Relaxed 7-Day Italy Self-Drive Road Trip With Itinerary from Pisa to Florence

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Tourist female in Pisa, Arno river, lamp and buildings reflection. Lungarno view.santa maria della spina
Blue hour twilight with Duomo and world famous Leaning Tower travel background in Tuscany.
Landscape with Pisa old town and Arno river, Tuscany, Italy.
 Tourists and locals enjoy a sunny day on the Corso Italia, the main shopping and dining street through the Tuscan city of Pisa, Italy.
Gothic church of Santa Maria della Spina, built around 1230 in the Pisan Gothic style.
Building in botanical garden of Pisa (Orto botanico di Pisa) in Italy
Photo of Tourists at the Primatial Metropolitan Cathedral of the Assumption of Mary in Pisa.
Carriage with horse in front of the leaning tower of Pisa
San Miniato, Pisa, Tuscany, Italy: the ancient catholic theological seminary in the picturesque old town.
Piazza Vittorio Emanuele square in the centre of Pisa city in Tuscany, Italy
Beautiful building of University on Piazza dei Cavalieri (Palazzo della Carovana) decorated with sgraffiti and sculptures of Grand Dukes of Tuscany. The statue depicts Cosimo I de' Medici. Pisa, Italy
The Cittadella Nuova now called the Giardino di Scotto or Giardino Scotto is an old fortress in Pisa, Italy
Piazza dei Cavalieri, Palazzo della Carovana, Palazzo dell'Orologio in Pisa, Italy. Architecture and landmark of Pisa. Cityscape of Pisa
Pisa, Italy. Leaning Tower of Pisa. Panoramic view in the evening. Aerial view
Aerial view of the Cattedrale di Santa Maria del Fiore in Florence, Italy, overlooking the city
Photo of Florence Aerial View of Ponte Vecchio Bridge during Beautiful Sunny Day, Italy.
Photo of Woman enjoys beautiful view on famous Duomo cathedral in Florence, standing on empty cathedral square during morning time.
Photo of Summer street cafe on Piazza della Repubblica in Florence, Toscana province, Italy.
Photo of Giotto's Campanile - An aerial dusk view of Giotto's Campanile and the historical Old Town of Florence, as seen from the top of Brunelleschi's Dome of the Florence Cathedral. Florence, Tuscany, Italy.
Photo of Ponte Vecchio, old bridge over Arno River, Florence, Tuscany, Italy.
Photo of The Colossus of the Apennines, majestic stone sculpture by Giambologna located in the park of Villa Demidoff in Florence, Italy.
Photo of Fountain of Neptune in Florence in early morning.
Photo of Sunset view of Florence, Ponte Vecchio, Palazzo Vecchio and Florence Duomo, Italy. Architecture and landmark of Florence. Cityscape of Florence.
Vintage carousel and tourists in Piazza della Repubblica (Republic Square) and the arch in honor of the first king of united Italy on background in Florence, Italy.
Photo of Arches of the Vasari Corridor (Corridoio Vasariano) in Florence, Tuscany, Italy. View of the Lungarno degli Archibusieri.
cheerful senior woman cycling with her electric mountain bike above downtown of Florence with stunning view over the old city, Tuscany, Italy
Facade of Palazzo Pitti palace with Gallery of Modern Art large building on Piazza dei Pitti square in historical centre of Florence city, blue sky white clouds, Tuscany, Italy
photo of view of Florence,Italy.
photo of view of Florence,Italy.
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Experience Italy like never before on this 7-day relaxed road trip, traversing through Pisa, Florence, Siena, Greve in Chianti, Montefioralle, and Lucca. This self-drive vacation offers a tranquil journey through the heart-stopping beauty found in Italy.

This self-drive package allows you to travel through picture-perfect landscapes in Italy at a relaxed pace. Get a dose of comfort, fun, and recreation in Pisa, Florence, Siena, Greve in Chianti, Montefioralle, and Lucca. Make yourself at home at top-rated hotels and stay 2 nights in Pisa and 4 nights in Florence. Finally, taste the local food and enjoy a refreshing drink at the most popular restaurants and bars along your road trip route in Italy.

Freedom of choice is key to a relaxing road trip in Italy. For your self-drive vacation, we’ll offer you a selection of the best rental vehicles with CDW insurance. Upon arrival in Pisa, you’ll collect your rental car of choice. From there, you’ll begin your 7-day journey across Italy and discover its unique culture, history, and diverse scenery.

Experience the essence of leisurely self-drive exploration across Italy with our handpicked selection of accommodations. From relaxed stays at renowned 5-star hotels offering magnificent views to comfortable 3-star options that cater to budget-conscious travelers, we ensure your journey is optimized for relaxation and comfort. Discover the perfect place to stay and unwind as you embark on a laid-back adventure in Italy.

