Stiletto X Charter
Capt. Jay grew up sailing Stilettos on Hatteras Island. He went on to design, develop, and build the new Stiletto X Series — a complete reimagining of the iconic beach cat for the modern era. The boat you're chartering is one he built himself.
The Stiletto X is the highest-performance vessel in the Hatteras Community Sailing fleet. It's faster, more capable, and a more visceral sailing experience than anything else on the Sound. Available for sunset sails, half-day charters, and full-day adventures — at the Stiletto X price point.
And yes — if you fall in love with it, it's for sale. Or Capt. Jay can build you one.
What's Included - Capt. Jay at the helm — the man who built the boat - Junior sailor mate — crew support aboard (works for tips, always appreciated) - Cooler with ice — bring your own drinks and snacks - Porta-pot or marine head — vessel equipped for comfort - Bluetooth speaker — your playlist, your sail - Chloe — she sails with Capt. Jay; first come, first served
Charter fees support Hatteras Community Sailing's 501(c)3 mission: free and reduced-cost youth sailing for Hatteras Island kids.
What’s Included
- Designed and built by Capt. Jay
- Licensed USCG captain (Capt. Jay)
- Junior sailor mate (works for tips)
- Cooler stocked with ice
- Porta-pot or marine head aboard
- Bluetooth music
- Chloe the golden retriever (first come first served)
- Highest-performance cat in the fleet
- Available sunset, half-day, or full day
- For sale — or build-to-order
- Supports youth sailing mission
Hatteras Community Sailing is a 501(c)3 nonprofit. Your program fee funds our youth sailing scholarships, community sailing days, and fleet maintenance — keeping sailing accessible to everyone on the Outer Banks. No child is turned away for inability to pay.
Learn about our mission →Select your vessel — your charter is a private, all-inclusive flat rate for the boat.
Questions? Contact us before booking.