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

Perfect travel plans
Everything included
Fully customizable

Description

Included

Flights
Select dates
Hotel
Select dates
Car rental
Select dates
Tours & tickets
Select dates
Travel plan
All inclusive app
Travel agent
24/7 fast service

Description

Escape the ordinary with this exciting 8-day road trip through Italy. Explore the diverse landscapes, lively cities, and beyond. Pack your bags, hit the road, and prepare for an unforgettable journey!

This perfectly planned road trip itinerary in Italy takes you through some of the best places to see in the country. You will spend 2 nights in Pisa, 2 nights in Florence, 2 nights in Siena, and 1 night in Rome. Anticipate well-spent days sightseeing, eating delicious food, and experiencing the highlights of each destination!

With this travel package, you can choose from an extensive selection of accommodations along your road trip route in Italy. We have handpicked the best hotels and places to stay across the country, including options for each budget. Whether you are in the mood for luxurious 5-star hotels or budget-friendly bed and breakfasts, we have got you covered.

Upon arriving in Pisa, the rental vehicle of your choice will be ready for collection. From there, the road trip can begin! Experience the ultimate freedom and uncover Italy on your own terms.

An expertly curated travel plan makes sure you don’t miss out on any of the best things to see and do on your road trip in Italy. Trevi Fountain and Colosseum are just a couple of the bucket-list attractions that await your discovery. Marvel at the remarkable Pantheon, learn more about the unique Piazza Navona, and immerse yourself in the vibrant atmosphere of Ponte Vecchio.

As you hit the open road and drive through Pisa, Florence, Siena, San Quirico d'Orcia, Pienza, Montepulciano, Montalcino, Castelnuovo dell'Abate, Rome, and Orvieto, you will also enjoy plenty of opportunities to uncover hidden gems and experience the authentic charm of Italy. Whether you are exploring enchanting towns and villages, discovering scenic routes, or indulging in local cuisine, there is always something new and exciting to experience in Italy.

Throughout your road trip in Italy, take breaks from sightseeing to explore your favorite destinations' top shopping streets and markets. Discover unique souvenirs that will forever remind you of your self-drive adventure in Italy.

This package offers an all-in-one solution for your trip planning - choose flights, a rental car, accommodation, attractions, and tours that suit your needs and desires. You can customize each day of your road trip itinerary with flexible trip planning before and after booking.

The best services in Italy fill up quickly, so book your spot early. Select a date and start planning your road trip in Italy today!

Read more

Travel details

Set your travel details to find the best price

Flights

Round trip
Round trip
Travel dates

Travelers

Rooms

Flights

Compare and choose from the best flights to Pisa

Car

Choose from the best car rental deals or see all options

Driver’s age is 30 - 65
I live in

Itinerary summary

See a summary of the itinerary that you can fully customize

Days
Destination
Attractions
Overnight
Day
City & Overnight
Attractions
“Tuttomondo” (Keith Haring)
Leaning Tower of PisaPiazza del Duomo, PisaPisa CathedralCentral MarketGalleria dell'AccademiaCathedral of Santa Maria del Fiore
Ponte VecchioUffizi Gallerypiazza della SignoriaBasilica of Santa Croce in Florencepiazzale MichelangeloOltrarno
Fortezza MediceaBasilica of San DomenicoFontebrandaSiena Cathedralpiazza del CampoTower of Mangia
Chapel VitaletaPalazzo Piccolomini, PienzaPorta al PratoFortezza MediceaFortress of MontalcinoAbbey of Sant'Antimo
ColosseumRoman ForumTrevi FountainPantheonPiazza Navona
Orvieto CathedralMuseo dell'Opera del DuomoOrvieto subterraneaWell of St Patrick
Palazzo Gambacorti

Personalize your itinerary

Customize tours under each day and destination

Day 1

Day 1

  • Pisa - Arrival day
  • More
  • “Tuttomondo” (Keith Haring)
  • More

Say hello to Pisa! Your exciting road trip through Italy is just about to start. Navigating the top places to see in the region is a breeze with a car. The rental vehicle of your choice will be ready for pickup upon your arrival in the city. You will stay in Pisa for 1 night before you continue your adventure!

