Caribbean Sailing: Explore Anguilla's Little Bay

Embark on an authentic sailing adventure to Little Bay in Anguilla. Snorkel in the crystal-clear waters, indulge in a delicious lunch, and relax on a classic Caribbean Rum Runner.

Duration: 3 hours
Cancellation: 24 hours
Highlights
  • Tradition Sailing Charters - Experience an unforgettable journey aboard a historic and traditionally rigged Classic West Indian Sloop. Built in 1978, Tradition was originally used to transport cargo throughout the Lesser Antilles, Caribbean, including the clandestine trade of rum. It stands as one of the last remaining vessels of its kind.
    The…
What's Included
  • GST (Goods and Services Tax)
  • Unlimited drinks (open bar)
  • Water and other non-alcoholic drinks
  • Towels
  • Use of snorkeling equipment
What's Not Included
  • Gratuities
  • Transportation to/from attractions
Additional Information

Experience the genuine charm of sailing on a traditional Caribbean “Rum Runner” from the past as Tradition navigates to one of Anguilla’s secret gems, Little Bay.
Little Bay is a breathtaking sanctuary, home to turtles, nesting pelicans, tropic birds, and majestic cliffs, making it an essential stop on your Anguilla adventure. Leap from the side of…

Location
Sandy Ground Road
Departure Point: Sandy Ground Dinghy Dock, Sandy Ground Village Directions: The Captain will pick you up in our tender from the Sandy Ground Dinghy Dock, centrally located in Sandy Ground Village.
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Customer Ratings
5.0
(43 Ratings)
5 stars
4 stars
3 stars
2 stars
1 star
Luxlovernyc
Feb 11, 2026
Don't miss a sail on this lovely ship with a fantastic crew - Our sail on Tradition was a highlight of a great week-long visit to Anguilla. There were six of us in total on the 3-hour sail. It was a gorgeous day (a lucky break in a week of mixed weather) and we had a fantastic time with Captain Deb and her stellar crew. We spent about an hour under sail to Little Bay, where several of our group snorkeled for an hour or more and others simply enjoyed floating in the water with noodles, amid turtles and other sea life. Rum punches or other drinks happily handed out to those afloat when asked. We got a lot of great stories about the boat and its history and about the island as well. Drinks of all kinds were provided, along with towels, noodles, snorkel equipment, even sun screen if needed. A lovely and relaxing way to spend a beautiful morning. Highly recommended.
Review provided by Tripadvisor
Btggo
Jan 25, 2026
Excellent half day trip. So much fun and great staff. - Deb and her crew took us on a great half day trip to little bay. They were super accommodating, gave us time for snorkeling and provided plenty of rum punch! We brought our own snorkel gear but there is no need, they have all the gear you need on the boat. They also provide nice towels for drying off after you’ve finished in the water. It was a wonderful way to experience the beautiful coast of Anguilla.
Review provided by Tripadvisor
Kathleen
May 1, 2025
Absolutely relaxing adventure! - Loved the crew, very knowledgeable and accommodating to each individual passenger. Breathtaking views! Highly recommend to anyone who is interested in sailing! Worry free and fun!
Review provided by Tripadvisor
Rpt5120zf
Apr 7, 2025
World Class Service! - We have been coming to Anguilla for over 10 years and this was the first year we took this sail. Shame on us - as we have been missing out on this incredibly fun experience! From the moment of first contact, throughout the sail, snorkeling and lunch, to disembarkment, it was absolutely perfect. Laurie, Deb and Marie were fantastic hosts and sailors, with no detail too small for them. It is rare to find this level of service anywhere in the world, let alone a beautiful sailboat. We will definitely be repeat customers!
Review provided by Tripadvisor
991rossanad
Mar 27, 2025
Fun on the water - This was a wonderful half day on the water. Our hosts Deb and Laurie were great. We appreciated learning some history of the island, as well as the beautiful ship Traditions herself. Sailing, snorkeling, swimming, topped off with ice cold beverages like rum punch and rose wine….what more can you ask for?! Will definitely book another visit next time we come to Anguilla
Review provided by Tripadvisor
Rossana_d
Mar 27, 2025
This was a delightful... - This was a delightful half day on the water. Our hosts Deb and Laurie were great. We appreciated learning about the island, as well as the ship Tradition herself. Sailing, snorkeling, swimming, topped off with ice cold beverages ( rum punch, rose wine, beer, water) ….what’s not to love about that?! We will definitely book again next time we visit Anguilla
Review provided by Viator
Rocksideridge
Mar 1, 2025
Great thing to do in Anguilla - What a great experience. The crew are just lovely, lovely people. It was great to watch them sail and see what a physically intensive sport it is! Next time we are in Anguilla we will do the sunset cruise! Loved it - and the old boat is just so beautiful and well taken care of.
Review provided by Tripadvisor
Ronni_g
Feb 20, 2025
Friendly staff - Very friendly staff very knowledgeable of the Island a very nice morning. A fun time I would do it again next time I return.
Review provided by Viator
Bb686
Feb 13, 2025
💙 Ocean 💙 - Our second trip on Tradition was just as memorable as the first - and we can’t wait to come back for more! This is an absolutely beautiful boat, with amazing history that Capt. Laurie shares with you. Both Laurie and Deb are incredibly welcoming and their passion to share their love of the boat and sailing with others is so infectious. Snorkeling at Little Bay this time was fantastic - with a few sea turtles and a stingray! This is a must when visiting Anguilla
Review provided by Tripadvisor
Andrew
Jan 24, 2025
Incredibly Fun Day!! - We went out on Traditions for a Morning Sail & Snorkeling Trip. Laurie, Deb and Crew were just so awesome. The boat is so cool, Laurie with his knowledge and his sailing stories (AndThe Pump House) Deb makes the best Rum Punch Anywhere!! The sail was great, the snorkeling was great, the day was great. Next time. Sunset or Prickly Pear!! Thank you.
Review provided by Tripadvisor
From $255
up to 12 guests
1 - Adult
Cancellation: Free cancellation up to 24 hours before the start of your experience (local time).