6-Day Italy Self-Drive Road Trip With Itinerary from Florence traveling west to Siena

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Photo of Florence Aerial View of Ponte Vecchio Bridge during Beautiful Sunny Day, Italy.
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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.
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Photo of Siena in Italy by SimonRei
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Photo of Siena, Italy. Aerial view of Piazza del Campo with Palazzo Pubblico and Torre del Mangia.
photo of view of Siena, Italy. Charming medieval city in Tuscany known for its stunning cathedral, Torre del Mangia, beautiful piazzas, and the famous Palio horse race.
photo of view of Siena, medieval town in Tuscany, with view of the Dome Bell Tower of Siena Cathedral, Mangia Tower and Basilica of San Domenico, Italy
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photo of view of Medieval San Gimignano hill town with skyline of medieval towers, including the stone Torre Grossa. Province of Siena, Tuscany, Italy.
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Experience the freedom of the open road in Italy as you embark on an unforgettable 6-day road trip! This experience caters to every traveler, featuring destinations like Florence, Siena, San Gimignano, Greve in Chianti, Pisa, and Lucca.

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 and 2 nights in Siena. 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, Siena, San Gimignano, Greve in Chianti, Pisa, and Lucca, 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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Driver’s age is 30 - 65
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Days
Destination
Attractions
Overnight
Day
City & Overnight
Attractions
Cathedral of Santa Maria del Fiore
piazzale MichelangeloBasilica of Santa Croce in Florencepiazza della SignoriaUffizi GalleryPonte VecchioOltrarno
Fortezza MediceaBasilica of San DomenicoSiena CathedralPubblico Palacepiazza del CampoTower of Mangia
Porta San GiovanniPiazza del Duomo, San GimignanoTown Hall, Picture Gallery and Great TowerChiesa di Sant'AgostinoCastle of VerrazzanoVilla Calcinaia - Conti Capponi
Piazza del Duomo, PisaLeaning Tower of PisaWalls of LuccaPorta San PietroPiazza dell'Anfiteatro
Central Market

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Day 1

Day 1

  • Florence - Arrival day
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  • Cathedral of Santa Maria del Fiore
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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 Cathedral Of Santa Maria Del Fiore, 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 Florence. 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 Florence, 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.

Let the evening flow smoothly from dinner to drinks at Manifattura, a top-rated bar in the area. For other recommendations, Se·sto On Arno Rooftop Bar provides a perfect setting for rounding out your night with style and great drinks. Likewise, Il Vinile offers a memorable night with diverse drink options and excellent service.

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 4 km, 1 hour 5 min

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

On day 2 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.

A visit to Oltrarno in Florence is a must on the agenda today. This neighborhood is full of hidden gems and character, perfect for a leisurely stroll. Plus, you’ll be close to some of the city’s most famous sights.

Florence is home to plenty of attractions that offer family-friendly attractions, romantic experiences, and scenic views! Start at Piazzale Michelangelo, an impressive observation deck that is worthwhile a visit in the city. Nearby, you’ll find Basilica Of Santa Croce In Florence, enchanting visitors with its culturally significant appeal. Continue your exploration at Piazza Della Signoria. This public square is one of the city’s most widely recognized 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 Uffizi Gallery. After exploring the art gallery, head to the globally renowned Ponte Vecchio.

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.

Visit Via de' Tornabuoni in Florence for an unforgettable shopping experience. Browse unique boutiques and luxurious stores, each offering delightful surprises. Find unique souvenirs or items to take home. After shopping, explore what Via de' Tornabuoni has to offer, including attractions, essential services, and vibrant community activities.

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

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.

Unwind after your meal by stepping into Bar 50 Rosso. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Bitter Bar offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Archea Brewery, another top-rated bar in the area.

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

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Day 3

Day 3

  • Florence
  • Siena
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Drive 77 km, 1 hour 45 min

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

Embark on another extraordinary experience on day 3 of your road trip in Italy. Today, you will make 1 stop and experience some of the highlights of Siena. At the end of the day, you will enjoy the comforts of a top-rated hotel in Siena, which will be your home away from home for 2 nights.

Today's adventure in Florence promises more breathtaking discoveries and enriching experiences! Begin at Fortezza Medicea (siena). This historic monument is a highlight of any visit in the city. Then, enjoy Basilica Of San Domenico, another stunning attraction that never fails to captivate visitors. Next, head over to Siena Cathedral, one of the city’s most interesting attractions, known for its culturally significant features.