Pisa is a beautiful city with plenty to discover. If you arrive before check-in time or prefer to get started on your sightseeing right away, we recommend checking out “tuttomondo” (keith Haring), or just taking a stroll in the city center. Soak in the lovely atmosphere and sit down for a bit to eat or drink.

Make your way to your chosen hotel. Check-in typically starts between 2 and 4 PM in Pisa. Make yourself at home and enjoy some downtime before heading out again.

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

Treat yourself to a delightful dinner at Anima di Grano Pizzeria Napoletana Pisa Italy, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try il Mercante? It's another excellent option with a diverse menu. Consider reserving a table at La Ghiotteria as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Pisa.

Extend your evening after a delightful meal by visiting Jeffer Cocktails & Friends, which offers the perfect atmosphere for a night out. Moreover, Le Parisien Wine Bar is another popular option for a drink or two. Likewise, Las Volta Cocktailbar also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

Raise a toast to the start of your 8-day road trip in Italy!

Read more
Day 2

Day 2

  • Pisa
  • Florence
  • More

Drive 90 km, 1 hour 58 min

  • Leaning Tower of Pisa
  • Piazza del Duomo, Pisa
  • Pisa Cathedral
  • Central Market
  • Galleria dell'Accademia
  • Cathedral of Santa Maria del Fiore
  • More

On day 2 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 Pisa and Florence. In the evening, you’ll end up in Florence, where you will stay for 2 nights.

Today, you'll explore some of the most beautiful places in Pisa, including a monument, a public square, a church, a food market, an art gallery and much more! Start your day with a visit to Leaning Tower Of Pisa. This iconic 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 breathtaking places you will experience today.

One of the best things about exploring Pisa on a self-guided tour is that you set the pace. There’s plenty of time for detours and discovering hidden gems. When you’re ready for your next stop, make your way to Pisa Cathedral, an up-and-coming church in the city. If you’re up for more discoveries, don’t forget to reserve some time for Central Market and Galleria Dell'accademia. End your day with a visit to Cathedral Of Santa Maria Del Fiore, an extraordinary church that’s sure to leave a lasting impression.

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.

As dinnertime approaches, it's time to head out for a bite to eat in Florence. 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 lovely dining experience at Ristorante Oliviero 1962, a popular restaurant in Florence. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Florence at Di Poneta Novoli, 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 Caffe San Firenze. It’s yet another ideal choice to enhance your time 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.

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

Read more
Day 3

Day 3

  • Florence
  • More

Drive 7 km, 52 min

  • Ponte Vecchio
  • Uffizi Gallery
  • piazza della Signoria
  • Basilica of Santa Croce in Florence
  • piazzale Michelangelo
  • Oltrarno
  • More

On day 3 of your road trip, you will have an entire day to explore Florence. You’ll stay in Florence for 1 night and discover all the best things to see and do in the area.

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.

Florence is home to plenty of attractions that offer fun adventures, romantic experiences, and scenic views! Start at Ponte Vecchio, a timeless historical landmark that is worthwhile a visit in the city. Nearby, you’ll find Uffizi Gallery, enchanting visitors with its romantic appeal. Continue your exploration at Piazza Della Signoria. This public square is one of the city’s most famous 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 Basilica Of Santa Croce In Florence. After exploring the church, head to the famous Piazzale Michelangelo.

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.

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

Treat yourself to a delicious dinner at Ditta Artigianale, an excellent option for tonight's dining. Looking for something different? Trattoria Da Burde offers a tantalizing alternative with its diverse menu. And don’t miss Casa Toscana. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Florence.

