When my dad asked me if I could plan a 10-day trip in Florence & Tuscany for our extended family (12 people in total), I was admittedly daunted by the task. It took a lot of research and planning, but miraculously, I managed to pull it off--and we had a fantastic vacation! Whether you’re a history buff eager to explore Renaissance masterpieces, a food lover seeking authentic Tuscan flavors, or an outdoor enthusiast yearning for scenic bike rides (all of whom were family members I had to accommodate on my trip), this week-long itinerary will guide you through the very best that Tuscany has to offer.

From rolling hills adorned with vineyards to charming medieval towns steeped in history, Tuscany offers an unforgettable experience for every traveler.

I am sharing all the research, planning and travel insights that went into crafting our 7-day itinerary in Tuscany, in the hopes of saving you a TON of time planning the perfect 1 week Tuscan vacation. This comprehensive travel guide will equip you with practical tips, hidden gems, and must-see attractions, ensuring you maximize your time in Tuscany

The Ultimate 1 Week Tuscany Itinerary & Travel Guide

Overview of Tuscany

One thing that I discovered in the process of planning our family vacation in Tuscany – the region is bigger than I realized! Before I get into the itinerary (and you make the same mistakes that I did), I think it makes sense to have a quick geography lesson about Italy’s most famous region. 

Located in central Italy, Tuscany spans from the Mediterranean Sea on its west coast all the way east to Arezzo and all the way south to Grosseto. The capital of Tuscany is Florence, but cities like Pisa, Arezzo and Siena are also within Tuscany’s boundaries. While it is an iconic land of rolling hills, winding roads, and cypress trees, there is more to it than initially meets the eye.

The state of Tuscany is actually split into ten smaller provinces, mostly named after the large city in the province (ex: Arezzo, Firenze, Lucca). If you’re looking for the quintessential Tuscan countryside experience, I would recommend focusing on the provinces of Firenze (which includes Chianti), Siena, and Pisa. This will save you time on driving, while also giving you the iconic experiences you come to Tuscany looking for.

Tuscany Travel Logistics

Arrival & Departure

Florence is the most logical place to start a 1 week trip in Tuscany. If you’re flying in from outside of Italy, Florence Airport (FLR) is your best bet in terms of finding flights. Essentially, you’ll make a big loop circuit through Tuscany, ending back at the same airport you came in to. 

Another airport to consider is Bologna Guglielmo Marconi Airport (BLQ). It’s about 45 minutes north of Florence, but it’s a good alternative. You might be able to find slightly cheaper rental cars and flights. Plus, I think Bologna is great, and it’s worth a day or two of your time. Especially for foodies. You're going to love the Emilia Romagna region.

A final option to consider, especially if you are traveling for a longer time in Italy, is flying into Rome. From Rome-Fiumicino Airport, there are direct high-speed trains to Florence. You can choose either the Leonardo Express, a Regionale FL1 train, or a high-speed Alta Velocità (AV) train. The AV train is ideal if you’re not planning to spend any time in Rome and want to get straight on to Florence from the airport.

Best times of the year to visit Tuscany

Due to its extreme popularity, Tuscany is most enjoyable during shoulder season. Summers are known for being busy and very hot. May and September are simply gorgeous with lovely weather, smaller crowds, and more affordable rates. May is Poppy season in Tuscany, so you can see these large fields of beautiful red flowers. Sunflower season starts in June and can last into July. Wine harvest typically begins in early to mid September. I would avoid January & February as many restaurants and shops are closed. 

How to Get Around Tuscany

To see Tuscany easily and comfortably, especially on limited time, a car is essential. While I'm a big fan of train travel in Europe, Tuscany is one of the places where you really need a car to fully experience it. The small towns are not easily accessible with public transportation, and you will miss a lot of highlights without access to a car. 

Using this itinerary, you shouldn’t have to drive more than about an hour or two between towns depending on your exact accommodation.

If you are arriving in Florence, I would recommend picking up and dropping off the rental car there. The smaller the car, the better because Italian towns have VERY narrow roads. Parking with a large vehicle is… stressful. Make sure you’ve got an all-inclusive insurance package. If you’re inexperienced driving in Italy, it is very probable that your car ends up with small dings and scrapes.

