Antigua Barbuda Hamptons Challenge Regatta

Calling all Sailors! The Antigua & Barbuda Hamptons Challenge Regatta is back!  Register your crew today and win the BIGGEST AMATEUR SAILING PRIZE on the East Coast.  This is a handicapped race using ratings provided by PHRF of Eastern Long Island.

  • Saturday, August 9th – 11am Skippers meeting, Race starts 12pm
  • $100 Early Bird Registration by August 1st
  • CLICK HERE to REGISTER
  • NOR: Noyack Bay and the vicinity of Gardiner’s Bay
  • 1st Prize Overall – includes airfare, charter boat for Antigua Sailing Week 2026, hotel accommodations in Antigua and registration fees to compete in Antigua Sailing Week (April 25 – May 1, 2026) for Captain and crew of five.
REGISTER

REFER 5 FRIENDS & WIN A TRIP TO ANTIGUA!!!

In an effort to attract more boats to participate in this years’ Antigua Barbuda Hamptons Challenge Regatta on Sat August 9th – the Antigua Barbuda Tourism Authority is offering Round Trip Airfare plus  4 Nights- 5 Days Accommodations for two, on Antigua- for any Captain who registers their own boat to race this year + refers 5 new Captains who register and compete in the race!

To receive this prize, the referred Captains must be FIRST TIME ENTERIES to the ABHC and must enter the name of the REFERRING CAPTAIN on the entry form when registering.

  • Prize Trip Certificate will be presented at the Awards Party on August 9th
  • Trips to take place between August 30, 2025, and August 31, 2026
  • Subject to availability*Any Blackout dates will be listed on the certificate
  • Winners are responsible for taxes *Hotel levy tax or $5 per person per night, paid to hotel locally upon arrival.

Taste of the Caribbean Regatta Awards Party

Everyone is welcome to come celebrate and dance the evening away. Enjoy great music, delicious food, open bar and signature cocktails!

  • Saturday August 9th 5:30pm–8:30pm
  • $100 pp advance tickets sales ($110 at the door)
  • Bell & Anchor Restaurant– 3253 Noyac Rd, Sag Harbor
  • Post-race Awards Party to benefit i-tri girls
TICKETS

The Antigua and Barbuda Hamptons Festival benefits i-tri which is an inclusive, community-based program that fosters self-respect, personal empowerment, self-confidence, positive body image, and healthy lifestyle choices for adolescent girls.

i-tri girls train mind, body, and spirit to complete a youth-distance triathlon as a metaphor for life’s journey, giving them the opportunity and the tools to achieve seemingly impossible goals. Along their way to the finish line, i-tri girls develop strong habits and attitudes which last a lifetime. This program is always free of charge to every participant.

Get in Touch

If you want to know more or have questions, please don’t hesitate to contact us.

    Our Sponsors

    Antigua Sailing Week

    Antigua and Barbuda Hamptons Challenge and Festival Returns August 12

    When Rob and Theresa Roden chartered a boat in the Caribbean for their honeymoon in 1995, the couple fell in love with Antigua and Barbuda, their people and their culture. READ FULL ARTICLE