Tuscany is world renowned for a reason. The rolling hills covered in vineyards are absolutely breathtaking, the Chianti is amazing and the food is divine. I had decently high expectations and every expectation was met or surpassed. While the winding {sometimes very narrow} roads were a bit of a surprise to me, they were 100% worth it- even as someone who gets very car sick. Tuscany definitely needs to be on your bucket list! Here are my top tips on what to do in Tuscany!
Itinerary
You could honestly spend as much time or as little time as you want in Tuscany! For us with two kids, I would have loved one more day at least so we could experience few other surrounding cities. But I do feel as though we had a decent amount of time to experience Tuscany! If the weather was warmer we would have relaxed by the pool more as well. But the food, wine, views & company made for a perfect getaway!
- Day 1- Drove from Verona to Tuscany
- Day 2- Explore cities, eat delicious food & drink incredible wines
- Day 3- Explore cities, eat delicious food & drink incredible wines
- Day 4- Explore cities, eat delicious food & drink incredible wines
- Day 5- Drove from Tuscany to Pisa
Airport/Train Stations
- Florence International Airport (FLR)
- Pisa International Airport (PSA)
- Firenze Santa Maria Novella (Firenze SMN)
Hotel
- My parents rented this home for our whole family to stay together and we would 110% rent it again. It is located walking distance to a cute little town with a handful of restaurants, is walking distance to a delicious winery, has a private pool, ample space and was absolutely stunning!! It was a true, cozy Tuscan villa and felt straight out of a RomCom. The grounds are spectacular! My parents actually talked about renting it for a full month and having friends come visit them because they enjoyed the home and location so much!
Restaurants
- Lunch/Dinner
- We hired two private chefs (recommended by our host) for two of the nights and 110% recommend you do the same! They came and cooked in our home and it was so much fun!! Literally one of the highlights of the trip! We learned how to make different types of pasta & ate delicious local dishes made from family recipes that have been passed down for generations! The chefs were Susanna Civeli {susannaciveli @ yahoo.it- she taught us to make pasta}
- Antica Macelleria Cecchini :: An 8th generation, famous butcher shop specializing in fresh cut meats (specifically the Florentine steak)
- Ristoro Di Lamole :: One of the most praised restaurants in the region. Their Zucchini pie with pecorino sauce and fresh truffles is an amazing appetizer. Reservations are highly recommended- so try booking this in advance!
Transportation
- We drove everywhere, other than the little city we stayed in/walking distance to.
- Hire a driver. If you plan on drinking quite a bit of Chianti, you may want to look into a driver or a tour. We didn’t take one since we had our two little kids with us, but I would definitely contemplate it in the future!
Recommendations
Cities Worth Visiting
- Castellina in Chianti :: A small, but quaint town full of restaurants and stores. Check out Via delle Votle, San Salvatore, and Rocca. We really liked this cute little city.
- Radda in Chianti :: This walled village is full of stores, alleys and squares. Visit Palazzo del Podesta and Prepositura di San Niccolo (a church dating back to 1200)
- Siena :: Visit the Contrada della Lupa, Piazza del Campo di Siena, Siena Cathedral and simply walk downtown!
Wineries
Tuscany is FILLED with delicious Chianti wines and so many of them have stunning views. These are a few of my recommendations, but also see the map I link below for more suggestions.
- Fattoria Le Fonti :: This is the winery located right next to the home we rented. It was so good, the view was stunning and we drank their wines at home just about every night!
- Fontodi
- Tenuta Casenuove
- Le Cinciole
- Azienda Agricola Montefioralle Winery
- Castello dei Rampolla
Must See Attractions
Our top priorities in Tuscany were to relax, eat delicious food and drink good wine. And that’s exactly what we did! I actually made a Google Map with tons of recommendations here! You’ll find cities that were recommended to me, restaurant suggestions, landmark suggestions, winery suggestions, viewpoint suggestions and more! Some of these spots we did make it to, others we didn’t. But we were very impressed by the spots we did make it to!
It’s also worth noting Tuscany is known for their truffles! White truffle season is October-December, Black winter truffle season is December-March and Black summer truffle season is May-September.
