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.

Leaning Tower Of Pisa is an ideal stop early in the day. This wondrous monument is a must-visit in the city. When you’re ready for your next discovery, continue to Piazza Del Duomo, Pisa, which may be one of the most stunning places you will experience today.

When you’re ready to jump back into the car and say goodbye to Pisa, you’ll hit the road in the direction of Florence. This drive usually takes around 1 hour 23 min.

One of our top recommendations for your sightseeing is Basilica Of Santa Croce In Florence. Spend some time admiring the culturally significant features of the church before you continue to your next stop. Then, head to Uffizi Gallery. This extraordinary art gallery is a traveler-favorite in the city.

If you're keen to see more, continue to Ponte Vecchio. Feed your curiosity by learning something new about the historical landmark. Next, take your journey to Piazza Della Signoria, a widely recognized public square.

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 lovely meal at Ristorante Oliviero 1962, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Di Poneta Novoli is another top choice with a popular menu. You could also check for a table at Caffe San Firenze. As an establishment that consistently gains high praises from customers, it’s an ideal choice in Florence tonight.

After your meal, keep the night alive at a bar like Manifattura, known for its lively atmosphere. Se·sto On Arno Rooftop Bar is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Il Vinile offers an excellent atmosphere for those looking to amp up the evening.

Say good night to Florence and look forward to another great day of your road trip in Italy!

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

Oltrarno is a fantastic place you can explore today in Florence. This neighborhood is a testament to the city’s character, and it's easy to spend hours just walking around and admiring the surroundings. Soak in the Florence-way-of-life and visit all the nearby sights.

Check out the interesting church, Basilica Di Santa Maria Novella, Firenze (fi). Afterward, continue to Central Market, a food market every traveler should visit. As you explore Florence’s charming streets, take in the lively atmosphere and get to know the character of the city.

Next, make your way to Galleria Dell'accademia. This locally renowned art gallery is an essential stop. Following that, head to Cathedral Of Santa Maria Del Fiore, another must-visit site that will enhance your experience. Don’t forget to stop by Piazzale Michelangelo, a famous observation deck in the city.

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 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.

Make sure to reserve a table at Ditta Artigianale, an iconic dining spot in Florence. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Trattoria Da Burde, a popular restaurant in Florence. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Casa Toscana, a hidden gem nestled in Florence. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Let the evening flow smoothly from dinner to drinks at Bar 50 Rosso, a top-rated bar in the area. For other recommendations, Bitter Bar provides a perfect setting for rounding out your night with style and great drinks. Likewise, Archea Brewery offers a memorable night with diverse drink options and excellent service.

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

On day 4 of your road trip in Italy, your travel plans include 2 stops at the most scenic, wondrous, and interesting places in the region. Siena and San Gimignano are on today's agenda. In the evening, you’ll end up in Siena, where you will stay for 2 nights.

Embrace the thrill of the open road as you wave goodbye to Florence and set your GPS to Siena. 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 1 hour 12 min. Upon reaching Siena, 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 Siena Cathedral, a popular church in Siena. Explore its enchanting features at your own pace before you continue your journey to your next attraction, Piazza Del Campo. This top-rated public square is a top recommendation in the area.

When you’re ready to explore more, Tower Of Mangia is an excellent choice. Spend some time discovering what some claim to be the most culturally significant monument in the region. Next, continue your sightseeing at the up-and-coming Basilica Of San Domenico and discover what makes this church unique.

When you arrive in San Gimignano, it's time to take a break from the road.

Set out on a self-guided sightseeing tour at Porta San Giovanni and explore the UNESCO world heritage-designated features. Next, make your way to Piazza Del Duomo, another highlight in San Gimignano.

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 delicious dinner at Enoteca I Terzi, an excellent option for tonight's dining. Looking for something different? Ristorante Tar-Tufo offers a tantalizing alternative with its diverse menu. And don’t miss Antica Trattoria Papei. Known for great service, it’s a fantastic choice for tonight in Siena.

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at Meet Life Cafè, a well-loved spot among locals and tourists. Or, head to Maudit Pub. This bar boasts a welcoming environment that is perfect for winding down. You could also continue your night at Bar Impero Siena, another top-rated place in the area.

Relax and recharge in preparation for another adventurous day in Italy!

On day 5 of your road trip, you'll get the chance to experience Castelnuovo Berardenga, San Regolo, Greve in Chianti, and Greti. At the end of the day, you'll drive back to Siena, where you still have 1 night left to stay.

When you’ve had your share of Siena, prepare for your next destination. Admire the views and listen to some good music as you drive in the direction of Castelnuovo Berardenga. Your travel time is around 27 min.

Savor the day by heading to Fèlsina S.p.a., an intriguing winery that draws visitors from near and far.

Continue your road trip and head to your next destination, San Regolo. This car ride takes around 19 min.

