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

Day 2 of your road trip will take you to the best attractions Florence has to offer. Cherish the 2 nights you have left in the city and use the provided itinerary to discover what to see in Florence.

Make time for Galleria Dell'accademia, a well-known art gallery that is worthwhile a visit in the city. Nearby, you’ll find Piazza Della Signoria, enchanting visitors with its noteworthy appeal. Continue your exploration at Ponte Vecchio. This historical landmark is one of the city’s most timeless 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 notable Basilica Of Santa Croce In Florence. Lastly, wrap up today’s self-guided sightseeing tour with a visit to Piazzale Michelangelo, a place of history-steeped interest in Florence.

Don’t forget to check out all the popular tours and experiences you can add to your travel plans in Italy. You can explore and select activities under each day of your itinerary.

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

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

Cap off your dinner by heading to Bar 50 Rosso, ideal for a leisurely evening with a drink in hand. Bitter Bar is another bar that offers an enjoyable setting. Similarly, Archea Brewery is also a popular place to go on a night out, perfect for relaxing and socializing.

Raise your glass to another unforgettable day in Italy!

On day 3 of your road trip, you’ll start and end your day in Florence, where you still have 1 night left. You'll spend part of the day exploring places of interest outside the immediate city, including Pisa and Lucca.

Continue your road trip and head to your next destination, Pisa. This car ride takes around 1 hour 16 min.

Spend your afternoon discovering Piazza Del Duomo, Pisa, a timeless public square known for its historic features. Next, continue your sightseeing at Leaning Tower Of Pisa, a globally renowned monument.

After soaking in Pisa’s unique atmosphere, jump into the car with a full heart and drive in the direction of your next destination: Lucca. Expect your car journey to take a minimum of 32 min. When you arrive in Lucca, it's time to take a break from the road.

Enjoy sightseeing at your own pace and allow yourself time to explore the beautiful surroundings. Take your self-guided tour to Guinigi Tower, an underrated monument that everyone visiting Lucca should see. Next, head to San Michele In Foro. This stunning church is one of the most increasingly popular attractions in the region.

If you're keen to see more, don’t miss out on Mura Di Lucca, a romantic historical landmark popular among locals as well as travelers.

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

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

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.

After enjoying a fulfilling meal, continue your evening at Gosh*, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Antico Caffè Del Moro - Art Bar Firenze offers a welcoming atmosphere for easing into the nightlife. Similarly, Quelo Bar provides an excellent environment for a relaxed and enjoyable evening.

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

Dive into day 4 of your remarkable road trip in Italy. Today you'll explore 2 destinations, including Siena and San Gimignano. At the end of the day, you’ll unwind at one of the finest accommodations in Siena, where you'll spend 2 nights.

Fasten your seatbelt and make your way to your next stop — Siena, home to many well-known sights in the region. Keep in mind that your travel time from Florence to Siena may take around 1 hour 12 min without traffic disruptions. Upon arrival in Siena, we highly recommend checking out some of the top attractions.

Spend your afternoon discovering Siena Cathedral, an interesting church known for its grand features. Next, continue your sightseeing at Piazza Del Campo, an impressive public square.

If you're starting to feel hungry, this is a great time for a break at a nearby restaurant or cafe. When you're ready for more, stop by Pubblico Palace and uncover the details of this respected palace.

Once you're ready to continue your road trip, it's time to buckle up and drive, eagerly anticipating your arrival in San Gimignano.

Our first attraction recommendation in San Gimignano is Parco Della Rocca, an up-and-coming park that draws attention for its romantic features. Spend some time soaking in the atmosphere before continuing to Sangimignano1300, a heritage-rich museum that stands out in the city.

Time flies when you're having fun! But don't forget to stop for a bit to eat and drink between your adventures. When you're rested and recharged, head to Piazza Del Duomo, an underrated public square that offers a unique experience.

At the end of the day, you will drive to Siena, where you'll have a room waiting for you at the perfect place to stay. Check in and enjoy some downtime.

