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

Experience an unparalleled adventure on day 2 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 vibrant destinations - Florence. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Florence. You will spend 2 nights here for some well-deserved relaxation.

Today’s agenda in Ancona includes an observation deck, a church, an art gallery, a historical landmark, a public square and much more! Piazzale Michelangelo is must-visit observation deck and a great starting point for the day. Next, continue your journey to Basilica Of Santa Croce In Florence, a notable church, located just a leisurely stroll away. Next, head to Uffizi Gallery, a romantic art gallery, also available for your discovery today.

Each stop on today’s itinerary promises to leave you with lasting memories and a deeper appreciation for Ancona. When you're ready, let your sightseeing route take you to the wondrous Ponte Vecchio. If you’re looking for more, Piazza Della Signoria is also an astonishing attraction that is worthwhile a visit.

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.

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.

Savor the flavors at Ristorante Oliviero 1962, a top pick for dinner tonight. Alternatively, Di Poneta Novoli beckons with its unique menu offerings. Also, consider Caffe San Firenze. With its consistent customer satisfaction, it’s an excellent option for dining in Florence tonight.

Keep the evening going at Manifattura, a great choice for enjoying the after-dinner hours with a drink. You could also go to Se·sto On Arno Rooftop Bar, which offers a similarly pleasant setting and great drinks. Another option is Il Vinile, which provides an inviting environment for unwinding after a busy day out.

As the sun sets on another day of adventure, rest up and recharge for the next leg of your road trip in Italy.

Wake up to day 3 of your extraordinary road trip in Italy. With 1 night left in Florence, we encourage you to seize the day and discover the unexplored beauty of the city’s surroundings!

Florence is home to plenty of attractions that offer family-friendly attractions, romantic experiences, and scenic views! Start at Santa Maria Della Spina, an increasingly popular church that is worthwhile a visit in the city. Nearby, you’ll find Piazza Del Duomo, Pisa, enchanting visitors with its stunning appeal. Continue your exploration at Leaning Tower Of Pisa. This monument is one of the city’s most globally renowned 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 Guinigi Tower. After exploring the monument, head to the beloved San Michele In Foro. Lastly, wrap up today’s self-guided sightseeing tour with a visit to Mura Di Lucca, a place of enchanting interest in Florence.

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

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.

Savor the flavors at Ditta Artigianale, a top pick for dinner tonight. Alternatively, Trattoria Da Burde beckons with its unique menu offerings. Also, consider Casa Toscana. With its consistent customer satisfaction, it’s an excellent option for dining 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.

Savor another day of unforgettable experiences in Italy!

Dive into day 4 of your remarkable road trip in Italy. Today you will explore Siena and Greti, 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 Siena. You’ll stay here for 1 night.

Today’s route brings family-friendly attractions, scenic views, and photo-friendly spots. The first attraction of today is Fortezza Medicea (siena). This frequently visited monument is a picture-perfect place to see in Florence. Continue your discovery at Fontebranda, a photogenic 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 notable church offers a history-steeped encounter with Florence. Next, make your way to Piazza Del Campo to add another highlight to your day. After that, visit Pubblico Palace, a locally appreciated palace that’s sure to impress. If you’re up for more, end your self-guided sightseeing tour at Villa Calcinaia - Conti Capponi, an up-and-coming 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.

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

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.

Following your dinner, dive into the local bar culture at Meet Life Cafè. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Maudit Pub, the perfect place for those looking to experience the best of the nightlife. Similarly, Bar Impero Siena provides excellent drinks and a great atmosphere, ensuring a memorable night out.

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

On day 5 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 2 destinations, Santa Maria degli Angeli and Perugia. When you’re not sightseeing, take time to relax at your selected hotel in Perugia, where you’ll be staying for 1 night.

Today’s itinerary in Siena covers several incredible sights, including a church, a public square, a castle, a historical landmark and much more! Start your adventure at Basilica Of San Francesco D'assisi. This notable church is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the visually striking wonders of Piazza Del Comune, a must-see public square in the town.

Consider stopping for a small bite to eat or a drink at a local eatery to keep your energy going. When you’re ready, continue your discovery with a visit to Rocca Maggiore. This up-and-coming castle offers an enriching experience. For a change of pace, head to Rocca Paolina, where you can take in eye-catching features. Conclude your self-guided sightseeing tour with a visit to Perugia Cathedral and Piazza Iv Novembre. These sights offer a fulfilling end to a perfect day.

When you’re done exploring for the day, you’ll drive to your hotel in Perugia. 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 Perugia. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.

Make sure to reserve a table at Ristorante Settimo Sigillo, an iconic dining spot in Perugia. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Caffè Baglioni, a popular restaurant in Perugia. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Bar Pellas, a hidden gem nestled in Perugia. 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, Tommi Bar stands out as an excellent choice for a post-dinner cocktail. Alternatively, Valentina offers an ideal atmosphere to enjoy the pleasures of the night. Caffe Dal Perugino is also a great option that provides a perfect setting for a relaxing evening.

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

On day 6 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 Urbino and San Vittore. In the evening, you’ll end up in Ancona, where you will stay for 1 night.

Start by visiting Palazzo Ducale, a prime spot to begin your journey. This breathtaking palace is sure to impress. Next on your list is Galleria Nazionale Delle Marche, another must-visit landmark and frequently visited museum renowned for its picture-perfect features.

While exploring and sightseeing, take time to savor the culture of Perugia by sampling some local delicacies. When you’re ready for more sightseeing, head to Frasassi Caves. This instagrammable cave system is an essential place to visit for anyone looking for the full Perugia experience. We also recommend visiting San Vittore Alle Chiuse, an often recommended church.

At the end of the day, you will drive to Ancona, 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 Ancona's most popular restaurants, and connect with friendly locals for an authentic adventure.

Enjoy a delicious meal at Amarcord, a highly-rated dining destination in Ancona. If you're eager to try something different, consider Bontà delle Marche, another top spot with a tantalizing menu. You might also want to secure a reservation at Ristorante Pizzeria Da Romano. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Ancona this evening.

After your meal, keep the night alive at a bar like Alla Tazza D'oro, known for its lively atmosphere.

Raise your glass to another unforgettable day in Italy!