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.

Enjoy the perfect balance of relaxation and exploration in Ancona today. One of the most top-rated attractions included on the itinerary is Piazzale Michelangelo. This enchanting observation deck will help you start your sightseeing on top. Then, take a leisurely stroll to Basilica Of Santa Croce In Florence and learn what makes this culturally significant church unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the extraordinary Uffizi Gallery. After exploring the art gallery, head to Ponte Vecchio. This timeless historical landmark is a highlight in Ancona. As your day continues, stop by Piazza Della Signoria, known for its romantic features.

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

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.

Continue the enjoyment post-dinner at Manifattura, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Se·sto On Arno Rooftop Bar offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out Il Vinile. This bar is a favorite among both locals and visitors looking for a delightful evening out filled with laughter and fun.

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, where you'll stay for 1 night more.

Get ready for a day filled with family-friendly attractions, romantic experiences, and scenic views in the charming city of Florence. Your adventure starts at Santa Maria Della Spina, an underrated local hot spot. Another notable attraction to explore is Piazza Del Duomo, Pisa. This timeless public square is known for its grand appeal.

After soaking in the highlights of these sights, take some time to wander Florence's streets and immerse yourself in the local atmosphere. When you're ready to continue your sightseeing adventure, head to Leaning Tower Of Pisa. This historic monument offers a fascinating experience that many visitors find memorable. Guinigi Tower is also worth visiting, along with San Michele In Foro. These standout landmarks offer unique experiences that add to the day’s enjoyment. End your day at Mura Di Lucca. This frequently visited historical landmark provides a fitting finale to your sightseeing.

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.

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.

Continue your evening by exploring the vibrant nightlife scene at Bar 50 Rosso, a prime destination for a thrilling night out. Also, don’t forget to check out Bitter Bar, a bar that offers unique local touches. Likewise, Archea Brewery provides an excellent alternative for a fun evening.

Raise your glass and celebrate another amazing day of your road trip in Italy!

On day 4 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 2 destinations, Siena and Greti. When you’re not sightseeing, take time to relax at your selected hotel in Siena, where you’ll be staying for 1 night.

Today’s route brings family-friendly attractions, breathtaking views, and picturesque spots. The first attraction of today is Fortezza Medicea (siena). This curiosity-inducing monument is an awe-inspiring 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 captivating church offers an inviting encounter with Florence. Next, make your way to Piazza Del Campo to add another highlight to your day. After that, visit Pubblico Palace, a curiosity-inducing palace that’s sure to impress. If you’re up for more, end your self-guided sightseeing tour at Villa Calcinaia - Conti Capponi, a beloved 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 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.

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 savoring a delicious meal, step into the vibrant nightlife at Meet Life Cafè, where the evening is just getting started. In the same way, Maudit Pub offers a unique charm perfect for experiencing the local bar scene in Siena. Bar Impero Siena is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

Raise your glass to another unforgettable day 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.

Get ready for a day filled with family-friendly attractions, scenic views, and photo-friendly spots in the charming town of Siena. Your adventure starts at Basilica Of San Francesco D'assisi, a captivating local hot spot. Another notable attraction to explore is Piazza Del Comune. This beloved public square is known for its majestic appeal.

After soaking in the highlights of these sights, take some time to wander Siena's streets and immerse yourself in the local atmosphere. When you're ready to continue your sightseeing adventure, head to Rocca Maggiore. This romantic castle offers a fascinating experience that many visitors find memorable. Rocca Paolina is also worth visiting, along with Perugia Cathedral. These standout landmarks offer unique experiences that add to the day’s enjoyment. End your day at Piazza Iv Novembre. This frequently visited public square provides a fitting finale to your sightseeing.

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.

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

Enjoy a delicious meal 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.

Say good night to Perugia and look forward to another great day of your road trip 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.

Set out on a day brimming with fun adventures, breathtaking views, and picturesque spots. Start at the popular Palazzo Ducale, a picture-perfect palace in Perugia. Next, go to Galleria Nazionale Delle Marche.

After visiting Palazzo Ducale and Galleria Nazionale Delle Marche, have a stroll along Perugia's streets and take in the local charm. Continue your sightseeing by heading to Frasassi Caves. This stunning cave system offers a unique experience. San Vittore Alle Chiuse is another noteworthy attraction 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.

Treat yourself to a wonderful meal at Amarcord, a top-rated dining spot in Ancona. If you're in the mood for something new, try Bontà delle Marche, another premier location with a delectable menu. You might also want to book a table at Ristorante Pizzeria Da Romano. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Ancona.

Following your dinner, dive into the local bar culture at Alla Tazza D'oro. Enjoy this evening's relaxed ambiance with delightful drinks.

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