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

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!

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!

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!

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!