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

On day 2 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 Florence. In the evening, you’ll end up in Florence, where you will stay for 2 nights.

Prepare for a day full of fun adventures, romantic experiences, and breathtaking views. When you’re ready, kick off your sightseeing adventure at Piazzale Michelangelo. This astonishing observation deck is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Basilica Of Santa Croce In Florence, one of the city’s best highlights.

Next, check out Uffizi Gallery, one of the most famous places to see in Ancona. This art gallery is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, Ponte Vecchio. Wander around and soak in the history-steeped atmosphere this historical landmark offers. Then, head to Piazza Della Signoria, a top-rated public square that adds another dimension to your day.

When you’re done exploring for the day, you’ll drive to your hotel in Florence. Check in and spend some time relaxing before you head out to tour the city.

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.

Have a fantastic dining experience at Ristorante Oliviero 1962, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Di Poneta Novoli offers an enticing alternative with its varied menu. Additionally, Caffe San Firenze 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 Manifattura, known for its inviting atmosphere. Se·sto On Arno Rooftop Bar is another great option if you’re looking for a place to get the night started. Similarly, Il Vinile provides a great setting to enjoy the night away.

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

On day 3 of your road trip, you’ll start and end your day in Florence, where you'll stay for 1 night more.

Enjoy the perfect balance of relaxation and exploration in Florence today. One of the most underrated attractions included on the itinerary is Santa Maria Della Spina. This majestic church will help you start your sightseeing on top. Then, take a leisurely stroll to Piazza Del Duomo, Pisa and learn what makes this breathtaking public square unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the wondrous Leaning Tower Of Pisa. After exploring the monument, head to Guinigi Tower. This curiosity-inducing monument is a highlight in Florence. As your day continues, stop by San Michele In Foro, known for its breathtaking features. Lastly, don’t forget to check out the often recommended Mura Di Lucca. Enjoy exploring this incredible historical landmark at your own pace.

When you’re done exploring for the day, you’ll return to Florence and your accommodation.

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.

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.

Following your dinner, dive into the local bar culture at Bar 50 Rosso. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Bitter Bar, the perfect place for those looking to experience the best of the nightlife. Similarly, Archea Brewery provides excellent drinks and a great atmosphere, ensuring a memorable night out.

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

Experience an unparalleled adventure on day 4 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 2 vibrant destinations - Siena and Greti. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Siena. You will spend 1 night here for some well-deserved relaxation.

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 stunning monument is an up-and-coming place to see in Florence. Then, wander over to Fontebranda. If symbolic sites excite you, this historical landmark will be right up your alley. Nearby, you’ll also find Siena Cathedral. This visually striking 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 a spectacular 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 picture-perfect Pubblico Palace. Take a moment to appreciate the fascinating details of this beloved palace. Wrap up your self-guided tour of Florence's top attractions with a visit to Villa Calcinaia - Conti Capponi.

At the end of the day, you will drive to Siena, 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 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.

Dine in style at Enoteca I Terzi, a top recommendation for dinner tonight. Or, for a change of pace, Ristorante Tar-Tufo boasts a menu that's sure to impress. Also, be sure to check out Antica Trattoria Papei. Known as a local hotspot, it’s a great choice for tonight in Siena.

Continue the enjoyment post-dinner at Meet Life Cafè, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Maudit Pub offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out Bar Impero Siena. This bar is a favorite among both locals and visitors looking for a delightful evening out filled with laughter and fun.

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

Discover a day packed with family-friendly attractions, breathtaking views, and photo-friendly spots in Siena. Begin your sightseeing with Basilica Of San Francesco D'assisi. This well-known church is one of the top attractions in the town. Proceed to Piazza Del Comune, another must-visit attraction.

As you wander through the inviting streets of Siena, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to Rocca Maggiore. This locally appreciated castle is a traveler-favorite. Not far away, you’ll find Rocca Paolina, another key site on your sightseeing itinerary. Perugia Cathedral is yet another highly recommended place to visit nearby, offering plenty to discover for curious travelers. Conclude your day at Piazza Iv Novembre and uncover why it's recognized as one of the town's most frequently visited attractions.

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.

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

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.

Explore the vibrant nightlife at Tommi Bar after your meal, a hub for lively evenings and memorable moments. Or, head to Valentina for a great selection of flavorful drinks and a charming setting. Furthermore, Caffe Dal Perugino is perfect for those looking to extend their night with a touch of local flavor.

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

Embark on another extraordinary experience on day 6 of your road trip in Italy. Today, you will make 2 stops and experience some of the highlights of Urbino and San Vittore. At the end of the day, you will enjoy the comforts of a top-rated hotel in Ancona, which will be your home away from home for 1 night.

Today’s route brings family-friendly attractions, breathtaking views, and photo-friendly spots. The first attraction of today is Palazzo Ducale. This locally renowned palace is a historic place to see in Perugia. Continue your discovery at Galleria Nazionale Delle Marche, a picture-perfect museum with stories to tell.

As you stroll around Perugia, take in the distinct atmosphere and learn what makes this town so unique. Maximize your sightseeing with a visit to Frasassi Caves. This interesting cave system offers an awe-inspiring encounter with Perugia. Next, make your way to San Vittore Alle Chiuse to add another highlight to your day. Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day in Perugia.

When you’re done exploring for the day, you’ll drive to your hotel in Ancona. 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 Ancona. Enjoy a satisfying meal that will recharge you for tonight's adventures.

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

Extend your evening after a delightful meal by visiting Alla Tazza D'oro, which offers the perfect atmosphere for a night out.

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