, stingrays and reef fish, then swim to the beach or rest on the shaded deck. Snorkel gear, towels, swim aids and an open bar of beer, wine, rum punch and soft drinks are included; children from age 4 are welcome.

Step-by-step itinerary

Sail and snorkel at Little Bay

• Board Tradition at Sandy Ground dock
• Receive history and safety briefing
• Enjoy 1-1.5 hour sail to Little Bay
• Snorkel and explore marine life
• Swim to beach or jump off rock
• Relax on deck with drinks

The Experience

Tradition leaves from a small wooden dock in Sandy Ground. The captain gives a short history of the vessel and a safety briefing, then the crew raises the sails—and you're invited to help work them if you want to. The sail to Little Bay takes 1 to 1.5 hours, long enough to feel the rhythm of the boat and the Caribbean wind without the day becoming a journey. The captain and crew are happy to show you the ropes or leave you to watch the water.

Once anchored at Little Bay, you have an hour in the water. The snorkel gear and swim aids are there, but so is the choice: dive in to hunt for turtles and stingrays, swim to the small beach, jump off the famous Little Bay Rock, or stay on deck under the shade with a cold drink and watch the cliffs rise behind the bay. The cooler is stocked with beer, wine, rum punch and soft drinks—no limit, no tab.

Little Bay itself is the draw: a secluded cove ringed by cliffs, home to nesting pelicans and tropic birds, and shallow enough that the marine life—turtles, stingrays, reef fish—moves close to the surface. The water is warm and buoyant. Towels and gear stay with you the whole time.

What’s included

• Snorkel gear, towels and swim aids.
• unlimited beer, wine, rum punch and soft drinks.
• pickup and transfer from the Sandy Ground dock.
• use of the boat's shaded deck between water time.

Good to know

Easy physical level

Operated by Tradition Sailing Charters

Is this one for you?Choose this shared sailing and snorkeling trip if you want to meet other travelers and split costs; book a private charter instead if you prefer your own dedicated crew and boat.

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Top questions

What is Tradition, the boat on this tour?

Tradition is a classic West Indian sloop built in 1978 to carry cargo up and down the Lesser Antilles, including a past life smuggling rum. It's one of the last surviving vessels of its kind, traditionally rigged and still sailed by hand.

Can I help sail the boat, or do I just ride?

The captain and crew are happy to show you the ropes and let you help raise and trim the sails if you want to. It's optional—you can participate as much or as little as you like.

What kind of marine life will I see while snorkeling at Little Bay?

Little Bay is home to sea turtles, stingrays, and reef fish in shallow, clear water. The bay also hosts nesting pelicans and tropic birds on the cliffs above.

Is the open bar really unlimited?

Yes. The cooler is fully stocked with beer, wine, rum punch and non-alcoholic drinks, and there's no limit or tab—everything is included in the tour price.

How long is the sail each way, and how much time do I spend snorkeling?

The sail to Little Bay takes 1 to 1.5 hours. Once you arrive, you have about an hour in the water to snorkel, swim to the beach, jump off the rock or relax on the shaded deck.

Can children go on this tour?

Yes, children are welcome from age 4. Swim aids and snorkel gear are provided, and the crew can help younger swimmers stay safe and comfortable in the water.