The Classic Regatta

A St. Petersburg sailing tradition since 2010 - bringing sailors together and supporting Neighborly Meals on Wheels.

The Classic Regatta began in 2010 as the Good Old Boat Regatta, combining a fun day on the water with a commitment to giving back to the community. Over the years, the event has raised well over $100,000 for Neighborly and its Meals on Wheels program, helping provide meals and support to seniors throughout Pinellas County.

In 2015, the event became The Classic Regatta, and for many years participation was reserved for boats at least 20 years old.

This year, we’re opening the starting line to everyone. Old boat, new boat, classic cruiser, seasoned racer.  If you sail, you’re invited to join us.

At the heart of the Classic Regatta is a fun pursuit race, where boats start at different times based on their handicaps, giving boats of different speeds the chance to race together and creating the possibility of an exciting finish as the fleet converges near the end. It’s competitive enough to be interesting, but the emphasis has always been on getting out on the water, enjoying some friendly competition, and bringing the sailing community together.

And the fun doesn’t end at the finish line. After racing, sailors, friends, and guests gather for the Classic Regatta After Party to celebrate, swap stories, and enjoy an evening together.

The regatta has been held every year since 2010 with just one exception: 2024, when Hurricane Milton forced its cancellation.

For 2026, we’re continuing the tradition — welcoming more boats, bringing more sailors together, and continuing to support a great local cause.

Whatever year is on your boat’s documentation, come sail with us.