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.

Bring your curiosity for today’s adventure around Ancona. Some of the city’s most loved attractions await! Piazzale Michelangelo is the perfect place to start. This observation deck is one of the most spectacular places to visit in Ancona. Next, head to Galleria Dell'accademia, a notable art gallery, known for its eye-catching 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 Central Market. This eye-catching food market is a highly recommended experience. Nearby, you'll also find Basilica Di Santa Maria Novella, Firenze (fi). Visit these for an interesting touch to your journey.

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.

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.

Dine in style at Ristorante Oliviero 1962, a top recommendation for dinner tonight. Or, for a change of pace, Di Poneta Novoli boasts a menu that's sure to impress. Also, be sure to check out Caffe San Firenze. Known as a local hotspot, it’s a great choice for tonight in Florence.

Round off your dining experience by visiting Manifattura, a prime location for a drink. Alternatively, explore the distinctive characteristics of Se·sto On Arno Rooftop Bar, a bar catering to every mood and preference. Il Vinile likewise offers a unique atmosphere, perfect for a memorable night out.

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

On day 3 of your road trip, you will have an entire day to explore Florence. You’ll stay in Florence for 2 nights and discover all the best things to see and do in the area.

Bring your curiosity for today’s adventure around Florence. Some of the city’s most loved attractions await! Cathedral Of Santa Maria Del Fiore is the perfect place to start. This church is one of the most widely recognized places to visit in Florence. Next, head to Ponte Vecchio, a globally renowned historical landmark, known for its enchanting 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 Uffizi Gallery. This historic art gallery is a highly recommended experience. Nearby, you'll also find Palazzo Vecchio and Piazza Della Signoria. Visit these for an interesting touch to your journey. Finish the day with a visit to Basilica Of Santa Croce In Florence, a respected church 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 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.

Enjoy a delicious meal 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.

Keep the excitement of the evening going by visiting a bar or two. Bar 50 Rosso is an excellent place to start. You could also check out Bitter Bar, offering a different kind of charm. A last recommendation for the day is Archea Brewery. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

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

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

Today’s well-planned self-sightseeing route offers several fun adventures, scenic views, and picturesque spots. Whether you decide to explore Florence on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss. Piazza Del Duomo, Pisa is the first of them. Spend some time admiring this breathtaking public square before continuing your journey. Pisa Cathedral is your next stop. This often recommended church is one of the best-rated sights in Florence.

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 Angelo Caduto. To round off your sightseeing experience, visit Leaning Tower Of Pisa.

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

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 Buca Mario, 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 Agricola Toscana, 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 Eataly 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.

After enjoying a fulfilling meal, continue your evening at Gosh*, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Antico Caffè Del Moro - Art Bar Firenze offers a welcoming atmosphere for easing into the nightlife. Similarly, Quelo Bar provides an excellent environment for a relaxed and enjoyable evening.

Raise your glass to another unforgettable day 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!

Today’s agenda in Siena includes a winery and a castle. Antinori Nel Chianti Classico is must-visit winery and a great starting point for the day. Next, continue your journey to Castle Of Verrazzano, an up-and-coming castle, located just a leisurely stroll away. Next, head to Castello Di Brolio, a romantic castle, also available for your discovery today.

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

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.

Savor the flavors at Osteria Quattro Venti, a top pick for dinner tonight. Alternatively, Fischi per Fiaschi beckons with its unique menu offerings. Also, consider Osteria da Divo. With its consistent customer satisfaction, it’s an excellent option for dining in Siena tonight.

Extend your evening after a delightful meal by visiting Charlie Mixology Bar Di Aldinucci Riccardo, which offers the perfect atmosphere for a night out. Moreover, Bar Pinacoteca is another popular option for a drink or two. Likewise, San Paolo Pub also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

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

Today, you'll explore some of the most beautiful places in Siena, including a castle, a church, a monument, a public square, an archeological site and much more! Start your day with a visit to Castel Sant'angelo. This top-rated castle is a must-visit in the city. When you’re ready for your next discovery, continue to Basilica Di Santa Maria Maggiore, which may be one of the most culturally significant places you will experience today.

