7-Day Italy Self-Drive Road Trip With Itinerary from Ancona to Florence, Siena, and Perugia

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

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Ancona allows for both. Start by heading to Piazzale Michelangelo. This top-rated observation deck provides an insightful glimpse into the city's identity. Next, discover Basilica Of Santa Croce In Florence, a culturally significant church, promising a delightful encounter.

Continue your sightseeing with a visit to Uffizi Gallery, an impressive art gallery. When you’re done, don’t forget to make a stop at the globally renowned Ponte Vecchio. Round off your day at Piazza Della Signoria, another gem in Ancona with culturally significant features to discover.

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 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.

Make sure to reserve a table at Ristorante Oliviero 1962, 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 Di Poneta Novoli, 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 Caffe San 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.

After your meal, keep the night alive at a bar like Manifattura, known for its lively atmosphere. Se·sto On Arno Rooftop Bar is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Il Vinile offers an excellent atmosphere for those looking to amp up the evening.

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

On day 3 of your road trip in Italy, you’ll start and end your day in Florence, but spend the day exploring what’s beyond the city. Since you will return to Florence for 1 night more, there’s no need to rush. Experience Pisa and Lucca to the fullest today with this curated day itinerary!

Today's adventure in Florence promises more breathtaking discoveries and enriching experiences! Begin at Santa Maria Della Spina. This history-steeped church is a highlight of any visit in the city. Then, enjoy Piazza Del Duomo, Pisa, another UNESCO world heritage-listed attraction that never fails to captivate visitors. Next, head over to Leaning Tower Of Pisa, one of the city’s most iconic attractions, known for its UNESCO world heritage-designated features.

If you’re looking for more, spend time soaking in the atmosphere of Guinigi Tower. This enchanting monument is frequented by locals and tourists alike. To complete your memorable day, make sure to visit San Michele In Foro, a locally appreciated church, and take a stroll around the area. If you want to extend your self-guided sightseeing tour, go check out Mura Di Lucca before you head back to your hotel.

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

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

Make sure to reserve a table at Ditta Artigianale, 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 Trattoria Da Burde, 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 Casa Toscana, a hidden gem nestled in Florence. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

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.

Relax and recharge in preparation for another adventurous day in Italy!

On day 4 of your road trip in Italy, you will get a true taste of the freedom a self-drive vacation in Europe entails. Today’s travel plans include stops at the most scenic, wondrous, and interesting places in Siena and Greti. In the evening, you’ll end up in Siena, where you will stay for 1 night.

Today’s route brings family-friendly attractions, scenic views, and picturesque spots. The first attraction of today is Fortezza Medicea (siena). This intriguing monument is a historic place to see in Florence. Continue your discovery at Fontebranda, a heritage-rich historical landmark with stories to tell.

As you stroll around Florence, take in the distinct atmosphere and learn what makes this city so unique. Maximize your sightseeing with a visit to Siena Cathedral. This locally renowned church offers a visually striking encounter with Florence. Next, make your way to Piazza Del Campo to add another highlight to your day. After that, visit Pubblico Palace, an increasingly popular palace that’s sure to impress. If you’re up for more, end your self-guided sightseeing tour at Villa Calcinaia - Conti Capponi, a locally appreciated winery in the city. Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day in Florence.

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.

Enjoy a delicious meal at Enoteca I Terzi, a top-rated dining destination in Siena. If you're in the mood to try something new, consider Ristorante Tar-Tufo, another top spot with a mouthwatering menu. You might also want to secure a reservation at Antica Trattoria Papei. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Siena this evening.

Cap off your dinner by heading to Meet Life Cafè, ideal for a leisurely evening with a drink in hand. Maudit Pub is another bar that offers an enjoyable setting. Similarly, Bar Impero Siena is also a popular place to go on a night out, perfect for relaxing and socializing.

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 5 of your remarkable road trip in Italy. Today you will explore Santa Maria degli Angeli and Perugia, 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 Perugia. You’ll stay here for 1 night.

Bring your curiosity for today’s adventure around Siena. Some of the town’s most loved attractions await! Basilica Of San Francesco D'assisi is the perfect place to start. This church is one of the most captivating places to visit in Siena. Next, head to Piazza Del Comune, a frequently visited public square, known for its enchanting features.

In between the sights, don’t hesitate to take small detours to explore local stores and eateries. When you’re ready to continue your adventure, head to Rocca Maggiore. This culturally significant castle is a highly recommended experience. Nearby, you'll also find Rocca Paolina and Perugia Cathedral. Visit these for an interesting touch to your journey. Finish the day with a visit to Piazza Iv Novembre, a visually striking public square in Siena.

At the end of the day, you will drive to Perugia, 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 Perugia's best restaurants.

Don’t miss out on dining at Ristorante Settimo Sigillo, a top-rated dining destination in Perugia. If you're in the mood to try something new, consider Caffè Baglioni, another top spot with a mouthwatering menu. You might also want to secure a reservation at Bar Pellas. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Perugia this evening.

Continue your lively evening at Tommi Bar, a perfect place for winding down or revving up the night, depending on which mood you’re in. Valentina is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Caffe Dal Perugino ensures a night out tailored to your taste.

Celebrate another amazing day of your road trip adventure in Italy!

On day 6 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 2 destinations, Urbino and San Vittore. When you’re not sightseeing, take time to relax at your selected hotel in Ancona, where you’ll be staying for 1 night.

Perugia is brimming with adventures. Today’s wonderful stops include a palace, a museum, a cave system, a church and much more! Begin your sightseeing adventure at the well-known Palazzo Ducale and allow yourself time to explore. Just a short distance away you'll find your next stop, Galleria Nazionale Delle Marche, an UNESCO world heritage-listed museum that draws visitors from far and near.

Continue your journey to Frasassi Caves, one of the town’s most notable spots that you shouldn’t miss. Another great site to visit is the frequently visited San Vittore Alle Chiuse.

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

As you explore more of Ancona, 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.

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

After enjoying a fulfilling meal, continue your evening at Alla Tazza D'oro, ideal for those looking to unwind with a drink in a comfortable setting.

Head back to your accommodation in Ancona and get some rest in preparation for another magical day of your road trip in Italy!