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

Day 2 offers an itinerary packed with the best things to see in Ancona. You’ll stay in Ancona for 1 night more, offering you enough time to explore at a relaxed pace.

Ancona is brimming with adventures.

Experience Passetto, an up-and-coming monument in the city. Then, head to Cathedral Basilica Of St. Cyriacus and soak in the ambiance of this historic church.

There are many interesting places to see in Ancona, and when you are ready for more, go to Arch Of Trajan. This is one of the city’s most up-and-coming picture-perfect spots of interest. After exploring the monument, visit the increasingly popular Lazzaretto Of Ancona. Not far away, you'll also find State Tactile Museum Omero. This museum is a detailed highlight in Ancona. Before wrapping up your self-guided sightseeing tour, head to Parco Belvedere Posatora, an underrated park in the city.

Don’t forget to check out all the popular tours and experiences you can add to your travel plans in Italy. You can explore and select activities under each day of your itinerary.

As dinnertime approaches, it's time to head out for a bite to eat. If you are looking to dine at a popular restaurant in Ancona, it's often a good idea to reserve a table in advance.

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.

Continue your evening by exploring the vibrant nightlife scene at Alla Tazza D'oro, a prime destination for a thrilling night out.

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

Your itinerary for day 3 of your road trip in Italy includes 1 stop and features some of the highlights of Urbino. At the end of the day, enjoy the comforts of a top-rated hotel in Urbino, where you'll spend 1 night.

Fortezza Albornoz makes a great addition to your morning plans. This locally appreciated castle is a breathtaking place to see in Ancona. Continue your discovery at Casa Santi, a historic museum with stories to tell.

As you stroll around Ancona, take in the distinct atmosphere and learn what makes this town so unique. Maximize your sightseeing with a visit to Galleria Nazionale Delle Marche. This curiosity-inducing museum offers a picture-perfect encounter with Ancona. Next, make your way to Palazzo Ducale to add another highlight to your day. After that, visit Oratory Of St John The Baptist, Urbino, a locally appreciated church that’s sure to impress. Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day in Ancona.

When you’re done exploring for the day, you’ll drive to your hotel in Urbino. Check in and relax before you head out to tour the town.

As dinnertime approaches, it's time to head out for a bite to eat. If you are looking to dine at a popular restaurant in Urbino, it's often a good idea to reserve a table in advance.

As the day draws to a close, take a moment to unwind and prepare for the next exciting chapter of your road trip in Italy.

Experience an unparalleled adventure on day 4 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 place, which are San Gimignano. At the end of the day, you will retreat to the hotel of your choice in San Gimignano, where will spend 1 night.

Chiesa Di Sant'agostino is perfect for a self-paced visit during the day. This photogenic church is sure to impress. Next on your list is Parco Della Rocca, another must-visit landmark and beloved park renowned for its enchanting features.

While exploring and sightseeing, take time to savor the culture of Urbino by sampling some local delicacies. When you’re ready for more sightseeing, head to Sangimignano1300. This eye-catching museum is an essential place to visit for anyone looking for the full Urbino experience. We also recommend visiting Porta San Giovanni, a worthwhile monument. Nearby, you'll also find Galleria Continua, ready to add charm to your journey. End your self-guided sightseeing tour with a stop at Piazza Del Duomo and wrap up your day with its culturally significant appeal.

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

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

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

On day 5 of your road trip in Italy, your travel plans include 1 stop at the most scenic, wondrous, and interesting places in the region. Florence are on today's agenda. In the evening, you’ll end up in Florence, where you will stay for 2 nights.

The Boboli Gardens is must-visit botanical garden and a great option for a daytime tour of the area. Continue your journey to Piazzale Michelangelo, a spectacular observation deck, located just a leisurely stroll away. Next, head to Basilica Of Santa Croce In Florence, a heritage-rich church, also available for your discovery today.

Each stop on today’s itinerary promises to leave you with lasting memories and a deeper appreciation for San Gimignano. When you're ready, let your sightseeing route take you to the astonishing Uffizi Gallery. If you’re looking for more, Ponte Vecchio is also a wondrous attraction that is worthwhile a visit. Lastly, don’t miss Palazzo Vecchio, a place of romantic interest in the city.

After soaking up all the sights on today's itinerary, you'll be ready to head to 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.

Florence is a place where the culinary landscape is as diverse as its attractions. So before the day ends, treat your palate to a taste of local cuisine at one of the best restaurants in Florence.

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.

If you’re not ready to end the night just yet, Manifattura offers a perfect venue to relax and savor a drink. Similarly, Se·sto On Arno Rooftop Bar is well-suited for those looking to unwind in a social setting. Il Vinile is another excellent spot to enjoy a nightcap after a delightful meal.

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

On day 6 of your road trip, you'll get the chance to experience Pisa. At the end of the day, you'll drive back to Florence, where you still have 1 night left to stay.

Your adventure in Florence is only getting started when you visit Piazza Del Duomo, Pisa, a timeless local hot spot. Another notable attraction to explore is Pisa Cathedral. This up-and-coming church is known for its UNESCO world heritage-listed appeal.

