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

Dive into day 2 of your remarkable road trip in Italy. Today you will explore Florence, 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 2 nights.

Today’s well-planned self-sightseeing route offers several fun adventures, romantic experiences, and scenic views. Whether you decide to explore Ancona on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss. The Boboli Gardens is the first of them. Spend some time admiring this romantic botanical garden before continuing your journey. Ponte Vecchio is your next stop. This world-famous historical landmark is one of the best-rated sights in Ancona.

Consider grabbing some lunch or a light snack to keep your energy going. Beyond the above-mentioned attractions, today is also the perfect time to visit Basilica Of Santa Croce In Florence. This heritage-rich church is a sight to behold. To round off your sightseeing experience, visit Uffizi Gallery and Piazza Della Signoria.

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.

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.

Dine in style at Ristorante Oliviero 1962, a top recommendation for dinner tonight. Or, for a change of pace, Di Poneta Novoli boasts a menu that's sure to impress. Also, be sure to check out Caffe San Firenze. Known as a local hotspot, it’s a great choice for tonight in Florence.

Unwind after your meal by stepping into Manifattura. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Se·sto On Arno Rooftop Bar offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Il Vinile, another top-rated bar in the area.

Raise your glass and celebrate another amazing day of your road trip 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.

Today’s route brings family-friendly attractions, breathtaking views, and picturesque spots. The first attraction of today is Piazza Del Duomo, Pisa. This iconic public square is a culturally significant place to see in Florence. Continue your discovery at Leaning Tower Of Pisa, a breathtaking monument 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 Piazza Dell'anfiteatro. This popular public square offers an enchanting encounter with Florence. Guinigi Tower 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 Florence.

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

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

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 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.

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

Embark on another extraordinary experience on day 4 of your road trip in Italy. Today, you will make 2 stops and experience some of the highlights of Siena and Greti. 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.

Today’s route brings fun adventures, breathtaking views, and photo-friendly spots. The first attraction of today is Fortezza Medicea (siena). This up-and-coming monument is a historic place to see in Florence. Continue your discovery at Tower Of Mangia, a picture-perfect monument 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 Piazza Del Campo. This famous public square offers a romantic encounter with Florence. Pubblico Palace 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 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.

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

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.

To truly maximize your evening out, consider visiting Meet Life Cafè after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Maudit Pub, another bar with an inviting ambiance. Similarly, Bar Impero Siena also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

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.

Experience an unparalleled adventure on day 5 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 2 vibrant destinations - Santa Maria degli Angeli and Perugia. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Perugia. You will spend 1 night here for some well-deserved relaxation.

Savor the day by visiting some of the best places to see in Siena, including a church, a castle, a historical landmark, a public square and much more! Start your adventure at Basilica Of San Francesco D'assisi. This notable church is a must-visit for travelers looking for a unique holiday experience. Make your way to Rocca Maggiore located in Siena for an enchanting atmosphere.

Next, immerse yourself in the setting of Basilica Di Santa Chiara. Its awe-inspiring features will captivate you. After the church, continue your tour of the town with a visit to Rocca Paolina. This historical landmark has a photogenic appeal. For a change of pace, head to Perugia Cathedral. As one of the most worthwhile attractions in Siena, this church is an excellent place to end your self-guided tour.

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.

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.

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.

After enjoying a fulfilling meal, continue your evening at Tommi Bar, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Valentina offers a welcoming atmosphere for easing into the nightlife. Similarly, Caffe Dal Perugino provides an excellent environment for a relaxed and enjoyable evening.

Head back to your accommodation in Perugia and get some rest in preparation for another magical day of your road trip 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.

Today’s agenda in Perugia includes a museum, a palace, and a cave system. Casa Santi is must-visit museum and a great starting point for the day. Next, continue your journey to Galleria Nazionale Delle Marche, an intriguing museum, located just a leisurely stroll away. Next, head to Palazzo Ducale, an UNESCO world heritage-listed palace, also available for your discovery today.

Each stop on today’s itinerary promises to leave you with lasting memories and a deeper appreciation for Perugia. If you’re looking for more, Frasassi Caves is also a notable attraction that is worthwhile a visit.

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.

Enjoy a lovely dining experience at Amarcord, a popular restaurant in Ancona. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Ancona at Bontà delle Marche, 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 Ristorante Pizzeria Da Romano. It’s yet another ideal choice to enhance your time in Ancona tonight.

Continue your evening by exploring the vibrant nightlife scene at Alla Tazza D'oro, a prime destination for a thrilling night out.

Get a good night's sleep and look forward to another great day on the road in Italy!