Tuscany was the perfect place to start my Europe 2023 vacation. The birthplace of the Italian renaissance, Florence was the most beautiful city I have visited in Italy. It had the right mix of art and culture, with an incredible range of casual and upscale eateries. We spent the first two days in Florence and the third day in Chianti. Looking back on my itinerary, I am still impressed by how much ground we covered in those 72 hours.
Table of contents
Getting here
When we booked, there were no direct flights from NYC to Florence. We ended up booking a flight with a stopover in Brussels. Why Brussels? It was the only option that worked with our timing.
We ended up being delayed by over an hour in NYC, meaning we arrived late to Brussels and missed our connection. With only one flight from Brussels to Florence a day, we had to choose an alternate solution. They weren’t great – our choices were to fly to Rome, then Florence or to Zurich, then Florence. My concern was that if the next flight were delayed, we could miss our connection and that would be even more time lost. We decided to fly to Rome then take a train to Florence. I figured we might as well make it to Rome – since there were way more trains running that route than flights, it seemed like the least risky solution.
It worked out pretty well – the train took less than 2 hours, and we still managed to get to Florence on the same day, albeit 6 hours late.
But, lesson learned – going forward I’ll only book flights that have multiple options on the same day for the same route.
Food
Tuscany was one of my favorite food destinations of the trip. I’m still impressed by how much we squeezed in!
Would eat again
After a long day visiting Tuscan vineyards, we were looking for a quick and simple dinner. On route to a pizza restaurant we had Googled moments before, we stumbled upon a small street full of people eating paninis, all with the same wrapper. We found ourselves in the middle of four panini shops, all with the same name: All’Antico Vinaio.
Ordering was simple. You stand in line and choose from one of the preset menu items. They allow a bit of customization on the sauces and toppings, but only one meat per sandwich. One massive sandwich is 10€.
The sandwich was delicious. We shared a mortadella panini with soft cheese, sundried tomato spread and arugula. It was so good, I wished I could have had it again the next day before we left.
Caffee Gilli is the oldest coffee shop in Florence. It’s the perfect spot for a coffee, cocktail, or dessert break. Inside, there’s a coffee bar where you can grab a quick espresso or check out the pastry cases, and outside there is an expansive covered patio.
The patio was really comfortable. Even in the peak afternoon hours, the wait for a seat was only a few minutes. At times it was hard to flag down a waiter, but the coffee and desserts were enjoyable.
We stopped here on our way to Chianti. Located in a residential neighborhood, it was out of the way from everywhere else we went, so I basically saw this as our only chance.
We went on Sunday morning around 11 am, and their large parking lot was already full. The terrace and interior tables were 80% seated with locals having an early lunch. Every single person I saw was Italian and the staff spoke a very limited amount of English. I ordered by pointing to various crostatas, cookies and croissants.
I’m glad we made the time to stop by because these were probably the most authentic Italian pastries we had throughout the trip. While I wouldn’t encourage you to go out of your way to come here, if you’re headed out to the Italian countryside, definitely make this a pit stop on the way over.
I chose Gunè because I was looking for Italian food with a modern twist. Stepping into their elegant blue dining room definitely felt like a departure from the classic Florentine architecture. Gunè struck the right level of formality that I was looking for – upscale, without being stuffy. They have tasting menus in the 60€ to 75€ range, and à la carte options.
The food and presentation were phenomenal. We started the meal with an assortment of amuse-bouches, followed by two perfectly al dente pastas covered in a divine sauce. The cocktails were also a fun part of the experience – the presentation of the cocktails was really good. One of them was served in a teacup and came paired with a flavored foam in a spoon.
I enjoyed this meal a lot and would recommend it if you’re looking for a nice dinner without a super high price tag or buttoned-up vibe.
We stumbled upon this tiny wine bar after having dinner at Gunè and trying to knock on a few out-of-service wine doors. We stopped in because it looked like a cozy place to have a glass of wine and was filled with locals. They had 6 seats at the bar and a bench with a few small tables. A lot of people had taken glasses of wine and chairs to drink outside in the street. Behind the bar, three waiters poured glasses of Italian wine and made snacks from cheese, charcuterie and a small toaster.
We took a seat at the bar and were served some amazing Italian wine. We were given slices of cheese to snack on and ordered an incredible crostini – a piece of fresh bread was slathered with sausage meat, covered with cheese, then toasted until the cheese was bubbling. While the staff’s English was limited, it was just enough for us to order or get wine recommendations.
