Up next in our spotlight series is the Heritage Cup Regatta and Rendezvous hosted by Sea Cliff Yacht Club. Just east of New York City, this regatta provides a scenic Long Island backdrop with a fun and festive atmosphere. Michael Emmert talked with the CYOA about what makes the Heritage Cup so special.

What is the history and tradition behind this regatta, and how does it influence the experience for participants?

Michael Emmert: The Heritage Cup regatta has become an integral part of the Classic Yacht Challenge Series though the Classic Yacht Owners Association since its inception in 2006. The Heritage Cup's humble beginnings trace back to a moment of inspiration during our Rhodes Golden-Eye campaign competing in every event in the series. We got word that the Mayors Cup in Manhattan for the following weekend was unexpectedly canceled due to lack of participation. Determined to keep the spirit of classic boat racing alive, a brave decision was made to start a regatta in Western Long Island Sound at very short notice. After some begging and pleading with renowned figure Jim Cassidy, founder of Heritage Marine Insurance—who was kind of the Godfather of the series— I received his blessing to make it part of the series. Against all odds, and over three hundred phone calls to classic boat owners, the inaugural Heritage Cup saw 13 passionate participants coming together in the name of tradition and camaraderie.

What sets the fleet of classic yachts at your regatta apart from other similar events? Are there specific types of yachts or notable vessels that regularly participate?

ME: Over the years, the event expanded to include the beloved Good Old Boat class, welcoming boats designed 25 years ago or older, and even introducing a junior sailing scholarship fund to provide opportunities for underprivileged youth to join the sailing community.

What is special at your event to celebrate the classic yacht racing community during the event?

ME: Although facing challenges such as the Covid pandemic and changing yacht clubs, the Heritage Cup has persevered and continues to thrive, now calling Sea Cliff Yacht Club in Hempstead Harbor its home. The picturesque surroundings of the historic Sea Cliff Village offer a stunning backdrop for spectators to witness the thrilling competition among vintage, classic, and good old boats each year. Hempstead harbor allows us to start and finish the regatta less than five minutes from the mooring field, which allows us to showcase these magnificent yachts from land and sea.

What aspects of your regatta make it a must-attend event for sailors and enthusiasts—whether it’s the location, race format, social atmosphere, or something else?

ME: Looking ahead, we are dedicated to making each Heritage Cup regatta more enjoyable and exciting than the last. From lively live bands to memorable JAM THE DOCK award parties, there are always new elements to look forward to and experience on race day. The Village of Sea Cliff is the oldest incorporated village in the United States. It is a short walk up the hill to the town of bars and restaurants. Making it a must see destination for racers.

How does your regatta engage the wider community, and are there unique activities or events that connect spectators and non-sailors with the world of classic yachts?

ME: Heritage Cup regatta is where the legacy of classic boat racing and the spirit of community come together in a celebration of history and passion. Our premier social event is the Sea Cliff Yacht Club JAM THE DOCK party, an event that promises to be the talk of the sailing community! At Sea Cliff Yacht Club, we firmly believe that the essence of a great party lies in creating unforgettable moments that bring people together. The JAM THE DOCK party takes place on the SCYC pier, where the magic of our vibrant community shines against the backdrop of stunning views of Hempstead Harbor’s Mooring Field, and the picturesque village of Sea Cliff. The dock party is not just an event; it's an experience that you wouldn't want to miss! This captivating gathering is open to all - participants, friends, families, and esteemed members of the yacht club. As we come together, we believe that the more, the merrier, and the more participants we have, the more enjoyable and memorable the celebration becomes.

The first regattas of the 2025 Classic Yacht Challenge Series are just around the corner! Sign up today to make sure you're part of all the action!