From Florence To Sienna and Rome: A 7-Day Tuscany Itinerary

Traveling abroad is one of those experiences that stays with you long after the trip is over. It’s thrilling, transformative, and yes, a little nerve-wracking too. Before my first trip to Italy (and first time making a visit to Tuscany!), I felt that exact mix of excitement and nervousness. Stepping into a new country with a different language, customs, and culture can be intimidating. But as soon as I arrived, I realized how magical and unforgettable this region is. From the rolling hills and medieval towns to the vineyard-covered countryside and rich history, Tuscany is like a scene pulled straight from a dream.

To help ease your worries and make sure you get the most out of your time there, I’ve put together a detailed itinerary filled with all the recommendations, tips, and highlights you’ll need to explore Tuscany with confidence. I promise, you’ll fall in love with it just like I did!

Tuscany Itinerary

Planning a trip to Tuscany can definitely feel a little overwhelming at first—there’s just so much to see and do! But trust me, once you’ve got a solid itinerary, it all falls into place. Tuscany is hands down my favorite place in the world, and I know firsthand how important it is to have a plan. This guide is designed to help take the guesswork out of your planning so you can experience all the best parts of Tuscany, whether it’s your first time or you’re returning for more.

Before we dive into the daily breakdown, let’s cover the basics: where Tuscany is, how to get there, and how many days I recommend based on your style of trip. From iconic cities like Florence and Siena to charming hill towns, scenic drives, wineries, and some hidden gems, this itinerary covers it all. By the end of it, you’ll have a clear, inspiring roadmap for making your Tuscany adventure both seamless and unforgettable.

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Where Is Tuscany

Tuscany is a region located in central Italy and is famous for its breathtaking countryside, historic towns, and mouthwatering food and wine. It sits right between Rome and northern Italy, and it’s super easy to reach—just a 1.5 to 2-hour train ride from Rome. Florence is the main city in Tuscany, but there are so many other incredible towns to explore, like Siena, Lucca, Pisa, San Gimignano, Montepulciano, and Pienza. Each one has its own unique charm, from medieval architecture to rolling hills and endless vineyards. Whether you’re into art, food, or just want to relax in one of the most beautiful places in the world, Tuscany has something for everyone.

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How Many Days In Tuscany Is Enough

How long you should spend in Tuscany depends on the kind of trip you’re planning. If you’re just passing through as part of a larger Italy itinerary, I’d recommend spending at least two or three nights—especially if you’re near Florence. This will give you enough time to visit a couple of wineries, explore a few hill towns, and soak in the views of the countryside. But fair warning: even with just a short stay, you’ll find yourself wishing you had more time. I know I did! On my first trip, we only had two nights, and it’s the one thing I would’ve changed.

Tuscany is a place you can easily spend 3, 5, 7, or even 9+ days in Tuscany exploring. Every corner has something new to discover from charming villages, historic cities, scenic drives, and of course, plenty of pasta and wine along the way.

What To Do In Tuscany Italy

Visit A Winery

Tuscany and wine go hand-in-hand, so you absolutely can’t visit without tasting some of the region’s world-renowned wines. Whether it’s the bold Chianti, rich Brunello di Montalcino, or the smooth Vino Nobile di Montepulciano, there’s something for every wine lover to savor. Many vineyards offer guided tastings, tours, and even cooking classes that give you a deeper dive into the region’s winemaking traditions. Be sure to plan ahead, especially during the summer or harvest season when spots fill up quickly! A quick tip: bring a light jacket or scarf for those cool wine cellars, and don’t forget to pace yourself. Tuscany’s wines are so delicious, it’s easy to get carried away!

Take A Scenic Drive

Renting a car is one of the best ways to explore Tuscany, and I highly recommend it since public transportation is not always the most convenient for exploring the countryside or smaller towns. It gives you the freedom for a road trip to discover hidden gems, charming towns, and stunning landscapes at your own pace. We rented a car and it is super easy upon arriving in Florence and rent your car in Florence from airport, making it a seamless start to your adventure.

Once you’re on the road, the Val d’Orcia is a must-see, with its postcard-perfect views of rolling hills, cypress trees, and picturesque stone farmhouses. Drive during the daylight and stop often—there are so many spots to pull over and take in the views. A little tip: bring a reliable map (cell service can be spotty in some areas), snacks, and make sure your tank is full for longer drives. Trust me, the freedom and the views make it so worth it!

Explore Hilltop Towns

Tuscany is home to some of Italy’s most enchanting medieval towns, like San Gimignano, Montepulciano, Pienza, and Cortona. These hilltop gems are best explored on foot, so make sure to pack comfortable shoes (trust me, you’ll be walking a lot) and bring a camera, because the views are too stunning not to capture. I recommend visiting in the morning or late afternoon to avoid the crowds and get that perfect light for your photos. Each town has its own unique charm, from cobblestone streets and artisan shops to local markets and breathtaking panoramic views. If you’re the type who loves a bit of adventure and exploring fast-paced destinations, these day trips are absolutely perfect for you.

