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Helly Hansen Sailing World Regatta Series | 19 – 26 October, 2024


The Most Popular Weekend Racing Series in the United States.

The Helly Hansen Sailing World Regatta Series, features an exciting multi-city sailboat racing circuit held in the United States.

Sail with us throughout the year in St. PetersburgSan DiegoAnnapolisChicago, Marblehead, and then for the final regatta in the series, and the most prestigious to attend, the Helly Hansen Sailing World Regatta Series Championship hosted by Sunsail in the beautiful British Virgin Islands in October.

What’s New?

The Helly Hansen Sailing World Regatta Series will continue the traditions that have made it a sailor-favorite series like its post-racing parties and social events at each yacht club, and awarding one top-finishing team at each regatta a chance to compete in the overall season championship, held in the British Virgin Islands in October.

Want to join? Fill out the form below and a Holiday Planner will contact you.

For full pricing and to book your place on the Tahiti Pearl Regatta, please contact a member of the sales team on +1 877 378 7508 or fill out the form below.

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Pricing and Booking Information

Choose the option that suits you:




Sample Regatta Schedule



  • 8:30 am – Mandatory Skippers Meeting at Sunsail base pool deck (waivers due)
  • 12:00 pm – Complete yacht briefing and dock out
  • 1:00 pm – Rendezvous at Cooper Island Beach Club mooring field, Manchineel Bay,
  • During race, leave dinghy on a mooring early to save spot
  • 2:00 pm – Warning Signal for Leg 1 (The Channel Islands)
  • Overnight mooring/anchorage at Cooper Island Beach Club mooring field
  • 5:00 pm – Helly Hansen hosts sundowners on the dock


  • Depart Cooper Island (recommend early departure)
  • Rendezvous at The Baths for exploration
  • 12:00 pm – Warning Signal for Leg 2 (The Baths to Bitter End Yacht Club)
  • Competitor moorings provided by Bitter End Yacht Club
  • 6:00 pm – Dockside Welcome Toast
  • Free evening


  • Bitter End Lay Day
  • Wing & Dinghy Challenge, Games & more
  • Competitor moorings provided by Bitter End Yacht Club
  • 5:00pm – Mount Gay Rum drink contest
  • Free evening


  • 10:00 am – Warning Signal for Leg 3 & 4 (Virgin Gorda to Sandy Cay)
  • Leg 3 – Virgin Gorda to Scrub Island
  • Leg 4 – Scrub Island to Sandy Cay
  • Overnight mooring/anchoring at Jost van Dyke
  • Free evening


  • 10:00 am – Warning Signal for Leg 5 (Sandy Cay to Norman Island)
  • Norman Island In-Port Race(s): intention to run 2 buoy races
  • 6:30 pm – Helly Hansen Awards at Pirates Bight Bar


  • Cruising Day
  • Optional check-in boats at the Sunsail Base, Road Town, Tortola


  • 11:00am – Check in boats at the Sunsail Base, Road Town, Tortola

Special Mentions

What’s Included in Regatta Package

What’s Not Included in Regatta Package

View Our Yachts

Sunsail 41 underway
Sunsail 454L catamaran under sail

Sail in the British Virgin Islands

With warm weather throughout the year, steady trade winds, calm currents and a kaleidoscope of aquamarine waters and bougainvillea-clad hillsides, Tortola is a sailor’s paradise. This is the yacht charter capital of the Caribbean and arguably the most famous sailing destination in the world. Here you’ll find sheltered, yacht-filled harbors, sun-soaked white-sand beaches, delightful pirate bars and awe-inspiring dives. Explore the sailing grounds.

Official Regatta Information

The information given in this section is just to give you a basic idea about the various regattas.

For more up-to-date information about organising authorities, racing rules and regulations, programmes, racing classes, handicap systems, entry, etc., visit https://www.sailingworld.com/regatta-series/.

Find out more

For more information about this event and pricing call us at +1 877 378 7508 or check out the regatta website here.

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