Tuscany. One of the largest and most-visited regions in Italy. It is no wonder that it tops many people's bucket lists with land comprising of vast plains, gorgeous green rolling hills, hundreds of vineyards and lots of quaint, medieval hillside towns. It is such a beautiful place words cannot describe and that photos don't do justice topped off with some of the most delicious food and wine around. If this dreamy destination is not on your list, it should be. And for a decent chunk of time. There is so much to see and do in Tuscany that you really should plan to spend at least a week to get a taste of the wonderful culture. And then you should go back and do more. Better yet, you should just move there like Diane Lane does in Under the Tuscan Sun. But if that cannot happen well then here is a list of 7 places to see on your next trip to Tuscany that will have you longing for more.
A street in Florence
PISA
Home of the Leaning Tower and pretty much nothing else. A half day is more than enough in this touristy city and trains run regularly here every day from Florence (about a 30 min ride). The Leaning Tower can be found in Piazza dei Miracoli. It is free to wander the grounds but you have to buy a ticket to climb it. I've never felt the need to do that. There are tons of tourists here so you will probably just want to get your picture and turn right around. Avoid eating or drinking near the Leaning Tower because those places tend to rip off tourists. Instead stop at Il Crudo in nearby Piazza Cairoli (Piazza Cairoli 8) for a delicious panino.
An obligatory picture with the Leaning Tower
FIESOLE
Another great day trip from Florence, this charming little town is located up on the hills slightly north of the city so has a spectacular view and also has a cute little piazza with trattorias and gelaterias. Make sure you wander the side streets up the hill because there are spectacular views once you reach the top. If you are staying in Florence and unable to spend time exploring the Tuscan countryside but want a taste for it, this is the place to go. It is a quick 20 minutes on ATAF bus number 7 from Piazza San Marco. Purchase your tickets inside the tabaccheria. Make sure to validate (stamp) your ticket in the machine as soon as you board the bus.
Views from Fiesole
SIENA
Another major city of Tuscany but smaller than Florence and a little over an hour south. You will want at least a full day to explore this city. Piazza del Campo is the main square full of places to eat and bustling with people. Definitely fun to wander around. For an amazing Tuscan meal off the beaten path in a super cute tiny square with a great outside patio, visit Enoteca I Terzi (Via dei Termini 7). Also, the Duomo (Piazza del Duomo 8) is supposedly one of the most beautiful cathedrals in Tuscany, especially the interior. Other than that have fun and get lost wandering the streets, my most favorite activity.
Lunch al fresco at Enoteca I Terzi
CERTALDO ALTO
Definitely a lesser known town in Tuscany, my husband and I stumbled upon this place when we were searching for a town with a city hall to get married. This one definitely fit the bill-- old and medieval, perched up high on a hill with gorgeous views of the rolling Tuscan countryside, quaint, and filled with cobblestone streets for strolling. Cars need a special permit to drive up here so visitors must park at the town below (Certaldo proper) and take the funiculare up the hill, which just adds to the charm. It is a really small town that you don't need a full day for but is a great place to relax outside with some wine and bruschetta at a cute little cafe like Enoteca Boccaccio (Via Boccaccio 37) taking in the scenery. It's about 45 min to an hour south of Florence.
The quaint town of Certaldo Alto
SAN GIMIGNANO
Another quaint medieval town great for wandering around located about an hour south of Florence. A few hours are perfect for exploring the many cute streets lined with shops and places to grab a bite or drink. This town produces one of the few white wines in Tuscany, Vernaccia, and it's pretty good so make sure to have a glass! The views on the drive to town are so amazing and exactly how you would picture Tuscany. This town can get pretty crowded but escape the masses and have a delicious panino and glass of wine for lunch at dal Bertelli (Via Capassi 30), a cute little spot off the main tourist drag that offers local ingredients.
The towers of San Gimignano
MONTERIGGIONI
This small, fortified medieval town still has its walls intact. Walk along the walls for amazing views of Tuscany and relax in its piazza with an espresso or prosecco. You don't need more than 2 hours here because it is so small. It's about an hour south of Florence and on the way to Siena.
The view from the walls of Monteriggioni
Not mentioned in the list above but something everyone should include in their trip is a visit to a winery. There are literally hundreds in Tuscany to choose from whether it be a huge, well-established brand or a small, family-owned name. On my last trip, I visited the new Antinori Winery (Via Cassia per Siena 133, Bargino) which was down the street from where we were staying. Antinori is a huge production (some bottles can be found in the States) and the facilities were nothing short of spectacular. On my next trip, however, I plan to make it to some of the smaller, independently-owned wineries for a more intimate experience. Here is a helpful site that lists all the wineries in the Chianti region of Tuscany and here is another helpful resource that includes some other Tuscan wine regions as well. Be sure to check the winery's own website to make sure they are still in business and for more details on their hours.
The crew at Antinori Winery
Curious about where to stay? You could choose to stay in Florence which serves as a good home base and has plenty of hotels. For a splurge, stay at the Westin or St. Regis which are centrally-located, on the river Arno and housed in buildings with beautiful architecture that make you think for second you're in a museum. OR, you could opt to stay in the countryside in an agriturismo which is an excellent and affordable option (you will just need a car). What is an agriturismo you ask? Well, my next post will be all about it and the agriturismo that I stayed at, so check back soon or follow me to receive a notification.
Wondering about Florence? Read my post on that here.
Not on this list but a top priority for my next trip to Tuscany are the towns of Montalcino and Montepulciano for their exceptional wine-- Vino Nobile and Brunello. If you've been to either of these places, I'd love to hear all about it including any wineries you visited. Leave me a comment below, per favore!
And as always, if you have any specific questions about Tuscany I encourage you to ask away! Happy traveling :)