We’ll introduce you to some of the best travel destinations in Italy. This relaxed road trip features the stunning Ponte Vecchio. Another highlight of this self-drive tour is the captivating Leaning Tower Of Pisa.

Traveling leisurely through Italy means you could spend as much time as you want at the magnificent Piazza Del Duomo, Pisa. With this travel plan, you could also soak in the atmosphere of the memorable Piazzale Michelangelo. Get close to the spectacular Cathedral Of Santa Maria Del Fiore and the wonderful Piazza Della Signoria. You’ll have plenty of time to take in each attraction's unique features, learn its unique history, and appreciate it to the fullest.

Enjoy strolling through Italy's shopping hotspots near your accommodation. Visit shops, discover the locals’ way of life, or try various specialties. Don't forget to bring home a piece of the country that will remind you of your relaxing vacation in Italy.

Between sightseeing, you can make the most of your downtime and join a popular tour in Italy. This relaxed road trip also gives you plenty of time to stroll through Italy's shopping hotspots. Through these experiences, you'll have plenty of opportunities to discover the locals’ way of life and soak in the rich cultural heritage of the Italy.

This self-drive vacation package includes everything you need for a stress-free, easy road trip through Italy. You’ll have a cozy place to stay for 6 nights, with a selection of top-rated breakfast and restaurant options nearby. We'll also provide you with the best rental car you can use throughout the 7 days of your self-drive road trip in Italy. On top of all that, you also have the option to add flights to your travel plan and personalize each day of your itinerary by adding tours and tickets.

This self-drive package includes 24/7 travel support and a step-by-step guide. You can access the guide at any point of your journey through our mobile app, where you can also keep and organize your travel documents.

Spend an amazing 7-day vacation in Italy and get to know more about this fantastic destination. Choose your travel dates and plan a laid-back and relaxed road trip in Italy today!

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Driver’s age is 30 - 65
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Itinerary summary

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Days
Destination
Attractions
Overnight
Day
City & Overnight
Attractions
Knights' Square
Leaning Tower of PisaPiazza del Duomo, PisaBasilica of Santa Maria NovellaCentral MarketGalleria dell'AccademiaCathedral of Santa Maria del Fiore
Ponte VecchioUffizi Gallerypiazza della SignoriaBasilica of Santa Croce in Florencepiazzale MichelangeloOltrarno
Pinacoteca NazionaleSiena Cathedralpiazza del CampoTower of MangiaFortezza Medicea
Castle of VerrazzanoFattoria ViticcioVilla Calcinaia - Conti Capponi
Piazza dell'AnfiteatroGuinigi TowerSt Martin CathedralPiazza NapoleonePalazzo Ducale di LuccaWalls of Lucca
Palazzo Blu

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Day 1

Day 1

  • Pisa - Arrival day
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  • Knights' Square
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Your relaxed road trip through Italy starts when you reach the incredible city of Pisa, where you'll stay for 1 night. You'll pick up your rental car in Pisa and begin your adventure in Italy.

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.

As afternoon approaches, head to your chosen hotel in Pisa. Check-in typically starts around 2 to 4 PM at hotels in Italy. We recommend staying at a hotel in a central location for easy access to the best attractions, restaurants, and bars in the city.

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.

Don’t miss out on dining at Anima di Grano Pizzeria Napoletana Pisa Italy, a top-rated dining destination in Pisa. If you're in the mood to try something new, consider il Mercante, another top spot with a mouthwatering menu. You might also want to secure a reservation at La Ghiotteria. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Pisa this evening.

A visit to a top-rated local bar is one of the most refreshing ways to cap off a beautiful night in Pisa.

Unwind after your meal by stepping into Jeffer Cocktails & Friends. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Le Parisien Wine Bar offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Las Volta Cocktailbar, another top-rated bar in the area.

Raise a toast as you look back into the highlights of today’s laid-back and relaxed road trip adventure in Italy. Enjoy your first taste of Pisa as you soak in the city’s unique vibe.

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Day 2

Day 2

  • Pisa
  • Florence
  • More

Drive 90 km, 2 hours 4 min

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

Day 2 of your self-drive tour in Italy is your opportunity to see and experience the diversity of the country. You’ll stay in Florence for 4 nights. Along the route of your relaxed road trip, you can get a glimpse of the locals’ way of life and visit some of the most amazing locations in Italy.

Today's adventure in Pisa promises more breathtaking discoveries and enriching experiences! Begin at Leaning Tower Of Pisa. This historic monument is a highlight of any visit in the city. Then, enjoy Piazza Del Duomo, Pisa, another breathtaking attraction that never fails to captivate visitors. Next, head over to Basilica Di Santa Maria Novella, Firenze (fi), one of the city’s most interesting attractions, known for its symbolic features.

