Two-Week Italy Self-Drive Road Trip With Itinerary from Ancona traveling south to Urbino, San Gimignano, Florence, Siena, Santa Maria degli Angeli, Perugia, Rome, and Sorrento

On day 2 of your road trip, you will have an entire day to explore Ancona. You’ll stay in Ancona for 1 night and discover all the best things to see and do in the area.

Today's adventure in Ancona promises more breathtaking discoveries and enriching experiences! Begin at Passetto. This visually striking monument is a highlight of any visit in the city. Then, enjoy Cathedral Basilica Of St. Cyriacus, another monumental attraction that never fails to captivate visitors. Next, head over to Arch Of Trajan, one of the city’s most frequently visited attractions, known for its picture-perfect features.

If you’re looking for more, spend time soaking in the atmosphere of Lazzaretto Of Ancona. This culturally significant museum is frequented by locals and tourists alike. To complete your memorable day, make sure to visit State Tactile Museum Omero, an up-and-coming museum, and take a stroll around the area. If you want to extend your self-guided sightseeing tour, go check out Parco Belvedere Posatora before you head back to your hotel.

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 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.

Enjoy a lovely dining experience at Amarcord, a popular restaurant in Ancona. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Ancona at Bontà delle Marche, 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 Ristorante Pizzeria Da Romano. It’s yet another ideal choice to enhance your time in Ancona tonight.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Alla Tazza D'oro stands out as an excellent choice for a post-dinner cocktail.

Savor another day of unforgettable experiences in Italy!

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

Get ready for a day filled with family-friendly attractions, scenic views, and picturesque spots in the charming town of Ancona. Your adventure starts at Fortezza Albornoz, a beloved local hot spot. Another notable attraction to explore is Casa Santi. This worthwhile museum is known for its picture-perfect appeal.

After soaking in the highlights of these sights, take some time to wander Ancona's streets and immerse yourself in the local atmosphere. When you're ready to continue your sightseeing adventure, head to Galleria Nazionale Delle Marche. This picture-perfect museum offers a fascinating experience that many visitors find memorable. Palazzo Ducale is also worth visiting, along with Oratory Of St John The Baptist, Urbino. These standout landmarks offer unique experiences that add to the day’s enjoyment.

At the end of the day, you will drive to Urbino, where you'll have a room waiting for you at the perfect place to stay. Check in and enjoy some downtime.

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

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

Dive into day 4 of your remarkable road trip in Italy. Today you will explore San Gimignano, 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 San Gimignano. You’ll stay here for 1 night.

Bring your curiosity for today’s adventure around Urbino. Some of the village’s most loved attractions await! Chiesa Di Sant'agostino is the perfect place to start. This church is one of the most curiosity-inducing places to visit in Urbino. Next, head to Parco Della Rocca, an underrated park, known for its romantic 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 Sangimignano1300. This historic museum is a highly recommended experience. Nearby, you'll also find Porta San Giovanni and Galleria Continua. Visit these for an interesting touch to your journey. Finish the day with a visit to Piazza Del Duomo, an inviting public square in Urbino.

After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of your accommodation in San Gimignano. San Gimignano 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 San Gimignano. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.

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

On day 5 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.

Set out on a day brimming with family-friendly attractions, romantic experiences, and breathtaking views. Start at the popular The Boboli Gardens, an enchanting botanical garden in San Gimignano. Next, go to Piazzale Michelangelo.

After visiting The Boboli Gardens and Piazzale Michelangelo, have a stroll along San Gimignano's streets and take in the local charm. Continue your sightseeing by heading to Basilica Of Santa Croce In Florence. This culturally significant church offers a unique experience. Uffizi Gallery is another noteworthy attraction worthwhile a visit. End your self-guided sightseeing tour on top with a visit to Ponte Vecchio, one of the most enchanting places to visit in San Gimignano. If you still have some time left for sightseeing, we also recommend stopping by Palazzo Vecchio.

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.

Treat yourself to a wonderful meal at Ristorante Oliviero 1962, a top-rated dining spot in Florence. If you're in the mood for something new, try Di Poneta Novoli, another premier location with a delectable menu. You might also want to book a table at Caffe San Firenze. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Florence.

After enjoying a fulfilling meal, continue your evening at Manifattura, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Se·sto On Arno Rooftop Bar offers a welcoming atmosphere for easing into the nightlife. Similarly, Il Vinile provides an excellent environment for a relaxed and enjoyable evening.

Raise your glass to another unforgettable day in Italy!