One of the best things about exploring Siena 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 Trevi Fountain, a timeless monument in the city. If you’re up for more discoveries, don’t forget to reserve some time for Pantheon and Piazza Navona. End your day with a visit to Largo Di Torre Argentina, a notable archeological site that’s sure to leave a lasting impression.

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.

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

Don’t miss out on dining at La Bottega Roma, a top-rated dining destination in Rome. If you're in the mood to try something new, consider Pasta In Corso, another top spot with a mouthwatering menu. You might also want to secure a reservation at Trattoria Vecchia Roma. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Rome this evening.

Continue the enjoyment post-dinner at La Botticella Of Poggi Giovanni, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Almalu Trastevere offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out Bar Viminale Di Pepi Maurilio. This bar is a favorite among both locals and visitors looking for a delightful evening out filled with laughter and fun.

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

On day 8 of your road trip, you’ll start and end your day in Rome, but spend part of the day exploring places of interest outside the immediate city. On today's itinerary, you'll find attractions in Vatican City and Rome. You still have 2 nights left in Rome.

Trastevere is a neighborhood that stands out as one of the must-see places in Vatican City. Take a moment to explore its distinct atmosphere, and don’t miss the popular sightseeing spots just a short walk away. For another highlight, head to Via del Corso, a street offering its own unique experiences.

Start by visiting St. Peter's Basilica, a prime spot to begin your journey.

We also recommend visiting Piazza Del Popolo, a top-rated public square.

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

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

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.

Explore the vibrant nightlife at Sant' Eustachio Caffè after your meal, a hub for lively evenings and memorable moments. Or, head to Yellowsquare Rome for a great selection of flavorful drinks and a charming setting. Furthermore, Caffè Portofino is perfect for those looking to extend their night with a touch of local flavor.

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

Day 9 of your road trip across Italy promises a magnificent time exploring Rome. You have 1 night left in Rome. Take the opportunity to experience more of the best attractions and activities in the city.

Today’s route brings fun adventures, breathtaking views, and photo-friendly spots. The first attraction of today is Colosseum. This world-famous archeological site is a breathtaking place to see in Rome. Continue your discovery at Arch Of Constantine, a picture-perfect monument with stories to tell.

As you stroll around Rome, take in the distinct atmosphere and learn what makes this city so unique. Maximize your sightseeing with a visit to Roman Forum. This wondrous archeological site offers a culturally significant encounter with Rome. Next, make your way to Capitoline Museums to add another highlight to your day. After that, visit Piazza Di Spagna, a world-famous public square that’s sure to impress. If you’re up for more, end your self-guided sightseeing tour at Spanish Steps, an astonishing public square 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 Rome.

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

Don’t miss out on dining at Hotel de Russie, a top-rated dining destination in Rome. If you're in the mood to try something new, consider La Taverna Italiana, another top spot with a mouthwatering menu. You might also want to secure a reservation at The Parrot Bar. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Rome this evening.

Continue the enjoyment post-dinner at The Apartment Bar Roma, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Hotel Hassler Roma offers a vibrant space for indulging in well-crafted drinks and engaging conversation.

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

Embark on another extraordinary experience on day 10 of your road trip in Italy. Today, you will make 2 stops and experience some of the highlights of Alberi and Sorrento. At the end of the day, you will enjoy the comforts of a top-rated hotel in Sorrento, which will be your home away from home for 2 nights.

Rome is brimming with adventures. Today’s wonderful stops include an observation deck, a museum, and a church. Begin your sightseeing adventure at the beloved Belvedere Sorrento and allow yourself time to explore. Just a short distance away you'll find your next stop, Museo Correale Di Terranova, a picture-perfect museum that draws visitors from far and near.

Continue your journey to Cathedral Of Saints Philip And James, one of the village’s most increasingly popular spots that you shouldn’t miss.

At the end of the day, you will drive to Sorrento, 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 Sorrento. If you are looking to dine at a popular restaurant in the town, it's often a good idea to reserve a table in advance.