Did I miss anything?
What would you add to the list or what would you like to know more about?
For more Italy tips and posts, click here!
These photos are gorgeous! I have never been but it is definitely on my bucket list! Thank you for sharing!
Definitely one of my dream destinations. Every since I saw the movie, Under The Tuscan Sun.
I have heard much about Tuscany, but have never visited. It sounds like wine is part of the daily lifestyle!
If I ever have the opportunity to visit Tuscany, I’m going to use this as a guide on what to do. Love it.
It sounds wonderful! I would love to visit Tuscany one day and see and do it all!
Although Italian, I have been in Tuscany many years ago now. I remember the infinite heat of the same, but also the beauties to take your breath away. Every day is a new experience and a journey through history!
I love the detailed itinerary. And the pictures are stunning. Will consider Tuscany as another travel destination.
The sky and the nature looks breathtaking!! I love all your pictures, it does look like an exciting trip.
What a lovely experience to share with your whole family. I can imagine how much fun it must have been to have a private chef demonstrating how to prepare Italian meals – and delicious, too! We spent part of a day in Chianti on a wine-tasting tour, and it had so much charm. Your photos brought me right back! I agree that more time spent in Tuscany is always a good idea.
I LOVE Tuscany…the food, the people, the landscape, the history! Did I say food? Loved looking at your photos!
These travel photos are lovely. I’d love to take my family in here too! There are so many great things to do and eat.
Ooohhhh…excellent then! Thanks on the tip about getting a driver, when I am here. I wouldn’t want my eyes to miss out on any sight-seeing!
Glad to see the Tuscany post with your kid. I have a 10-year-old and we are planning to take him to Italy next year. This post will come handy.
Tuscany looks stunning. I have never been before and would really love too… think I would like to stay where you did as from the sounds of it, it left quite an impression. Plus being close to Fattoria Le Fonti is an added bonus
Tuscany is a dream, isn’t it? I love your itinerary and the experiences you had, especially hiring the private chef- how amazing that would be. The wineries and villages you visited some I’ve been to, but there are many that I have not and hope to one day return.
Oh! How much I loved reading this as it brought back some of the most amazing memories from Tuscany. The cobbled streets, the medieval architecture, the endless vineyard views. Loved the fact that you rented a home and had some absolutely memorable local interactions! Having local chefs on a holiday is so much better than eating at restaurants! I remember visiting San Gimignano and the shopping for handmade soaps in its cutesy market!
Amazing pictures. We are just back from a 3 week trip to Tuscany. We did everything by public transport and walking, what was just fine. We also did some wine tasting. There were some wineries we could walk to or take the bus. Food is so delicious in the area.
oh wow… the view is simply breathtaking! I would take so many pictures of the scenery just like you did! lovely shots! I would love to visit Castellina in Chianti someday.
Such nice pictures! Wish i could visit some time and see these views for myself!
Love the itinerary that you made. Explore cities, eating delicious food & drink incredible wines pretty much sums up my ideal vacation. We’d love to visit Tuscany in the future. Thank you for sharing with us your wonderful experience.
Wonderful photos! Tuscany should be on everyone’s travel bucket list. Siena piqued my curiosity after reading your list of worthwhile cities to visit. I’m sure dining at Ristoro di Lamole with such beautiful views is fantastic! It’s also an excellent idea to sample Chianti wines. I’m also interested in learning more about their varied seasonal truffles, so I’ll keep track of that.
Tuscany does look a great place for a relax! Seems like everywhere you went you were presented with beautiful views. Not just the nature, but the small town as well. I’m not a wine drinker, but I can see how they tasted great by seeing you enjoyed them.
It sounds so amazing! Hiring chefs to come cook in your home would definitely bea highlight for me too. I can’t imagine a better Tuscany vacation than what you have pictured here!
This is a great showcase for places and things to do in Tuscany. We are staying in Arezzo in July and have also hired a chef to come and cook for us for a meal with friends and family. I definitely need to think about visiting both Siena and Chianti during my stay. I hadn’t looked into them until your recommendation and they look great.