6-Day Italy Self-Drive Road Trip With Itinerary from Florence to San Gimignano and Montefioralle and surrounding area

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Description

Explore the best of Italy on a 6-day road trip! Uncover hidden gems and experience the rich culture firsthand as you journey through Florence, Pisa, Lucca, San Gimignano, Siena, Montefioralle, Santa Maria degli Angeli, and Cortona. 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 Florence, 1 night in San Gimignano, and 1 night in Montefioralle. 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 Florence, 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 Florence, Pisa, Lucca, San Gimignano, Siena, Montefioralle, Santa Maria degli Angeli, and Cortona, 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
Oltrarno
Cathedral of Santa Maria del Fiorepiazza della SignoriaPonte VecchioUffizi GalleryBasilica of Santa Croce in Florencepiazzale MichelangeloThe Boboli Gardens
Pisa CathedralPiazza del Duomo, PisaLeaning Tower of PisaWalls of LuccaSt Martin CathedralPiazza del Duomo, San Gimignano
Fortezza MediceaBasilica of San DomenicoSiena Cathedralpiazza del CampoPorta PispiniCastello di Brolio
Eremo delle CarceriRocca MaggioreBasilica of San Francesco d'AssisiParterre
Central Market

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Day 1

Day 1

  • Florence - Arrival day
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  • Oltrarno
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Say hello to Florence! 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 Florence for 2 nights before you continue your adventure!

Florence 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 Oltrarno, a must-see neighborhood, and 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 Florence. 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 Florence, it's often a good idea to reserve a table in advance.

Enjoy a lovely meal at Ristorante Oliviero 1962, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Di Poneta Novoli is another top choice with a popular menu. You could also check for a table at Caffe San Firenze. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Florence tonight.

Keep the evening going at Manifattura, a great choice for enjoying the after-dinner hours with a drink. You could also go to Se·sto On Arno Rooftop Bar, which offers a similarly pleasant setting and great drinks. Another option is Il Vinile, which provides an inviting environment for unwinding after a busy day out.

Raise a toast to the start of your 6-day road trip in Italy!

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Day 2

Day 2

  • Florence
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Drive 14 km, 1 hour 15 min

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

Day 2 offers a multitude of experiences. You will stay in Florence for 1 night more, offering you enough time to explore at a relaxed pace.

Today’s itinerary in Florence covers several incredible sights, including a church, a public square, a historical landmark, an art gallery, an observation deck, a botanical garden and much more! Start your adventure at Cathedral Of Santa Maria Del Fiore. This impressive church is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the grand wonders of Piazza Della Signoria, a must-see public square in the city.

Consider stopping for a small bite to eat or a drink at a local eatery to keep your energy going. When you’re ready, continue your discovery with a visit to Ponte Vecchio. This wondrous historical landmark offers an enriching experience. For a change of pace, head to Uffizi Gallery, where you can take in historic features. Conclude your self-guided sightseeing tour with a visit to Basilica Of Santa Croce In Florence and Basilica Of Santa Croce In Florence. These sights offer a fulfilling end to a perfect day.

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.

Experience shopping bliss at Florence as you explore Mercato Centrale. Take a leisurely stroll through unique and shops, where local treasures are waiting to be found. Beyond shopping, Mercato Centrale offers more options, including unique attractions, key services, and vibrant events.

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

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.

Continue your lively evening at Bar 50 Rosso, a perfect place for winding down or revving up the night, depending on which mood you’re in. Bitter Bar is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Archea Brewery ensures a night out tailored to your taste.

Raise your glass to another unforgettable day in Italy!

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Day 3

Day 3

  • Florence
  • San Gimignano
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Drive 195 km, 3 hours 36 min

  • Pisa Cathedral
  • Piazza del Duomo, Pisa
  • Leaning Tower of Pisa
  • Walls of Lucca
  • St Martin Cathedral
  • Piazza del Duomo, San Gimignano
  • More

Embark on another extraordinary experience on day 3 of your road trip in Italy. Today, you will make 3 stops and experience some of the highlights of Pisa, Lucca, and San Gimignano. At the end of the day, you will enjoy the comforts of a top-rated hotel in San Gimignano, which will be your home away from home for 1 night.

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Florence allows for both. Start by heading to Pisa Cathedral. This underrated church provides an insightful glimpse into the city's identity. Next, discover Piazza Del Duomo, Pisa, a symbolic public square, promising a delightful encounter.

Continue your sightseeing with a visit to Leaning Tower Of Pisa, a wondrous monument. When you’re done, don’t forget to make a stop at the underrated Mura Di Lucca. Round off your day at St Martin Cathedral, another gem in Florence with picture-perfect features to discover.

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

As you explore more of San Gimignano, 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.

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

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Day 4

Day 4

  • San Gimignano
  • Montefioralle
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Drive 105 km, 2 hours 54 min

  • Fortezza Medicea
  • Basilica of San Domenico
  • Siena Cathedral
  • piazza del Campo
  • Porta Pispini
  • Castello di Brolio
  • More

On day 4 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 Siena and San Regolo. In the evening, you’ll end up in Montefioralle, where you will stay for 1 night.

Bring your curiosity for today’s adventure around San Gimignano. Some of the city’s most loved attractions await. Fortezza Medicea (siena) is the perfect place to start. This monument is one of the most often recommended places to visit in San Gimignano. Next, head to Basilica Of San Domenico, a frequently visited church, known for its picture-perfect 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 Siena Cathedral. This culturally significant church offers a unique experience that is highly recommended. Meanwhile, Piazza Del Campo adds its own distinct charm to your journey. Finish your day with a visit to Porta Pispini, a stunning historical landmark in San Gimignano.

After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of your accommodation in Montefioralle. Montefioralle 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 Montefioralle's best restaurants.

Treat yourself to a delicious dinner at La Castellana, an excellent option for tonight's dining. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Montefioralle.

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

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Day 5

Day 5

  • Montefioralle
  • Florence
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Drive 363 km, 5 hours 22 min

  • Eremo delle Carceri
  • Rocca Maggiore
  • Basilica of San Francesco d'Assisi
  • Parterre
  • More

Experience an unparalleled adventure on day 5 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 2 vibrant destinations - Santa Maria degli Angeli and Cortona. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Florence. You will spend 1 night here for some well-deserved relaxation.

Today’s itinerary in Montefioralle covers several incredible sights, including a monastery, a castle, a church, a park and much more! Start your adventure at Eremo Delle Carceri. This intriguing monastery is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the history-steeped wonders of Rocca Maggiore, a must-see castle in the town.

Consider stopping for a small bite to eat or a drink at a local eatery to keep your energy going. When you’re ready, continue your discovery with a visit to Basilica Of San Francesco D'assisi. This locally renowned church offers an enriching experience. For a change of pace, head to Parterre, where you can take in romantic features.

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.

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 meal at Ristorante Buca Mario, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Agricola Toscana is another top choice with a popular menu. You could also check for a table at Eataly Firenze. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Florence tonight.

Unwind after your meal by stepping into Gosh*. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Antico Caffè Del Moro - Art Bar Firenze offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Quelo Bar, another top-rated bar in the area.

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 6

Day 6

  • Florence - Departure day
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  • Central Market
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Day 6 of your road trip in Italy is your departure day. This is your chance to catch a last glimpse of Florence 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, we recommend visiting Central Market, an eye-catching food market before you head out.

On your last day in Italy, take time to indulge in shopping at Florence’s popular marketplace, San Lorenzo Market. 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 Florence.

Enjoy a lovely meal at Tijuana, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Djària - American Bar is another top choice with a popular menu.

You’ll then say farewell to Florence. 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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