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.

Immerse yourself in Ancona’s rich culture with today's sightseeing itinerary. Start your journey at Piazzale Michelangelo. This history-steeped observation deck is sure to ignite your curiosity. Next, dive into the photogenic features of Basilica Of Santa Croce In Florence, a must-visit church 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 Uffizi Gallery, an impressive art gallery. For a change of scene, check out Ponte Vecchio, known for its respected features. We also recommend visiting Piazza Della Signoria. This public square is a must for anyone looking to experience the city to the fullest.

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

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.

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.

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

Greet day 3 of your road trip in Italy with a smile and start your day with a hearty breakfast. You will return to Florence for your remaining 1 night in the city later today, but first, it’s time for some exploring! On the agenda for this day, you’ll find only the best things to see and do in Pisa and Lucca.

Discover a day packed with family-friendly attractions, romantic experiences, and scenic views in Florence. Begin your sightseeing with Santa Maria Della Spina. This underrated church is one of the top attractions in the city. Proceed to Piazza Del Duomo, Pisa, another must-visit attraction.

As you wander through the inviting streets of Florence, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to Leaning Tower Of Pisa. This world-famous monument is a traveler-favorite. Not far away, you’ll find Guinigi Tower, another key site on your sightseeing itinerary. San Michele In Foro is yet another highly recommended place to visit nearby, offering plenty to discover for curious travelers. Conclude your day at Mura Di Lucca and uncover why it's recognized as one of the city's most curiosity-inducing attractions.

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.

Don’t miss out on dining at Ditta Artigianale, a top-rated dining destination in Florence. If you're in the mood to try something new, consider Trattoria Da Burde, another top spot with a mouthwatering menu. You might also want to secure a reservation at Casa Toscana. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Florence this evening.

To truly maximize your evening out, consider visiting Bar 50 Rosso after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Bitter Bar, another bar with an inviting ambiance. Similarly, Archea Brewery also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

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.

Set out on a day brimming with family-friendly attractions, breathtaking views, and photo-friendly spots. Start at the locally appreciated Fortezza Medicea (siena), a breathtaking monument in Florence. Next, go to Fontebranda.

After visiting Fortezza Medicea (siena) and Fontebranda, have a stroll along Florence's streets and take in the local charm. Continue your sightseeing by heading to Siena Cathedral. This inviting church offers a unique experience. Piazza Del Campo is another noteworthy attraction worthwhile a visit. End your self-guided sightseeing tour on top with a visit to Pubblico Palace, one of the most breathtaking places to visit in Florence. If you still have some time left for sightseeing, we also recommend stopping by 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 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.

Enjoy a delicious meal at Enoteca I Terzi, a highly-rated dining destination in Siena. If you're eager to try something different, consider Ristorante Tar-Tufo, another top spot with a tantalizing menu. You might also want to secure a reservation at Antica Trattoria Papei. With a reputation for consistently satisfying customers, it’s an excellent 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.

Savor another day of unforgettable experiences 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.

Brace yourself for today’s incredible lineup of attractions in Siena, featuring fun adventures, scenic views, and picturesque spots. Start at Basilica Of San Francesco D'assisi, a notable church in the town. Then, head to Piazza Del Comune and soak in the ambiance of this romantic public square.

There are many interesting places to see in Siena, and when you are ready for more, go to Rocca Maggiore. This is one of the town’s most worthwhile symbolic spots of interest. After exploring the castle, visit the worthwhile Rocca Paolina. Not far away, you'll also find Perugia Cathedral. This church is a monumental highlight in Siena. Before wrapping up your self-guided sightseeing tour, head to Piazza Iv Novembre, a locally appreciated public square in the town.

At the end of the day, you will drive to Perugia, 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 Perugia, 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 Ristorante Settimo Sigillo, a popular restaurant in Perugia. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Perugia at Caffè Baglioni, 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 Bar Pellas. It’s yet another ideal choice to enhance your time in Perugia tonight.

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.

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 6 of your remarkable road trip in Italy. Today you will explore Urbino and San Vittore, 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 Ancona. You’ll stay here for 1 night.

Bring your curiosity for today’s adventure around Perugia. Some of the town’s most loved attractions await! Palazzo Ducale is the perfect place to start. This palace is one of the most captivating places to visit in Perugia. Next, head to Galleria Nazionale Delle Marche, a locally appreciated museum, known for its breathtaking features.

In between the sights, don’t hesitate to take small detours to explore local stores and eateries. When you’re ready to continue your adventure, head to Frasassi Caves. This awe-inspiring cave system is a highly recommended experience. Nearby, you'll also find San Vittore Alle Chiuse. Visit these for an interesting touch to your journey.

After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of your accommodation in Ancona. Ancona offers plenty of top-rated hotels for every travel budget. Take some time to relax before you go out again.

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

Treat yourself to a delightful dinner at Amarcord, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Bontà delle Marche? It's another excellent option with a diverse menu. Consider reserving a table at Ristorante Pizzeria Da Romano as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Ancona.

Cap off your dinner by heading to Alla Tazza D'oro, ideal for a leisurely evening with a drink in hand.

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