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

Make sure to reserve a table at Enoteca I Terzi, an iconic dining spot in Siena. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Ristorante Tar-Tufo, a popular restaurant in Siena. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Antica Trattoria Papei, a hidden gem nestled in Siena. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Meet Life Cafè stands out as an excellent choice for a post-dinner cocktail. Alternatively, Maudit Pub offers an ideal atmosphere to enjoy the pleasures of the night. Bar Impero Siena is also a great option that provides a perfect setting for a relaxing evening.

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

On day 5 of your road trip, you’ll start and end your day in Siena, where you have 1 night left to stay.

Once you're ready to continue your road trip, it's time to buckle up and drive, eagerly anticipating your arrival in San Regolo. This drive usually takes around 36 min, without any stops or traffic disruptions.

Castello Di Brolio is a beloved castle we recommend visiting today. Discover its visually striking features before continuing your self-guided tour.

Once you're ready to continue your road trip, it's time to buckle up and drive, eagerly anticipating your arrival in Castellina in Chianti. This drive usually takes around 40 min, without any stops or traffic disruptions.

One of our top recommendations for your sightseeing is Tumulo Di Montecalvario. Spend some time admiring the respected features of the archeological site before you continue to your next stop. Then, head to Rocca Di Castellina In Chianti. This beloved castle is a traveler-favorite in the hamlet.

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

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 Siena, it's often a good idea to reserve a table in advance.

Savor the flavors at Osteria Quattro Venti, a top pick for dinner tonight. Alternatively, Fischi per Fiaschi beckons with its unique menu offerings. Also, consider Osteria da Divo. With its consistent customer satisfaction, it’s an excellent option for dining in Siena tonight.

Let the evening flow smoothly from dinner to drinks at Charlie Mixology Bar Di Aldinucci Riccardo, a top-rated bar in the area. For other recommendations, Bar Pinacoteca provides a perfect setting for rounding out your night with style and great drinks. Likewise, San Paolo Pub offers a memorable night with diverse drink options and excellent service.

Raise your glass to another unforgettable day in Italy!

On day 6 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 2 destinations, including Santa Maria degli Angeli and Perugia. When you’re not sightseeing, take time to relax at your chosen hotel in Florence, where you’ll be staying for 1 night.

Throughout the day, make sure to take breaks to appreciate the surroundings.

After soaking in Siena’s unique atmosphere, jump into the car with a full heart and drive in the direction of your next destination: Santa Maria degli Angeli. Expect your car journey to take a minimum of 1 hour 36 min. When you arrive in Santa Maria degli Angeli, it's time to take a break from the road.

Enjoy sightseeing at your own pace and allow yourself time to explore the beautiful surroundings. Take your self-guided tour to Basilica Of San Francesco D'assisi, a locally renowned church that everyone visiting Santa Maria degli Angeli should see. Next, head to Rocca Maggiore. This history-steeped castle is one of the most increasingly popular attractions in the region.

Embrace the thrill of the open road as you wave goodbye to Santa Maria degli Angeli and set your GPS to Perugia. While on the road, immerse yourself in your favorite road trip tunes or sample the sounds from a local radio station. This car ride usually takes around 34 min. Upon reaching Perugia, unwind, observe, and explore. The best things to do, see, and eat are waiting for you.

Enjoy sightseeing at your own pace and allow yourself time to explore the beautiful surroundings. Take your self-guided tour to The Fontana Maggiore, a locally appreciated monument that everyone visiting Perugia should see. Next, head to Piazza Iv Novembre. This history-steeped public square is one of the most increasingly popular attractions in the region.

If you're keen to see more, don’t miss out on Perugia Cathedral, a photogenic church popular among locals as well as travelers.

After soaking up all the sights on today's itinerary, you'll be ready to head to your accommodation in Florence. Florence offers plenty of top-rated hotels for every travel budget. Take some time to relax before you go 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.

Treat yourself to a wonderful meal at Tijuana, a top-rated dining spot in Florence. If you're in the mood for something new, try Djària - American Bar, another premier location with a delectable menu. You might also want to book a table at The Florence Irish Pub. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Florence.

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