Tuscany 1 Week Itinerary

Day 0: Arrival in Florence 

As I suggested above, Florence is the best place to start a 1 week itinerary in Tuscany. It is the capital of Tuscany, and has an immense amount of art and history to discover. I would strongly recommend that you start or end your Italian holiday with a few extra days in Florence. For the purposes of this blog post, I am going to keep my Florence suggestions to a minimum. I want to focus mostly on other places in Tuscany.

If you are interested, you can read a separate itinerary specifically about the best things to see & do in Florence for first-time visitors. When it comes to planning your extra time in Florence, I would say 2 days is good. 3 days or more is ideal. While you could see the highlights in about 36 hours, I think Florence is better enjoyed slowly. It gives you time to dive into the museums and stories that make Florence such a unique destination in Italy.

Day 1: Siena 

With its medieval architecture and vibrant atmosphere, Siena is the perfect introduction to Tuscany. Stroll through Siena’s winding streets, where the medieval architecture seems frozen in time. At its heart lies the uniquely fan-shaped Piazza del Campo, one of Europe’s most magnificent medieval squares. This piazza is the location of Palio di Siena, a thrilling horse race held twice a year in Siena that’s been a local tradition since the 1600s. During our visit, preparations for the race were underway, and we got to see one of the racing teams on a procession through the city. 

As you walk around Siena, you’ll pass charming shops offering locally crafted ceramics, leather goods, and the delectable panforte—a traditional Sienese fruit and nut cake. 

Be sure to visit the Siena Cathedral, a masterpiece of Gothic architecture. Its intricate facade, striped marble columns, and dazzling mosaic floors make it one of the most impressive churches in Italy. Inside, you’ll find works by Michelangelo, Donatello, and Pisano, along with a remarkable frescoed library. Climb the tower for sweeping views of the surrounding countryside.

Day 2: Medieval Tuscan Towns 

Today, explore three of Tuscany’s most picturesque villages, each with its own character and charm. Begin with San Gimignano, often called the "Medieval Manhattan" for its iconic towers. Once a symbol of each family's wealth and power, these 14 towers are a striking reminder of the town’s medieval past. Wander through the town’s narrow streets, where artisans sell handcrafted ceramics, olive oil, and saffron—a specialty of the area. 

Grab gelato at Gelateria Dondoli in San Gimignano, rated as the two-time gelato world champion. As you can tell from my TikTok video about this gelato, I loved it!! You'll most likely find a line, but the line moves really quickly. I tried two of the signature flavors – saffron & pine nut and raspberry & rosemary. Both flavors were distinct and strong, and utterly delicious. Plus, the gelato had the perfect creamy texture. I think it deserved to win the award as world's best gelato!

Next, visit Volterra, a town known for its fascinating Etruscan roots and alabaster craftsmanship. The ancient city walls and the Porta all’Arco date back to the 4th century BC. Yeah, that's right -- there was a thriving civilization in Italy that predates even the Romans. Volterra’s Roman theater, alabaster workshops, and the hauntingly beautiful Medici Fortress make it a destination filled with both history and mystery.

Conclude your day in Monteriggioni, a tiny fortified town that appears as if it’s been plucked from a medieval fairytale. Walk along the ancient walls, where you’ll find panoramic views of the rolling Tuscan hills. As evening falls, enjoy a quiet dinner at a local trattoria and soak up the serene ambiance of this medieval wonder.

Day 3: Tuscan Adventures

You've had a few lovely days of sightseeing in Tuscany, so now it is time for some adrenaline activities. Or at least the Tuscan version of adventure activities. Start your day with a stunning sunrise hot air balloon ride, a truly magical way to see Tuscany. We went with Tuscany Ballooning, and had a fabulous time. Really an unforgettable experience!

The balloon departed near Cerbaia, gliding peacefully above the region’s iconic rolling hills and vineyards. Get a glimpse of my experience with my TikTok video about our sunrise ballooning! It’s a view that perfectly captures the natural beauty of Tuscany, all awash with a beautiful morning glow. As the balloon touched back down to earth, we were greeted with a celebratory glass of prosecco and a light breakfast. 

In the afternoon, embark on a truffle-hunting adventure, one of Tuscany’s most beloved culinary traditions. Accompanied by a 3rd generation truffle hunter from Oressea Farms, we set out for a truffle hunt with their specially trained dogs. Certain species of dogs are most commonly used in truffle hunting, and they are trained from birth to hunt for the fragrance of the truffle.