When you're ready for some sights, head to Castello Di Brolio, a curiosity-inducing castle in San Regolo. Explore its visually striking features at your own pace before you continue your journey.

Set your GPS to Greve in Chianti and hit the road. Expect a journey of approximately 59 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Greve in Chianti beckons with new experiences!

Our first attraction recommendation in Greve in Chianti is Castle Of Verrazzano, an intriguing castle that draws attention for its visually striking features.

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.

Make sure to reserve a table at Osteria Quattro Venti, an iconic dining spot in Siena. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Fischi per Fiaschi, a popular restaurant in Siena. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Osteria da Divo, a hidden gem nestled in Siena. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Cap off your dinner by heading to Charlie Mixology Bar Di Aldinucci Riccardo, ideal for a leisurely evening with a drink in hand. Bar Pinacoteca is another bar that offers an enjoyable setting. Similarly, San Paolo Pub is also a popular place to go on a night out, perfect for relaxing and socializing.

Relax and recharge in preparation for another adventurous day 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.

As you explore Santa Maria degli Angeli’s charming streets, take in the lively atmosphere and get to know the character of the town.

Fasten your seatbelt and make your way to your next stop — Santa Maria degli Angeli, home to many well-known sights in the region. Keep in mind that your travel time from Siena to Santa Maria degli Angeli may take around 1 hour 36 min without traffic disruptions. Upon arrival in Santa Maria degli Angeli, we highly recommend checking out some of the top attractions.

Enjoy sightseeing at your own pace and allow yourself time to explore the beautiful surroundings. Take your self-guided tour to Basilica Of San Francesco D'assisi, a locally renowned church that everyone visiting Santa Maria degli Angeli should see. Next, head to Piazza Del Comune. This enchanting public square is one of the most curiosity-inducing attractions in the region.

If you're keen to see more, don’t miss out on Rocca Maggiore, a romantic castle popular among locals as well as travelers.

Once you're ready to continue your road trip, it's time to buckle up and drive, eagerly anticipating your arrival in Perugia. This drive usually takes around 34 min, without any stops or traffic disruptions.

Our first attraction recommendation in Perugia is Perugia Cathedral, a frequently visited church that draws attention for its heritage-rich features. Spend some time soaking in the atmosphere before continuing to Piazza Iv Novembre, a history-steeped public square that stands out in the town.

Time flies when you're having fun! But don't forget to stop for a bit to eat and drink between your adventures. When you're rested and recharged, head to The Fontana Maggiore, an intriguing monument that offers a unique experience.

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.

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

Savor the flavors at Ristorante Settimo Sigillo, a top pick for dinner tonight. Alternatively, Caffè Baglioni beckons with its unique menu offerings. Also, consider Bar Pellas. With its consistent customer satisfaction, it’s an excellent option for dining in Perugia tonight.

To truly maximize your evening out, consider visiting Tommi Bar after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Valentina, another bar with an inviting ambiance. Similarly, Caffe Dal Perugino also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

Take some time to reflect on your day and savor another beautiful night in Italy.

On day 7 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 2 destinations, including Orvieto and Lucca. When you’re not sightseeing, take time to relax at your chosen hotel in Pisa, where you’ll be staying for 1 night.

Orvieto’s wonders await as you prepare for another journey on the road, leaving the breathtaking surroundings of Perugia behind. This drive usually takes around 1 hour 17 min. Orvieto welcomes you with a multitude of unique vacation experiences.

Savor the day by heading to Well Of St. Patrick, an interesting monument that draws visitors from near and far.

Fasten your seatbelt and make your way to your next stop — Orvieto, home to many well-known sights in the region. Keep in mind that your travel time from Perugia to Orvieto may take around 1 hour 17 min without traffic disruptions. Upon arrival in Orvieto, we highly recommend checking out some of the top attractions.

When you're ready for some sights, head to Orvieto Cathedral, a notable church in Orvieto. Explore its history-steeped features at your own pace before you continue your journey to your next attraction, Pozzo Della Cava. This locally appreciated cave is a top recommendation in the area.

Lucca’s wonders await as you prepare for another journey on the road, leaving the breathtaking surroundings of Orvieto behind. This drive usually takes around 2 hours 33 min. Lucca welcomes you with a multitude of unique vacation experiences.

For a more meaningful self-guided tour of the village's best attractions, visit Mura Di Lucca, an often recommended historical landmark 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 Piazza Dell'anfiteatro and admire its romantic features.

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.

Have a fantastic dining experience at Ristorante Capodimonte Pisa, a highly recommended choice for tonight's dinner. If you're looking to mix things up, La Locanda Dei Pisani Doc Pisa offers an enticing alternative with its varied menu. Additionally, Baribaldi Pisa is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Pisa.

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.

Savor another day of unforgettable experiences in Italy!