The ambiance was so relaxed. The customers were familiar with the staff and came in and out to smoke cigarettes or take walks. The wine bar seemed to operate on the honor system. When someone walked out with a glass of wine, it was up to them to come back and make sure they closed their tab (and let the waiter know what it was they even ordered). Part way through our evening, the owner gave one of the waiters 5€. She left and came back a few minutes later with a cup of gelato that she, the owner and another waiter shared.
It was one of our favorite spots, and we would definitely come back.
While my original intention was to have breakfast here, I obviously ended up sleeping in, so we popped in for lunch after seeing the statue of David. While the food itself wasn’t particularly remarkable, the ambiance definitely was.
Half of the space is a restaurant and bar, while the other half is a store selling flowers and houseware. Tables are interspersed throughout the store portion as well. A grand piano sits amongst vases of flowers, washed with natural light from a skylight. They also had a few tables on the patio or right next to large windows looking into the street. I don’t think I could ever find a space like this in NYC.
If I lived here, I could see this becoming a regular spot to pop into for a coffee, pastries and browsing.
This was our first meal in Florence. I’m admittedly not a huge steak fan, so I wasn’t originally sure if Florentine steak would be on my list. I eventually decided to squeeze it in after reading so much about it.
It turned out to be the best steak I had had in my life and I am so glad I booked it. The steak was cooked perfectly and had such a great smoky flavor from the wood-burning grill they used.
The restaurant itself is in a cool space – once a bookstore, it has been repurposed to an upscale dining room with a private space on the mezzanine surrounded by shelves of wine.
Vivoli is the first gelato store in Florence and is well known on social media for its affogato. The shop is small and tucked away – to one side is the coffee bar and to the other, the gelato. You order and pay at the register by the entrance and hand your receipt to a server behind each respective counter.
The affogato was definitely the highlight of the visit, not just because of how photogenic it was, but because of how creamy and rich it was. I’ve had a few affogatos in the US, but the top notch espresso and gelato, as well as the proportion of each component was just top notch.
Good, but not essential
I found Locale because it’s listed as one of the 50 Best Bars in the World. Even though they don’t take reservations for the bar, we were able to walk in and get a table easily around 9 pm. By 11 pm, people were lining up outside. The interior design is cool – the bar area feels like a dimly lit greenhouse with its glass ceilings and plants, while the different rooms in the restaurant (and the bathrooms) have more of an upscale vibe.
While it was a fun place to have drinks, the drinks themselves didn’t stand out much, especially compared to some of the other bars I’ve been to on the list.
Perchè No! is one of the more popular gelato shops in Florence and was on almost all of the lists I read. Reflecting on all the gelato I had throughout this trip, and more generally, I wouldn’t say this one particularly stood out to me. It was good, but the flavors were on the more mild side. Next time in Florence, I would try a different spot.
Rivoire is considered the best chocolate shop in Florence, but when I went there, it felt like the emphasis was more on the coffee/cocktail bar and pastries than on chocolates. I tried a few pastries and chocolates, and everything was good, but I was a little disappointed by the limited chocolate selection.
Culture
Must See
Accademia Gallery (Michelangelo’s David)
The statue of David was much more stunning (and larger) in person than I expected. While the gallery is crowded, the statue is mounted in a way that creates a stunning viewing experience, and makes it easy to admire regardless of how many people are there. Walking into the gallery, David is the first thing you see at the end of a long corridor. A large skylight allows natural light to shine directly onto the statue.
Other than seeing David, we also enjoyed walking through a long room filled with busts.
Make sure to buy tickets weeks ahead of time, especially if you’re planning on going during peak season. Allocate extra time for the visit because the museum can run behind schedule. We were let in 15 minutes after our designated time.
I had always heard a lot about Milan’s duomo, but didn’t realize what a sight Florence’s would be. We stumbled upon it on our way to dinner and were immediately struck its elegance and beauty. The white marble was in stunning and stark contrast to the sky and surrounding buildings. It’s free and easy to take a look inside, but the exterior is the main highlight.
Officina Profumo Farmaceutica di Santa Maria Novella (Via della Scala 16, 50123)
I’d seen this gorgeous body products store featured in several social media posts. It was actually more beautiful than I expected. Vibrant colorful florals were placed throughout the space. It’s fun to browse, and if you’re in the market for luxury soaps, scents or lotions, a great place to buy.
The one drawback of visiting was how busy it was. That made it a little more difficult to appreciate or browse.
Piazzale Michelangelo
Piazzale Michelangelo is a viewpoint overlooking all of Florence. Those who are interested can hike to the top, but we drove there on our way back from Chianti. Parking was a little hard to find, but we found a spot in a very narrow street close to the viewpoint.