After soaking in the highlights of these sights, take some time to wander Florence's streets and immerse yourself in the local atmosphere. When you're ready to continue your sightseeing adventure, head to Leaning Tower Of Pisa. This UNESCO world heritage-listed monument offers a fascinating experience that many visitors find memorable. Knights' Square is also worth visiting, along with Palazzo Blu. These standout landmarks offer unique experiences that add to the day’s enjoyment. End your day at Santa Maria Della Spina. This up-and-coming church provides a fitting finale to your sightseeing.

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. If you are looking to dine at a popular restaurant in Florence, it's often a good idea to reserve a table in advance.

Enjoy a delicious meal at Ditta Artigianale, a highly-rated dining destination in Florence. If you're eager to try something different, consider Trattoria Da Burde, another top spot with a tantalizing menu. You might also want to secure a reservation at Casa Toscana. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Florence this evening.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Bar 50 Rosso stands out as an excellent choice for a post-dinner cocktail. Alternatively, Bitter Bar offers an ideal atmosphere to enjoy the pleasures of the night. Archea Brewery is also a great option that provides a perfect setting for a relaxing evening.

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

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

Experience Fortezza Medicea (siena), an increasingly popular monument in the city. Then, head to Basilica Of San Domenico and soak in the ambiance of this picture-perfect church.

There are many interesting places to see in Florence, and when you are ready for more, go to Siena Cathedral. This is one of the city’s most popular enchanting spots of interest. After exploring the church, visit the often recommended Pubblico Palace. Not far away, you'll also find Piazza Del Campo. This public square is an UNESCO world heritage-designated highlight in Florence. Before wrapping up your self-guided sightseeing tour, head to Tower Of Mangia, an intriguing monument in the city.

When you’re done exploring for the day, you’ll drive to your hotel in Siena. Check in and relax 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 Siena. Enjoy a satisfying meal that will recharge you for tonight's adventures.

Treat yourself to a delicious dinner at Enoteca I Terzi, an excellent option for tonight's dining. Looking for something different? Ristorante Tar-Tufo offers a tantalizing alternative with its diverse menu. And don’t miss Antica Trattoria Papei. Known for great service, it’s a fantastic choice for tonight in Siena.

Continue the enjoyment post-dinner at Meet Life Cafè, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Maudit Pub offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out Bar Impero Siena. This bar is a favorite among both locals and visitors looking for a delightful evening out filled with laughter and fun.

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

Dive into day 8 of your remarkable road trip in Italy. Today you'll explore 1 destination, including Santa Maria degli Angeli. At the end of the day, you’ll unwind at one of the finest accommodations in Santa Maria degli Angeli, where you'll spend 1 night.

Make a stop at Basilica Of Santa Maria Degli Angeli. This well-known church is a must-visit for travelers looking for a unique holiday experience. Make your way to Eremo Delle Carceri located in Siena for another exciting encounter.

Next, immerse yourself in the setting of Rocca Maggiore. Its symbolic features will captivate you. After the castle, continue your tour of the village with a visit to Basilica Of San Francesco D'assisi. Visitors usually appreciate the UNESCO world heritage-designated features of this church. Next up is Portico Of Monte Frumentario, a highly recommended historical landmark. For a change of pace, head to Piazza Del Comune. As one of the most increasingly popular attractions in Siena, this public square is the perfect place to end your self-guided sightseeing tour.

At the end of the day, you will drive to Santa Maria degli Angeli, 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 Santa Maria degli Angeli. Enjoy a relaxing evening as you savor delicious local cuisine.

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

Say good night to Santa Maria degli Angeli and look forward to another great day of your road trip in Italy!

Your itinerary for day 9 of your road trip in Italy includes 1 stop and features some of the highlights of Perugia. At the end of the day, enjoy the comforts of a top-rated hotel in Perugia, where you'll spend 1 night.

Enjoy all that National Archaeological Museum Of Umbria has to offer. This is an intriguing museum you should not miss. Another must-see is Rocca Paolina, an often recommended historical landmark in Santa Maria degli Angeli.

When you’re ready for the next sight, head to Carducci Gardens. From there, take a leisurely stroll to Perugia Cathedral, another of the city’s up-and-coming attractions. We recommend continuing your self-guided tour at Piazza Iv Novembre, a history-steeped place of interest in the city. If time allows, add The Fontana Maggiore to your itinerary. This underrated monument offers the perfect finishing touch to your day in Santa Maria degli Angeli.

After soaking up all the sights on today's itinerary, you'll be ready to head to 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 a true cultural experience.

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 consistently gains high praises from customers, it’s an ideal choice in Perugia tonight.

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.

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

Experience an unparalleled adventure on day 10 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 2 places, which are Vatican City and Rome. At the end of the day, you will retreat to the hotel of your choice in Rome, where will spend 2 nights.

