Toscana
September 2026
4 Days
Driving in the heart of Milan seemed a bit too intimidating so we took a 20 minute taxi ride to Linate airport to pick up a rental car to start the drive to Tuscany. The rolling hills of the region are home to over 3,000 wineries and the famous Sangiovese grape. Agriturismos are popular throughout the region where you can stay on a working farm ranging from basic farmhouses to ultra-luxurious estates.
There are dozens of picturesque towns to visit throughout the region from the center of the Renaissance in Florence, to the medieval stronghold of Siena, and smaller towns of Volterra, Montepulciano, and San Gimignano.
Contents
Daily Itinerary
Pit stop in Maranello to visit the home of Ferrari
Arrival at our Tuscan farm
Dinner overlooking the Tuscan hills
Wine tasting with views at Altezza
Cool off in the pool
Day trip to the unique piazza of Siena
Try the local dish wild boar ragù
Dinner on the farm overlooking San Gimignano at Fattoria Poggio Alloro
Drive to the Manhattan of the Middle Ages at San Gimignano
Escape the rain for lunch at Dulcisinfundo Bistrot
Best gelato in the world at Gelateria Dondoli
Rental Car
Locauto Linate Airport - Florence Airport: $569
Hotels
Al Gelso Bianco: $4,087 for 4 nights
▸ Family run farm and winery located midway between Florence and Siena with 7 apartments on the property and offering a number of activities for adults and children.
Al Gelso Bianco - Barberino Tavarnelle, Italy 2026
Food (With Beli Ranking)
Osteria Il Vinao (8.8) - Small restaurant we just walked into that didn't seem to have many tourists (or people at all) and turned out to be maybe our best meal of the trip.
Fattoria Poggio Alloro (8.4) - Farm with views of San Gimignano serving a traditional Italian meal outdoors - if you want more of any courses, just let them know.
Dulcisinfundo Bistrot (7.7) - We got caught in the rain so just ducked into this restaurant and it turned out to be pretty good! Modern looking but serving traditional Tuscan food, not to be confused with Ristorante Dulcisinfundo.
Gelateria Dondoli - Renowned as the best gelato in the world, it lives up to the hype and is not to be missed despite the lines.
Full Itinerary
Day 1
Ferrari Museum
From Milan we took the A1 highway straight to Florence which runs right past Maranello, the home of Ferrari. There are not many brands that are more "Italian" than Ferrari so even if you're not a huge car person, the museum is worth a stop if you happen to be in the area.
Museo Ferrari - Maranello, Italy 2026
Al Gelso Bianco
On our drive, the A1 was incredibly backed up due to an accident so we got off the highway and drove through the winding Tuscan hills before finally arriving to our small farm in the early evening. We originally had planned to go to a restaurant for dinner, but because we arrived so late we ended up just having dinner on the farm which happened to be BBQ night.
It turned out to be good that our drive took so much longer because having dinner outside with the sun setting behind the rolling hills was the most incredible night we had on our trip. There were also a number of families along with the family who ran the farm so this was also much more relaxing than being in crowded Milan restaurants with a toddler.
Al Gelso Bianco - Barberino Tavarnelle, Italy 2026
Day 2
Altezza Winery
With over 3,000 wineries in Tuscany you don't have to go very far to find a wine tasting. Altezza wasn't too far from our farm and we had lunch with our wine as well. The truffle lasagna they served might have been the single best dish we ate on our trip. The winery is just a 5 minute drive from San Gimignano so the views of the famous towers were amazing, feeling similar to our winery visit in Montserrat in Spain.
Altezza Winery - San Gimignano, Italy 2026
Pool Time
After our wine and a quick supermarket stop, we spent the rest of the afternoon by the pool on the farm with spritzes.
Al Gelso Bianco - Barberino Tavarnelle, Italy 2026
Day 3
Siena
From our farm, Siena was only about a 40 minute drive away. In the middle ages, Siena rivaled Florence in power and its architecture is well preserved today with the uniquely shell-shaped Piazza del Campo still serving as the city's epicenter. The medieval roads are narrow and winding up and down the hills the city is built on.
As we drove, parking is only available outside the city walls. We parked in the train station parking lot without issue, and although there are a number moving ramps that take you up to the city level I expect there's always at least a few out of operation. At least this was the case for us and carrying a baby and stroller up the stairs was no joke.
