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

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Explore the best of Italy on a 8-day road trip! Uncover hidden gems and experience the rich culture firsthand as you journey through Pisa, Lucca, Florence, Siena, San Gimignano, Castellina in Chianti, Bologna, Modena, Montale Rangone, and Parma. This road trip itinerary in Italy seamlessly combines exploration with relaxation.

This perfectly planned road trip itinerary in Italy takes you through some of the best places to see in the country. You will spend 3 nights in Pisa, 3 nights in Florence, and 1 night in Modena. 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. Ponte Vecchio and Leaning Tower Of Pisa are just a couple of the bucket-list attractions that await your discovery. Marvel at the remarkable Piazza Del Duomo, Pisa, learn more about the unique Piazzale Michelangelo, and immerse yourself in the vibrant atmosphere of Cathedral Of Santa Maria Del Fiore.

As you hit the open road and drive through Pisa, Lucca, Florence, Siena, San Gimignano, Castellina in Chianti, Bologna, Modena, Montale Rangone, and Parma, 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!

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Itinerary summary

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Days
Destination
Attractions
Overnight
Day
City & Overnight
Attractions
Knights' Square
Piazza del Duomo, PisaPisa CathedralLeaning Tower of PisaWalls of LuccaSt Martin CathedralPiazza dell'Anfiteatro
piazzale MichelangeloBasilica of Santa Croce in FlorenceUffizi GalleryPonte VecchioCathedral of Santa Maria del Fiorepiazza della Signoria
piazza del CampoSiena CathedralBasilica of San DomenicoFortezza MediceaPiazza del Duomo, San Gimignano
Poggio AmorelliTumulo di MontecalvarioRocca di Castellina in Chianti
Basilica of San DomenicoPiazza Santo StefanoTwo TowersPiazza MaggioreBologna CathedralFountain of Neptune, Bologna
Parco archeologico e museo all'aperto della Terramara di MontaleParma CathedralTeatro RegioGiuseppe Garibaldi Monument
Palazzo Gambacorti

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Day 1

Day 1

  • Pisa - Arrival day
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  • Knights' Square
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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 2 nights 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 Knights' Square, 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.

Make sure to reserve a table at Anima di Grano Pizzeria Napoletana Pisa Italy, 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 il Mercante, 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 La Ghiotteria, a hidden gem nestled in Pisa. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Continue the enjoyment post-dinner at Jeffer Cocktails & Friends, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Le Parisien Wine Bar offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out Las Volta Cocktailbar. This bar is a favorite among both locals and visitors looking for a delightful evening out filled with laughter and fun.

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

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Day 2

Day 2

  • Pisa
  • More

Drive 46 km, 1 hour 43 min

  • Piazza del Duomo, Pisa
  • Pisa Cathedral
  • Leaning Tower of Pisa
  • Walls of Lucca
  • St Martin Cathedral
  • Piazza dell'Anfiteatro
  • More

Wake up to day 2 of your extraordinary road trip in Italy. With 1 night left in Pisa, we encourage you to seize the day and discover the unexplored beauty of the city’s surroundings!

Today’s agenda in Pisa includes a public square, a church, a monument, a historical landmark and much more! Piazza Del Duomo, Pisa is must-visit public square and a great starting point for the day. Next, continue your journey to Pisa Cathedral, a beloved church, located just a leisurely stroll away. Next, head to Leaning Tower Of Pisa, a symbolic monument, also available for your discovery today.

Each stop on today’s itinerary promises to leave you with lasting memories and a deeper appreciation for Pisa. If you’re looking for more, Mura Di Lucca is also an intriguing attraction that is worthwhile a visit. Lastly, don’t miss St Martin Cathedral, an underrated gem to see in the city.

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

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.

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.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Bar Mocambo, known for its inviting atmosphere. Tree is another great option if you’re looking for a place to get the night started. Similarly, Chupiteria provides a great setting to enjoy the night away.

