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

Experience an unparalleled adventure on day 2 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 vibrant destinations - Florence. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Florence. You will spend 3 nights here for some well-deserved relaxation.

Today's adventure in Ancona promises more breathtaking discoveries and enriching experiences! Begin at Piazzale Michelangelo. This history-steeped observation deck is a highlight of any visit in the city. Then, enjoy Galleria Dell'accademia, another heritage-rich attraction that never fails to captivate visitors. Next, head over to Central Market, one of the city’s most locally renowned attractions, known for its visually striking features.

If you’re looking for more, spend time soaking in the atmosphere of Basilica Di Santa Maria Novella, Firenze (fi). This enchanting church is frequented by locals and tourists alike. To complete your memorable day, make sure to take a stroll around the area.

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.

Cap off your dinner by heading to Manifattura, ideal for a leisurely evening with a drink in hand. Se·sto On Arno Rooftop Bar is another bar that offers an enjoyable setting. Similarly, Il Vinile is also a popular place to go on a night out, perfect for relaxing and socializing.

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

Day 3 of your road trip across Italy promises a magnificent time exploring Florence. You have 2 nights left in Florence. Take the opportunity to experience more of the best attractions and activities in the city.

Discover a day packed with fun adventures, romantic experiences, and scenic views in Florence. Begin your sightseeing with Cathedral Of Santa Maria Del Fiore. This widely recognized church is one of the top attractions in the city. Proceed to Ponte Vecchio, 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 Uffizi Gallery. This spectacular art gallery is a traveler-favorite. Not far away, you’ll find Palazzo Vecchio, another key site on your sightseeing itinerary. Piazza Della Signoria is yet another highly recommended place to visit nearby, offering plenty to discover for curious travelers. Conclude your day at Basilica Of Santa Croce In Florence and uncover why it's recognized as one of the city's most well-known attractions.

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 meal at Ditta Artigianale, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Trattoria Da Burde is another top choice with a popular menu. You could also check for a table at Casa Toscana. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Florence tonight.

Round off your dining experience by visiting Bar 50 Rosso, a prime location for a drink. Alternatively, explore the distinctive characteristics of Bitter Bar, a bar catering to every mood and preference. Archea Brewery likewise offers a unique atmosphere, perfect for a memorable night out.

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

On day 4 of your road trip, you’ll start and end your day in Florence, where you'll stay for 1 night more.

Start your adventure at Piazza Del Duomo, Pisa. This wondrous public square is a must-visit for travelers looking for a unique holiday experience. Make your way to Pisa Cathedral located in Florence for another exciting encounter.

Next, immerse yourself in the setting of Angelo Caduto. After the sightseeing destination, continue your tour of the city with a visit to Leaning Tower Of Pisa. Visitors usually appreciate the noteworthy features of this monument.

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

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 Ristorante Buca Mario, 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 Agricola Toscana, 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 Eataly Firenze. It’s yet another ideal choice to enhance your time in Florence tonight.

Cap off your dinner by heading to Gosh*, ideal for a leisurely evening with a drink in hand. Antico Caffè Del Moro - Art Bar Firenze is another bar that offers an enjoyable setting. Similarly, Quelo Bar is also a popular place to go on a night out, perfect for relaxing and socializing.

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

Wake up to day 6 of your extraordinary road trip in Italy. With 1 night left in Siena, we encourage you to seize the day and discover the unexplored beauty of the city’s surroundings!

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Siena allows for both. Start by heading to Antinori Nel Chianti Classico. This underrated winery provides an insightful glimpse into the village's identity. Next, discover Castle Of Verrazzano, a visually striking castle, promising a delightful encounter.

Continue your sightseeing with a visit to Castello Di Brolio, a locally appreciated castle.

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

After a long day of exploring, sit down for a delicious dinner at a top-rated restaurant in Siena. Enjoy a satisfying meal that will recharge you for tonight's adventures.

