Osteria Giocondo Brings Italian Charm to Downtown Winter Park
I think I’ve found my new favorite spot right in the heart of downtown Winter Park! Osteria Giocondo recently opened on Main Street, giving us a cozy place to gather, connect, and enjoy a drink with some Italian-inspired small bites. It’s owned and operated by Devil’s Thumb Ranch, so you can expect the same luxury, attention to detail, and high-quality experience they’re known for - without the drive!
This charming little spot sits in the same building as Vasquez Creek Inn and Volario’s (also part of the Devil’s Thumb family), directly across Highway 40 from Hideaway Park + the Rendezvous Event Center. The space has actually been empty for a few years, but longtime locals might remember it as Caffe Giocondo (a coffee shop serving breakfast and lunch), so they've officially switched gears from the AM to the PM scene, with typical hours 5-9pm Wednesday through Saturday.
THE VIBE
Marked by elegant yet cozy furniture and décor, the space is laid out with connection in mind. Think plush leather couches, velvet rust-orange armchairs, and low coffee tables that invite you to settle in. Even the small tables for two don’t feel like your typical restaurant seating - it’s more like pulling up a chair at a friend’s place. No hard wooden chairs to be found! The whole vibe is designed to make you linger and soak in a little Italian aperitivo culture, a pre-dinner ritual built around drinks, light bites, and an unhurried atmosphere where lingering and enjoying time together is the goal.
And that’s exactly what Osteria Giocondo has created: a place to slow down, sip a glass of wine, and be present with your crew. They’re blending a bit of Italian tradition with our beloved après-ski rhythm, and it just works.
You can make it a full meal by ordering a mix of their “small bites,” or use it as the perfect starting point for dinner. When you’re ready for something heartier, just head next door to Volario’s for hand-tossed pizza, freshly rolled pasta, surf-and-turf entrées, and more Italian-inspired deliciousness.
THE FOOD
The menu at Osteria Giocondo is designed for sharing with its selection of small bites. They offer classic house-made bread like rosemary-and–sea salt focaccia, plus a whole lineup of cicchetti (small, snack-sized plates): marinated olives, wagyu meatballs, arancini, olive tapenade bruschetta, and even a charcuterie board if you’re ready to go big!
On the lighter side, the piccola insalata selection brings fresh options like burrata with marinated tomatoes, a bright caprese salad, or a peppery fennel-arugula combo. And if you’re craving something more substantial, their pizzettes (mini pizzas) deliver: go for a simple Margherita, a mushroom-and-truffle Fungo, or a tangy, sweet-and-savory number with goat cheese, Calabrese, pickled onions, and honey. They even offer a gluten-free crust!
Another fun option is their wine and cheese pairing - perfect for anyone who wants to sample a little bit of everything. You’ll get the chef’s selection of three Italian cheeses, each paired with a 2-ounce pour of one of their wines.
THE DRINKS
Osteria Giocondo prides itself on its wine selection: bubbly Prosecco, crisp whites like Sauvignon and Pinot Grigio, a rosé, and a solid selection of reds from Chianti to a rich Super Tuscan. Be sure to check out their weekly wine feature! On the beer front, they’ve got a mix of craft and classic brews: light lagers, juicy IPAs, a milk stout, plus gluten-free and non-alcoholic options. And for cocktails? Fresh takes like their "Limonata" made with their homemade limoncello pay homage to the Italian countryside. They also have non-alcholic beers (including a gluten-reduced option) as well as some fun mocktails (like the Grapefruit Mule). With a little something for everyone, it's even easier to cozy in and stay awhile!
EAT WELL, LAUGH OFTEN, LOVE MUCH
The team at Osteria Giocondo lives by the motto “mangia bene, ridi spesso, ama molto!” - eat well, laugh often, and love much. And they’ve created a space and a menu that make all three come naturally. It’s the perfect complement to mountain living.
If you’re feeling the pull of Grand County’s slower pace and are considering investing in a mountain property, let’s connect! I’d love to hear about your real estate goals and share my wealth of knowledge gathered from decades of living and working in this beautiful place I get to call home.
Posted by Leah Bishop on
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