If you’re looking for more, spend time soaking in the atmosphere of Pubblico Palace. This UNESCO world heritage-listed palace is frequented by locals and tourists alike. To complete your memorable day, make sure to visit Piazza Del Campo, a famous public square, and take a stroll around the area. If you want to extend your self-guided sightseeing tour, go check out Tower Of Mangia before you head back to your hotel.

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

As you are wrapping up for the day, treat yourself to a satisfying dinner at a nice restaurant in Siena. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.

Treat yourself to a delicious dinner at Enoteca I Terzi, an excellent option for tonight's dining. Looking for something different? Ristorante Tar-Tufo offers a tantalizing alternative with its diverse menu. And don’t miss Antica Trattoria Papei. With its reputation for pleasing customers, it’s a fantastic 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.

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

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Day 4

Day 4

  • Siena
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Drive 154 km, 3 hours 1 min

  • Porta San Giovanni
  • Piazza del Duomo, San Gimignano
  • Town Hall, Picture Gallery and Great Tower
  • Chiesa di Sant'Agostino
  • Castle of Verrazzano
  • Villa Calcinaia - Conti Capponi
  • More

On day 4 of your road trip in Italy, you’ll start and end your day in Siena, but spend the day exploring what’s beyond the city. Since you will return to Siena for 1 night more, there’s no need to rush. Experience San Gimignano, Greve in Chianti, and Greti to the fullest today with this curated day itinerary!

Siena is brimming with adventures. Today’s wonderful stops include a monument, a public square, a museum, a church, a castle, a winery and much more! Begin your sightseeing adventure at the often recommended Porta San Giovanni and allow yourself time to explore. Just a short distance away you'll find your next stop, Piazza Del Duomo, a culturally significant public square that draws visitors from far and near.

Continue your journey to Palazzo Comunale, Pinacoteca, Torre Grossa, one of the village’s most increasingly popular spots that you shouldn’t miss. Another great site to visit is the beloved Chiesa Di Sant'agostino. When you're finished at the church, Castle Of Verrazzano awaits your visit. This castle is an enchanting highlight on today's itinerary. Last up is a winery - the intriguing Villa Calcinaia - Conti Capponi.

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

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

Treat yourself to a wonderful meal at Osteria Quattro Venti, a top-rated dining spot in Siena. If you're in the mood for something new, try Fischi per Fiaschi, another premier location with a delectable menu. You might also want to book a table at Osteria da Divo. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Siena.

Cap off your dinner by heading to Charlie Mixology Bar Di Aldinucci Riccardo, ideal for a leisurely evening with a drink in hand. Bar Pinacoteca is another bar that offers an enjoyable setting. Similarly, San Paolo Pub is also a popular place to go on a night out, perfect for relaxing and socializing.

Savor another day of unforgettable experiences in Italy!

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Day 5

Day 5

  • Siena
  • Florence
  • More

Drive 238 km, 3 hours 53 min

  • Piazza del Duomo, Pisa
  • Leaning Tower of Pisa
  • Walls of Lucca
  • Porta San Pietro
  • Piazza dell'Anfiteatro
  • More

On day 5 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 2 destinations, Pisa and Lucca. When you’re not sightseeing, take time to relax at your selected hotel in Florence, where you’ll be staying for 1 night.

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Siena allows for both. Start by heading to Piazza Del Duomo, Pisa. This iconic public square provides an insightful glimpse into the city's identity. Next, discover Leaning Tower Of Pisa, a breathtaking monument, promising a delightful encounter.

Continue your sightseeing with a visit to Mura Di Lucca, an underrated historical landmark. When you’re done, don’t forget to make a stop at the frequently visited Porta San Pietro. Round off your day at Piazza Dell'anfiteatro, another gem in Siena with awe-inspiring features to discover.

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 you explore more of Florence, 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.

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

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.

Celebrate another amazing day of your road trip adventure 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, begin at Central Market. This well-known food market is a popular place to see in the city.

On your last day in Italy, take time to indulge in shopping at Florence’s popular marketplace, Mercato Centrale. 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.

Treat yourself to a delicious dinner at Tijuana, an excellent option for tonight's dining. Looking for something different? Djària - American Bar offers a tantalizing alternative with its diverse menu. And don’t miss The Florence Irish Pub.

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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