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

Your itinerary for day 2 of your road trip in Italy includes 2 stops and features some of the highlights of Pisa and Florence. At the end of the day, enjoy the comforts of a top-rated hotel in Florence, where you'll spend 2 nights.

Start your day at Leaning Tower Of Pisa. This picture-perfect monument is a globally renowned place to see in Pisa. Then, wander over to Piazza Del Duomo, Pisa. If majestic sites excite you, this public square will be right up your alley.

Florence’s wonders await as you prepare for another journey on the road, leaving the breathtaking surroundings of Pisa behind. This drive usually takes around 1 hour 23 min. Florence welcomes you with a multitude of unique vacation experiences.

For a more meaningful self-guided tour of the city's best attractions, visit Basilica Of Santa Croce In Florence, a locally renowned church that is sure to impress. Take in the surroundings and enjoy the freedom of exploring at your own pace before you continue your journey. Next, head to Uffizi Gallery and admire its instagrammable features.

When you’re ready, continue to Ponte Vecchio, a timeless historical landmark beloved by locals and tourists alike. Don't miss out on Piazza Della Signoria, another highlight of the area that promises a memorable visit.

When you’re done exploring for the day, you’ll drive to your hotel in Florence. Check in and relax 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 Florence. Enjoy a relaxing evening as you savor delicious local cuisine.

Enjoy a delicious meal at Ristorante Oliviero 1962, a top-rated dining destination in Florence. If you're in the mood to try something new, consider Di Poneta Novoli, another top spot with a mouthwatering menu. You might also want to secure a reservation at Caffe San Firenze. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Florence this evening.

Cap off your dinner by heading to Manifattura, ideal for a leisurely evening with a drink in hand. Se·sto On Arno Rooftop Bar is another bar that offers an enjoyable setting. Similarly, Il Vinile is also a popular place to go on a night out, perfect for relaxing and socializing.

Relax and look forward to more memorable moments to come!

Day 3 of your road trip will take you to the best attractions Florence has to offer. Cherish the 1 night you have left in the city and use the provided itinerary to discover what to see in Florence.

A visit to Oltrarno is a must on the agenda today. This neighborhood is full of hidden gems and character, perfect for a leisurely stroll. Plus, you’ll be close to some of the city’s most famous sights.

Your adventure in Florence is only getting started when you visit Basilica Di Santa Maria Novella, Firenze (fi), a popular local hot spot. Another notable attraction to explore is Central Market. This interesting food market is known for its enchanting appeal.

After soaking in the highlights of these sights, take some time to wander Florence's streets and immerse yourself in the local atmosphere. When you're ready to continue your sightseeing adventure, head to Galleria Dell'accademia. This heritage-rich art gallery offers a fascinating experience that many visitors find memorable. Cathedral Of Santa Maria Del Fiore is also worth visiting, along with Piazzale Michelangelo. These standout landmarks offer unique experiences that add to the day’s enjoyment.

Don’t forget to check out all the popular tours and experiences you can add to your travel plans in Italy. You can explore and select activities under each day of your itinerary.

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

Treat yourself to a wonderful meal at Ditta Artigianale, a top-rated dining spot in Florence. If you're in the mood for something new, try Trattoria Da Burde, another premier location with a delectable menu. You might also want to book a table at Casa Toscana. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Florence.

Extend your evening after a delightful meal by visiting Bar 50 Rosso, which offers the perfect atmosphere for a night out. Moreover, Bitter Bar is another popular option for a drink or two. Likewise, Archea Brewery also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

Get a good night's sleep and look forward to another great day on the road in Italy!

On day 4 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 2 destinations, including Siena and San Gimignano. When you’re not sightseeing, take time to relax at your chosen hotel in Siena, where you’ll be staying for 2 nights.

When you’ve had your share of Florence, prepare for your next destination. Admire the views and listen to some good music as you drive in the direction of Siena. Your travel time is around 1 hour 12 min.

Enjoy sightseeing at your own pace and allow yourself time to explore the beautiful surroundings. Take your self-guided tour to Siena Cathedral, a notable church that everyone visiting Siena should see. Next, head to Piazza Del Campo. This romantic public square is one of the most famous attractions in the region.

If you're keen to see more, don’t miss out on Tower Of Mangia, a respected monument popular among locals as well as travelers. Basilica Of San Domenico is an excellent attraction to visit next. Spend some time learning more about this underrated church before you continue your journey.

Continue your road trip and head to your next destination, San Gimignano.

Spend your afternoon discovering Porta San Giovanni, a locally appreciated monument known for its breathtaking features. Next, continue your sightseeing at Piazza Del Duomo, an underrated public square.

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

Siena is a place where the culinary landscape is as diverse as its attractions. So before the day ends, treat your palate to a taste of local cuisine at one of the best restaurants in Siena.

Treat yourself to a delightful dinner at Enoteca I Terzi, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Ristorante Tar-Tufo? It's another excellent option with a diverse menu. Consider reserving a table at Antica Trattoria Papei as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Siena.

Continue your evening by exploring the vibrant nightlife scene at Meet Life Cafè, a prime destination for a thrilling night out. Also, don’t forget to check out Maudit Pub, a bar that offers unique local touches. Likewise, Bar Impero Siena provides an excellent alternative for a fun evening.

As the day draws to a close, take a moment to unwind and prepare for the next exciting chapter of your road trip in Italy.

On day 5 of your road trip, you’ll start and end your day in Siena, where you still have 1 night left. You'll spend part of the day exploring places of interest outside the immediate city, including Castelnuovo Berardenga, San Regolo, Greve in Chianti, and Greti.

