The Ultimate Tuscany Road Trip Itinerary (2 Weeks)

A two-week Tuscany road trip is ideal to fully soak in all the amazing sights, sounds, and flavors this region has to offer. With 14 days, you can leisurely explore each destination, savor the local cuisine, and truly immerse yourself in the Tuscan lifestyle. However, if you’re short on time, don’t worry! You can still experience much of Tuscany in a week or less.

While many Tuscan road trip guides focus solely on the popular spots like Florence and Pisa, I wanted to cover the full Tuscan experience, starting with the iconic cities and extending to the hidden gems. You’ll find many quaint towns and villages that you haven’t heard of here!

This map shows all the must-see stops on your Tuscany road trip. I’ll break down each destination in detail below and share tips to make your adventure as smooth and enjoyable as possible.

• Boboli Gardens: Need a break from the hustle and bustle? Head to these lush gardens behind the Pitti Palace for a relaxing stroll or a picnic. Springtime here is absolutely beautiful.
• Mercato Centrale: Explore this vibrant market where you can sample local cheeses, cured meats, and fresh produce. It’s a great spot for lunch or to pick up picnic supplies.
• Oltrarno District: Cross the river to discover this trendy neighborhood filled with artisan workshops, cozy cafes, and some of the best trattorias in the city. It’s a great place to explore in the evening.
• Piazzale Michelangelo: This square is my absolute favorite viewpoint of the city. From this vantage point, you have sweeping panoramic views of the Arno River and the Florentine skyline.

After soaking in the art and history of Florence, it’s time to head to Lucca and Pisa, two Tuscan gems that offer their own unique charms. Lucca, a city surrounded by Renaissance-era walls, is known for its well-preserved medieval architecture and relaxed atmosphere. Pisa, of course, is famous worldwide for its iconic Leaning Tower, but there’s so much more to explore.

Start your journey in Lucca, a charming walled city that feels like stepping back in time. The massive, intact Renaissance walls that encircle the city are perfect for a leisurely bike ride or walk, offering beautiful views and a unique perspective of the city.

• Lucca Walls (Le Mura di Lucca): Start your day with a leisurely bike ride or walk along the top of Lucca’s impressive city walls. These wide, tree-lined paths offer great views of the city and are perfect for a morning workout.
• Piazza dell’Anfiteatro: This unique oval-shaped square was once a Roman amphitheater. Now, it’s a lively hub filled with cafes and shops. I love grabbing a gelato here and soaking in the lively atmosphere.
• Torre Guinigi (Guinigi Tower): Climb to the top of this medieval tower, which is crowned with a small garden of oak trees. The panoramic views of Lucca’s rooftops and surrounding countryside are stunning.
• Lucca Cathedral (San Martino): Don’t miss the intricate facade and impressive artworks inside this beautiful cathedral. Look out for the Volto Santo, a revered wooden crucifix said to have been carved by Nicodemus.

Next up on our Tuscan road trip are the enchanting hill towns of San Gimignano and Volterra. These are some of my favorite stops in Tuscany! While it’s possible to visit both of them as a day trip, I recommend staying overnight for 1-2 nights to take it slow and fully experience their quintessential Tuscan charm.

San Gimignano, known as the “Town of Fine Towers” and “Medieval Manhattan” is famous for its stunning medieval skyline. Volterra, with its Etruscan roots, offers a fascinating blend of ancient history and charming streets. These towns are a step back in time and perfect for exploring on foot. Add these spots to your itinerary:

• Volterra Roman Theatre: This well-preserved Roman theater dates back to the 1st century BC. It’s a fascinating glimpse into the ancient past and a must-see for history buffs.
• Palazzo dei Priori: The oldest town hall in Tuscany, this building dominates Volterra’s main square. Climb the tower for panoramic views and explore the historic rooms inside.
• Etruscan Museum (Museo Etrusco Guarnacci): Volterra has deep Etruscan roots, and this museum houses one of Italy’s most important collections of Etruscan artifacts. The intricate funerary urns and sculptures are particularly interesting.
• Volterra Cathedral (Duomo di Volterra): This beautiful cathedral features a mix of architectural styles and a stunning interior. The adjacent Baptistery is also worth a visit for its octagonal design and peaceful ambiance.

Volterra is famous for its alabaster, and you can visit workshops to see artisans at work. It’s a great place to pick up a unique souvenir. Also, don’t miss the opportunity to taste Vernaccia di San Gimignano, a celebrated white wine native to the area. Many local wineries offer tastings and tours.