Treat yourself to a delightful dinner at Frankie's Pizza Bar Sorrento Brunch & Vegan, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Bougainvillea? It's another excellent option with a diverse menu. Consider reserving a table at Banana Split as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Sorrento.

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at Leone Rosso Café, a well-loved spot among locals and tourists. Or, head to Hotel Antiche Mura Sorrento. This bar boasts a welcoming environment that is perfect for winding down.

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

On day 11 of your road trip in Italy, you’ll start and end your day in Sorrento, but spend the day exploring what’s beyond the town. Since you will return to Sorrento for 1 night more, there’s no need to rush. Experience Positano and Ravello to the fullest today with this curated day itinerary!

Discover a day packed with family-friendly attractions, romantic experiences, and natural wonders in Sorrento. Begin your sightseeing with Costiera Amalfitana Positano. This often recommended beach is one of the top attractions in the village. Proceed to Giardini Principessa Di Piemonte, another must-visit attraction.

As you wander through the inviting streets of Sorrento, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to Villa Rufolo. This interesting historical landmark is a traveler-favorite.

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

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

Enjoy a lovely dining experience at Fuoro51, a popular restaurant in Sorrento. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Sorrento at Hotel Bellevue Syrene, 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 Hotel Villa Fiorita. It’s yet another ideal choice to enhance your time in Sorrento tonight.

Head back to your accommodation in Sorrento and get some rest in preparation for another magical day 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.

Set out on a day brimming with fun adventures, scenic views, and photo-friendly spots. Start at the frequently visited Etruscan Arch, a picture-perfect historical landmark in Sorrento. Next, go to Perugia Cathedral.

After visiting Etruscan Arch and Perugia Cathedral, have a stroll along Sorrento's streets and take in the local charm. Continue your sightseeing by heading to Piazza Iv Novembre. This awe-inspiring public square offers a unique experience. The Fontana Maggiore is another noteworthy attraction worthwhile a visit.

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.

Enjoy a lovely meal at Ristorante Settimo Sigillo, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Caffè Baglioni is another top choice with a popular menu. You could also check for a table at Bar Pellas. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Perugia tonight.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Tommi Bar stands out as an excellent choice for a post-dinner cocktail. Alternatively, Valentina offers an ideal atmosphere to enjoy the pleasures of the night. Caffe Dal Perugino is also a great option that provides a perfect setting for a relaxing evening.

Raise your glass to another unforgettable day in Italy!

Greet day 13 of your road trip in Italy with a smile and start your day with a hearty breakfast. You will return to Perugia 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 Perugia and Santa Maria degli Angeli.

Today, you'll explore some of the most beautiful places in Perugia, including a historical landmark, a church, a public square, a castle and much more! Start your day with a visit to Rocca Paolina. This underrated historical landmark is a must-visit in the city. When you’re ready for your next discovery, continue to Basilica Of San Francesco D'assisi, which may be one of the most stunning places you will experience today.

One of the best things about exploring Perugia 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 Del Comune, an underrated public square in the city. If you’re up for more discoveries, don’t forget to reserve some time for Basilica Di Santa Chiara and Rocca Maggiore.

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

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

Dine in style at La Taverna, a top recommendation for dinner tonight. Or, for a change of pace, Ristorante del Sole boasts a menu that's sure to impress. Also, be sure to check out Al Mangiar Bene. Known as a local hotspot, it’s a great choice for tonight in Perugia.

Continue your lively evening at Caffè Fortebraccio, a perfect place for winding down or revving up the night, depending on which mood you’re in. Caffe Del Banco is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Dempsey's Perugia 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.

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.

Perugia is home to plenty of attractions that offer family-friendly attractions, photo-friendly spots, and history-rich sites! Start at Villa Colloredo Mels Museum, an underrated museum that is worthwhile a visit in the town. Nearby, you’ll find Basilica Cattedrale Di San Flaviano, enchanting visitors with its culturally significant appeal. Continue your exploration at Leopardi's House. This museum is one of the town’s most up-and-coming spots.

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.

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.

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

Savor another day of unforgettable experiences in Italy!