On day 6 of your road trip, you’ll start and end your day in Florence, but spend part of the day exploring places of interest outside the immediate city. On today's itinerary, you'll find attractions in Pisa. You still have 1 night left in Florence.

Bring your curiosity for today’s adventure around Florence. Some of the city’s most loved attractions await! Piazza Del Duomo, Pisa is the perfect place to start. This public square is one of the most world-famous places to visit in Florence. Next, head to Pisa Cathedral, a worthwhile church, known for its culturally significant 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 Leaning Tower Of Pisa. This picture-perfect monument is a highly recommended experience. Nearby, you'll also find Knights' Square and Palazzo Blu. Visit these for an interesting touch to your journey. Finish the day with a visit to Santa Maria Della Spina, an inviting church in Florence.

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 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.

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at Bar 50 Rosso, a well-loved spot among locals and tourists. Or, head to Bitter Bar. This bar boasts a welcoming environment that is perfect for winding down. You could also continue your night at Archea Brewery, another top-rated place in the area.

Head back to your accommodation in Florence and get some rest in preparation for another magical 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, Siena. 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 adventure in Florence promises more breathtaking discoveries and enriching experiences! Begin at Fortezza Medicea (siena). This culturally significant monument is a highlight of any visit in the city. Then, enjoy Basilica Of San Domenico, another breathtaking attraction that never fails to captivate visitors. Next, head over to Siena Cathedral, one of the city’s most popular attractions, known for its enchanting features.

If you’re looking for more, spend time soaking in the atmosphere of Pubblico Palace. This historic palace is frequented by locals and tourists alike. To complete your memorable day, make sure to visit Piazza Del Campo, a spectacular public square, and take a stroll around the area. If you want to extend your self-guided sightseeing tour, go check out Tower Of Mangia before you head back to your hotel.

At the end of the day, you will drive to Siena, 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 Siena, 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 delightful dinner at Enoteca I Terzi, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Ristorante Tar-Tufo? It's another excellent option with a diverse menu. Consider reserving a table at Antica Trattoria Papei as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Siena.

Extend your evening after a delightful meal by visiting Meet Life Cafè, which offers the perfect atmosphere for a night out. Moreover, Maudit Pub is another popular option for a drink or two. Likewise, Bar Impero Siena 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!

Embark on another extraordinary experience on day 8 of your road trip in Italy. Today, you will make 1 stop and experience some of the highlights of Santa Maria degli Angeli. At the end of the day, you will enjoy the comforts of a top-rated hotel in Santa Maria degli Angeli, which will be your home away from home for 1 night.

Today’s route brings family-friendly attractions, scenic views, and picturesque spots. The first attraction of today is Basilica Of Santa Maria Degli Angeli. This notable church is a stunning place to see in Siena. Continue your discovery at Eremo Delle Carceri, a picturesque monastery with stories to tell.

As you stroll around Siena, take in the distinct atmosphere and learn what makes this village so unique. Maximize your sightseeing with a visit to Rocca Maggiore. This increasingly popular castle offers a history-steeped encounter with Siena. Next, make your way to Basilica Of San Francesco D'assisi to add another highlight to your day. After that, visit Portico Of Monte Frumentario, an often recommended historical landmark that’s sure to impress. If you’re up for more, end your self-guided sightseeing tour at Piazza Del Comune, a beloved public square in the village. Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day in Siena.

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

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

Round off your dining experience by visiting Bibenda Assisi Wine Tasting & Gourmet Food, Olive Oil And Chocolate Tastings, a prime location for a drink.

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 9 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 1 night here for some well-deserved relaxation.

Prepare for a day full of family-friendly attractions, picturesque spots, and history-rich sites. When you’re ready, kick off your sightseeing adventure at National Archaeological Museum Of Umbria. This curiosity-inducing museum is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Rocca Paolina, one of the city’s best highlights.

Next, check out Carducci Gardens, one of the most frequently visited places to see in Santa Maria degli Angeli. This park is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, Perugia Cathedral. Wander around and soak in the culturally significant atmosphere this church offers. Then, head to Piazza Iv Novembre, a top-rated public square that adds another dimension to your day. Finally, visit the increasingly popular The Fontana Maggiore, the last of our attraction recommendations for today.

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.

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.

Dine in style at Ristorante Settimo Sigillo, a top recommendation for dinner tonight. Or, for a change of pace, Caffè Baglioni boasts a menu that's sure to impress. Also, be sure to check out Bar Pellas. Known as a local hotspot, it’s a great choice for tonight in Perugia.

