Snowbirds, Slices, and Success: How An Italian Affair and Florida Chefs Workshop Make Seasonal Food Business Work

The Rise of the Snowbird Food Entrepreneur

Every winter, as flocks of northerners head south in search of sunshine, a unique kind of migration follows close behind — food trucks, bakers, chefs, and culinary creators bringing their businesses to Florida for the season. These snowbird food entrepreneurs have discovered how to keep operations thriving year-round by tapping into Florida’s bustling winter event scene. But making it all work — licenses, logistics, and lunch rushes — requires more than just passion. It requires a reliable Food Truck Commissary in Pinellas County that understands the unique needs of mobile food vendors.

That’s where Florida Chefs Workshop comes in. As a leading Food Truck Commissary in St. Pete, our shared-use kitchen provides a licensed, health-inspected home base for operators like Aaron Jolley, owner of An Italian Affair. What began as a small-town pizzeria in upstate New York has grown into a seasonal food truck success story, with Aaron serving sizzling slices at some of Florida’s top festivals and events — supported each winter by a trusted Food Truck Commissary in St. Pete that helps keep operations running smoothly.

An Italian Affair: From Massena to Mobile Success

Before there was a food truck rolling into Florida festivals, there was a cozy pizza shop in Massena, New York. In 1995, Aaron Jolley opened An Italian Affair, starting with just 1,200 square feet, a few seats, and a focus on takeout and delivery. But what he lacked in space, he made up for in flavor. Using high-quality ingredients, scratch-made dough, and all-natural cheese, Aaron built a loyal following that kept coming back for more.

As demand grew, so did the restaurant. By 2007, An Italian Affair had expanded to seat over 100 guests, added a full beer and wine list, and evolved into a full-service Italian eatery known for big portions and bold flavors. It was a hometown favorite — not just a place to eat, but a gathering spot that reflected the heart of the community.

But Aaron wasn’t done growing.

He added a mobile unit — a custom-built pizza truck — bringing his famous slices to events and festivals throughout the region. Soon after came Doughboy’s Donuts, a bright blue mini-donut trailer serving hot, fresh treats. These mobile extensions of his brand allowed him to reach new audiences while maintaining the same quality and charm that made his restaurant a local staple.

With both wheels and a reputation, Aaron was ready for a new kind of adventure — one that would eventually roll down south.

Why Go South for the Winter? The Snowbird Advantage

For many food truck operators, winter means downtime — fewer festivals, frigid temps, and frozen revenue. But savvy entrepreneurs like Aaron Jolley have found a smarter way: follow the sun. By heading south each winter, Aaron keeps his mobile business active while other trucks sit in storage. And Florida? It’s the perfect destination.

With year-round outdoor events, a thriving tourism industry, and countless seasonal residents (many of whom are fellow Northerners), Florida’s winter market is bursting with opportunity. From golf tournaments and First Friday festivals to food truck rallies and community celebrations, there’s no shortage of places to park and serve.

Aaron’s red pizza truck — a crowd favorite in upstate New York — becomes a winter mainstay at some of Florida’s top events, including:

• The PGA Valspar Championship

• First Friday in Tarpon Springs

• The Seminole Recreation Center’s Annual Food Truck Rally

  
  

His signature slices and mini donuts bring a taste of New York to the Sunshine State, satisfying cravings and building a new following that returns year after year.

But thriving as a snowbird food vendor isn’t just about showing up — it’s about showing up prepared. And that’s where the real planning begins.

Making It Work: The Logistics Behind Seasonal Food Trucking

Running a food truck is no small feat — and running one in two different states is a whole different level of challenge. For snowbird entrepreneurs like Aaron Jolley, it takes more than a tank of gas and a GPS to get from Massena to St. Pete. It takes careful planning, regulatory know-how, and a solid operational base in both regions.

Here’s what it really takes to keep a seasonal food truck business running smoothly across state lines:

✔️ Dual Licensing & Health Inspections

Each state — and often each county — has its own rules for mobile food vendors. Aaron maintains proper licenses and health certifications for both New York and Florida, ensuring full compliance wherever he serves.

✔️ Commissary Kitchen Access

Florida law requires mobile food operators to be affiliated with a licensed commissary kitchen for food prep, storage, and sanitation. Without one, you can’t legally operate — which is why having a reliable Food Truck Commissary in St. Pete is essential (we’ll get to that in the next section).

✔️ Transporting Equipment & Supplies

From specialty ovens to ingredient stockpiles, bringing a truck south means knowing what to pack, what to source locally, and how to get everything on the road without skipping a beat.

✔️ Event Scheduling & Permits

Landing spots at high-traffic events requires advance planning, local contacts, and a good reputation. Aaron has built strong relationships across both states, allowing him to secure great placements season after season.