Truffles, which cannot be easily cultivated, occur naturally in the wild, typically near the roots of certain tree species under damp conditions. Go behind-the-scenes of our Tuscany truffle hunt with my TikTok video about the experience.

Hunting for truffles is like any other kind of hunting – you are not guaranteed to find truffles! The dog will lead the way, sniffing out the coveted truffles hidden underground. All of a sudden, the dog will bolt away and start digging beneath a tree. Then the owner will run over and remove the truffle from the ground. We got to keep (and cook!) everything that we found on the hunt.

Day 4: Chianti 

Chianti is a region synonymous with wine, rolling hills, and charming villages. We became really familiar with Chianti during our trip, since our villa was located in the heart of Chianti. There are a number of cute small towns to visit in Chianti, and I think one of the best ways to visit them is on two wheels! 

Gear up for an exhilarating bike tour through Chianti, following the iconic route of the Eroica, Tuscany’s celebrated vintage bike race.

We had an absolutely fabulous guided bike ride with Elizabeth from Tuscany Bicycle. Based in Gaiole In Chianti, Elizabeth founded her business a few years ago on a dream. She has grown it to a premier bike tour and rental outfitter in Chianti. You can create a custom bike route in Chianti, based on your fitness level, interests and desired length of ride. The shop can equip you with everything you need for a safe & comfortable ride, from helmets to e-bikes. 

Towns & Attractions to Visit in Chianti:

• Gaiole in Chianti: this is where you’ll begin your ride if you rent from Tuscany Bicycle. It is a vibrant hub for cyclists and the birthplace of the Eroica race itself. Pop into La Bottega with outfit yourself in authentic Italian bike gear, like jerseys and branded t-shirts.
• Ceramiche Rampini: bring the look of Tuscany home with you in the form of pottery. Each hand-painted ceramic is unique, featuring vibrant colors and patterns inspired by the Tuscan landscape. If you get to chatting with the artists, you might even hear juicy stories about their celebrity clients.
• Radda in Chianti: medieval town perched atop a hill. Enjoy a coffee or a pastry at a local café, taking in the views over the vineyards below. Radda’s stone streets and fortress-like buildings capture the medieval essence of Chianti
• Greve in Chianti: charming village with a weekly farmer’s market. Grab a snack at Antica Macelleria Falorni, a historic artisanal butcher shop. You’ll be greeted by an enticing display of cured meats, cheeses, and other regional delicacies. Try the famous wild boar salami.
• Castellina in Chianti: Known for its impressive medieval walls and hidden passageways, Castellina is a picturesque place to wind down from the ride. Take a stroll along the Via delle Volte, a covered walkway offering panoramic views
• Panzano: a beautiful village that is known as “Tuscany’s meat city,” in large part thanks to Dario Cecchini, an eccentric celebrity butcher with a mini beef empire. No one can wield a bloody meat cleaver better, much less while reciting Dante.

Day 5: Chianti 

For your second day in Chianti, why not enjoy one of the region’s most beloved products – WINE! One of my dad’s primary goals from our 1 week trip in Tuscany was discovering new wines. So we spent a lot of time exploring and learning about Tuscan wines, especially Chianti Classico.

Chianti Classico DOCG is a celebrated wine born in the heart of Tuscany, crafted by ~400 wineries in a specific region between Florence and Siena. You might even recognize the black rooster from its labels!

The wine is made primarily from Sangiovese grapes, with at least 80% Sangiovese required to earn the Chianti Classico label. Chianti is known for its deep ruby red color and vibrant, aromatic profile. Distinguished by its balanced acidity, medium-to-full body, and firm tannins, Chianti Classico DOP is as elegant as it is versatile. 

Chianti Wineries to Try

• Antinori nel Chianti Classico: innovative winery seamlessly merging modern architecture with nature. Carved into the hills of Chianti, this winery was designed to respect the landscape while celebrating Tuscany’s renowned wine culture. Join a guided tour through its stunning cellars, where the latest winemaking techniques meet centuries-old tradition. 
• Ricasoli Winery: one of the oldest wine estates in Italy and the birthplace of Chianti Classico wine. Dating back to the 12th century, Ricasoli’s sprawling vineyards, medieval castle, and ancient cellars tell the story of Tuscany’s deep-rooted winemaking heritage. A visit here is pricier than other places in Chianti, but I promise it is worth it. The Ricasoli family’s influence on Tuscan wine is legendary, and this visit offers a profound appreciation for the history and craftsmanship that define this region.