If you’re looking for more, spend time soaking in the atmosphere of Central Market. This visually striking food market is frequented by locals and tourists alike. To complete your memorable day, make sure to visit Galleria Dell'accademia, a captivating art gallery, and take a stroll around the area. If you want to extend your self-guided sightseeing tour, go check out Cathedral Of Santa Maria Del Fiore before you head back to your hotel.

You’ll be staying at the incredible city of Florence in this laid-back road trip in Italy. You'll stay here for 4 nights.

Exploring the food culture in Florence offers you an exciting chance to connect with locals and experience diversity along your relaxed road trip. When you’re ready to eat, we recommend you visit one of the best dining spots in the city.

Make sure to reserve a table at Ristorante Oliviero 1962, 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 Di Poneta Novoli, 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 Caffe San Firenze, a hidden gem nestled in Florence. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

If you’re not yet ready to call it a night, head back out to celebrate your vacation with a drink. This is a great time to slow down, look back at your day, and raise a toast to your wonderful holiday in Italy.

Following your dinner, dive into the local bar culture at Manifattura. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Se·sto On Arno Rooftop Bar, the perfect place for those looking to experience the best of the nightlife. Similarly, Il Vinile provides excellent drinks and a great atmosphere, ensuring a memorable night out.

Raise your glass and relax after another big day of your leisurely paced road trip in Italy!

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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 leisurely self-drive tour across Italy, you’ll go deep into Florence, where you'll stay for 3 nights, and see some of the city’s unforgettable attractions. To learn more of the city's culture, you'll also dine at the most popular restaurants in Florence, and meet locals along the way!

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.

Today's adventure in Florence promises more breathtaking discoveries and enriching experiences! Begin at Ponte Vecchio. This romantic historical landmark is a highlight of any visit in the city. Then, enjoy Uffizi Gallery, another romantic attraction that never fails to captivate visitors. Next, head over to Piazza Della Signoria, one of the city’s most impressive attractions, known for its remarkable features.

If you’re looking for more, spend time soaking in the atmosphere of Basilica Of Santa Croce In Florence. This culturally significant church is frequented by locals and tourists alike. To complete your memorable day, make sure to visit Piazzale Michelangelo, a famous observation deck, and take a stroll around the area.

Make the most of your time in the country by joining activities that let you discover more about Italy. Check out all of the tours you can join this day of your leisurely self-drive holiday in Italy and ensure the experience of a lifetime.

Exploring new places makes you hungry. Luckily, Florence has multiple restaurants that offer fantastic dining experiences to continue your laid-back and stress-free discovery of the city.

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

A visit to a top-rated local bar is one of the most refreshing ways to cap off a beautiful night 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.

Grab a drink and enjoy every passing minute of this night of your relaxed road trip experience in Italy!

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Day 4

Day 4

  • Florence
  • More

Drive 153 km, 2 hours 52 min

  • Pinacoteca Nazionale
  • Siena Cathedral
  • piazza del Campo
  • Tower of Mangia
  • Fortezza Medicea
  • More

On day 4 of your relaxed road trip, you’ll start your self-paced adventure in Florence and visit amazing attractions in Siena destinations, just outside of the city. You still have 2 nights left in Florence. This means today is also another excellent opportunity to dine at some of the top-rated restaurants and bars in the area.

A blend of family-friendly attractions, photo-friendly spots, and historic treasures await you in Florence on today’s itinerary. First up is the locally appreciated art gallery, Pinacoteca Nazionale. Afterward, continue to Siena Cathedral, a church 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 Piazza Del Campo. This impressive public square is an essential stop. Following that, head to Tower Of Mangia, another must-visit site that will enhance your experience. Don’t forget to stop by Fortezza Medicea (siena), a curiosity-inducing monument in the city.

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

When it’s time to eat, the city has a variety of restaurants and cuisines to suit your palate and complement your relaxed road trip experience. Take a leisurely walk around Florence, while looking for a place to eat. Or, check out our top recommendations and treat yourself to a nice meal.

Enjoy a lovely dining experience at Ristorante Buca Mario, 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 Agricola Toscana, 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 Eataly Firenze. It’s yet another ideal choice to enhance your time in Florence tonight.

As the day is coming to an end, retreat to your hotel for some rest, or head out to a bar to celebrate your time in Florence. The bars in Florence make the perfect setting for a laid-back drink and chilled hangout with your travel companions.

Continue your lively evening at Gosh*, a perfect place for winding down or revving up the night, depending on which mood you’re in. Antico Caffè Del Moro - Art Bar Firenze is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Quelo Bar ensures a night out tailored to your taste.