Don’t miss out on dining at Osteria Quattro Venti, a top-rated dining destination in Siena. If you're in the mood to try something new, consider Fischi per Fiaschi, another top spot with a mouthwatering menu. You might also want to secure a reservation at Osteria da Divo. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Siena this evening.

If you’re not ready to end the night just yet, Charlie Mixology Bar Di Aldinucci Riccardo offers a perfect venue to relax and savor a drink. Similarly, Bar Pinacoteca is well-suited for those looking to unwind in a social setting. San Paolo Pub is another excellent spot to enjoy a nightcap after a delightful meal.

Raise your glass to another unforgettable day in Italy!

On day 7 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, Rome. When you’re not sightseeing, take time to relax at your selected hotel in Rome, where you’ll be staying for 3 nights.

Get ready for an exciting day in Siena. Today’s sightseeing agenda includes a castle, a church, a monument, a public square, an archeological site and much more! Begin your adventure at Castel Sant'angelo. This is a widely recognized castle you should not miss. Another must-see is Basilica Di Santa Maria Maggiore, a popular church in Siena.

When you’re ready for the next sight, head to Trevi Fountain. From there, take a leisurely stroll to Pantheon, another of the city’s timeless attractions. We recommend continuing your self-guided tour at Piazza Navona, a grand place of interest in the city. If time allows, add Largo Di Torre Argentina to your itinerary. This popular archeological site offers the perfect finishing touch to your day in Siena.

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

As you explore more of Rome, 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 La Bottega Roma, a top-rated dining spot in Rome. If you're in the mood for something new, try Pasta In Corso, another premier location with a delectable menu. You might also want to book a table at Trattoria Vecchia Roma. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Rome.

If you’re not ready to end the night just yet, La Botticella Of Poggi Giovanni offers a perfect venue to relax and savor a drink. Similarly, Almalu Trastevere is well-suited for those looking to unwind in a social setting. Bar Viminale Di Pepi Maurilio is another excellent spot to enjoy a nightcap after a delightful meal.

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.

One of the most iconic places you can visit today in Vatican City is Trastevere. Allow yourself some time to explore this neighborhood and discover its unique quirks. You'll also find many of the best sightseeing spots nearby. You can also explore Via del Corso, a street that offers a glimpse into local life and culture.

Set out on a day brimming with fun adventures, romantic experiences, and scenic views. Next, go to Sistine Chapel.

Piazza Del Popolo is another noteworthy attraction worthwhile a visit.

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

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

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.

Extend your evening after a delightful meal by visiting Sant' Eustachio Caffè, which offers the perfect atmosphere for a night out. Moreover, Yellowsquare Rome is another popular option for a drink or two. Likewise, Caffè Portofino also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

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

On day 9 of your road trip, you will have an entire day to explore Rome. You’ll stay in Rome for 1 night and discover all the best things to see and do in the area.

Enjoy the perfect balance of relaxation and exploration in Rome today. One of the most globally renowned attractions included on the itinerary is Colosseum. This picture-perfect archeological site will help you start your sightseeing on top. Then, take a leisurely stroll to Arch Of Constantine and learn what makes this breathtaking monument unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the iconic Roman Forum. After exploring the archeological site, head to Capitoline Museums. This interesting museum is a highlight in Rome. As your day continues, stop by Piazza Di Spagna, known for its visually striking features. Lastly, don’t forget to check out the widely recognized Spanish Steps. Enjoy exploring this incredible public square at your own pace.

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.

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

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 your delicious meal, get a taste of the vibrant nightlife with a visit to The Apartment Bar Roma, known for its inviting atmosphere. Hotel Hassler Roma is another great option if you’re looking for a place to get the night started.

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 10 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 Alberi and Sorrento. In the evening, you’ll end up in Sorrento, where you will stay for 2 nights.

