Spread out for the full effect, with two or three bases to move around more easily
Tuscany has so many things to offer! Cities with countless amounts of art & incredible architecture, sandy beaches and hot springs to relax at, mountains for hiking adventures, vineyards and wineries where you can enjoy tastings, olive groves and cypresses to offer spectacular landscapes. Sometimes its seems like no matter how many days you plan on staying in Tuscany, it is just never enough.
Let's say from the start that 5 days will fly by and not be nearly enough, but if that's all you have, here is our recommendations on how you can plan 5 days in Tuscany in order to get a taste of the diversity and beauty of this area.
First, let's take Florence out of the equation
If this is your first time in Italy, then you need to dedicate a few days just to Florence. Stay in Florence and explore the museums, monuments, enjoying shopping and lots of delicious gelato. In this article we suggest an itinerary for seeing Florence in just 2 days so that you won't miss the top sights. The ideal solution is to find accommodations within the city walls, don't pick up a rental car just yet and plan an itinerary that will leave you satisfied that you have seen most of the main sights.
After your time in the Renaissance City, pick up a rental car and plan on spending 5 full days touring and exploring the Tuscan countryside, with two bases: one in the south and one in Chianti. This will offer various landscapes that make up the region of Tuscany.
Day 1 in Tuscany: Pisa & Lucca
You can leave the car behind for one more day (keeping your base in Florence), and visit these two destinations with public transport from Florence. Remember to buy your tower tickets BEFORE you go.
Pisa, as well as Florence, has to be seen at least once in your life. From Florence, there is a regional train that arrives in Pisa in about one hour. The city of Pisa is famous for beautiful Piazza dei Miracoli, where you'll find all of the major monuments and sights. Here is the magnificent Cathedral of Pisa, built in the 11th century, the splendid Baptistery of St. John, the monumental Camposanto (cemetery) and the striking Leaning Tower of Pisa, an international landmark that you must climb at least once in your lifetime! While you are going back to the train station, we suggest a tranquil walk along the Arno riverbanks enjoying this charming city in Tuscany. You could follow some of the tips we've included in our one day in Pisa itinerary.
After Pisa, head over to Lucca where you can experience the thrill of walking - or cycling! - along the city walls, strolling its charming medieval streets and visiting the fabulous marble-decorated churches. Don't miss out on Piazza dell'Anfiteatro and the archaeological remains under the 12th century church of Saints Giovanni and Reparata. Lucca is just a 30 minute train ride from Pisa, and the station is located just outside the city walls on the southern end, so the town is easy to see on foot in half a day.
Day 2 in Tuscany: A full day in Siena
Make Siena your base for two days, so you can enjoy the city nightlife, and take a day trip to explore one of the hot springs close by.
Siena, like Florence, merits being included in your short stay in Tuscany. Not just for the art, architecture and history but also for the small town feel, the magical skyline and its hospitality. There are several hotels that offer parking included, keeping you within walking distance for restaurants and sites.
Day 3 in Tuscany: A day in the Val d'Orcia
When you see a postcard of Tuscany, you see the Valdorcia. Gentle hills colored in green (or yellow) with lonely cypresses sitting atop the hills are typical landscapes of this area.
The most representative destinations are Montalcino and Montepulciano, also famous for their excellent red wines, Pienza and its Renaissance square, San Quirico d'Orcia and its gardens. The smaller towns such as Bagno Vignoni and Buonconvento also hold their own special charm. Buonconvento is technically in the Crete Senesi, which is between Siena and Val d'Orcia, so you can definitely explore more of it and its sights on the way down or back up.
Day 4 in Tuscany: Chianti
Chianti is synonymous with wine and wine tastings! You will have already experimented with the wines south of Siena in Montalcino and Montepulciano. Look for an accommodation on a wine estate and see everything up close.
Choose to follow one of our suggested itineraries in Chianti where you can wander through some of the quaint and picturesque towns of Chianti visiting vineyards, small shops and savoring the authentic flavors of Tuscany. A few of the more charming towns include San Donato in Poggio where you can walk to the local restaurants and experience a real medieval hamlet or Castellina in Chianti, one of the three original towns in the Chianti League.
The landscapes are spectacular, the vineyards are plentiful and everything is fairly close, so you will keep your driving times to a minimum. However, we do advise that if you want to be tasting the wines that you look into a guided wine tasting tour, or a private driver so you can be worry free!
Day 5 in Tuscany: San Gimignano & Volterra
You have been traveling quite a bit, so select an accommodation in the countryside where you can take a day off and just relax: by the pool, at a town market or simply enjoying a cooking lesson where you can eat your own prepared meal afterward!
This amazing little town is just right to fill in a half day and leave you some much deserved free time. San Gimignano has been left virtually untouched, the tall towers, quaint streets and outdoor cafes just beckon to you to stroll aimlessly. This UNESCO World Heritage Site since 1990, is the home to tasty saffron dishes and Vernaccia white wine. And if you are really curious there are several points of interest you can visit without taking up the whole day, starting with the Duomo and the civic museum in the Torre Grossa next door...and some of their great restaurants!
I suggest you take your time in San Gimignano as to not be in a hurry. If you however find yourself with some time on your hands, I suggest you head toward Volterra nearby. It is another medieval town in Tuscany that merits a visit to its historical center, also enjoying the drive and views between the two towns. Here is our recommended top sights to see in Volterra and more info on how to get there.
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