Tuscany Travel Guide: Where To Stay, What To Do and How to Make the Most of Your time in Italy
Over the past 1.5 years we’ve spent almost 2 months in Tuscany. And to say we fell in love is an understatement. Coming from LA, the slowness was an initial shock to the system but once we got into the flow, we truly came to understand the magic of living under the Tuscan sun. I’m beyond excited to share all the things we discovered during our last two visits, links to our AIRBNB hamlet, and tips for your next trip to Tuscany. Let’s go!
Best Tuscany Airbnb -
Tuscany Day Trip to Siena
Getting TO TUSCANY + Getting ARounD
The Florence Airport, located just a stone's throw away from the city center, offers convenient access to Tuscany's capital and its surrounding areas. Alternatively, Pisa International Airport presents another excellent option, boasting a wider range of international connections. You can also fly into Rome but be prepared for a 3-4hr road trip. All three airports have ample transportation options, including buses, trains, and rental cars, making it a smooth journey to immerse yourself in the beauty of Tuscany's rolling hills, historical towns, and world-class vineyards.
tip: Rome2rio is an extremely helpful resource for planning your routes + transportation options to get you from point A to B. In a country like Italy, with fabulous trains and public transportation, it is so helpful to see what is available and how to efficiently get to where you need to go.
One thing I didn’t know before we arrived last year: the region of Tuscany is vast! People talk about it like “oh I’m just going to Tuscany.” Tuscany is HUGE - the size of the state of New Jersey - so first things firsts: if you’re really planning to explore then I highly recommend renting a car. And this will be the most expensive part of your trip. We’ve found the best rental car deals on DISCOVER CARS + have used them many times over the past few years.
The good news is: lodging, food, wine and experiences are fairly inexpensive compared to the states! Especially the wine; I mean we’re talking incredible bottles for $15.
WHERE TO STAY
Most people typically come to Tuscany and stay in the northwest quandrant (if you kind of divide it into 4s) in cities like Florence, Pisa, Lucca, Siena. I’ll give you a minute to look at a map.
We took an entirely different route and decided to stay near Arezzo in a small medieval town called Anghiari which is on the east side boarding Umbria. Why? Honestly, I found this epic Airbnb and that was that! In talking with friends we met in our Airbnb hamlet (more on that below), many of whom have traveled in Tuscany before, they said our location was super special and unique because it wasn’t touristy or busy like other places in Tuscany. I LOVED our location because it was smack in the middle of Italy and we were easily able to take day trips to Siena, Rome, and Florence… even the beach on the east coast. Anghiari was also recently included in Travel + Leisure’s 12 Best Small Towns in Italy round-up.
If you are going to do Tuscany for less than a week and you’re looking for city vibes then I would recommend staying in Siena or Lucca. Florence would not be at the top of my list because it has just become so inundated with tourists over the past few years. If you’re looking for smaller, picturesque Italian towns try Montepulciano, Montalcino, San Miniato or Pienza. I’m also obsessed with the tiny village of Bagno Vignoni which is famous for it’s hot springs. Bagno Vignoni would be an incredible honeymoon spot or relaxing couples getaway.
There’s something super special about being out in the countryside without floods of tourists. If you do want to stay in Florence, Casa G Firenze is a beautiful boutique hotel that is central to everything. We absolutely loved the vibes and hospitality. You can see more of the property in my Tuscany highlight on IG.
Scroll down for specifics on our stay in Anghiari plus day trip recommendations for Tuscany.
Outside of Anghiari AIRBNB near Arezzo Italy
Gorgeous Tuscany Airbnb with multiple houses and communal pool
Tuscany Day TriPS
There is so much to see and do that you should be prepared to drive a lot. Tuscany is gorgeous, so there are worse things, but if you really want to get out there and see all there is to offer, you will be spending a lot of time in the car. For those “destination” spots like Florence, Siena, and Rome there are quick trains!
Go to the thermal springs in Bagno Vignoni (you have to see this video) - you can make full day or half-day reservations at this hotel. This was SO magical and a must do!
Drive to Siena to explore the city and make sure to have lunch at Pizzeria alle Scalette.
Hit the luxury outlets (40 minutes outside of Florence) - see details here
Train to Florence but be prepared for tourist insanity!
Train to Rome - make sure to check out my Rome Travel Guide that has a ton of resto recs.
Drive to Montepulciano to wine taste and explore the town. With its charming cobblestone streets, ancient walls, and stunning Renaissance architecture, Montepulciano truly captures the essence of Tuscany. You could 100% spend the full day wandering the streets and wine tasting.
Rent a classic car and get lost in the hills of Tuscany. Slow Drive Vintage Cars is your spot! If you do this, make sure to stop in San Miniato.
Visit the Beach in Senigallia and reach out to our friends at Tenuta Marino for private wine tasting - tell them I sent you
If you happen to be driving back to Rome to catch a flight, do a little detour the Saturnia Hot Springs. We weren’t able to make it this trip but I have heard nothing but amazing things!