Embrace the thrill of the open road as you wave goodbye to Siena and set your GPS to Castelnuovo Berardenga. While on the road, immerse yourself in your favorite road trip tunes or sample the sounds from a local radio station. This car ride usually takes around 27 min. Upon reaching Castelnuovo Berardenga, unwind, observe, and explore. The best things to do, see, and eat are waiting for you.

Enjoy sightseeing at your own pace and allow yourself time to explore the beautiful surroundings. Take your self-guided tour to Fèlsina S.p.a., a locally appreciated winery that everyone visiting Castelnuovo Berardenga should see.

It’s time to gear up for the next part of your road trip adventure. Under favorable conditions, your drive to San Regolo may take around 19 min. Upon your arrival in San Regolo, you’ll be greeted with the opportunity to do some sightseeing and exploring.

One of our top recommendations for your sightseeing is Castello Di Brolio. Spend some time admiring the visually striking features of the castle before you continue to your next stop.

When you’ve had your share of San Regolo, prepare for your next destination. Admire the views and listen to some good music as you drive in the direction of Greve in Chianti. Your travel time is around 59 min.

Enjoy sightseeing at your own pace and allow yourself time to explore the beautiful surroundings. Take your self-guided tour to Castle Of Verrazzano, an increasingly popular castle that everyone visiting Greve in Chianti should see.

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

Siena is a place where the culinary landscape is as diverse as its attractions. So before the day ends, treat your palate to a taste of local cuisine at one of the best restaurants in Siena.

Savor the flavors at Osteria Quattro Venti, a top pick for dinner tonight. Alternatively, Fischi per Fiaschi beckons with its unique menu offerings. Also, consider Osteria da Divo. With its consistent customer satisfaction, it’s an excellent option for dining in Siena tonight.

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.

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

Dive into day 6 of your remarkable road trip in Italy. Today you'll explore 2 destinations, including Santa Maria degli Angeli and Perugia. At the end of the day, you’ll unwind at one of the finest accommodations in Perugia, where you'll spend 1 night.

Set your GPS to Santa Maria degli Angeli and hit the road. Expect a journey of approximately 1 hour 36 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Santa Maria degli Angeli beckons with new experiences!

Set out on a self-guided sightseeing tour at Basilica Of San Francesco D'assisi and explore the historic features. Next, make your way to Piazza Del Comune, another highlight in Santa Maria degli Angeli. When you’re done exploring the public square, continue to Rocca Maggiore, a visually striking castle.

When you’re ready to jump back into the car and say goodbye to Santa Maria degli Angeli, you’ll hit the road in the direction of Perugia. This drive usually takes around 34 min.

Perugia Cathedral is an often recommended church we recommend visiting today. Discover its culturally significant features before continuing your self-guided tour to Piazza Iv Novembre, an awe-inspiring public square that’s well-regarded in the area.

Next, stop by The Fontana Maggiore, a culturally significant monument.

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

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

Dine in style at Ristorante Settimo Sigillo, a top recommendation for dinner tonight. Or, for a change of pace, Caffè Baglioni boasts a menu that's sure to impress. Also, be sure to check out Bar Pellas. Known as a local hotspot, it’s a great choice for tonight in Perugia.

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

Savor another day of unforgettable experiences in Italy!

On day 7 of your road trip in Italy, your travel plans include 2 stops at the most scenic, wondrous, and interesting places in the region. Orvieto and Lucca are on today's agenda. In the evening, you’ll end up in Pisa, where you will stay for 1 night.

Continue your road trip and head to your next destination, Orvieto. This car ride takes around 1 hour 17 min.

Spend your afternoon discovering Well Of St. Patrick, a locally renowned monument known for its historic features.

When you’ve had your share of Perugia, prepare for your next destination. Admire the views and listen to some good music as you drive in the direction of Orvieto. Your travel time is around 1 hour 17 min.

Enjoy sightseeing at your own pace and allow yourself time to explore the beautiful surroundings. Take your self-guided tour to Orvieto Cathedral, a locally renowned church that everyone visiting Orvieto should see. Next, head to Pozzo Della Cava. This standout cave is one of the most worthwhile attractions in the region.

Embrace the thrill of the open road as you wave goodbye to Orvieto and set your GPS to Lucca. While on the road, immerse yourself in your favorite road trip tunes or sample the sounds from a local radio station. This car ride usually takes around 2 hours 33 min. Upon reaching Lucca, unwind, observe, and explore. The best things to do, see, and eat are waiting for you.

When you're ready for some sights, head to Mura Di Lucca, a worthwhile historical landmark in Lucca. Explore its majestic features at your own pace before you continue your journey to your next attraction, Piazza Dell'anfiteatro. This captivating public square is a top recommendation in the area.

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

Indulge in a memorable dining experience at one of Pisa's most popular restaurants, and connect with friendly locals for a true cultural experience.

Don’t miss out on dining at Ristorante Capodimonte Pisa, a top-rated dining destination in Pisa. If you're in the mood to try something new, consider La Locanda Dei Pisani Doc Pisa, another top spot with a mouthwatering menu. You might also want to secure a reservation at Baribaldi Pisa. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Pisa this evening.

Let the evening flow smoothly from dinner to drinks at Bar Mocambo, a top-rated bar in the area. For other recommendations, Tree provides a perfect setting for rounding out your night with style and great drinks. Likewise, Chupiteria offers a memorable night with diverse drink options and excellent service.

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