Following your dinner, dive into the local bar culture at Tommi Bar. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Valentina, the perfect place for those looking to experience the best of the nightlife. Similarly, Caffe Dal Perugino provides excellent drinks and a great atmosphere, ensuring a memorable night out.

Savor another day of unforgettable experiences in Italy!

Dive into day 10 of your remarkable road trip in Italy. Today you will explore Vatican City and 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 2 nights.

Start your adventure at Sistine Chapel. This widely recognized chapel is a must-visit for travelers looking for a unique holiday experience. Make your way to St. Peter's Basilica located in Perugia for another exciting encounter.

Next, immerse yourself in the setting of Vatican Museums. After the art museum, continue your tour of the city with a visit to Spanish Steps. Visitors usually appreciate the enchanting features of this public square.

At the end of the day, you will drive to Rome, where you'll have a room waiting for you at the perfect place to stay. Check in and enjoy some downtime.

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

Savor the flavors at La Bottega Roma, a top pick for dinner tonight. Alternatively, Pasta In Corso beckons with its unique menu offerings. Also, consider Trattoria Vecchia Roma. With its consistent customer satisfaction, it’s an excellent option for dining in Rome tonight.

To truly maximize your evening out, consider visiting La Botticella Of Poggi Giovanni after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Almalu Trastevere, another bar with an inviting ambiance. Similarly, Bar Viminale Di Pepi Maurilio also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

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

Day 11 of your road trip will take you to the best attractions Rome has to offer. Cherish the 1 night you have left in Rome by discovering the best things there are to see and do in the city.

Today’s well-planned self-sightseeing route offers several fun adventures, romantic experiences, and scenic views. Whether you decide to explore Rome on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss. Villa Borghese Pinciana is the first of them. Spend some time admiring this history-steeped museum before continuing your journey. Colosseum is your next stop. This iconic archeological site is one of the best-rated sights in Rome.

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 Roman Forum. This breathtaking archeological site is a sight to behold. To round off your sightseeing experience, visit Trevi Fountain and Pantheon. If time allows, end your day with Castel Sant'angelo, a grand castle that offers a memorable conclusion to your exploration.

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 Rome. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.

Have a fantastic dining experience at RomAntica, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Coso Ristorante offers an enticing alternative with its varied menu. Additionally, DEROMA - Farine Romane is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Rome.

Continue your evening by exploring the vibrant nightlife scene at Sant' Eustachio Caffè, a prime destination for a thrilling night out. Also, don’t forget to check out Yellowsquare Rome, a bar that offers unique local touches. Likewise, Caffè Portofino provides an excellent alternative for a fun evening.

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

On day 12 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 Naples. In the evening, you’ll end up in Sorrento, where you will stay for 2 nights.

Get ready for an exciting day in Rome. Today’s sightseeing agenda includes a castle, a museum, and a street. Begin your adventure at Castel Sant'elmo. This is a notable castle you should not miss. Another must-see is Naples National Archaeological Museum, a captivating museum in Rome.

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

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.

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

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.

After savoring a delicious meal, step into the vibrant nightlife at Leone Rosso Café, where the evening is just getting started. In the same way, Hotel Antiche Mura Sorrento offers a unique charm perfect for experiencing the local bar scene in Sorrento.

Take some time to reflect on your day and savor another beautiful night 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 Sorrento for your remaining 1 night in the town 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 Ravello, Positano, Amalfi, and Atrani.

Today's adventure in Sorrento promises more breathtaking discoveries and enriching experiences! Begin at Fondazione Ravello. This awe-inspiring cultural center is a highlight of any visit in the village. Then, enjoy Costiera Amalfitana Positano, another peaceful attraction that never fails to captivate visitors.

If you’re looking for more, spend time soaking in the atmosphere of Collegiate Santa Maria Maddalena. This visually striking church is frequented by locals and tourists alike. To complete your memorable day, make sure to visit Villa Rufolo, a locally renowned historical landmark, and take a stroll around the area.

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

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.

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, Fauno Bar is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Sorrento.

Savor another day of unforgettable experiences in Italy!

On day 14 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, Pompei. When you’re not sightseeing, take time to relax at your selected hotel in Ancona, where you’ll be staying for 1 night.

A blend of family-friendly attractions, scenic views, and photo-friendly spots await you in Sorrento on today’s itinerary. First up is the popular archeological site, Archaeological Park Of Pompeii. Afterward, continue to Amphitheatre Of Pompeii, an archeological site every traveler should visit.

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

Have a fantastic dining experience at Pizzeria Pulcinella, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Donegal Irish Pub offers an enticing alternative with its varied menu. Additionally, Vino E Cucina Miscia is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Ancona.

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