Two-Week Italy Self-Drive Road Trip With Itinerary from Ancona traveling west to Florence, Siena, Rome, Sorrento, 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 3 nights.

Today’s well-planned self-sightseeing route offers several fun adventures, romantic experiences, and breathtaking 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. Piazzale Michelangelo is the first of them. Spend some time admiring this enchanting observation deck before continuing your journey. Galleria Dell'accademia is your next stop. This captivating art gallery 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 Central Market. This instagrammable food market is a sight to behold. To round off your sightseeing experience, visit Basilica Di Santa Maria Novella, Firenze (fi).

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.

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

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.

Continue your evening by exploring the vibrant nightlife scene at Manifattura, a prime destination for a thrilling night out. Also, don’t forget to check out Se·sto On Arno Rooftop Bar, a bar that offers unique local touches. Likewise, Il Vinile provides an excellent alternative for a fun evening.

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

Day 3 of your road trip will take you to the best attractions Florence has to offer. Cherish the 2 nights you have left in Florence by discovering the best things there are to see and do in the city.

Florence is home to plenty of attractions that offer family-friendly attractions, romantic experiences, and scenic views! Start at Cathedral Of Santa Maria Del Fiore, an impressive church that is worthwhile a visit in the city. Nearby, you’ll find Ponte Vecchio, enchanting visitors with its history-steeped appeal. Continue your exploration at Uffizi Gallery. This art gallery is one of the city’s most impressive spots.

Enjoy the freedom of exploring Florence at your own pace and find hidden gems along the way. If you want to see more picture-perfect spots, make sure to visit Palazzo Vecchio. After exploring the palace, head to the astonishing Piazza Della Signoria. Lastly, wrap up today’s self-guided sightseeing tour with a visit to Basilica Of Santa Croce In Florence, a place of heritage-rich interest in Florence.

Don’t forget to check out all the popular tours and activities you can add to your road trip itinerary. Italy is a beautiful travel destination that offers plenty of unique tours that will enhance your vacation experience. Explore and select your activities below.

As you are wrapping up for the day, treat yourself to a satisfying dinner at a nice restaurant in Florence. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.

Enjoy a lovely dining experience at Ditta Artigianale, a popular restaurant in Florence. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Florence at Trattoria Da Burde, 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 Casa Toscana. It’s yet another ideal choice to enhance your time in Florence tonight.

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.

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

At the end of the day, you'll drive back to Florence, where you'll stay for 1 night more.

Discover a day packed with fun adventures, scenic views, and picturesque spots in Florence. Begin your sightseeing with Piazza Del Duomo, Pisa. This iconic public square is one of the top attractions in the city. Proceed to Pisa Cathedral, 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 Angelo Caduto. This intriguing sightseeing destination is a traveler-favorite. Not far away, you’ll find Leaning Tower Of Pisa, another key site on your sightseeing itinerary.

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

As you are wrapping up for the day, treat yourself to a satisfying dinner at a nice restaurant in Florence. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.

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

Explore the vibrant nightlife at Gosh* after your meal, a hub for lively evenings and memorable moments. Or, head to Antico Caffè Del Moro - Art Bar Firenze for a great selection of flavorful drinks and a charming setting. Furthermore, Quelo Bar is perfect for those looking to extend their night with a touch of local flavor.

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

On day 6 of your road trip, you’ll start and end your day in Siena, where you'll stay for 1 night more.

Bring your curiosity for today’s adventure around Siena. Some of the village’s most loved attractions await! Antinori Nel Chianti Classico is the perfect place to start. This winery is one of the most frequently visited places to visit in Siena. Next, head to Castle Of Verrazzano, an intriguing castle, known for its awe-inspiring 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 Castello Di Brolio. This history-steeped castle is a highly recommended experience. Visit these for an interesting touch to your journey.

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

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.

Enjoy a delicious meal at Osteria Quattro Venti, a highly-rated dining destination in Siena. If you're eager to try something different, consider Fischi per Fiaschi, another top spot with a tantalizing menu. You might also want to secure a reservation at Osteria da Divo. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Siena this evening.

Keep the evening going at Charlie Mixology Bar Di Aldinucci Riccardo, a great choice for enjoying the after-dinner hours with a drink. You could also go to Bar Pinacoteca, which offers a similarly pleasant setting and great drinks. Another option is San Paolo Pub, which provides an inviting environment for unwinding after a busy day out.

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

Dive into day 7 of your remarkable road trip in Italy. Today you will explore Rome, 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 Rome. You’ll stay here for 3 nights.

Prepare for a day full of family-friendly attractions, romantic experiences, and breathtaking views. When you’re ready, kick off your sightseeing adventure at Castel Sant'angelo. This widely recognized castle is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Basilica Di Santa Maria Maggiore, one of the city’s best highlights.