Today’s itinerary in Rome covers several incredible sights, including an observation deck, a museum, and a church. Start your adventure at Belvedere Sorrento. This locally appreciated observation deck is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the picture-perfect wonders of Museo Correale Di Terranova, a must-see museum 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 Cathedral Of Saints Philip And James. This underrated church offers an enriching experience. These sights offer a fulfilling end to a perfect day.

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

Enjoy a lovely meal at Frankie's Pizza Bar Sorrento Brunch & Vegan, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Bougainvillea is another top choice with a popular menu. You could also check for a table at Banana Split. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Sorrento tonight.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Leone Rosso Café, known for its inviting atmosphere. Hotel Antiche Mura Sorrento is another great option if you’re looking for a place to get the night started.

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

Get ready for an exciting day in Sorrento. Today’s sightseeing agenda includes a beach, a park, and a historical landmark. Begin your adventure at Costiera Amalfitana Positano. This is an underrated beach you should not miss. Another must-see is Giardini Principessa Di Piemonte, an up-and-coming park in Sorrento.

When you’re ready for the next sight, head to Villa Rufolo.

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

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.

Have a fantastic dining experience at Fuoro51, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Hotel Bellevue Syrene offers an enticing alternative with its varied menu. Additionally, Hotel Villa Fiorita is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Sorrento.

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 12 of your remarkable road trip in Italy. Today you will explore 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 2 nights.

Brace yourself for today’s incredible lineup of attractions in Sorrento, featuring family-friendly attractions, breathtaking views, and photo-friendly spots. Start at Etruscan Arch, a curiosity-inducing historical landmark in the city. Then, head to Perugia Cathedral and soak in the ambiance of this photogenic church.

There are many interesting places to see in Sorrento, and when you are ready for more, go to Piazza Iv Novembre. This is one of the city’s most underrated visually striking spots of interest. After exploring the public square, visit the often recommended 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.

Have a fantastic dining experience at Ristorante Settimo Sigillo, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Caffè Baglioni offers an enticing alternative with its varied menu. Additionally, Bar Pellas is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Perugia.

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.

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

On day 13 of your road trip in Italy, you’ll start and end your day in Perugia, but spend the day exploring what’s beyond the city. Since you will return to Perugia for 1 night more, there’s no need to rush. Experience Perugia and Santa Maria degli Angeli to the fullest today with this curated day itinerary!

Today’s well-planned self-sightseeing route offers several fun adventures, picturesque spots, and history-rich sites. Whether you decide to explore Perugia on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss. Rocca Paolina is the first of them. Spend some time admiring this symbolic historical landmark before continuing your journey. Basilica Of San Francesco D'assisi is your next stop. This locally renowned church is one of the best-rated sights in Perugia.

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 Piazza Del Comune. This grand public square is a sight to behold. To round off your sightseeing experience, visit Basilica Di Santa Chiara and Rocca Maggiore.

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

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

Savor the flavors at La Taverna, a top pick for dinner tonight. Alternatively, Ristorante del Sole beckons with its unique menu offerings. Also, consider Al Mangiar Bene. With its consistent customer satisfaction, it’s an excellent option for dining in Perugia tonight.

After enjoying a fulfilling meal, continue your evening at Caffè Fortebraccio, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Caffe Del Banco offers a welcoming atmosphere for easing into the nightlife. Similarly, Dempsey's Perugia provides an excellent environment for a relaxed and enjoyable evening.

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

Experience an unparalleled adventure on day 14 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 vibrant destinations - Recanati. 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.

Savor the day by visiting some of the best places to see in Perugia, including a museum and a church. Start your adventure at Villa Colloredo Mels Museum. This intriguing museum is a must-visit for travelers looking for a unique holiday experience. Make your way to Basilica Cattedrale Di San Flaviano located in Perugia for another exciting encounter.

Next, immerse yourself in the setting of Leopardi's House. Its photogenic features will captivate you.

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.

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

Don’t miss out on dining 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.

To truly maximize your evening out, consider visiting Alla Tazza D'oro after dinner. This bar is known for offering some of the best drinks and vibes in the city.

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