Savor the rest of the night and celebrate another incredible relaxed road trip adventure in the magical Florence!

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Day 5

Day 5

  • Florence
  • More

Drive 58 km, 1 hour 47 min

  • Castle of Verrazzano
  • Fattoria Viticcio
  • Villa Calcinaia - Conti Capponi
  • More

On day 5 of your relaxed road trip across Italy, you’ll explore the area around Florence, where you’ll be staying for another 1 night. With so many fun and inspiring experiences to offer, a tour of Florence will make you fall even more in love with the city and uniqueness of Italy.

Today’s agenda in Florence includes a castle and a winery. Castle Of Verrazzano is must-visit castle and a great starting point for the day. Next, continue your journey to Fattoria Viticcio, a worthwhile winery, located just a leisurely stroll away. Next, head to Villa Calcinaia - Conti Capponi, a romantic winery, also available for your discovery today.

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

After a laid-back day of exploring top attractions in the area, it’s an excellent idea to sit down for a lovely and peaceful dinner. We’ve collected the most recommended restaurants in the city for you, so you can check out the menus and make your reservation in advance.

Don’t miss out on dining at Tijuana, a top-rated dining destination in Florence. If you're in the mood to try something new, consider Djària - American Bar, another top spot with a mouthwatering menu. You might also want to secure a reservation at The Florence Irish Pub. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Florence this evening.

A visit to a top-rated local bar is one of the most refreshing ways to cap off a beautiful night in Florence.

Raise your glass to celebrate another day of your laid-back and relaxed road trip experience in Italy!

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Day 6

Day 6

  • Florence
  • Pisa
  • More

Drive 112 km, 2 hours 2 min

  • Piazza dell'Anfiteatro
  • Guinigi Tower
  • St Martin Cathedral
  • Piazza Napoleone
  • Palazzo Ducale di Lucca
  • Walls of Lucca
  • More

Day 6 of your relaxed road trip across Italy promises an exciting agenda full of discovery. You’ll start your day in the city of Lucca and drive in the direction of the city of Pisa for some laid-back sightseeing. You’ll end your day in the city of Pisa, where you’ll stay for 1 night.

Today’s agenda in Florence includes a public square, a monument, a church, a palace, a historical landmark and much more! Piazza Dell'anfiteatro is must-visit public square and a great starting point for the day. Next, continue your journey to Guinigi Tower, a frequently visited monument, located just a leisurely stroll away. Next, head to St Martin Cathedral, a culturally significant church, also available for your discovery today.

Each stop on today’s itinerary promises to leave you with lasting memories and a deeper appreciation for Florence. When you're ready, let your sightseeing route take you to the popular Piazza Napoleone. If you’re looking for more, Palazzo Ducale Di Lucca is also a locally appreciated attraction that is worthwhile a visit. Lastly, don’t miss Mura Di Lucca, a place of history-steeped interest in the city.

Continue your laid-back road trip exploration of the best attractions in Italy at Pisa. Select from top hotels and accommodations in the city to recharge and rejuvenate.

After a laid-back day of exploring top attractions in the area, it’s an excellent idea to sit down for a lovely and peaceful dinner. We’ve collected the most recommended restaurants in the city for you, so you can check out the menus and make your reservation in advance.

Savor the flavors at Ristorante Capodimonte Pisa, a top pick for dinner tonight. Alternatively, La Locanda Dei Pisani Doc Pisa beckons with its unique menu offerings. Also, consider Baribaldi Pisa. With its consistent customer satisfaction, it’s an excellent option for dining in Pisa tonight.

After dinner, you can choose between heading back to your hotel to recharge, taking a leisurely stroll, or going out to a bar for a relaxed drink in great company.

Round off your dining experience by visiting Bar Mocambo, a prime location for a drink. Alternatively, explore the distinctive characteristics of Tree, a bar catering to every mood and preference. Chupiteria likewise offers a unique atmosphere, perfect for a memorable night out.

Raise your glass in celebration of your freedom and relaxed road trip adventure in Italy!

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Day 7

Day 7

  • Pisa - Departure day
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  • Palazzo Blu
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Day 7 of your relaxed road trip in Italy is your departure day. If you have a flight to catch, you’ll drop off your rental car well in advance before your departure. Choose a late flight to enjoy a stress-free last day in Pisa.

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

If you're up for some more sightseeing, begin at Palazzo Blu. This beloved art gallery is a popular place to see in the city.

Unwind and look back at the past 7 days of your relaxed road trip over a bite to eat. This is your chance to enjoy one last traditional meal in Pisa or just grab something light to keep you going.

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

Give yourself enough time to wave goodbye to Pisa and begin your journey home. The unforgettable experiences you’ve collected along your 7-day relaxed road trip in Italy is a story you will tell for the rest of your life.

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