Available languages
3 hours
Mobile ticket
Indulge in an authentic sailing experience on a classic Caribbean "Rum Runner" of yesteryear as Tradition sails to one of Anguilla's hidden treasures, Little Bay.
Home to turtles, nesting pelicans, tropic birds and magnificent cliffs, Little Bay is a stunning oasis and a “must do” on your Anguilla itinerary. Dive off the side of Tradition and feast your eyes on a panorama of spectacular marine life as you snorkel through the warm, buoyant waters of the Caribbean.
Suitable for all physical fitness levels
For a full refund, cancel at least 24 hours before the scheduled departure time.
GST (Goods and Services Tax)
Unlimited drinks (open bar)
Water and other non-alcoholic drinks
Towels
Use of Snorkelling equipment
Gratuities
Transportation to/from attractions
Tradition Sailing Charters
Enjoy a "once in a lifetime experience" sailing onboard a historical and traditionally rigged, Classic West Indian Sloop. Tradition, built in 1978 to sail cargo up and down the Lesser Antilles, Caribbean (including smuggling rum!), is one of the last surviving vessels of her kind. The Captain will pick you up on the small wooden dock in Sandy Ground, and transfer you to Tradition. Once the Captain gives a short history of Tradition and a safety briefing, the crew will raise the sails while you enjoy a delightful 1-1.5 hour sail to the gorgeous and secluded Little Bay. The captain and crew are always happy to show you the ropes, if you'd like to participate in the sailing.
Little Bay
Once at anchor in Little Bay, spend the next hour exploring the delightful marine life, including turtles and stingrays, using the complimentary snorkel gear and swim aids. Swim to the beach, jump off the famous Little Bay Rock, or simply, relax on the boat's shaded deck enjoying a cold beer, chilled glass of wine, rum punch, or your favorite beverage. This all-inclusive adventure includes a fully stocked cooler with alcoholic and non-alcoholic beverages, snorkeling gear, towels, swim aids and an authentic sailing experience onboard the last surviving sail-trading vessel of its kind.
41 reviews
Total reviews and rating from Viator & Tripadvisor
Kathleen S,
May 1, 2025
- Review from Tripadvisor
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!



rpT5120ZF,
Apr 7, 2025
- Review from Tripadvisor
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!
991rossanad,
Mar 27, 2025
- Review from Tripadvisor
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


Rossana D,
Mar 27, 2025
- Review from Viator
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
rocksideridge,
Mar 1, 2025
- Review from Tripadvisor
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.
Ronni G,
Feb 20, 2025
- Review from Viator
Very friendly staff very knowledgeable of the Island a very nice morning. A fun time I would do it again next time I return.
BB686,
Feb 13, 2025
- Review from Tripadvisor
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


Andrew S,
Jan 24, 2025
- Review from Tripadvisor
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.




Matt T,
Jan 4, 2025
- Review from Viator
Great experience! Crew were fantastic and extremely friendly and knowledgeable. Highly recommend spending the time aboard the charter


theolliesofwp,
Jun 14, 2024
- Review from Tripadvisor
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".


Operated by Tradition Sailing Charters