• Rated by TripAdvisor as Anguilla’s #1 Sailing Adventure
  • Tradition Sailing Charters offers an authentic Caribbean sailing experience
  • We’re excited to share our passion of sailing on our beloved Classic West Indian sloop with you!


Nothing says authentic Caribbean experience like a stunning, romantic sunset sail on Tradition, one of the last sail trading vessels of her kind. This 2.5 hour sunset sail offers the best views of the sun setting on Anguilla and will be a guaranteed highlight of your tropical vacation in paradise.

Sip our famous signature Champagne cocktail or enjoy other cocktails from our Premium open bar. We’ll sail our way along the Anguilla coastline and enjoy the scenic beauty of Little Bay, Crocus Bay, and Katouche Bay.

While you revel in this unique view of the sun setting on Anguilla (ever hopeful for a Green Flash), we’ll serve up a feast of delicious platters our house-made hors d’oeuvres. While you’re dining on our cocktail hour feast, watch for the first stars to make their appearance as we make our way back to Sandy Ground.

  • Day 1 - Sunset Sail Tour

    2.5 Hour Sunset Sail along the Anguilla Coastline

    Mondays, Wednesdays, Fridays
    4:30 to 7 pm (November 1 to February 28)
    5 pm to 7:30 pm (March 1 to August 30)

    Enjoy the beautiful sunsets and views on the waters of Anguilla while enjoying cocktails and delicious platters.

  • Personalized & Professional Service
  • Unlimited Signature Champagne Cocktails
  • Premium Open Bar
  • Delicious Freshly Made Hors D’oeuvres
  • Gratuities for the crew
  • Hotel/Villa Transfers

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