5-Day Italy Self-Drive Road Trip With Itinerary from Florence to Siena and surrounding area

Day 2 of your road trip will take you to the best attractions Florence has to offer. Cherish the 1 night you have left in Florence by discovering the best things there are to see and do in the city.

Get ready for an exciting day in Florence. Today’s sightseeing agenda includes a church, a public square, a historical landmark, an art gallery, an observation deck and much more! Begin your adventure at Cathedral Of Santa Maria Del Fiore. This is a famous church you should not miss. Another must-see is Piazza Della Signoria, an impressive public square in Florence.

When you’re ready for the next sight, head to Ponte Vecchio. From there, take a leisurely stroll to Uffizi Gallery, another of the city’s astonishing attractions. We recommend ending your self-guided tour of the city with an enchanting observation deck. Piazzale Michelangelo is a truly remarkable place to visit in Florence.

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 Via de' Tornabuoni. Take a leisurely stroll through unique boutiques and high-end shops, where local treasures are waiting to be found. Beyond shopping, Via de' Tornabuoni offers more options, including unique attractions, key services, and vibrant events.

After a long day of exploring, sit down for a delicious dinner at a top-rated restaurant in Florence. Enjoy a satisfying meal that will recharge you for tonight's adventures.

Enjoy a lovely meal at Ditta Artigianale, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Trattoria Da Burde is another top choice with a popular menu. You could also check for a table at Casa Toscana. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Florence tonight.

Extend your evening after a delightful meal by visiting Bar 50 Rosso, which offers the perfect atmosphere for a night out. Moreover, Bitter Bar is another popular option for a drink or two. Likewise, Archea Brewery also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

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

On day 3 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 Siena, where you’ll be staying for 1 night.

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

Begin your journey at Piazza Del Duomo, Pisa and explore the stunning features. Next, make your way to Leaning Tower Of Pisa, another highlight in the city.

Lucca’s wonders await as you prepare for another journey on the road, leaving the breathtaking surroundings of Pisa behind. This drive usually takes around 31 min. Lucca welcomes you with a multitude of unique vacation experiences.

Your self-guided tour starts at Mura Di Lucca, an underrated historical landmark that is sure to impress. Take in the surroundings and enjoy the freedom of exploring before you continue your journey. Next, head to Piazza Napoleone and admire its romantic features. When you’re ready, continue to Piazza Dell'anfiteatro, a captivating public square beloved by locals and tourists alike.

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.

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

Enjoy a lovely dining experience at Enoteca I Terzi, a popular restaurant in Siena. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Siena at Ristorante Tar-Tufo, 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 Antica Trattoria Papei. It’s yet another ideal choice to enhance your time in Siena tonight.

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!

Experience an unparalleled adventure on day 4 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 2 vibrant destinations - Siena and San Gimignano. 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 route brings family-friendly attractions, romantic experiences, and breathtaking views. The first attraction of today is Piazza Del Campo. This widely recognized public square is an enchanting place to see in Siena. Continue your discovery at Siena Cathedral, a romantic church with stories to tell.

As you stroll around Siena, take in the distinct atmosphere and learn what makes this city so unique. Maximize your sightseeing with a visit to Basilica Of San Domenico. This underrated church offers a culturally significant encounter with Siena. Fortezza Medicea (siena) is the last of our recommendations for today. Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day in Siena.

As you’ve unraveled the marvels of Siena, it’s time to gear up for the next part of your road trip adventure. Under favorable conditions, your drive to San Gimignano may take around 50 min. Upon your arrival in San Gimignano, you’ll be greeted with the opportunity to do some sightseeing and exploring.

Spend your afternoon discovering Piazza Del Duomo, a curiosity-inducing public square known for its enchanting features.

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

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.

Make sure to reserve a table at Ristorante Buca Mario, an iconic dining spot in Florence. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Agricola Toscana, a popular restaurant in Florence. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Eataly Firenze, a hidden gem nestled in Florence. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Cap off your dinner by heading to Gosh*, ideal for a leisurely evening with a drink in hand. Antico Caffè Del Moro - Art Bar Firenze is another bar that offers an enjoyable setting. Similarly, Quelo Bar 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!