One-Week Italy Self-Drive Road Trip With Itinerary from Pisa to Florence, Siena, and Perugia

Experience an unparalleled adventure on day 2 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 2 vibrant destinations - Pisa and Florence. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Florence. You will spend 2 nights here for some well-deserved relaxation.

Get ready for an exciting day in Pisa. Today’s sightseeing agenda includes a monument, a public square, a church, an art gallery, a historical landmark and much more! Begin your adventure at Leaning Tower Of Pisa. This is an iconic monument you should not miss. Another must-see is Piazza Del Duomo, Pisa, a globally renowned public square in Pisa.

When you’re ready for the next sight, head to Basilica Of Santa Croce In Florence. From there, take a leisurely stroll to Uffizi Gallery, another of the city’s famous attractions. We recommend continuing your self-guided tour at Ponte Vecchio, a visually striking place of interest in the city. If time allows, add Piazza Della Signoria to your itinerary. This famous public square offers the perfect finishing touch to your day in Pisa.

When you’re done exploring for the day, you’ll drive to your hotel in Florence. Check in and spend some time relaxing before you head out to tour the city.

After a long day of exploring, sit down for a delicious dinner at a top-rated restaurant in Florence. Enjoy a satisfying meal that will recharge you for tonight's adventures.

Treat yourself to a delightful dinner at Ristorante Oliviero 1962, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Di Poneta Novoli? It's another excellent option with a diverse menu. Consider reserving a table at Caffe San Firenze as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Florence.

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at Manifattura, a well-loved spot among locals and tourists. Or, head to Se·sto On Arno Rooftop Bar. This bar boasts a welcoming environment that is perfect for winding down. You could also continue your night at Il Vinile, another top-rated place in the area.

Celebrate another amazing day of your road trip adventure in Italy!

Day 3 of your road trip across Italy promises a magnificent time exploring Florence. You have 1 night left in Florence. Take the opportunity to experience more of the best attractions and activities in the city.

At the top of the list of things to do today is to explore Oltrarno, a neighborhood that captures the true essence of Florence. Take your time to uncover its best sides and enjoy its proximity to many of the area’s best attractions.

Today’s itinerary in Florence covers several incredible sights, including a church, a food market, an art gallery, an observation deck and much more! Start your adventure at Basilica Di Santa Maria Novella, Firenze (fi). This interesting church is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the picture-perfect wonders of Central Market, a must-see food market in the city.

Consider stopping for a small bite to eat or a drink at a local eatery to keep your energy going. When you’re ready, continue your discovery with a visit to Galleria Dell'accademia. This locally renowned art gallery offers an enriching experience. For a change of pace, head to Cathedral Of Santa Maria Del Fiore, where you can take in history-steeped features. Conclude your self-guided sightseeing tour with a visit to Piazzale Michelangelo. These sights offer a fulfilling end to a perfect day.

Don’t forget to check out all the popular tours and activities you can add to your road trip itinerary. Italy is a beautiful travel destination that offers plenty of unique tours that will enhance your vacation experience. Explore and select your activities below.

After a day of adventure, treat yourself to an exquisite dinner at one of Florence's best restaurants.

Treat yourself to a delightful dinner at Ditta Artigianale, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Trattoria Da Burde? It's another excellent option with a diverse menu. Consider reserving a table at Casa Toscana as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Florence.

Unwind after your meal by stepping into Bar 50 Rosso. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Bitter Bar offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Archea Brewery, another top-rated bar in the area.

Savor another day of unforgettable experiences in Italy!

Dive into day 4 of your remarkable road trip in Italy. Today you will explore Siena and San Gimignano, where you will have the opportunity to experience all the top things to see and do. At the end of the day, you’ll unwind at one of the finest accommodations in Siena. You’ll stay here for 2 nights.

Brace yourself for today’s incredible lineup of attractions in Florence, featuring fun adventures, romantic experiences, and scenic views. Start at Siena Cathedral, a popular church in the city. Then, head to Piazza Del Campo and soak in the ambiance of this visually striking public square.

There are many interesting places to see in Florence, and when you are ready for more, go to Tower Of Mangia. This is one of the city’s most curiosity-inducing UNESCO world heritage-listed spots of interest. After exploring the monument, visit the beloved Basilica Of San Domenico. Not far away, you'll also find Porta San Giovanni. This monument is an UNESCO world heritage-designated highlight in Florence. Before wrapping up your self-guided sightseeing tour, head to Piazza Del Duomo, an often recommended public square in the city.

At the end of the day, you will drive to Siena, where you'll have a room waiting for you at the perfect place to stay. Check in and enjoy some downtime.

Indulge in a memorable dining experience at one of Siena's most popular restaurants, and connect with friendly locals for an authentic adventure.

Enjoy a lovely meal at Enoteca I Terzi, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Ristorante Tar-Tufo is another top choice with a popular menu. You could also check for a table at Antica Trattoria Papei. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Siena tonight.

