The Ultimate Wine Window Trail in Florence
POV: you’re scrolling on TikTok and see these cute little windows in Florence. No, they’re not Italian fairy doors—they’re buchette del vino (wine windows), and they’re the OG takeout service.
Florence’s wine windows offer that perfect mix of history, cultural immersion, and uniqueness that creates an experience you’ll never shut up about. Unlike the crowds at the Duomo or Uffizi, the wine windows give you a peek into the more intimate, local side of Florence that many travelers miss.
These tiny architectural archways also just might be the most underrated “bar crawl” in all of Florence, and I'm about to put you on the perfect trail to see our favorite ones. Be forewarned: this self-guided wine window walking tour just might be the highlight of your Florence adventure.
Some history you actually want to know
Before I reveal our trail, let’s take a second to appreciate the history of these lil guys: wine windows were created during the plague (read: OG pandemic) in the 1600s as a contactless way for businesses and wealthy families to sell wine directly to the public while social distancing (shoutout 2020). They would pass wine through these windows, collect payment, and disinfect coins with vinegar. Basically, they invented Uber Eats 400 years ago.
The Ultimate Wine Window Trail (aka, our perfect route)
By starting at Wine Window Matteoni and ending at DiVin Boccone, you’ll move through diverse neighborhoods while keeping the walking distance manageable (about 25 minutes total without stops). So, grab your most comfortable shoes (because cobblestones + cute sandals = blisters), charge your phone, and follow our signature trail for a perfect wine-filled stroll through Florence.
1. Wine Window Matteoni
The Hidden One
First off, we’re taking you to one of the only ground-level wine windows in the city. And while we usually tell travelers to look up (from their phones) while walking around, here we need to make an exception, because you’ll only find Wine Window Matteoni by looking down.
This wine window almost looks like a wine jail, with a little wooden door and bell slotted between iron bars. You might have to get on your knees to retrieve your glass, but oh man is it worth it. Don’t be afraid to ask the server to take your photo – it’s a wild perspective (see it on Instagram.)
Pro tip: Before your next stop on the trail, sidequest to its neighbor, the oldest pharmacy in the world: Officina Profumo-Farmaceutica di Santa Maria Novella. This one-of-a-kind locale has been crafting beautiful fragrances, remedies and herbal products with locally sourced ingredients since 1221.
2. Osteria Belle Donne
The Aesthetic One
Next, we’re hitting up one of the most popular (and photographed) windows: Osteria Belle Donne. The floral installation that surrounds the wine window makes an incredible backdrop for pics. Their window is part of a restaurant that serves traditional Tuscan cuisine, perfect for adding a lunch or dinner spot along your journey (just be sure to make a reservation).
Pro tip: Stop by on Friday nights when they sometimes offer special tastings of local Tuscan wines through the window. Ask for their “buchetta special” and you might get a surprise!
3. Cafe Odeon
The Artsy One
Cafe Odeon’s wine window is surrounded by contemporary local art, creating a cool juxtaposition between Renaissance architecture and modern creativity. The window itself features unique decorative elements not seen in the others, including tiny carved grape motifs (s’cute!)
Pro tip: Cafe Odeon occasionally hosts pop-up events where local artists sketch portraits of customers that are then delivered through the wine window. Check their Instagram for upcoming dates!
4. BABAE
The Trendy One
BABAE famously became one of the first establishments to revive the tradition during COVID in 2020. Their window serves not just wine, but also craft cocktails! It’s owned by siblings Claudio and Chiara, who will happily explain Babae’s history while serving you. This place is also Stanley Tucci-approved, as seen on “Stanley Tucci—Searching for Italy.”
Pro tip: Their signature “Buchetta Negroni” is served exclusively through the window and comes in a souvenir flask. Perfect for sipping while wandering the nearby streets of the Oltrarno district.
5. Fiaschetteria Fantappié
The Quiet One
This wine window is located at a wine shop slightly off the beaten path, giving “I have this little place that nobody knows about” energy. It’s also just a stone’s throw from the IG-famous Fotoautomatica vintage photo booth.
When we arrived, we were immediately greeted by the owner, Alessia—the wine shop has been in her family since 1947. She was the sweetest human to chat with and even let us cosplay as wine window-istas, experiencing the window from both sides. Before we headed to the next window, Alessia even helped us pick us a bottle to take home from the vast floor-to-ceiling wine shelves.
Pro tip: This spot is in a quieter neighborhood where you'll find fewer tourists and more locals, perfect for chatting up some Florentines who might share other local recommendations. (They know this city far better than TikTok.)
6. DiVin Boccone
The Foodie One
End your trail at DiVin Boccone, where the wine window is part of a Pugliese wine bar. From the outside, you’d never know that a cozy wine cellar lies within, making it almost feel like a wine and cheese speakeasy.
DiVin Boccone takes the wine window concept to a whole new level by serving not just drinks, but also small bites and FULL bottles of wine through their buchetta. Their window is distinctive for its rustic iron detailing and the small bell that customers ring for service. Hopefully the owner, Massimiliano (one of our favorite Florentine humans), is around to tell you about the Amarone.
You’ll want to stay for a glass (or three) in the wine cellar as the perfect way to celebrate completing the trail. Trust us, their aperitivo selection is unmatched.
Pro tip(s): Their bufala mozzarella and mortadella changed our lives, please don’t leave without trying it. If you have a big group, order the Michelangelo platter to split. They also ship their wines to the US for an authentic souvenir!
How to make the most of this trail
Best times to go:
Start around 2 pm to catch the best lighting for photos and finish just in time for aperitivo hour. Alternatively, late afternoon to early evening (5–8 pm) is a sweet spot when most windows are active and still beautifully lit for photos. Golden hour in Italy, baby!
Outfit check: Wear something that pops against the neutral stone backgrounds—think bold colors or patterns for maximum contrast.
Fuel up: Most of these spots serve food or are near cafes, so you can snack your way through the city. Also, don’t forget to drink water (stay hydrated, bestie).
Sidequests: Each stop on this trail puts you close to other amazing spots worth checking out—from hidden gardens to local boutiques. Don’t rush between windows; instead, use them as anchors for exploring the surrounding areas.
Learn a few Italian phrases: The locals appreciate it, and it makes for a more authentic experience. Start with “Posso fare una foto?” (Can I take a photo?)
Why this matters beyond the aesthetic
These wine windows aren’t just photo ops—they're literal survivors. They’ve witnessed centuries of history, including multiple plagues, world wars, and countless tourists. By visiting and sharing these historical gems, you're helping preserve a unique part of Florence’s cultural heritage while experiencing something genuinely unique.
So take that Insta and pat yourself on the back.
Cin cin! 🍷
Arielle
