10-Day Italy Self-Drive Road Trip With Itinerary from Pisa to Florence, San Gimignano, Santa Maria degli Angeli, and Rome

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 places, which are Pisa and Florence. At the end of the day, you will retreat to the hotel of your choice in Florence, where will spend 2 nights.

Experience Leaning Tower Of Pisa, a wondrous monument in the city. Then, head to Piazza Del Duomo, Pisa and soak in the ambiance of this breathtaking public square.

Once you're ready to continue your road trip, it's time to buckle up and drive, eagerly anticipating your arrival in Florence. This drive usually takes around 1 hour 18 min, without any stops or traffic disruptions.

Ponte Vecchio is a world-famous historical landmark we recommend visiting today. Discover its romantic features before continuing your self-guided tour to Uffizi Gallery, a standout art gallery that’s well-regarded in the area.

Next, stop by Piazza Della Signoria, a history-steeped public square.

At the end of the day, you will drive to Florence, 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 Florence's most popular restaurants, and connect with friendly locals for a true cultural experience.

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.

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 recharge in preparation for another adventurous day 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.

Make time for David, a locally renowned statue that is worthwhile a visit in the city. Nearby, you’ll find Galleria Dell'accademia, enchanting visitors with its photogenic appeal. Continue your exploration at Central Market. This food market is one of the city’s most well-known spots.

Enjoy the freedom of exploring Florence at your own pace and find hidden gems along the way. If you want to see more picture-perfect spots, make sure to visit Cathedral Of Santa Maria Del Fiore. After exploring the church, head to the captivating Basilica Of Santa Croce In Florence. Lastly, wrap up today’s self-guided sightseeing tour with a visit to Piazzale Michelangelo, a place of visually striking interest in Florence.

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.

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 Ditta Artigianale, a highly-rated dining destination in Florence. If you're eager to try something different, consider Trattoria Da Burde, another top spot with a tantalizing menu. You might also want to secure a reservation at Casa Toscana. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Florence this evening.

After savoring a delicious meal, step into the vibrant nightlife at Bar 50 Rosso, where the evening is just getting started. In the same way, Bitter Bar offers a unique charm perfect for experiencing the local bar scene in Florence. Archea Brewery is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

Relax and look forward to more memorable moments to come!

Your itinerary for day 4 of your road trip in Italy includes 2 stops and features some of the highlights of Siena and San Gimignano. At the end of the day, enjoy the comforts of a top-rated hotel in San Gimignano, where you'll spend 2 nights.

After soaking in Florence’s unique atmosphere, jump into the car with a full heart and drive in the direction of your next destination: Siena. Expect your car journey to take a minimum of 1 hour 9 min. When you arrive in Siena, it's time to take a break from the road.

Enjoy sightseeing at your own pace and allow yourself time to explore the beautiful surroundings. Take your self-guided tour to Palazzo Salimbeni, a worthwhile palace that everyone visiting Siena should see. Next, head to Piazza Del Campo. This enchanting public square is one of the most widely recognized attractions in the region.

If you're keen to see more, don’t miss out on Siena Cathedral, a history-steeped church popular among locals as well as travelers.

Continue your road trip and head to your next destination, San Gimignano. This car ride takes around 42 min.

Enjoy sightseeing at your own pace and allow yourself time to explore the beautiful surroundings. Take your self-guided tour to Porta San Giovanni, a beloved monument that everyone visiting San Gimignano should see. Next, head to Parco Della Rocca. This instagrammable park is one of the most worthwhile attractions in the region.

If you're keen to see more, don’t miss out on Piazza Del Duomo, an UNESCO world heritage-designated public square popular among locals as well as travelers.

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

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

Head back to your accommodation in San Gimignano and get some rest to prepare for another magical day of your road trip in Italy.

Greet day 5 of your road trip in Italy with a smile and start your day with a hearty breakfast. You have 1 night to stay in San Gimignano, so get ready to make the most of your time in the region. On the agenda for this day, you’ll find only the best things to see and do in Greve in Chianti, Montefioralle, and Greti.

It’s time to gear up for the next part of your road trip adventure. Under favorable conditions, your drive to Greve in Chianti may take around 56 min. Upon your arrival in Greve in Chianti, you’ll be greeted with the opportunity to do some sightseeing and exploring.

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

Once you're ready to continue your road trip, it's time to buckle up and drive, eagerly anticipating your arrival in Montefioralle. This drive usually takes around 10 min, without any stops or traffic disruptions.

Spend your afternoon discovering Fattoria Viticcio, a frequently visited winery known for its serene features.

It’s time to gear up for the next part of your road trip adventure. Under favorable conditions, your drive to San Gimignano may take around 56 min. Upon your arrival in San Gimignano, you’ll be greeted with the opportunity to do some sightseeing and exploring.

Spend your afternoon discovering Villa Calcinaia - Conti Capponi, a curiosity-inducing winery known for its respected features.

When you’re done exploring the area’s best attractions, you’ll drive back to your accommodation in San Gimignano.

San Gimignano 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 San Gimignano.

Savor another day of unforgettable experiences in Italy!