Know Before You Go: San Gimignano can get quite busy, especially in the summer. Arrive early in the morning or later in the afternoon to avoid the peak crowds. Volterra is generally less crowded, offering a more relaxed experience. Both towns have ZTL zones, so look for designated parking areas outside the town centers.

Spending a couple of days in Siena is an absolute must on your Tuscan road trip. Siena is like stepping into a medieval fairytale, with its narrow cobblestone streets, stunning Gothic architecture, and rich history.

• Palazzo Pubblico and Civic Museum: Located right in Piazza del Campo, this Gothic town hall is home to stunning frescoes, including the famous “Allegory of Good and Bad Government” by Ambrogio Lorenzetti.
• Enoteca Italiana: Wine lovers, this is your spot. Located in the Medici Fortress, this wine museum offers a deep dive into Italian wines, complete with tastings.
• Banchi di Sopra: This bustling main street is perfect for a leisurely stroll. Explore high-end boutiques, local shops, and plenty of cafes where you can take a break with some gelato. It’s a cool spot to enjoy an Aperol Spritz as well!
• Fonte Gaia: Check out this beautiful fountain in Piazza del Campo. The original 15th-century sculptures are now in a museum, but the replicas are still a sight to see.

Just a short drive from Siena, the walled town of Monteriggioni is a must-see stop on your Tuscany road trip. Perched atop a hill, this medieval fortress town offers well-preserved walls and towers, charming streets, and breathtaking views of the surrounding countryside.

Welcome to the heart of Tuscany’s wine country! The Chianti region is famous for its rolling hills, vineyards, olive groves, and charming villages. It’s the perfect place to relax, especially after exploring the bustling city of Siena.

Spending two days here allows you to fully immerse yourself in the region’s beauty and slower pace of life. But even 1 day will give you a taste of the region and its Chianti Classico wines. Beyond the vineyards, the region is dotted with medieval villages, stunning landscapes, and a wealth of history.

Enjoy some world-class wine and soak up the breathtaking scenery. Whether you’re a wine enthusiast or just love beautiful landscapes, Chianti will capture your heart.

After exploring Chianti, head back into the province of Siena to explore another magical rural area. Located just 1.5 hours away in Southern Tuscany, Val d’Orcia is the picture-perfect landscape of Tuscany you’ve seen in postcards. The rolling hills, cypress trees, and charming hilltop towns are absolutely stunning, which is why I had to include it in my ultimate Tuscany itinerary.

• Montepulciano: Famous for its Vino Nobile wine, this hilltop town is a must-visit. Start with a stroll down the main street, Via di Voltaia Nel Corso, lined with shops and cafes. Don’t miss the chance to visit Cantina Contucci or Cantina de’ Ricci for a wine tasting in an ancient cellar. Head to Piazza Grande for beautiful architecture and great views from the Palazzo Comunale tower.
• San Biagio Church: Just outside Montepulciano, this beautiful Renaissance church is set against a stunning backdrop of rolling hills. It’s a peaceful spot for some reflection and great photo opportunities.
• Pienza: Known as the “Ideal City” of the Renaissance, Pienza offers breathtaking views and charming streets. Wander through the Piazza Pio II and visit the Cathedral of Pienza. The town is also famous for its Pecorino cheese, so be sure to sample some at a local shop or market.
• Palazzo Piccolomini: This Renaissance palace in Pienza offers beautiful gardens and stunning views over the Val d’Orcia. It’s a great spot to relax and enjoy the scenery.

• Montalcino: This medieval town is renowned for its Brunello di Montalcino wine. Visit the fortress, La Fortezza, for panoramic views and wine tastings. Wander through the historic center, and stop by the Civic and Diocesan Museum of Sacred Art to see beautiful artworks and artifacts.
• Abbey of Sant’Antimo: Located just a short drive from Montalcino, this stunning Romanesque abbey is surrounded by serene countryside. It’s a peaceful and spiritual place, perfect for a quiet moment away from the crowds.
• Bagno Vignoni: This unique village is known for its thermal hot springs. The main square is actually a large thermal pool that dates back to Roman times. Relax in the warm waters and enjoy the historic ambiance.
• San Quirico d’Orcia: This small town features well-preserved medieval architecture and beautiful gardens. Stroll through the Horti Leonini, a 16th-century Italian garden, and visit the Collegiata di San Quirico, a Romanesque church with stunning portal sculptures.

If you’re looking to add a touch of relaxation to your Tuscan road trip, I highly recommend spending a spa day in Bagno Vignoni. This charming village in the Val d’Orcia region is renowned for its therapeutic thermal waters and picturesque setting, making it the perfect place to unwind and rejuvenate. It’s also a super romantic spot that makes it great for honeymoons in Tuscany.