One of the most widely recognized attractions included on the itinerary is Sistine Chapel.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the timeless Vatican Museums. After exploring the art museum, head to Spanish Steps. This impressive public square is a highlight in Perugia.

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

As dinnertime approaches, it's time to head out for a bite to eat. If you are looking to dine at a popular restaurant in Rome, it's often a good idea to reserve a table in advance.

Have a fantastic dining experience at La Bottega Roma, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Pasta In Corso offers an enticing alternative with its varied menu. Additionally, Trattoria Vecchia Roma is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Rome.

Keep the excitement of the evening going by visiting a bar or two. La Botticella Of Poggi Giovanni is an excellent place to start. You could also check out Almalu Trastevere, offering a different kind of charm. A last recommendation for the day is Bar Viminale Di Pepi Maurilio. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

Raise your glass to another unforgettable day 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 the city and use the provided itinerary to discover what to see in Rome.

Enjoy all that Villa Borghese Pinciana has to offer. This is a well-known museum you should not miss. Another must-see is Colosseum, an iconic archeological site in Rome.

When you’re ready for the next sight, head to Roman Forum. From there, take a leisurely stroll to Trevi Fountain, another of the city’s globally renowned attractions. We recommend continuing your self-guided tour at Pantheon, a culturally significant place of interest in the city. If time allows, add Castel Sant'angelo to your itinerary. This astonishing castle offers the perfect finishing touch to your day in Rome.

Don’t forget to check out all the popular tours and experiences you can add to your travel plans in Italy. You can explore and select activities under each day of your itinerary.

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

Treat yourself to a wonderful meal at RomAntica, a top-rated dining spot in Rome. If you're in the mood for something new, try Coso Ristorante, another premier location with a delectable menu. You might also want to book a table at DEROMA - Farine Romane. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Rome.

Let the evening flow smoothly from dinner to drinks at Sant' Eustachio Caffè, a top-rated bar in the area. For other recommendations, Yellowsquare Rome provides a perfect setting for rounding out your night with style and great drinks. Likewise, Caffè Portofino offers a memorable night with diverse drink options and excellent service.

Relax and look forward to more memorable moments to come!

On day 12 of your road trip in Italy, your travel plans include 1 stop at the most scenic, wondrous, and interesting places in the region. Naples are on today's agenda. In the evening, you’ll end up in Sorrento, where you will stay for 2 nights.

Start your day at Castel Sant'elmo. This breathtaking castle is a well-known place to see in Rome. Then, wander over to Naples National Archaeological Museum. If photogenic sites excite you, this museum will be right up your alley. Nearby, you’ll also find Spaccanapoli. This romantic street is a favorite among visitors.

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.

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

Don’t miss out on dining at Frankie's Pizza Bar Sorrento Brunch & Vegan, a top-rated dining destination in Sorrento. If you're in the mood to try something new, consider Bougainvillea, another top spot with a mouthwatering menu. You might also want to secure a reservation at Banana Split. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Sorrento this evening.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Leone Rosso Café stands out as an excellent choice for a post-dinner cocktail. Alternatively, Hotel Antiche Mura Sorrento offers an ideal atmosphere to enjoy the pleasures of the night.

Relax and look forward to more memorable moments to come!

Greet day 13 of your road trip in Italy with a smile and start your day with a hearty breakfast. You have 1 night to stay in Sorrento, so get ready to make the most of your time in the region. On the agenda for this day, you’ll find only the best things to see and do in Ravello, Positano, Amalfi, and Atrani.

Enjoy all that Fondazione Ravello has to offer. This is an up-and-coming cultural center you should not miss. Another must-see is Costiera Amalfitana Positano, an often recommended beach in Sorrento.

When you’re ready for the next sight, head to Amalfi Coast. From there, take a leisurely stroll to Collegiate Santa Maria Maddalena, another of the village’s often recommended attractions. We recommend continuing your self-guided tour at Villa Rufolo, a symbolic place of interest in the village.

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

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.

Don’t miss out on dining at Fuoro51, a top-rated dining destination in Sorrento. If you're in the mood to try something new, consider Hotel Bellevue Syrene, another top spot with a mouthwatering menu. You might also want to secure a reservation at Fauno Bar. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Sorrento this evening.

As the day draws to a close, take a moment to unwind and prepare for the next exciting chapter of your road trip in Italy.

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

Whatever your travel style is, Archaeological Park Of Pompeii is an essential stop in Sorrento. This locally renowned archeological site provides an insightful glimpse into the town's identity. Next, discover Amphitheatre Of Pompeii, a culturally significant archeological site, promising a delightful encounter.

After soaking up all the sights on today's itinerary, you'll be ready to head to 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.

Ancona is a place where the culinary landscape is as diverse as its attractions. So before the day ends, treat your palate to a taste of local cuisine at one of the best restaurants in Ancona.

Make sure to reserve a table at Pizzeria Pulcinella, an iconic dining spot in Ancona. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Donegal Irish Pub, a popular restaurant in Ancona. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Vino E Cucina Miscia, a hidden gem nestled in Ancona. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

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