Day 6: Val d’ Orcia

Perhaps the most picturesque part of Tuscany is Val d’Orcia, a UNESCO World Heritage landscape renowned for its golden hills, cypress-lined roads, and picturesque medieval towns. It looks like something out of a painting!

Start your journey in Montepulciano. Simply strolling around Montepulciano is stunning, thanks to its breathtaking Renaissance architecture. It is an ideal town for photographers.

Montepulciano is famed for its "Vino Nobile" or the Noble Wine. This was the exclusive wine drank by the Medici family during the height of their power in the Renaissance period. A visit to one of Montepulciano’s underground wine cellars, carved from ancient rock, offers a fascinating glimpse into local winemaking traditions and the opportunity to taste the exquisite Vino Nobile straight from the source.

Next, make your way to Pienza, a charming Renaissance town often called the “ideal city” due to its harmonious architecture and layout. Designed by Pope Pius II as an example of Renaissance urban planning, Pienza’s winding streets, flower-filled balconies, and stunning views of the Val d’Orcia countryside make it a truly idyllic destination. 

Pienza is also known for its famous Pecorino cheese. Pecorino is made from sheep’s milk and typically aged, creating a firm texture and distinctive, slightly tangy flavor. You can take a cheese making workshop at the family owned farm called Podere il Casale or simply eat a cheese themed meal at their farm-to-table restaurant. 

Day 7: Montalcino

Conclude your week in Tuscany with an unforgettable day of wine-tasting in the renowned Montalcino area, home of Brunello di Montalcino, one of Italy’s most prestigious wines. You can go behind-the-scenes of our Brunello wine tasting experiences on my TikTok video. If you find yourself with a bit of extra time in this area, make a quick stop at Abbazia di Sant'Antimo. Founded in the 9th century, this is a well-maintained Romanesque abbey nestled in the hills near Montalcino. Its elegant limestone structure and tranquil setting evoke a spiritual ambiance. 

Wineries to Visit in Montalcino

• Patrizia Cencioni Winery: a woman-run vineyard where you can stroll through the vineyards, explore the cellars, and enjoy a tasting. The welcoming atmosphere and dedication of the Cencioni family make this visit both educational and heartwarming.
• Capanna of Cencioni: renowned family-owned winery that has mastered the art of Brunello production. The location of this vineyard is stunning! You can get a panoramic view of Montalcino from below. They even have a wine & spa hotel if you want to spend the night. We did a vertical tasting here, which was a new experience for me. This means that, rather than sampling different wines from the vintner's selection, you sample the same wine, but from different years & harvests. Their Brunello was so rich with earthy flavors and deep complexity. I may or may not have shipped a few or their bottles home. 
• Podere Le Ripi: a biodynamic winery. The tour here includes insights into biodynamic agriculture and regenerative farming techniques. Admittedly, this wasn’t my favorite wine that we tried in Tuscany (and it is rather overpriced, imo), but I found the whole concept rather intriguing. Plus, the winery is beautiful and they have a great restaurant onsite.

Where to Stay in Tuscany

This is a BIG question when it comes to planning your perfect trip in Tuscany.  Essentially, there are three approaches you could take: 

1. Stay in one place for your entire trip, and use it as a base for exploring the entire region
2. Stay in a different place each night
3. Choose 1-2 home bases in a province and stay there for a couple of nights each. 

If you are going in a large group (like I did), booking a villa for the whole time is an amazing choice. Choose a villa somewhere more central like Chianti or around Siena, which gives you lots of easy day trip options. We stayed at Villa Le Pratola in Chianti, and had a fantastic stay. Nothing but positive things to say! 

If I was only traveling with my husband or a small group, I would probably choose to split time between two bases. I would choose an agritourism-type stay in a rural area in southern Tuscany and then I would choose a boutique hotel in a town like Siena or near Florence. This way, I can have two different, yet equally wonderful experiences. 

Have thoughts or questions about this Tuscany itinerary? Tell me in the comments!