Piazza del Campo - Siena, Italy 2026
Villa del Balbianello
The coast around Lake Como is lined with elegant villas, and although the Villa del Balbianello may not be as much of a household name as George Clooney's villa, you've almost certainly seen a picture of Lake Como from the viewpoint of this Villa. Most famously scenes in Casino Royale and Star Wars were filmed here.
Villa del Balbianello - Tremezzina, Italy 2026
Bellagio
Of the many towns situated on the shores of Lake Como, Bellagio is probably the most famous nicknamed the "Pearl of the Lake". The town sits right on the point where the lake splits in two, offering the most beautiful panoramic views of the lake. The cobblestone stairs take you uphill through the town, with tiny alleys and stairways shooting off where you'll find small shops and restaurants around every corner.
The view from the Salita Serbelloni is one of the most photographed spots on Lake Como.
Salita Serbelloni - Bellagio, Italy 2026
Dai Viga
With only an hour to spend in Bellagio, we didn't have time to sit down for a full lunch. After climbing up the Salita Serbelloni, we came across a small shop with a handful of standing tables outside and a line out the door. On a tight schedule, this was perfect - simple but pretty good pasta standing at a table outside before it was time to head back down to the boat.
Dai Viga - Bellagio, Italy 2026
The Brera district in Milan is widely regarded as the city's most chic neighborhood featuring cobblestone streets, art galleries, boutique stores, and many restaurants. Il Solferino was established in 1909 in the heart of Brera and features traditional MIlanese dishes like ossobuco and cotoletta alla Milanese.
The restaurant is stylish while still feeling traditional, helped by the no-nonsense waiters, and the food was very good. Although all of our dinners were quick given the baby's schedule, this would be an excellent place for dinner and drinks before continuing the night into the Brera nightlife.
Il Solferino - Milan, Italy 2026
Day 4
Galleria Vittorio Emanuele II
As Milan is one of the most famous fashion centers of the world, if you're going to do any shopping this is the place to do it. But, even if you aren't shopping you should at least walk through the Galleria, a remarkable 19th century shopping arcade with glass ceilings and home to the original Prada store.
Galleria Vittorio Emanuele II - Milan, Italy 2026
Ferrari Store
Of course we had to stop at the Ferrari Flagship store, just outside the Galleria. Here, you can buy everything Ferrari from Ferrari Legos, to Ferrari clothes, to historic F1 car parts.
Ferrari Store - Milan, Italy 2026
Duomo
Every European city has a church or cathedral at it's center, but in my opinion there are not so many that are that unique. While I would make that claim about the inside of the Duomo di Milano, the exterior is quite a marvel - and even then the view from the ground level is nothing.
Duomo di Milano - Milan, Italy 2026
The Duomo has terraces all around the roof that you can walk on - it's a bit of a climb up or you can pay a little extra to take the lift. Once you're on the terraces you can see up close the intricate carvings of the 96 gargoyles, 135 spires, and 3,400 statues adorning the exterior. A very cool experience, but make sure to book your tickets in advance if you want to go during sunset.
Terrazza del Duomo - Milan, Italy 2026
Navigli
The Navigli district is Milan's historic canal district, with the Naviglio Grande lined on both sides by dozens of places to eat and drink. The lively atmosphere begins in the early evening when the cocktail bars start filling up for aperitivo.
Navigli District - Milan, Italy 2026
After our aperitivo we had planned dinner at Posto di Conversazione, a restaurant on the canal serving traditional Milanese food. Unfortunately for us, a full Italian dinner after aperitivo proved a bit too much for the baby. The ossobucco I quickly ate was excellent though and this restaurant felt like an excellent place to spend an evening - the name does literally translate to "conversation place".
Posto di Conversazione - Milan, Italy 2026
Overall
Now that I had a chance to spend more than a day in Milan my overall impression is that while we enjoyed it, there's just many more places in Italy I would go to first. Milan is where the money is in Italy so you can find the best shopping, delicious restaurants, and excellent hotels. But it definitely falls more closely in the "another big city" bucket compared to some of Italy's other locations. I feel I can always be excited to go back to Rome, but I don't have that same feeling about Milan.
To see the next stop on this trip, go here to Tuscany