You’re Invited: A Day Of Sailing, Steel Drums & Cocktails — Supporting i-tri’s Mission To Empower Young Women
Antigua Barbuda Hamptons Challenge Regatta
Calling all Sailors!
Register for the Antigua Barbuda Hamptons Challenge Regatta coming up on Saturday, August 15th, in Sag Harbor, New York and compete for the largest amateur sailing prize on the East Coast!
The winning captain and crew of five will receive an all-expense-paid trip to compete in Antigua Sailing Week 2027.
SAILING IN FROM RHODE ISLAND, NYC, OR CONNECTICUT?
We’re rolling out the welcome mat — dockside. Breakwater Yacht Club is holding 4 overnight slips for boats making the trip in from Rhode Island, New York City, and Connecticut. The first 4 Captains from these regions to register their boat lock in a spot to tie up, no scrambling for dockage after a long sail down.
✓ 4 FREE overnight slips reserved at Breakwater Yacht Club for both Friday, Aug. 14th and Saturday, Aug 15th!
✓ Open exclusively to boats sailing in from RI, NYC & CT
✓ First 4 registered boats from these regions secure their slip — first come, first served
✓ Mention your home port when you register to be considered for a slip
Taste of the Caribbean Regatta Awards Party
The race is over, the sails are down, and it’s time to celebrate. Join us dockside as the sun sets over Sag Harbor to raise a glass to this year’s champions — steel drums pounding, rum punch flowing, and one incredible fleet of sailors trading sea stories long into the night. Every toast, every dance, and every ticket helps power i-tri girls, giving young women in our community the confidence and tools to chase their own finish lines.
- Saturday August 15th 5:30pm–8:30pm
- $100 pp advance tickets sales ($125 at the door)
- Bell & Anchor Restaurant– 3253 Noyac Rd, Sag Harbor
- Post-race Awards Party to benefit i-tri girls
More than a race — every mile you sail helps change a girl’s life.
The Antigua and Barbuda Hamptons Challenge 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 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