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.

Today, you'll explore some of the most beautiful places in Florence, including an art gallery, a public square, a historical landmark, a church, an observation deck and much more! Start your day with a visit to Galleria Dell'accademia. This locally renowned art gallery is a must-visit in the city. When you’re ready for your next discovery, continue to Piazza Della Signoria, which may be one of the most romantic places you will experience today.

One of the best things about exploring Florence on a self-guided tour is that you set the pace. There’s plenty of time for detours and discovering hidden gems. When you’re ready for your next stop, make your way to Ponte Vecchio, an iconic historical landmark in the city. If you’re up for more discoveries, don’t forget to reserve some time for Uffizi Gallery and Basilica Of Santa Croce In Florence. End your day with a visit to Piazzale Michelangelo, a top-rated observation deck that’s sure to leave a lasting impression.

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.

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.

Have a fantastic dining experience at Ditta Artigianale, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Trattoria Da Burde offers an enticing alternative with its varied menu. Additionally, Casa Toscana is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Florence.

After enjoying a fulfilling meal, continue your evening at Bar 50 Rosso, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Bitter Bar offers a welcoming atmosphere for easing into the nightlife. Similarly, Archea Brewery provides an excellent environment for a relaxed and enjoyable evening.

As the day draws to a close, take a moment to unwind and prepare for the next exciting chapter of your road trip in in Italy.

Embark on another extraordinary experience on day 3 of your road trip in Italy. Today, you will make 2 stops and experience some of the highlights of Pisa and Lucca. 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 1 night.

Discover a day packed with family-friendly attractions, scenic views, and picturesque spots in Florence. Begin your sightseeing with Piazza Del Duomo, Pisa. This globally renowned public square is one of the top attractions in the city. Proceed to Leaning Tower Of Pisa, another must-visit attraction that enhances the city’s allure.

As you wander through the inviting streets of Florence, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to Mura Di Lucca. This frequently visited historical landmark is a traveler-favorite. Not far away, you’ll find Piazza Napoleone, another key site on your sightseeing itinerary. Conclude your day at Porta San Pietro and uncover why it's recognized as one of the city's most up-and-coming attractions.

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 dinnertime approaches, it's time to head out for a bite to eat in Siena. 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 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.

Keep the evening going at Meet Life Cafè, a great choice for enjoying the after-dinner hours with a drink. You could also go to Maudit Pub, which offers a similarly pleasant setting and great drinks. Another option is Bar Impero Siena, which provides an inviting environment for unwinding after a busy day out.

As the day draws to a close, take a moment to unwind and prepare for the next exciting chapter of your road trip in in Italy.

Dive into day 4 of your remarkable road trip in Italy. Today you will explore Siena and San Gimignano, where you will have the opportunity to experience all the top things to see and do. At the end of the day, you’ll unwind at one of the finest accommodations in Florence. You’ll stay here for 1 night.

Siena is brimming with adventures. Today’s wonderful stops include a monument, a public square, and a church. Begin your sightseeing adventure at the up-and-coming Tower Of Mangia. Just a short distance away is Piazza Del Campo, an enchanting public square that draws visitors from far and near.

Continue your journey to Siena Cathedral, one of the city’s most notable spots that you shouldn’t miss. Another great site to visit is the beloved Basilica Of San Domenico. Last up on today’s itinerary is a monument. Make your way to Fortezza Medicea (siena) for some final sightseeing. Each attraction will leave you with lasting memories and a deeper appreciation for the rich heritage of Siena.

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

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

Dine in style at Ristorante Buca Mario, a top recommendation for dinner tonight. Or, for a change of pace, Agricola Toscana boasts a menu that's sure to impress. Also, be sure to check out Eataly Firenze. Known as a local hotspot, it’s a great choice for tonight in Florence.

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.

Savor another day of unforgettable experiences in Italy!