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
  • Unlimited drinks (open bar)
  • Use of snorkeling equipment
  • Towels
  • Water and other non-alcoholic drinks
  • Goods and Services Tax (GST)
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
(40 Ratings)
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1 star
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
Matt_t
Jan 4, 2025
Great experience! Crew... - Great experience! Crew were fantastic and extremely friendly and knowledgeable. Highly recommend spending the time aboard the charter
Review provided by Viator
Theolliesofwp
Jun 14, 2024
Perfect Day! - Just an amazing day onboard "Tradition"! Our family of (4) said it was the best part of our trip. The day was picture perfect, Laurie, Deb & Thomas were so welcoming, full of great stories and very accommodating to our every need. I especially loved the refills of rum punch with freshly grated nutmeg, great touch! The lunch was so delicious and fresh. We all wanted to book the sunset sail but just didn't have enough time. We will be back to Anguilla one day and first thing will be a sunset sail on "Tradition".
Review provided by Tripadvisor
Gnivr
Mar 17, 2024
A nostalgic day on a last of its kind sailing vessel!! - Just shared the experience of a lifetime sailing with these folks on this elegant and beautiful boat . They made the day extra special for my Grandchildren, and for me as well ! Not to be missed !
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).