Next, check out Trevi Fountain, one of the most world-famous places to see in Siena. This monument is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, Pantheon. Wander around and soak in the standout atmosphere this monument offers. Then, head to Piazza Navona, a top-rated public square that adds another dimension to your day. Finally, visit the locally renowned Largo Di Torre Argentina, 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 Rome. Rome 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 Rome's most popular restaurants, and connect with friendly locals for an authentic adventure.

Dine in style at La Bottega Roma, a top recommendation for dinner tonight. Or, for a change of pace, Pasta In Corso boasts a menu that's sure to impress. Also, be sure to check out Trattoria Vecchia Roma. Known as a local hotspot, it’s a great choice for tonight in Rome.

Continue your lively evening at La Botticella Of Poggi Giovanni, a perfect place for winding down or revving up the night, depending on which mood you’re in. Almalu Trastevere is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Bar Viminale Di Pepi Maurilio ensures a night out tailored to your taste.

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

Greet day 8 of your road trip in Italy with a smile and start your day with a hearty breakfast. You will return to Rome for your remaining 2 nights 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 Vatican City and Rome.

Set aside time today to explore Trastevere, a standout neighborhood that reflects the essence of the city. While you're there, you'll also be within reach of some of the city's top landmarks, making it easy to maximize your day. You might also want to visit Via del Corso, a street offering another perspective on the city.

Prepare for a day full of fun adventures, romantic experiences, and scenic views. When you’re ready, kick off your sightseeing adventure at St. Peter's Basilica. This globally renowned major basilica is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Sistine Chapel, one of the city’s best highlights.

Next, check out Vatican Museums, one of the most iconic places to see in Rome. This art museum is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, Piazza Del Popolo. Wander around and soak in the culturally significant atmosphere this public square offers.

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

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

Make sure to reserve a table at RomAntica, an iconic dining spot in Rome. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Coso Ristorante, a popular restaurant in Rome. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of DEROMA - Farine Romane, a hidden gem nestled in Rome. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

After savoring a delicious meal, step into the vibrant nightlife at Sant' Eustachio Caffè, where the evening is just getting started. In the same way, Yellowsquare Rome offers a unique charm perfect for experiencing the local bar scene in Rome. Caffè Portofino 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!

Day 9 offers a multitude of experiences. You will stay in Rome for 1 night more, offering you enough time to explore at a relaxed pace.

Today’s agenda in Rome includes an archeological site, a monument, a museum, a public square and much more! Colosseum is must-visit archeological site and a great starting point for the day. Next, continue your journey to Arch Of Constantine, a locally appreciated monument, located just a leisurely stroll away. Next, head to Roman Forum, a historic archeological site, also available for your discovery today.

Each stop on today’s itinerary promises to leave you with lasting memories and a deeper appreciation for Rome. When you're ready, let your sightseeing route take you to the captivating Capitoline Museums. If you’re looking for more, Piazza Di Spagna is also a world-famous attraction that is worthwhile a visit. Lastly, don’t miss Spanish Steps, a place of culturally significant interest in the city.

Don’t forget to check out all the popular tours and activities you can add to your road trip itinerary. Italy is a beautiful travel destination that offers plenty of unique tours that will enhance your vacation experience. Explore and select your activities below.

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

Treat yourself to a wonderful meal at Hotel de Russie, a top-rated dining spot in Rome. If you're in the mood for something new, try La Taverna Italiana, another premier location with a delectable menu. You might also want to book a table at The Parrot Bar. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Rome.

After enjoying a fulfilling meal, continue your evening at The Apartment Bar Roma, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Hotel Hassler Roma offers a welcoming atmosphere for easing into the nightlife.

Savor another day of unforgettable experiences in Italy!

On day 10 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 2 destinations, Alberi and Sorrento. When you’re not sightseeing, take time to relax at your selected hotel in Sorrento, where you’ll be staying for 2 nights.

Discover a day packed with fun adventures, romantic experiences, and scenic views in Rome. Begin your sightseeing with Belvedere Sorrento. This underrated observation deck is one of the top attractions in the village. Proceed to Museo Correale Di Terranova, another must-visit attraction.

As you wander through the inviting streets of Rome, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to Cathedral Of Saints Philip And James. This underrated church is a traveler-favorite.

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

As you explore more of Sorrento, 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.

Make sure to reserve a table at Frankie's Pizza Bar Sorrento Brunch & Vegan, an iconic dining spot in Sorrento. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Bougainvillea, a popular restaurant in Sorrento. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Banana Split, a hidden gem nestled in Sorrento. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Let the evening flow smoothly from dinner to drinks at Leone Rosso Café, a top-rated bar in the area. For other recommendations, Hotel Antiche Mura Sorrento provides a perfect setting for rounding out your night with style and great drinks.