If you’re not ready to end the night just yet, Bar 50 Rosso offers a perfect venue to relax and savor a drink. Similarly, Bitter Bar is well-suited for those looking to unwind in a social setting. Archea Brewery is another excellent spot to enjoy a nightcap after a delightful meal.

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

Read more
Day 4

Day 4

  • Florence
  • Siena
  • More

Drive 77 km, 1 hour 42 min

  • Fortezza Medicea
  • Basilica of San Domenico
  • Fontebranda
  • Siena Cathedral
  • piazza del Campo
  • Tower of Mangia
  • More

Dive into day 4 of your remarkable road trip in Italy. Today you will explore Siena, 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.

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Florence allows for both. Start by heading to Fortezza Medicea (siena). This often recommended monument provides an insightful glimpse into the city's identity. Next, discover Basilica Of San Domenico, a historic church, promising a delightful encounter.

Continue your sightseeing with a visit to Fontebranda, an underrated historical landmark. When you’re done, don’t forget to make a stop at the well-known Siena Cathedral. Not far away from the church, you will find the respected Tower Of Mangia, perfect for a quick visit. Round off your day at Piazza Del Campo, another gem in Florence with enchanting features to discover.

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.

As you explore more of Siena, you'll discover that its culinary landscape is as diverse as its attractions. Whether you're craving traditional dishes bursting with local flavors or innovative creations that push the boundaries of taste, you're sure to find a dining experience that satisfies your cravings.

Dine in style at Enoteca I Terzi, a top recommendation for dinner tonight. Or, for a change of pace, Ristorante Tar-Tufo boasts a menu that's sure to impress. Also, be sure to check out Antica Trattoria Papei. Known as a local hotspot, it’s a great choice for tonight in Siena.

Keep the excitement of the evening going by visiting a bar or two. Meet Life Cafè is an excellent place to start. You could also check out Maudit Pub, offering a different kind of charm. A last recommendation for the day is Bar Impero Siena. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

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

Read more
Day 5

Day 5

  • Siena
  • More

Drive 171 km, 3 hours 57 min

  • Chapel Vitaleta
  • Palazzo Piccolomini, Pienza
  • Porta al Prato
  • Fortezza Medicea
  • Fortress of Montalcino
  • Abbey of Sant'Antimo
  • More

Wake up to day 5 of your extraordinary road trip in Italy. With 1 night left in Siena, we encourage you to seize the day and discover the unexplored beauty of the city’s surroundings!

Immerse yourself in Siena’s rich culture with today's sightseeing itinerary. Start your journey at Chapel Vitaleta. This romantic church is sure to ignite your curiosity. Next, dive into the romantic features of Palazzo Piccolomini, Pienza, a must-visit palace in the town.

In between sights, stop by local stores, picturesque photo spots, and small eateries. When you’re ready for your next attraction, proceed to Porta Al Prato, a curiosity-inducing monument. For a change of scene, check out Fortezza Medicea, known for its visually striking features. We also recommend visiting Fortress Of Montalcino. This castle is a must for anyone looking to experience the town to the fullest. Lastly, end your day with a visit to Abbey Of Sant'antimo, yet another worthwhile attraction in Siena.

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

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

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.

Continue the enjoyment post-dinner at Charlie Mixology Bar Di Aldinucci Riccardo, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Bar Pinacoteca offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out San Paolo Pub. This bar is a favorite among both locals and visitors looking for a delightful evening out filled with laughter and fun.

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

Read more
Day 6

Day 6

  • Siena
  • Rome
  • More

Drive 242 km, 3 hours 37 min

  • Colosseum
  • Roman Forum
  • Trevi Fountain
  • Pantheon
  • Piazza Navona
  • More

On day 6 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, Rome. When you’re not sightseeing, take time to relax at your selected hotel in Rome, where you’ll be staying for 1 night.

A blend of fun adventures, scenic views, and picturesque spots await you in Siena on today’s itinerary. First up is the wondrous archeological site, Colosseum. Afterward, continue to Roman Forum, an archeological site every traveler should visit.

