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

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Explore Italy and discover its unique charm on this 7-day relaxed road trip through Pisa, Florence, Siena, Greve in Chianti, Montefioralle, and Lucca. Delight in a stress-free journey that focuses on exploration through the country's most captivating landscapes.

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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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.

Find your way to your hotel in Pisa. We recommend choosing a hotel in a central location for easy exploring. Check-in typically starts between 2 and 4 PM at hotels in Italy. Settle in and make plans for the evening.

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.

Enjoy a delicious meal at Anima di Grano Pizzeria Napoletana Pisa Italy, a highly-rated dining destination in Pisa. If you're eager to try something different, consider il Mercante, another top spot with a tantalizing menu. You might also want to secure a reservation at La Ghiotteria. With a reputation for consistently satisfying customers, it’s an excellent 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.

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 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.

Discover a day packed with family-friendly attractions, scenic views, and picturesque spots in Pisa. Begin your sightseeing with Leaning Tower Of Pisa. This world-famous monument is one of the top attractions in the city. Proceed to Piazza Del Duomo, Pisa, another must-visit attraction.

As you wander through the inviting streets of Pisa, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to Basilica Di Santa Maria Novella, Firenze (fi). This popular church is a traveler-favorite. Not far away, you’ll find Central Market, another key site on your sightseeing itinerary. Galleria Dell'accademia is yet another highly recommended place to visit nearby, offering plenty to discover for curious travelers. Conclude your day at Cathedral Of Santa Maria Del Fiore and uncover why it's recognized as one of the city's most spectacular attractions.

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

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.

Treat yourself to a wonderful meal at Ristorante Oliviero 1962, a top-rated dining spot in Florence. If you're in the mood for something new, try Di Poneta Novoli, another premier location with a delectable menu. You might also want to book a table at Caffe San Firenze. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Florence.

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.

After savoring a delicious meal, step into the vibrant nightlife at Manifattura, where the evening is just getting started. In the same way, Se·sto On Arno Rooftop Bar offers a unique charm perfect for experiencing the local bar scene in Florence. Il Vinile is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

Cherish every minute of your relaxed road trip vacation across 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

Day 3 of your relaxed road trip through Italy means 24 hours of making the best memories in Florence. You’ll go sightseeing at famous attractions in Florence. In the evening, you will experience one of the most popular dining spots in the city. So buckle up and prepare to be blown away by Florence!

Make sure to visit Oltrarno, a popular neighborhood in Florence. Spend some time wandering around the area and soak in its distinctive charm. You’ll also discover that several of the city’s must-see attractions are just around the corner.

A blend of family-friendly attractions, romantic experiences, and scenic views await you in Florence on today’s itinerary. First up is the globally renowned historical landmark, Ponte Vecchio. Afterward, continue to Uffizi Gallery, an art gallery 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 Della Signoria. This famous public square is an essential stop. Following that, head to Basilica Of Santa Croce In Florence, another must-visit site that will enhance your experience. Don’t forget to stop by Piazzale Michelangelo, an extraordinary observation deck in the city.

Italy makes the perfect setting for a calming but fun exploration. Aside from amazing sights, Italy also offers plenty of tours to enhance your relaxed road trip experience.

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.

Enjoy a lovely dining experience at Ditta Artigianale, 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 Trattoria Da Burde, 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 Casa Toscana. It’s yet another ideal choice to enhance your time in Florence tonight.

If you feel like it, head out to a bar to celebrate another fantastic day in Florence and take the pulse of the city’s nightlife. Enjoy the night without rushing to fully appreciate it.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Bar 50 Rosso, known for its inviting atmosphere. Bitter Bar is another great option if you’re looking for a place to get the night started. Similarly, Archea Brewery provides a great setting to enjoy the night away.

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

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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

Your laid-back and relaxed road trip in Italy continues on day 4, allowing you to create more unforgettable memories. Today’s travel plan offers you the chance to have a more in-depth understanding of Italy and its people by visiting the offerings and top attractions of Florence and beyond. With 2 nights left in Florence, you’ll have enough time to eat and unwind at popular restaurants and bars in the city.