Try A Cooking Class

If you’re looking for a fun and delicious way to dive into Tuscan culture, a cooking class is a must. Imagine learning to make pasta, pizza, or other traditional Tuscan dishes using fresh, local ingredients. Many classes take place on farms or at wineries, making the experience even more special. Whether you’re with a partner, family, or flying solo, it’s a hands-on activity that brings you closer to the food and the culture. Just be sure to bring an appetite, closed-toe shoes (you’ll be on your feet), and a sense of adventure—you’ll not only enjoy a fantastic meal but leave with new skills and recipes to recreate back home.

Enjoy A Thermal Spa

After days of sightseeing and exploring, there’s nothing quite like unwinding in one of Tuscany’s natural hot springs. The region is home to several thermal spas, offering a peaceful, rejuvenating experience. All you need is a swimsuit, a towel, and sandals. Also, be sure to check if you need to make a reservation in advance. Soaking in these healing waters is a perfect way to experience a more tranquil, relaxing side of Tuscany, leaving you refreshed and ready for your next adventure.

Visit the Leaning Tower of Pisa

No trip to Tuscany is complete without seeing the world-famous Leaning Tower of Pisa! Located in the charming city of Pisa, this iconic landmark is part of the stunning Piazza dei Miracoli, which also features a cathedral, baptistery, and cemetery. If you’re up for it, climb the tower (just make sure to get your timed tickets in advance) for breathtaking views of the city, but be prepared for the narrow spiral staircase! To avoid the crowds, I recommend visiting early in the morning or later in the afternoon. And of course, don’t forget your camera—you’ve got to snap that classic “holding up the tower” photo!

Tour Florence and Siena

While Tuscany is famous for its breathtaking countryside, its cities are just as exciting and full of charm. Florence is a treasure trove of Renaissance art and architecture, with must-see landmarks like the Duomo, Uffizi Gallery, and Ponte Vecchio. Meanwhile, Siena offers a more medieval vibe, with its stunning cathedral, historic square, and the famous Palio horse race. Both cities are perfect for day trips or longer stays, so make sure to wear comfy shoes because you’ll want to take your time wandering through their captivating streets.

Each of these activities shows a different side of what makes Tuscany so special. Whether you’re there for the food, the views, the culture, or just a bit of everything, Tuscany has it all and more.

Tuscany Italy Itinerary

3 day Tuscany Itinerary

Day One:

Arrive in Florence, Rent A Car at Florence Airport, Drive to Greve in Chianti, check in at Castello Vicciomaggio, wine tasting and dinner

Day Two:

Morning – Enjoy breakfast and the pool at the accommodation, Afternoon – Wine tour, lunch, and wine pairing experience at Castello di Verezzano

Day 3:

Enjoy breakfast and the pool before checking out. Take an optional day trip to San Gimignano (50 min.) or Pisa (1 hr. 20 min) before heading back to Florence to return your rental car and check in to your Florence accommodations.

Optional add-on: Spend a few days in Florence at the beginning or end of your visit.

5 Day Tuscany Itinerary

Day One:

Arrive in Florence, Rent A Car at Florence Airport, Drive to Greve in Chianti, check in at Castello Vicciomaggio, wine tasting and dinner

Day Two:

Morning – Enjoy breakfast and the pool at the accommodation, Afternoon – Wine tour, lunch, and wine pairing experience at Castello di Verezzano

Day 3:

Take a day trip to San Gimignano to explore the town, try Gelateria Dondoli, and enjoy lunch. Stop by Antinori Winery on your way back for a tasting.

Day 4:

Take an optional day trip to Pisa or Siena to explore the town and visit Piazza del Campo, or relax by the pool and enjoy your accommodations and the peaceful countryside.

Day 5:

Enjoy breakfast and the pool before checking out, or take an optional day trip before heading back to Florence to return your rental car and check in to your Florence accommodations.

Optional add-on: Spend a few days in Florence at the beginning or end of your visit.

Tuscany is one of those places that never fails to leave an impression.

Whether you’re sipping wine in Chianti, exploring the medieval streets of San Gimignano, or simply taking in the beauty of the rolling hills, it’s a region that fills your soul. No matter where you decide to stay or how you plan your days, Tuscany offers something magical around every corner. I hope this itinerary inspires your adventure and helps you make the most of your time in this stunning part of the world.

If you only have time for a Tuscan countryside day trip, here are some great options for a guided tour that you can book from Florence.

For more travel inspiration and tips to complete your Tuscany experience, check out my Where to Stay in Tuscany Region to find the perfect accommodation for your trip. If you’re a wine lover like me, don’t miss my guide on the Best Vineyards in Tuscany to Visit for some of the top spots to experience Tuscany’s wine culture. And if you’re planning to extend your travels to other parts of Italy, my complete Italy Itinerary will give you a perfect guide to explore Italy’s best destinations.Be sure to follow me on Instagram at @sierrainthecity for more travel inspiration and updates. Enjoy your trip to Tuscany, it’s a place you’ll never forget!