Round off your dining experience by visiting Meet Life Cafè, a prime location for a drink. Alternatively, explore the distinctive characteristics of Maudit Pub, a bar catering to every mood and preference. Bar Impero Siena likewise offers a unique atmosphere, perfect for a memorable night out.

Raise your glass to another unforgettable day in Italy!

On day 5 of your road trip, you’ll start and end your day in Siena, where you'll stay for 1 night more.

Enjoy the perfect balance of relaxation and exploration in Siena today. One of the most frequently visited attractions included on the itinerary is Fèlsina S. P. A. This enchanting winery will help you start your sightseeing on top. Then, take a leisurely stroll to Castello Di Brolio and learn what makes this respected castle unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the locally appreciated Castle Of Verrazzano. After exploring the castle, head to Villa Calcinaia - Conti Capponi. This intriguing winery is a highlight in Siena.

When you’re done exploring for the day, you’ll return to Siena and your accommodation.

As you are wrapping up for the day, treat yourself to a satisfying dinner at a nice restaurant in Siena. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.

Dine in style at Osteria Quattro Venti, a top recommendation for dinner tonight. Or, for a change of pace, Fischi per Fiaschi boasts a menu that's sure to impress. Also, be sure to check out Osteria da Divo. Known as a local hotspot, it’s a great choice for tonight in Siena.

Following your dinner, dive into the local bar culture at Charlie Mixology Bar Di Aldinucci Riccardo. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Bar Pinacoteca, the perfect place for those looking to experience the best of the nightlife. Similarly, San Paolo Pub provides excellent drinks and a great atmosphere, ensuring a memorable night out.

Head back to your accommodation in Siena and get some rest in preparation for another magical day of your road trip in Italy!

Embark on another extraordinary experience on day 6 of your road trip in Italy. Today, you will make 2 stops and experience some of the highlights of Santa Maria degli Angeli and Perugia. At the end of the day, you will enjoy the comforts of a top-rated hotel in Perugia, which will be your home away from home for 1 night.

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Siena allows for both. Start by heading to Basilica Of San Francesco D'assisi. This notable church provides an insightful glimpse into the town's identity. Next, discover Piazza Del Comune, a history-steeped public square, promising a delightful encounter.

Continue your sightseeing with a visit to Rocca Maggiore, an underrated castle. When you’re done, don’t forget to make a stop at the locally appreciated Perugia Cathedral. Not far away from the church, you will find the breathtaking The Fontana Maggiore, perfect for a quick visit. Round off your day at Piazza Iv Novembre, another gem in Siena with enchanting features to discover.

After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of your accommodation in Perugia. Perugia offers plenty of top-rated hotels for every travel budget. Take some time to relax before you go out again.

As dinnertime approaches, it's time to head out for a bite to eat in Perugia. If you are looking to dine at a popular restaurant in the city, it's often a good idea to reserve a table in advance.

Enjoy a delicious meal at Ristorante Settimo Sigillo, a top-rated dining destination in Perugia. If you're in the mood to try something new, consider Caffè Baglioni, another top spot with a mouthwatering menu. You might also want to secure a reservation at Bar Pellas. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Perugia this evening.

Continue your lively evening at Tommi Bar, a perfect place for winding down or revving up the night, depending on which mood you’re in. Valentina is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Caffe Dal Perugino ensures a night out tailored to your taste.

Head back to your accommodation in Perugia and get some rest in preparation for another magical day of your road trip in Italy!

On day 7 of your road trip in Italy, you will get a true taste of the freedom a self-drive vacation in Europe entails. Today’s travel plans include stops at the most scenic, wondrous, and interesting places in Orvieto and Lucca. In the evening, you’ll end up in Pisa, where you will stay for 1 night.

Enjoy the perfect balance of relaxation and exploration in Perugia today. One of the most well-known attractions included on the itinerary is Well Of St. Patrick. This breathtaking monument will help you start your sightseeing on top. Then, take a leisurely stroll to Orvieto Cathedral and learn what makes this history-steeped church unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the often recommended Pozzo Della Cava. After exploring the cave, head to Mura Di Lucca. This beloved historical landmark is a highlight in Perugia. As your day continues, stop by Piazza Dell'anfiteatro, known for its enchanting features.

When you’re done exploring for the day, you’ll drive to your hotel in Pisa. Check in and spend some time relaxing before you head out to tour the city.

As you are wrapping up for the day, treat yourself to a satisfying dinner at a nice restaurant in Pisa. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.

Savor the flavors at Ristorante Capodimonte Pisa, a top pick for dinner tonight. Alternatively, La Locanda Dei Pisani Doc Pisa beckons with its unique menu offerings. Also, consider Baribaldi Pisa. With its consistent customer satisfaction, it’s an excellent option for dining in Pisa tonight.

Unwind after your meal by stepping into Bar Mocambo. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Tree offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Chupiteria, another top-rated bar in the area.

Raise your glass and celebrate another amazing day of your road trip in Italy!