✔️ Consistency in Quality

Despite changing locations, Aaron maintains his commitment to the same scratch-made dough, all-natural cheese, and top-tier ingredients that built his following up north. Customers in Florida get the same An Italian Affair experience that Massena locals have loved for decades.

Operating seasonally isn't just a business choice — it’s a full-blown strategy. And like any good strategy, it works best with the right support behind it.

Florida Chefs Workshop: A Southern Base for Northern Brands

For food truck operators like Aaron Jolley, having a reliable home base is what transforms seasonal ambition into sustainable success. That’s where Florida Chefs Workshop comes in — not just as a kitchen, but as a strategic partner in Aaron’s winter operations.

Located in the heart of St. Petersburg, FL, Florida Chefs Workshop is a fully licensed, health-inspected Food Truck Commissary in Pinellas County, designed with mobile food businesses in mind. For seasonal vendors arriving from out of state, it’s the essential infrastructure that bridges the gap between arrival and operation.

Here’s how Aaron uses Florida Chefs Workshop as his winter headquarters:

🔹 Licensed Commissary Access

Florida law requires mobile food vendors to operate under a licensed commissary — and FCW provides that legal foundation. It’s where Aaron handles food prep, storage, cleaning, and sanitation to meet local health department standards.

🔹 Flexible Scheduling

As a shared-use commercial kitchen, FCW offers flexible rental options, which is ideal for snowbird vendors who don’t need year-round access but still demand full-service amenities during their season.

🔹 Central Location for Event Access

Situated in St. Pete, the kitchen provides convenient access to major events across the Tampa Bay area, allowing Aaron to roll out to festivals, food truck rallies, and golf tournaments with ease.

🔹 Professional, Reliable Environment

From day one, Aaron has trusted FCW for its clean, professional setup — and for the like-minded community of food entrepreneurs who call it home each winter. It's a space that supports growth, consistency, and the hustle that seasonal business demands.

Florida Chefs Workshop isn’t just a checkbox on an application — it’s the kind of place that understands what food truck operators need, because it was built specifically for them.

Snowbird Success in Action: Lessons from An Italian Affair

The story of Aaron Jolley and An Italian Affair is more than just a tale of great pizza — it’s a blueprint for how seasonal food entrepreneurs can build a business that moves with the market. By operating in New York during the summer and rolling into Florida for the winter, Aaron has created a year-round revenue stream without sacrificing the quality, consistency, or soul of his brand.

Here are a few key takeaways from his approach:

💡 Think Seasonally, Plan Strategically

Aaron doesn’t just “go south for the winter” — he plans his calendar, his licensing, and his logistics months in advance. His ability to maximize both northern and southern peak seasons is what gives him a competitive edge.

🏆 Your Commissary Is Your Backbone

Having a dependable Food Truck Commissary in St. Pete is a non-negotiable part of his operation. Florida Chefs Workshop gives him the tools, the licensing compliance, and the peace of mind he needs to focus on what matters most — serving great food.

🚚 Brand Consistency Travels Well

Whether in Massena or the middle of a Florida golf tournament, Aaron’s brand identity stays rock solid. Same quality, same flavors, same red pizza truck. That consistency is what keeps customers coming back, no matter the ZIP code.

🌴 Florida Isn’t Just for Tourists — It’s a Growth Market

Aaron’s seasonal model has introduced An Italian Affair to thousands of new customers — many of whom look for him year after year at local events. The Florida crowd isn’t just a stopgap — it’s a real part of his expanding customer base.

For food entrepreneurs considering a snowbird setup, Aaron’s journey proves that it’s not only possible — it’s a smart, scalable strategy. With the right foundation and a little flexibility, you can follow the sun and keep your business cooking all year long.

Bringing Your Business South? Start with the Right Kitchen.

The success of An Italian Affair shows that with the right planning, support, and mindset, a seasonal food truck business can thrive across state lines. Whether you're a lifelong restaurateur or a mobile vendor ready to chase the sun, the key to a smooth transition into Florida’s winter market starts with the right commissary partner.

At Florida Chefs Workshop, we’re proud to be that partner — offering licensed, flexible, and food truck–friendly kitchen space in the heart of St. Petersburg, FL. If you're looking for a reliable Food Truck Commissary in Pinellas County, we’re here to help make your seasonal journey a success.

And a big thank-you to Aaron Jolley and An Italian Affair for being one of our favorite seasonal clients since 2019. Your story continues to inspire us — and your pizza continues to win fans across the Sunshine State.

👉 Ready to bring your food business to Florida this winter?Let’s talk. Visit www.floridachefsworkshop.com or reach out to schedule a tour today.