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

On day 2 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, Florence. When you’re not sightseeing, take time to relax at your selected hotel in Florence, where you’ll be staying for 2 nights.

Savor the day by visiting some of the best places to see in Ancona, including an observation deck, a church, an art gallery, a historical landmark, a public square and much more! Start your adventure at Piazzale Michelangelo. This widely recognized observation deck is a must-visit for travelers looking for a unique holiday experience. Make your way to Basilica Of Santa Croce In Florence located in Ancona for another exciting encounter.

Next, immerse yourself in the setting of Uffizi Gallery. Its standout features will captivate you. After the art gallery, continue your tour of the city with a visit to Ponte Vecchio. Visitors usually appreciate the visually striking features of this historical landmark. Next up is Piazza Della Signoria, a highly recommended public square.

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.

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

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.

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.

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.

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

Immerse yourself in Florence’s rich culture with today's sightseeing itinerary. Start your journey at Santa Maria Della Spina. This romantic church is sure to ignite your curiosity. Next, dive into the historic features of Piazza Del Duomo, Pisa, a must-visit public square in the city.

In between sights, stop by local stores, picturesque photo spots, and small eateries. When you’re ready for your next attraction, proceed to Leaning Tower Of Pisa, a timeless monument. For a change of scene, check out Guinigi Tower, known for its culturally significant features. We also recommend visiting San Michele In Foro. This church is a must for anyone looking to experience the city to the fullest. Lastly, end your day with a visit to Mura Di Lucca, yet another often recommended attraction in Florence.

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.

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.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Bar 50 Rosso, known for its inviting atmosphere. Bitter Bar is another great option if you’re looking for a place to get the night started. Similarly, Archea Brewery provides a great setting to enjoy the night away.

Relax and reminisce about your day in Italy and look forward to more memorable moments to come!

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.

Get ready to discover some of the most iconic wonders in Florence, including a monument, a historical landmark, a church, a public square, a palace, a winery and much more! Start your day at Fortezza Medicea (siena). This picture-perfect monument is an up-and-coming place to see in Florence. Then, wander over to Fontebranda. If culturally significant sites excite you, this historical landmark will be right up your alley. Nearby, you’ll also find Siena Cathedral. This symbolic church is a favorite among visitors.

Florence offers plenty to explore, ensuring every moment of your visit is filled with excitement and discovery. If you're up for more, Piazza Del Campo is an extraordinary spot in the city that will captivate you with its unique charm. When you’re done at the public square, don’t forget to check out the culturally significant Pubblico Palace. Take a moment to appreciate the fascinating details of this increasingly popular palace. Wrap up your self-guided tour of Florence's top attractions with a visit to Villa Calcinaia - Conti Capponi.

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.

Don’t miss out on dining 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.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Meet Life Cafè, known for its inviting atmosphere. Maudit Pub is another great option if you’re looking for a place to get the night started. Similarly, Bar Impero Siena provides a great setting to enjoy the night away.

Take some time to reflect on your day and savor another beautiful night in Italy.

Embark on another extraordinary experience on day 5 of your road trip in Italy. Today, you will make 2 stops and experience some of the highlights of Santa Maria degli Angeli and Perugia. At the end of the day, you will enjoy the comforts of a top-rated hotel in Perugia, which will be your home away from home for 1 night.

Prepare for a day full of fun adventures, breathtaking views, and picturesque spots. When you’re ready, kick off your sightseeing adventure at Basilica Of San Francesco D'assisi. This notable church is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Piazza Del Comune, one of the town’s best highlights.

Next, check out Rocca Maggiore, one of the most curiosity-inducing places to see in Siena. This castle is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, Rocca Paolina. Wander around and soak in the heritage-rich atmosphere this historical landmark offers. Then, head to Perugia Cathedral, a top-rated church that adds another dimension to your day. Finally, visit the often recommended Piazza Iv Novembre, the last of our attraction recommendations for today.

After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of your accommodation in Perugia. Perugia 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 Perugia. Enjoy a satisfying meal that will recharge you for tonight's adventures.

Enjoy a lovely meal at Ristorante Settimo Sigillo, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Caffè Baglioni is another top choice with a popular menu. You could also check for a table at Bar Pellas. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Perugia tonight.

Round off your dining experience by visiting Tommi Bar, a prime location for a drink. Alternatively, explore the distinctive characteristics of Valentina, a bar catering to every mood and preference. Caffe Dal Perugino likewise offers a unique atmosphere, perfect for a memorable night out.

Savor another day of unforgettable experiences in Italy!

Experience an unparalleled adventure on day 6 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 2 vibrant destinations - Urbino and San Vittore. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Ancona. You will spend 1 night here for some well-deserved relaxation.

Discover a day packed with family-friendly attractions, scenic views, and photo-friendly spots in Perugia. Begin your sightseeing with Palazzo Ducale. This locally renowned palace is one of the top attractions in the town. Proceed to Galleria Nazionale Delle Marche, another must-visit attraction.

As you wander through the inviting streets of Perugia, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to Frasassi Caves. This well-known cave system is a traveler-favorite. Not far away, you’ll find San Vittore Alle Chiuse, another key site on your sightseeing itinerary.

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.

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.

Dine in style at Amarcord, a top recommendation for dinner tonight. Or, for a change of pace, Bontà delle Marche boasts a menu that's sure to impress. Also, be sure to check out Ristorante Pizzeria Da Romano. Known as a local hotspot, it’s a great choice for tonight in Ancona.

Explore the vibrant nightlife at Alla Tazza D'oro after your meal, a hub for lively evenings and memorable moments.

Raise your glass to another unforgettable day in Italy!