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 11 of your road trip, you’ll start and end your day in Sorrento, but spend part of the day exploring places of interest outside the immediate town. On today's itinerary, you'll find attractions in Positano and Ravello. You still have 1 night left in Sorrento.

Today’s itinerary in Sorrento covers several incredible sights, including a beach, a park, and a historical landmark. Start your adventure at Costiera Amalfitana Positano. This curiosity-inducing beach is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the enchanting wonders of Giardini Principessa Di Piemonte, a must-see park in the village.

Consider stopping for a small bite to eat or a drink at a local eatery to keep your energy going. When you’re ready, continue your discovery with a visit to Villa Rufolo. This captivating historical landmark offers an enriching experience. These sights offer a fulfilling end to a perfect day.

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

As you explore more of Sorrento, 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.

Savor the flavors at Fuoro51, a top pick for dinner tonight. Alternatively, Hotel Bellevue Syrene beckons with its unique menu offerings. Also, consider Hotel Villa Fiorita. With its consistent customer satisfaction, it’s an excellent option for dining in Sorrento tonight.

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 12 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 vibrant destinations - Perugia. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Perugia. You will spend 2 nights here for some well-deserved relaxation.

Today, you'll explore some of the most beautiful places in Sorrento, including a historical landmark, a church, a public square, a monument and much more! Start your day with a visit to Etruscan Arch. This curiosity-inducing historical landmark is a must-visit in the city. When you’re ready for your next discovery, continue to Perugia Cathedral, which may be one of the most monumental places you will experience today.

One of the best things about exploring Sorrento on a self-guided tour is that you set the pace. There’s plenty of time for detours and discovering hidden gems. When you’re ready for your next stop, make your way to Piazza Iv Novembre, a worthwhile public square in the city. If you’re up for more discoveries, don’t forget to reserve some time for The Fontana Maggiore.

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 are wrapping up for the day, treat yourself to a satisfying dinner at a nice restaurant in Perugia. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.

Enjoy a delicious meal at Ristorante Settimo Sigillo, a highly-rated dining destination in Perugia. If you're eager to try something different, consider Caffè Baglioni, another top spot with a tantalizing menu. You might also want to secure a reservation at Bar Pellas. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Perugia this evening.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Tommi Bar, known for its inviting atmosphere. Valentina is another great option if you’re looking for a place to get the night started. Similarly, Caffe Dal Perugino provides a great setting to enjoy the night away.

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

Wake up to day 13 of your extraordinary road trip in Italy. With 1 night left in Perugia, we encourage you to seize the day and discover the unexplored beauty of the city’s surroundings!

Start by visiting Rocca Paolina, a prime spot to begin your journey. This photogenic historical landmark is sure to impress. Next on your list is Basilica Of San Francesco D'assisi, another must-visit landmark and popular church renowned for its picture-perfect features.

While exploring and sightseeing, take time to savor the culture of Perugia by sampling some local delicacies. When you’re ready for more sightseeing, head to Piazza Del Comune. This UNESCO world heritage-listed public square is an essential place to visit for anyone looking for the full Perugia experience. We also recommend visiting Basilica Di Santa Chiara, a beloved church. Nearby, you'll also find Rocca Maggiore, ready to add charm to your journey.

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

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

Treat yourself to a delicious dinner at La Taverna, an excellent option for tonight's dining. Looking for something different? Ristorante del Sole offers a tantalizing alternative with its diverse menu. And don’t miss Al Mangiar Bene. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Perugia.

If you’re not ready to end the night just yet, Caffè Fortebraccio offers a perfect venue to relax and savor a drink. Similarly, Caffe Del Banco is well-suited for those looking to unwind in a social setting. Dempsey's Perugia is another excellent spot to enjoy a nightcap after a delightful meal.

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

On day 14 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 Recanati. In the evening, you’ll end up in Ancona, where you will stay for 1 night.

Set out on a day brimming with family-friendly attractions, picturesque spots, and historic treasures. Start at the increasingly popular Villa Colloredo Mels Museum, a history-steeped museum in Perugia. Next, go to Basilica Cattedrale Di San Flaviano.

After visiting Villa Colloredo Mels Museum and Basilica Cattedrale Di San Flaviano, have a stroll along Perugia's streets and take in the local charm. Continue your sightseeing by heading to Leopardi's House. This photogenic museum offers a unique experience.

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.

As dinnertime approaches, it's time to head out for a bite to eat in Ancona. 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.

Treat yourself to a delicious dinner at Amarcord, an excellent option for tonight's dining. Looking for something different? Bontà delle Marche offers a tantalizing alternative with its diverse menu. And don’t miss Ristorante Pizzeria Da Romano. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Ancona.

Keep the evening going at Alla Tazza D'oro, a great choice for enjoying the after-dinner hours with a drink.

Relax and recharge in preparation for another adventurous day in Italy!