Relax and reminisce about your day in Italy and look forward to more memorable moments to come!

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Day 3

Day 3

  • Pisa
  • Florence
  • More

Drive 89 km, 2 hours 2 min

  • piazzale Michelangelo
  • Basilica of Santa Croce in Florence
  • Uffizi Gallery
  • Ponte Vecchio
  • Cathedral of Santa Maria del Fiore
  • piazza della Signoria
  • More

On day 3 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 Florence. In the evening, you’ll end up in Florence, where you will stay for 3 nights.

Today’s well-planned self-sightseeing route offers several family-friendly attractions, romantic experiences, and breathtaking views. Whether you decide to explore Pisa on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss. Piazzale Michelangelo is the first of them. Spend some time admiring this visually striking observation deck before continuing your journey. Basilica Of Santa Croce In Florence is your next stop. This popular church is one of the best-rated sights in Pisa.

Consider grabbing some lunch or a light snack to keep your energy going. Beyond the above-mentioned attractions, today is also the perfect time to visit Uffizi Gallery. This historic art gallery is a sight to behold. To round off your sightseeing experience, visit Ponte Vecchio and Cathedral Of Santa Maria Del Fiore.

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

Savor the flavors at Ristorante Oliviero 1962, a top pick for dinner tonight. Alternatively, Di Poneta Novoli beckons with its unique menu offerings. Also, consider Caffe San Firenze. With its consistent customer satisfaction, it’s an excellent option for dining in Florence tonight.

Explore the vibrant nightlife at Manifattura after your meal, a hub for lively evenings and memorable moments. Or, head to Se·sto On Arno Rooftop Bar for a great selection of flavorful drinks and a charming setting. Furthermore, Il Vinile is perfect for those looking to extend their night with a touch of local flavor.

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

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Day 4

Day 4

  • Florence
  • More

Drive 185 km, 3 hours 40 min

  • piazza del Campo
  • Siena Cathedral
  • Basilica of San Domenico
  • Fortezza Medicea
  • Piazza del Duomo, San Gimignano
  • More

Greet day 4 of your road trip in Italy with a smile and start your day with a hearty breakfast. You will return to Florence for your remaining 2 nights in the city later today, but first, it’s time for some exploring! On the agenda for this day, you’ll find only the best things to see and do in Siena and San Gimignano.

Set out on a day brimming with family-friendly attractions, romantic experiences, and breathtaking views. Start at the famous Piazza Del Campo, a romantic public square in Florence. Next, go to Siena Cathedral.

After visiting Piazza Del Campo and Siena Cathedral, take time to explore Florence's streets and absorb its charm. Continue your sightseeing by heading to Basilica Of San Domenico. This culturally significant church offers a unique experience. Fortezza Medicea (siena) is another noteworthy stop. End your self-guided sightseeing tour on top with a visit to Piazza Del Duomo, one of the most history-steeped places to visit in Florence.

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

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 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.

Keep the excitement of the evening going by visiting a bar or two. Bar 50 Rosso is an excellent place to start. You could also check out Bitter Bar, offering a different kind of charm. A last recommendation for the day is Archea Brewery. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

Raise your glass to another unforgettable day in Italy!

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Day 5

Day 5

  • Florence
  • More

Drive 101 km, 2 hours 6 min

  • Poggio Amorelli
  • Tumulo di Montecalvario
  • Rocca di Castellina in Chianti
  • More

At the end of the day, you'll drive back to Florence, where you'll stay for 1 night more.

Savor the day by visiting some of the best places to see in Florence, including a winery, an archeological site, and a castle. Start your adventure at Poggio Amorelli. This beloved winery is a must-visit for travelers looking for a unique holiday experience. Make your way to Tumulo Di Montecalvario located in Florence for an enchanting atmosphere.

Next, immerse yourself in the setting of Rocca Di Castellina In Chianti. Its enchanting features will captivate you.

