Join us for the 16th edition of the Classic Regatta!

Enjoy a fun pursuit race on Tampa Bay followed by an after-party at the St. Petersburg Yacht Club. Co-sponsored by the St. Petersburg Sailing Association and St. Petersburg Yacht Club, this annual event raises funds for Neighborly Senior Care and its Meals on Wheels program.

Schedule:

• Optional Breakfast Buffet ($20) 09:00 am – 10:00 am  SPYC  (dine in the Quarterdeck)
• Competitors’ meeting 10:00 am   SPYC Quarterdeck  
• First Warning 1:00 pm Tampa Bay
• Social 4:00 pm SPYC Waterfront Room (free - cash bar)
• Buffet Dinner 5:00 pm  SPYC Waterfront Room (1 dinner included with boat entry; $35 otherwise)
• Awards 6:00 pm    

REGISTER YOUR BOAT
For skippers entering the Classic Regatta, use this link. Boat Entry Fee is $72. Includes $25 donation to Neighborly Senior Care, one buffet dinner, complimentary docking (subject to availability) and one long-sleeve performance shirt. 

CREW & GUEST RSVP / ORDERS
For crew and guests attending the party or ordering dinner, breakfast or shirts. Skippers are free to register their crew through this link.

Donate here 

(you can donate in the name of a boat or just make a general donation)

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. Much of this money was raised by the boats and crews themselves. The boat that raises the most money wins the coveted "Good Neighbor Award". 

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.