As you explore Siena’s charming streets, take in the lively atmosphere and get to know the character of the city. Next, make your way to Trevi Fountain. This iconic monument is an essential stop. Following that, head to Pantheon, another must-visit site that will enhance your experience. Don’t forget to stop by Piazza Navona, an iconic public square in the city.

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

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

Enjoy a delicious meal at La Bottega Roma, a highly-rated dining destination in Rome. If you're eager to try something different, consider Pasta In Corso, another top spot with a tantalizing menu. You might also want to secure a reservation at Trattoria Vecchia Roma. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Rome this evening.

Explore the vibrant nightlife at La Botticella Of Poggi Giovanni after your meal, a hub for lively evenings and memorable moments. Or, head to Almalu Trastevere for a great selection of flavorful drinks and a charming setting. Furthermore, Bar Viminale Di Pepi Maurilio is perfect for those looking to extend their night with a touch of local flavor.

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

Read more
Day 7

Day 7

  • Rome
  • Pisa
  • More

Drive 371 km, 4 hours 40 min

  • Orvieto Cathedral
  • Museo dell'Opera del Duomo
  • Orvieto subterranea
  • Well of St Patrick
  • More

Experience an unparalleled adventure on day 7 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 vibrant destinations - Orvieto. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Pisa. You will spend 1 night here for some well-deserved relaxation.

Bring your curiosity for today’s adventure around Rome. Some of the town’s most loved attractions await! Orvieto Cathedral is the perfect place to start. This church is one of the most notable places to visit in Rome. Next, head to Museo Dell'opera Del Duomo, an underrated museum, known for its respected features.

In between the sights, don’t hesitate to take small detours to explore local stores and eateries. When you’re ready to continue your adventure, head to Orvieto Underground. This historic cave system is a highly recommended experience. Nearby, you'll also find Well Of St. Patrick. Visit these for an interesting touch to your journey.

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.

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

Make sure to reserve a table at Ristorante Capodimonte Pisa, an iconic dining spot in Pisa. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of La Locanda Dei Pisani Doc Pisa, a popular restaurant in Pisa. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Baribaldi Pisa, a hidden gem nestled in Pisa. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Following your dinner, dive into the local bar culture at Bar Mocambo. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Tree, the perfect place for those looking to experience the best of the nightlife. Similarly, Chupiteria provides excellent drinks and a great atmosphere, ensuring a memorable night out.

Savor another day of unforgettable experiences in Italy!

Read more
Day 8

Day 8

  • Pisa - Departure day
  • More
  • Palazzo Gambacorti
  • More

Day 8 of your road trip in Italy is your departure day. This is your chance to catch a last glimpse of Pisa before saying goodbye to this wonderful destination. If you've still got time left, we recommend doing some last-minute shopping or sightseeing.

If you're up for some more sightseeing, begin at Palazzo Gambacorti. This increasingly popular palace is a popular place to see in the city.

On your last day in Italy, take time to indulge in shopping at Pisa’s popular marketplace. Look for keepsakes or souvenirs to remind you of your trip.

Before you conclude your road trip in Italy, drop by another restaurant for a last chance at a memorable dining experience in Pisa.

If you're eager to try something different, consider Ristorante alle Bandierine, another top spot with a tantalizing menu.

You’ll then say farewell to Pisa. Drive to the airport, return your car, and take the opportunity to get some last-minute souvenirs before you board your flight home. We wish you a pleasant journey and hope you leave with many wonderful memories of your road trip in Italy!

Read more

Similar travel packages

Discover other popular vacations in Italy

Link to appstore phone
Install Europe’s biggest travel app

Download Europe’s biggest travel marketplace to your phone to manage your entire trip in one place

Scan this QR code with your phone camera and press the link that appears to add Europe’s biggest travel marketplace into your pocket. Enter your phone number or email address to receive an SMS or email with the download link.