Wine Taste! this is an obvious one but surprisingly we didn’t do a lot of wine tasting during our month here, primarily because the tasting culture is not like the US. In the US it’s spend the day hoping between wineries, frolocking in the vineyards with picnics. In Tuscany, wine tasting is much more business like - taste and move on which is a little tough to do with a toddler. Here are recs from our sommelier friends though:
Antinori - definitely make reservations in advance
Dei Maria Caterina
Cantina Boscarelli
Poliziano
If you’re looking for other unique experiences there some to be had at Salvadonica (like picnic’ing in the vineyards) as well as Il Borro.
Outside of our 16th Century AIRBNB in Anghiari, Italy
View from store in Anghiari Italy
Details on our Tuscany Airbnb + DAILY LIFE AT THE HAMLET
We stayed at Poggiodoro, a charming 16th Century Villa in Anghiari and I couldn’t recommend it more. The house is beautiful and perfect for families or small groups.
If you’re bringing babes who are newly walking, make note that there are steep steps up to the second floor and the house is made of stone.
The house is heated in the floors (I think!) and it is magical / keeps the place feeling so warm and cozy.
During our stay last year (mid April - mid May) we experienced weather anywhere from 40 degrees to 75 degrees. This year it was in the 70s and gorgeous almost the entire time.
Although you can walk to a local cafe, I would consider this location to be a drive-to-your-destination kind of place.
The property is expansive (see below) so there is a ton of room to wander and roam.
Poggiodoro is part of a hamlet of houses and apartments that share a gorgeous pool (I mean, can you even believe that view?) If you can convince your friends + family to come, it would be incredible to rent out a few AIRBNBS in the hamlet for a week of Tuscan memories together.
It also backs into Il Cardo Bread + Breakfast which is another great place to stay if you’re looking to do a few days in Anghiari during your Tuscany adventure.
Logistics of Getting to Anghiari
Fly into Rome or Florence (closer) and rent a car + drive. Rome to Anghiari is 3 hrs. Florence to Anghiari is 1.5 hrs.
OR fly into Rome or Florence and train to Arezzo (nearest city to Anghiari). Once there, rent a car there and rive 25-30 minutes to Anghiari.
Day in the life Living in Anghiari
Our chill days looked a lot like this:
Wake up and cook breakfast. Something interesting and important to note: they don’t do breakfast in small Italian villages like they do in the states (no eggs, brunch, etc.)
Drive 5 minutes into the medieval walls of Anghiari or 12 minutes to the town of Sansepolcro and grab an espresso and croissant at a local cafe. Our faves:
Bar Teatro
Pasticceria Chieli - incredible pastries!
Walk through Anghiari or Sansepolcro - both gorgeous locations with beautiful architecture and walk streets. The old town of Sansepolcro is especially good for kids to run around! Anghiari is very hilly with magical vista views.
Make lunch or go out to a local spot in Anghiari or Sansepolcro
Hang by the pool at our AIRBNB or take our daughter to the playground at the local castle
Make dinner or go out to a local spot in Anghiari, Sansepolcro, or Arezzo. You can’t miss:
Cantina Del Granduca - all the pasta are to-die-for. Definitely e-mail the to make a resi.
Dirty Rat - a nice change of pace from pasta, pasta, pasta!
Restorante Nena
Il Feudo del Vicario - the bringoli pasta is incredible!
We did a TON of cooking during our stay. It was honestly one of my favorite parts of out trips! We typically went to the COOP or GALA grocery stores in Sansepolcro for all our needs. There are also amazing butchers and produce markets to be found in both Anghiari and Sansepolcro.
The hosts of Poggiodoro, a charming 16th Century Villa can also help coordinating special experiences for you like cooking classes, horseback riding, etc.
Luna and Mama in Anghiari Italy enjoying Pizza
Thermal Baths at Bagno Vignoni
LEARNINGS+ Challenges
Most people do not speak English in these smaller villages (like Anghiari) but we had no problem with our basic Italian and the Google translate app.
Google hours are not always right! We found that many many business do not update their hours on Google and were shocked when we would show up and they would be closed. It took a lot of trial and error!
Italian siesta is a real thing. Many businesses including grocery stores are closed from 1pm-4pm. We also found that many businesses are closed on Sundays and Mondays which was extremely challenging for us with groceries and meals (especially with a toddler), so it just required extra planning.
Italy Amazon delivers! It can take 2 - 3 days longer than you’re used to but you do still have access to many things on the interwebs.
Did I miss anything? Let me know if you have any Qs!
You can always book a call with me to chat Tuscany or Euro trip planning. I’m happy to help! xx - Ashley
We’ve spent almost two months in Portugal’s capital over the last year and I will never get tired of Lisbon’s captivating blend of old-world charm and modern allure. This travel guide is a long one but we wanted to make sure you had everything you needed in one place: where to stay, how to get around, the EDP top 5, and a list of over 90 places to eat, drink and have fun in Lisbon!