Bagno Vignoni is unique for its central thermal pool, which sits in the middle of the village square, surrounded by historic buildings. The village has been a spa destination since Roman times, and its healing waters have been praised for their therapeutic properties. A day here offers a serene escape from the hustle and bustle of sightseeing.

Here’s what to do:

As your Tuscan road trip continues, head east from Val d’Orcia to the beautiful towns of Arezzo and Cortona.

• Piazza Grande, Arezzo: Start in the heart of Arezzo at this beautiful sloping square, surrounded by historic buildings. It’s especially lively during the monthly antique market on the first Sunday of each month and the Saturday before.
• Basilica of San Francesco: Home to the famous fresco cycle “The Legend of the True Cross” by Piero della Francesca. The frescoes are a masterpiece of Renaissance art and absolutely worth seeing. Be sure to book tickets in advance.
• Arezzo Cathedral (Duomo di Arezzo): This stunning Gothic cathedral features beautiful stained glass windows and more frescoes by Piero della Francesca. The peaceful atmosphere makes it a lovely spot for some quiet reflection.
• Casa Vasari: Visit the home of Giorgio Vasari, a Renaissance painter, architect, and writer. The house is filled with his frescoes and offers a glimpse into his life and work.
• Medici Fortress (Fortezza Medicea): Climb up to this historic fortress for panoramic views over Arezzo and the surrounding countryside. It’s a great spot for a picnic or a leisurely stroll.

• Piazza della Repubblica: This lively square is the center of Cortona, featuring the impressive Palazzo Comunale with its clock tower. It’s a great place to start your exploration of the town.
• Santa Maria delle Grazie al Calcinaio: A beautiful Renaissance church located just outside the town walls, offering stunning architecture and serene surroundings.
• Diocesan Museum: Located in the former church of Gesù, this museum houses important works of art, including the famous “Annunciation” by Fra Angelico.
• Basilica of Santa Margherita: Situated at the top of Cortona, this basilica offers breathtaking views of the Val di Chiana and Lake Trasimeno. The climb up is worth it for the stunning vistas.
• Cortona’s Main Square (Piazza della Repubblica): The heart of Cortona, this lively square is perfect for people-watching. Grab a coffee or gelato and soak in the charming atmosphere.
• Etruscan Academy Museum: Learn about Cortona’s Etruscan heritage through a vast collection of artifacts, including ancient ceramics, bronze works, and more.
• Bramasole: Fans of “Under the Tuscan Sun” can visit the iconic villa featured in the book and movie. It’s a bit outside the town center, but a pleasant walk or short drive.
• Le Celle Monastery: Just a short drive from Cortona, this peaceful Franciscan monastery offers beautiful architecture and tranquil surroundings. It’s a perfect spot for a reflective walk.

Here’s some helpful information that will help you decide where to stay:

• Distance: Approximately 80 km (50 miles)
• Driving Time: About 1.5 hours
• Route: Take the A1/E35 Autostrada (also known as the Autostrada del Sole) northbound towards Florence. This highway offers a direct and fast route back to the city.

• Distance: Approximately 110 km (68 miles)
• Driving Time: About 1.5 to 2 hours
• Route: Head west on SP71 towards Camucia, then take the SR71 northbound to join the A1/E35 Autostrada towards Florence. Alternatively, take the scenic SS715, which passes through the beautiful Val di Chiana region before merging onto the A1/E35.

• Val di Chiana: If you have time, take a detour through the Val di Chiana for some last-minute picturesque views and charming small towns like Lucignano or Foiano della Chiana.
• Montepulciano: If you missed it earlier, a quick stop in Montepulciano for a final wine tasting or a stroll through its historic center is a great way to break up the drive.

Before you pack your bags and hit the road, here are a few key things to consider before embarking on your two-week adventure through Tuscany.

Tuscany is beautiful year-round, but the best time for a road trip depends on what you’re looking for. Here’s a quick breakdown:

• Spring (April to June): Spring is fantastic for mild weather and blooming landscapes. The countryside is lush and green, perfect for scenic drives and outdoor activities. Plus, it’s less crowded than the peak summer months.
• Summer (July to August): Summer brings warm temperatures and bustling towns. It’s a great time for festivals and outdoor dining, but be prepared for more tourists and higher prices. Make sure to book accommodations and attractions in advance.
• Autumn (September to October): Autumn is arguably the best time to visit. The weather is still pleasant, the summer crowds have thinned, and the vineyards are bustling with harvest activities. It’s also the season for wine festivals and truffle hunting.
• Winter (November to March): Winter is the off-season, offering a quieter experience with fewer tourists. While some attractions might have shorter hours, you’ll enjoy lower prices and the chance to experience Tuscany’s cozy, festive side. Christmas markets and hearty Tuscan cuisine are highlights.