Bring your curiosity for today’s adventure around Florence. Some of the city’s most loved attractions await! Pinacoteca Nazionale is the perfect place to start. This art gallery is one of the most locally appreciated places to visit in Florence. Next, head to Siena Cathedral, a locally renowned church, known for its visually striking 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 Piazza Del Campo. This UNESCO world heritage-designated public square is a highly recommended experience. Nearby, you'll also find Tower Of Mangia and Fortezza Medicea (siena). Visit these for an interesting touch to your journey.

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

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.

Treat yourself to a delicious dinner at Ristorante Buca Mario, an excellent option for tonight's dining. Looking for something different? Agricola Toscana offers a tantalizing alternative with its diverse menu. And don’t miss Eataly Firenze. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Florence.

As the day is coming to an end, stop at some of Florence’s best bars to celebrate this day of your slow-paced adventure in Italy.

If you’re not ready to end the night just yet, Gosh* offers a perfect venue to relax and savor a drink. Similarly, Antico Caffè Del Moro - Art Bar Firenze is well-suited for those looking to unwind in a social setting. Quelo Bar is another excellent spot to enjoy a nightcap after a delightful meal.

Raise your glass and toast to another unforgettable, laid-back road trip adventure in Italy!

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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, you’ll start your self-paced adventure in Florence and visit amazing attractions in Greve in Chianti, Montefioralle, and Greti destinations, just outside of the city. You still have 1 night 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.

Get ready for a day filled with family-friendly attractions, romantic experiences, and scenic views in the charming town of Florence. Your adventure starts at Castle Of Verrazzano, a frequently visited local hot spot. Another notable attraction to explore is Fattoria Viticcio. This curiosity-inducing winery is known for its enchanting appeal.

After soaking in the highlights of these sights, take some time to wander Florence's streets and immerse yourself in the local atmosphere. When you're ready to continue your sightseeing adventure, head to Villa Calcinaia - Conti Capponi. This romantic winery offers a fascinating experience that many visitors find memorable.

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

Mealtimes are the perfect opportunities to immerse yourself in the local culture of Italy. When you're not appreciating the best places to visit in Florence, explore the city like a local by trying out the best restaurants in the area.

Enjoy a delicious meal at Tijuana, a highly-rated dining destination in Florence. If you're eager to try something different, consider Djària - American Bar, another top spot with a tantalizing menu. You might also want to secure a reservation at The Florence Irish Pub. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Florence this evening.

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.

Raise your glass in celebration of your freedom and relaxed road trip adventure 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 leisurely self-drive tour in Italy is another opportunity for an in-depth travel experience in the country. You’ll stay in Pisa for 1 night.

Today’s route brings family-friendly attractions, romantic experiences, and scenic views. The first attraction of today is Piazza Dell'anfiteatro. This captivating public square is a stunning place to see in Florence. Continue your discovery at Guinigi Tower, a majestic monument with stories to tell.

As you stroll around Florence, take in the distinct atmosphere and learn what makes this city so unique. Maximize your sightseeing with a visit to St Martin Cathedral. This locally appreciated church offers a breathtaking encounter with Florence. Next, make your way to Piazza Napoleone to add another highlight to your day. After that, visit Palazzo Ducale Di Lucca, a worthwhile palace that’s sure to impress. If you’re up for more, end your self-guided sightseeing tour at Mura Di Lucca, a worthwhile historical landmark in the city. Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day in Florence.

In the city of Pisa, you’ll find plenty of stay options that will accommodate your need for rest and relaxation after spending your day on the road. Our top recommendations perfectly complement your relaxed road trip vacation in Italy.

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.

Take a stroll around the area, head back to your accommodation for the night, or continue your evening at one of the best-rated bars in the city.

Keep the evening going at Bar Mocambo, a great choice for enjoying the after-dinner hours with a drink. You could also go to Tree, which offers a similarly pleasant setting and great drinks. Another option is Chupiteria, which provides an inviting environment for unwinding after a busy day out.

Raise your glass and toast to another unforgettable, laid-back road trip adventure in Italy!

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Day 7

Day 7

  • Pisa - Departure day
  • More
  • Palazzo Blu
  • More

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 increasingly popular 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.

Have a fantastic dining experience at Restaurant -Pizzeria Il Mio Capriccio, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Ristorante alle Bandierine offers an enticing alternative with its varied 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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