I couldn’t have picked a better time to visit Tuscany, for so many reasons:
- Two weeks prior, the movie You, Me & Tuscany was released, so the vibes were already set.
- We went during shoulder season, so we experienced fewer crowds and grabbed round-trip tickets for $900.
- Because of the time of year, the weather wasn’t too hot or cold.
So you can imagine how magical this trip was. On top of the fact that it was the first Italian region I’ve visited, and surely won’t be my last. Below, I’m sharing the Black Girls You, Me & Tuscany Travel Guide. This included where I stayed, ate, and played.
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Where to Stay
W Florence
One of the first 5-star hotels I’ve ever stayed in, and it was a 10/10 experience. From the amenities to the customer service, they really made sure we were well taken care of. Speaking of amenities, they have restaurants on-site, a wellness area (including a gym and sauna), and a rooftop bar.
We started and ended our Tuscany trip at the W Florence, and it really set the tone. This hotel is fairly pricey (~$488 nightly), but my friend has a family/friend discount with Marriott that we used.








Locanda dei Logi
Located in the Tuscany countryside, specifically near the town of San Gimignano. This hotel is the epitome of what I imagined Tuscany would be. A winery and restaurant on-site, a pool overlooking the vineyard and the Tuscan hills, and nothing but relaxation and nature.
During our stay, we relaxed, napped and sunbathed by the pool, did wine tastings, and walked around the area. It was truly a moment of rest. Did I mention you can ship the wine from the vineyard home? My friend and I did, and I’m so happy we did because I didn’t in Portugal and still regret it!












Where to Eat
During our time in the countryside, everything we ate was at Locanda dei Logi’s on-site restaurant, Cantinetta dei Logi.
But in Florence, we ate at the following places:
Pino’s Sandwiches – Salumeria Verdi
Known for their authentic Italian sandwiches made fresh every day, this place is a great spot for a quick lunch. I ordered the BEEGS, which includes: prosciutto, mozzarella, roasted red peppers, sun-dried tomatoes, and pesto or hot sauce. Everyone was so friendly inside; the owner, Pino, was actually taking and making orders. When he asked if I wanted pesto or hot sauce, I was indecisive, so he added both, which was delicious!


A popular spot for gelato and affogato, they’ve been making homemade ice cream since 1930. This was my first time trying affogato (I’m not a big coffee drinker), and I loved it! When we arrived, there was a line, which seems typical, and it moved rather quickly because of their seamless system. You order and pay via kiosk, bring your ticket to the counter, and wait for your order to be called.



W Florence
While we did stay at the hotel, you don’t need to be a guest to eat breakfast, lunch, or dinner. We had dinner and breakfast here, which were great. The dinner menu is small, but we just wanted to eat and sleep after landing in Florence.


Cooking Class
I think it’s only right to take a cooking class while in Florence, and there are tons to choose from. We booked a pasta-and-tiramisu cooking class via GetYourGuide, and it was amazing. We learned how to make ravioli and pappardelle pasta, while drinking unlimited wine—what’s not to love? And we were gifted a Michelangelo apron, which we wore during class.






Wine Window
You can’t come to Florence without checking out the different wine windows around the city. These “Buchetta del Vino” (little wine doors) started in the 1600s to safely sell food and wine during the plague. And they were definitely revived during COVID. The process is simple: knock on the door, order (they usually have a menu nearby), pay (cash or card), enjoy!
There are quite a few scattered throughout the city, I’d suggest using Google Maps to find one(s) closest to you. Below, I’m sharing a few that I had saved:
- Buchetta del Vino Belle Donne
- Osteria Bella Donne Wine Window
- Wine Window Matteoni (Buchetta del Vino)
- Osteria e Vinaino Cicalone (we visited this location!)



Osteria del Giglio
Located 1 minute away from our hotel, this place is your traditional Tuscan-style restaurant. We ordered bruschetta, ceaser salad, and veal slow-cooked Florentine style. Everything was absolutely delicious, and the service was good and quick.


Where to Play
I noticed a lot of the things to do in Tuscany also revolve around food (e.g., wine tasting and cooking classes). So look back to the “where to play” section above for additional ideas.
Galleria dell’Accademia di Firenze
This is where you can see Michelangelo’s sculpture, David. I’d suggest buying your ticket in advance and not doing what we did, which is show up. Thankfully, we were able to buy tickets on the spot, but we paid about €10 more. I think us visiting Tuscany during their shoulder season saved us, so please buy your tickets in advance.



Shop at the Markets
There are a few markets to check out, especially leather markets, as Florence is known for its centuries-old leather craftsmanship.



Ponte Vecchio
This bridge (meaning Old Bridge) is the only surviving bridge from World War II and is now a tourist attraction. Many come for sunrise and/or sunset; we came during sunset, which was nice.



Fotoautomatica
A fotoautomatica is an original analog photobooth, and like wine windows, there are several of these scattered around Florence. I went to a location less than 3 minutes from the hotel, and it cost €3. You’ll need exact change as it doesn’t take card payments. Also, it does take several minutes for the photobooth to print your strip, so be patient.