It’s a great photo opp. The view of all the red Florentine rooftops is iconic.
Ponte Vecchio
Ponte Vecchio is an old bridge in Florence filled with jewelry stores. The stores range from local shops to Rolex and Patek Philippe. While I wasn’t in the market for any jewelry, it was fun walking the bridge both during the day when the shops are open, and at night after they have closed.
Because the stores sit on the bridge, they all have small windows that look onto the Arno river. They’re really cute – almost like looking at a hanging picture. Keep in mind that a lot of stores are reluctant to let you take photos. (One of the shops was kind enough to let me snap a couple).
Wine Tasting in Chianti
If you’re short on time, I wouldn’t say that I would pick this over exploring Florence, but if you have some extra time, it’s definitely a worthwhile day trip. The vineyards were more beautiful than anything I’d seen in Napa, and of course, the Tuscan countryside food was delicious.
Getting there
The best way to access the Tuscan countryside is by car. Originally, I wanted to hire a private driver for the day – wine tasting is a lot more fun when everyone can drink. Ultimately what I found is that they were in pretty limited supply and more expensive than what I was looking for (550€ for 12 hours).
Initially, I was reluctant to rent a car because of the hassle, especially for only one day. But, amazingly, when I asked my hotel concierge for advice, they were able to book the car for me and have it dropped off at the hotel. When I was done with the car, all I had to do was bring it back to the hotel and they would return it for me. All in, this cost me 160€. The rental was for a full 24 hours, included overnight parking, and was incredibly convenient.
If you’re worried about driving in the countryside, don’t be. The roads were in good condition and easy to navigate. Just make sure to go slowly! Sometimes the roads for two-way traffic can be a bit on the small side and lack visibility on sharp turns.
Once again underestimating how tired I would be, we were an hour late to our reservation. But, thanks to the help of our hotel, the vineyard held our table, which was located on the terrace with the best view of the countryside. We had booked the wine tasting and light lunch for 60€ per person. (It was definitely not light).
When we arrived at the vineyard, we were greeted by a sommelier who gave us a quick tour of the winery, then took us through our wine tasting and food pairing. The wine was great, but the food was truly phenomenal. Everything was incredibly fresh, homemade and clean. We started with a trio of bruschetta, prosciutto, and cantaloupe, followed by a cheese plate, a main pasta (we had funghi and bolognese), and a dessert (tiramisu and cheesecake). An olive oil and balsamic vinegar tasting were also included in the experience.
The service was probably one of the best parts. The vineyard was incredibly accommodating even though we were an hour late and everyone was very friendly. They made sure that each table had a lot of 1:1 attention with their sommelier.
The timing ended up working out well – just as we had finished lunch, it began to rain and they had to close the terrace.
Vineyard 2: Antinori nel Chianti Classico
After Poggio Amorelli, we drove 30 minutes back towards Florence to Antinori, one of the best known vineyards in Tuscany.
The vineyard was gorgeous. I had never imagined that a vineyard could be so architecturally modern and striking. Driving in felt like driving into a futuristic resort.
After parking, we made our way upstairs to the top floor, which overlooked the gorgeous Tuscan hills. We sat down for lunch at their restaurant Rinuccio 1180 on the terrace. We opted for a lighter lunch since we had just come from a big meal at Poggio, and it was probably for the best given the food was average.
We chose a bottle of wine for the table, and that was great. If I were to come back, I would skip the food and opt for a wine tasting.
Sad we missed
Because of our flight mishap, we missed our scheduled time to visit the Uffizi and weren’t able to fit it in on another day.
Accommodations
The Westin Excelsior
The service at the Westin was fantastic. Working with the concierge leading up to my trip was really helpful in making reservations at the restaurants and vineyards, and adjusting them on the days when we were too tired to meet our planned schedule.
The room was comfortable and spacious. In the mornings, free coffee is served in the lobby. While the lobby area was nice, it wasn’t particularly big or beautiful.
Would I stay here again? Maybe. If I did, I would choose a better room. This time I opted for the most basic room choice, and I was pretty disappointed by the complete lack of a view. I’m not kidding, the room looked out onto another wall of the hotel.
Itinerary

After arriving in Florence later than expected, we just managed to squeeze in dinner at Regina Bistecca where I had the best steak I’ve ever eaten, and drinks at Locale Firenze.

We had a great day combining sightseeing, shopping and eating.

We spent the day at two beautiful Tuscan vineyards.