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

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 San Gimignano to Santa Maria degli Angeli may take around 2 hours 8 min without traffic disruptions. Upon arrival in Santa Maria degli Angeli, we highly recommend checking out some of the top attractions.

Set out on a self-guided sightseeing tour at Basilica Of San Francesco D'assisi and explore the stunning features. Next, make your way to Porta San Giacomo, another highlight in Santa Maria degli Angeli. When you’re done exploring the sightseeing destination, continue to Portico Of Monte Frumentario, a culturally significant historical landmark.

Nearby, you will also find Rocca Maggiore. This curiosity-inducing castle is a top place to see in the area. Lastly, head to Basilica Di Santa Chiara, a picture-perfect church that is perfect for some final exploring in the town.

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

Santa Maria degli Angeli 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 Santa Maria degli Angeli.

Round off your dining experience by visiting Bibenda Assisi Wine Tasting & Gourmet Food, Olive Oil And Chocolate Tastings, a prime location for a drink.

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

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

Once you're ready to continue your road trip, it's time to buckle up and drive, eagerly anticipating your arrival in Rome. This drive usually takes around 2 hours 25 min, without any stops or traffic disruptions.

One of our top recommendations for your sightseeing is Colosseum. Spend some time admiring the picture-perfect features of the archeological site before you continue to your next stop. Then, head to Roman Forum. This globally renowned archeological site is a traveler-favorite in the city.

If you're keen to see more, continue to Pantheon. Feed your curiosity by learning something new about the monument. Next, take your journey to Trevi Fountain, a world-famous monument. Conclude your sightseeing at Spanish Steps, known for its visually striking features.

At the end of the day, you will drive to Rome, 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 Rome, it's often a good idea to reserve a table in advance.

Dine in style at La Bottega Roma, a top recommendation for dinner tonight. Or, for a change of pace, Pasta In Corso boasts a menu that's sure to impress. Also, be sure to check out Trattoria Vecchia Roma. Known as a local hotspot, it’s a great choice for tonight in Rome.

Let the evening flow smoothly from dinner to drinks at La Botticella Of Poggi Giovanni, a top-rated bar in the area. For other recommendations, Almalu Trastevere provides a perfect setting for rounding out your night with style and great drinks. Likewise, Bar Viminale Di Pepi Maurilio offers a memorable night with diverse drink options and excellent service.

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

On day 8 of your road trip, you’ll start and end your day in Rome, where you have 1 night left to stay.

Via del Corso is a fantastic place you can explore today in Vatican City. This street 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 Vatican City-way-of-life and visit all the nearby sights.

Catch Piazza Del Popolo before the crowds roll in. This enchanting public square is sure to ignite your curiosity. Next, dive into the symbolic features of Piazza Navona, a must-visit public square in the city.

Continue your road trip and head to your next destination, Vatican City, Vatican City. This car ride takes around 12 min.

Next, make your way to St. Peter's Basilica, another highlight in Vatican City.

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

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 Rome, it's often a good idea to reserve a table in advance.

Enjoy a lovely dining experience at RomAntica, a popular restaurant in Rome. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Rome at Coso Ristorante, another great place to eat. With a menu designed to impress, it promises a journey of flavors that will leave you captivated. A third option to check out is the top-rated DEROMA - Farine Romane. It’s yet another ideal choice to enhance your time in Rome tonight.

Continue your lively evening at Sant' Eustachio Caffè, a perfect place for winding down or revving up the night, depending on which mood you’re in. Yellowsquare Rome is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Caffè Portofino ensures a night out tailored to your taste.

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

On day 9 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, including Orvieto. When you’re not sightseeing, take time to relax at your chosen hotel in Pisa, where you’ll be staying for 1 night.

Set your GPS to Orvieto and hit the road. Expect a journey of approximately 1 hour 35 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Orvieto beckons with new experiences!

Our first attraction recommendation in Orvieto is Well Of St. Patrick, an interesting monument that draws attention for its awe-inspiring features.

When you’ve had your share of Rome, 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 35 min.

For a more meaningful self-guided tour of the village's best attractions, visit Orvieto Cathedral, 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 Museo Dell'opera Del Duomo and admire its heritage-rich features.

When you’re ready, continue to Orvieto Underground, a locally appreciated cave system beloved by locals and tourists alike. Don't miss out on Torre Del Moro Orvieto, another highlight of the area that promises a memorable visit. Not far away, you’ll also find Pozzo Della Cava, a respected place to see that you won’t regret spending some extra time discovering.

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.

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.

Enjoy a lovely meal at Ristorante Capodimonte Pisa, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, La Locanda Dei Pisani Doc Pisa is another top choice with a popular menu. You could also check for a table at Baribaldi Pisa. As an establishment that consistently gains high praises from customers, it’s an ideal choice in Pisa tonight.

After enjoying a fulfilling meal, continue your evening at Bar Mocambo, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Tree offers a welcoming atmosphere for easing into the nightlife. Similarly, Chupiteria provides an excellent environment for a relaxed and enjoyable evening.

As the sun sets, rest up and recharge for the next leg of your road trip in Italy.