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

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.

Don’t miss out on dining at Ristorante Buca Mario, a top-rated dining destination in Florence. If you're in the mood to try something new, consider Agricola Toscana, another top spot with a mouthwatering menu. You might also want to secure a reservation at Eataly Firenze. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Florence this evening.

Let the evening flow smoothly from dinner to drinks at Gosh*, a top-rated bar in the area. For other recommendations, Antico Caffè Del Moro - Art Bar Firenze provides a perfect setting for rounding out your night with style and great drinks. Likewise, Quelo Bar offers a memorable night with diverse drink options and excellent service.

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

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Day 6

Day 6

  • Florence
  • Modena
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Drive 159 km, 2 hours 55 min

  • Basilica of San Domenico
  • Piazza Santo Stefano
  • Two Towers
  • Piazza Maggiore
  • Bologna Cathedral
  • Fountain of Neptune, Bologna
  • More

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

Florence is home to plenty of attractions that offer family-friendly attractions, photo-friendly spots, and historic treasures! Start at Basilica Of San Domenico, a worthwhile church that is worthwhile a visit in the city. Nearby, you’ll find Piazza Santo Stefano, enchanting visitors with its romantic appeal. Continue your exploration at Two Towers. This monument is one of the city’s most captivating 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 Piazza Maggiore. After exploring the public square, head to the often recommended Bologna Cathedral. This church will wrap up today’s self-guided sightseeing tour 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 Modena. Modena offers plenty of top-rated hotels for every travel budget. Take some time to relax before you go out again.

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

Enjoy a delicious meal at Dispensa Emilia_ Via Emilia Est Modena, a top-rated dining destination in Modena. If you're in the mood to try something new, consider Trattoria Aldina, another top spot with a mouthwatering menu. You might also want to secure a reservation at Ristorante Europa 92 Ristorante Pavarotti. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Modena this evening.

Continue your lively evening at Chiaro Cafe', a perfect place for winding down or revving up the night, depending on which mood you’re in. Major Tom is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Cesare Modena — Caffè Malagoli Dal 1934 ensures a night out tailored to your taste.

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

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Day 7

Day 7

  • Modena
  • Pisa
  • More

Drive 268 km, 3 hours 29 min

  • Parco archeologico e museo all'aperto della Terramara di Montale
  • Parma Cathedral
  • Teatro Regio
  • Giuseppe Garibaldi Monument
  • More

Embark on another extraordinary experience on day 7 of your road trip in Italy. Today, you will make 2 stops and experience some of the highlights of Montale Rangone and Parma. At the end of the day, you will enjoy the comforts of a top-rated hotel in Pisa, which will be your home away from home for 1 night.

Get ready for an exciting day in Modena. Today’s sightseeing agenda includes an archeological site, a church, an opera house, a monument and much more! Begin your adventure at Parco Archeologico E Museo All'aperto Della Terramara Di Montale. This is a beloved archeological site you should not miss. Another must-see is Parma Cathedral, a worthwhile church in Modena.

When you’re ready for the next sight, head to Teatro Regio. From there, take a leisurely stroll to Giuseppe Garibaldi Monument, another of the village’s up-and-coming attractions.

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

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.

Enjoy a lovely meal at Restaurant -Pizzeria Il Mio Capriccio, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Ristorante alle Bandierine is another top choice with a popular menu. You could also check for a table at Barrique Cocktail And Bistrot. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Pisa tonight.

Keep the evening going at Bar Livorno, a great choice for enjoying the after-dinner hours with a drink.

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

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Day 8

Day 8

  • Pisa - Departure day
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  • Palazzo Gambacorti
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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 often recommended palace is a popular place to see in the city.

Explore local shops for souvenirs to remember your trip or find unique gifts for loved ones.

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

Treat yourself to a delightful dinner at Anita Osteria, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try La corte di San Leonardo? It's another excellent option with a diverse 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!

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