To fully appreciate Tuscany’s charm, I recommend a two-week road trip. This allows you to explore at a relaxed pace, savoring each destination without feeling rushed. With 14 days, you can cover Florence, Siena, the Chianti region, Val d’Orcia, and more, enjoying the best of Tuscany’s culture, history, and landscapes.

However, if you’re short on time, a week-long trip can still give you a good taste of Tuscany. Focus on the highlights, like Florence, Siena, and a couple of charming hill towns. Just be prepared to prioritize your must-see spots and perhaps save some adventures for a future trip.

Whether you have a few days or two weeks, Tuscany promises an unforgettable journey filled with beauty, history, and incredible food and wine. Enjoy planning your trip and get ready for an amazing adventure!

If time allows, your best bet is to stay in each of those major destinations from the itinerary above. This will allow you to save time on driving every day and experience each place like a local.

However, if you’re looking for more simplicity, consider splitting the trip into 2-3 accommodations. This will make it less of a hassle to constantly pack your bags and be on the go. Here’s a breakdown of what I recommend:

• Florence (or just outside) for 4-5 nights
• Siena for 4-5 nights
• Val d’Orcia for 3-4 nights

While my itinerary covers the must-see spots in Tuscany, there are a few other hidden gems you might want to add to your adventure if you have extra time:

Planning a road trip through Tuscany is super exciting, but you might have some questions. Here are answers to common queries to help you plan your adventure.

If you’re short on time but want to experience the highlights, here’s a condensed 5-day itinerary:

• Day 1: Florence: Explore iconic sites like the Duomo, Uffizi Gallery, and Ponte Vecchio. Wander through the vibrant streets and enjoy a meal in the Oltrarno district.
• Day 2: Siena: Visit the stunning Piazza del Campo, climb the Torre del Mangia for great views, and marvel at the frescoes in the Basilica of San Domenico.
• Day 3: San Gimignano and Volterra: Discover the medieval towers of San Gimignano, then head to Volterra to explore its Etruscan roots and the Roman theater.
• Day 4: Chianti Region: Spend the day wine tasting in Greve in Chianti and visiting charming villages like Panzano. Enjoy the scenic drives through vineyards and olive groves.
• Day 5: Pisa and Lucca: Check out the Leaning Tower of Pisa and the beautiful Piazza dei Miracoli, then head to Lucca for a bike ride along the city walls and a stroll through its historic center.

Start in Florence and head south to Siena. From there, visit San Gimignano and Volterra, then travel through the Chianti region. Finally, loop back north to visit Pisa and Lucca before returning to Florence. This route ensures minimal backtracking and maximizes your time enjoying each destination.

The total driving time for the main route is about 7 to 8 hours, depending on traffic and exact routes taken.

Absolutely! Here’s a sample 7-day itinerary:

• Day 1: Florence: Explore the city’s rich art and history.
• Day 2: Siena: Discover the medieval charm of Siena.
• Day 3: San Gimignano and Volterra: Experience these picturesque hill towns.
• Day 4: Chianti Region: Enjoy wine tasting and scenic drives.
• Day 5: Pisa: Visit the Leaning Tower and other historical sites.
• Day 6: Lucca: Bike along the city walls and explore the historic center.
• Day 7: Return to Florence: Spend your final day soaking up more of Florence or take a scenic drive through the countryside.

Yes, there are tolls on major highways (autostrade) in Tuscany. Be sure to have cash or a credit card ready for toll booths. Using a Telepass, if available, can make the journey smoother. Remember to also check for ZTL (limited traffic zones) in cities like Florence and Siena to avoid fines.

Exploring Tuscany without a car is definitely possible, though it requires a bit more planning and flexibility. The region is well-connected by trains and buses, making it easy to travel between major cities like Florence, Pisa, Siena, and Arezzo. Use Trenitalia and Italo for trains, and SITA, Tiemme, and Lazzi for buses.

For places not easily accessible by public transport, consider joining organized tours. These tours often include transportation, guides, and sometimes meals and wine tastings. Cycling and walking are also great ways to explore Tuscany’s scenic landscapes and charming villages.

Though remember- driving a car is your best way to get around Tuscany and visit all the stops on this itinerary!

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