MOST POPULAR 6 HOURS 4+ YEARS
SHARED PRICKLY PEAR LOBSTER LUNCH DAY SAIL.
This amazing sail to the Paradise island Prickly Pear is a day of indulgence that begins the moment your feet touch the deck of Tradition and only ends when we wave you goodbye. We’ll greet your with Morning Mimosas or a glass of freshly squeezed orange juice and feast on succulent grilled Caribbean lobster.BOOK NOW LEARN MORE 
ANGUILLA PARADISE SAILING CRUISES
We’re excited to have the opportunity to share our passion of sailing on our beloved Classic West Indian sloop with you! Book one of our Anguilla boat charters and get ready for the experience of a lifetime.
If you’re a hard-core sailor, a fair weather boater, or even if you’ve never set foot on a sailboat before, we’re here to provide an unforgettable Anguilla sailing experience!
POPULAR SAILING PACKAGES
Shared Prickly Pear Lobster Lunch Day Sail
This amazing sail to the Paradise island Prickly Pear is a day of indulgence that begins the moment your feet touch the deck of Tradition and only ends when we wave you goodbye. We’ll greet your with Morning Mimosas or a glass of freshly squeezed orange juice and feast on succulent grilled Caribbean lobster.
2.5 HOURS 18+ YEARS FROM $255.00
Shared Sunset Sailing Cruise
Nothing says sublime like a Sundowners sail on Tradition. This 2 hour 30 minute sunset sail on Tradition will be a guaranteed highlight of your tropical vacation in paradise.
3 HOURS 4+ YEARS FROM $209.00
Shared Little Bay Half Day Sail and Snorkel Adventure
Our Half Day Sail & Snorkeling Adventure to Little Bay is the perfect solution for families with small children.
MORE ABOUT TRADITION SAILING
Rated by TripAdvisor as Anguilla’s #1 Sailing Adventure, Tradition Sailing Charters offers an authentic Caribbean sailing experience.
Tradition was hand-crafted, in 1978, on the beach in Carriacou, Grenada. Built for sail trading through the Caribbean, she worked the trade winds, carrying cargo – including contraband from St. Barthelemy where the smuggling trade in alcohol and cigarettes thrived until as recently as the 1990’s.
