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 of your road trip will take you to the best attractions Ancona has to offer. Cherish the 1 night you have left in the city and use the provided itinerary to discover what to see in Ancona.

Whatever your travel style is, Passetto is an essential stop in Ancona. This increasingly popular monument provides an insightful glimpse into the city's identity. Next, discover Cathedral Basilica Of St. Cyriacus, a stunning church, promising a delightful encounter.

Continue your sightseeing with a visit to Arch Of Trajan, a frequently visited monument. When you’re done, don’t forget to make a stop at the locally appreciated Lazzaretto Of Ancona. Not far away from the museum, you will find the stunning Parco Belvedere Posatora, perfect for a quick visit. Round off your day at State Tactile Museum Omero, another gem in Ancona with photogenic features to discover.

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 Ancona's most popular restaurants, and connect with friendly locals for a true cultural experience.

Make sure to reserve a table at Amarcord, 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 Bontà delle Marche, 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 Ristorante Pizzeria Da Romano, a hidden gem nestled in Ancona. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Alla Tazza D'oro, known for its inviting atmosphere.

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 place, which are Urbino. At the end of the day, you will retreat to the hotel of your choice in Urbino, where will spend 1 night.

It’s time to gear up for the next part of your road trip adventure. Under favorable conditions, your drive to Urbino may take around 1 hour 23 min. Upon your arrival in Urbino, you’ll be greeted with the opportunity to do some sightseeing and exploring.

Fortezza Albornoz is a frequently visited castle we recommend visiting today. Discover its picture-perfect features before continuing your self-guided tour to Casa Santi, a historic museum that’s well-regarded in the area.

Next, stop by Galleria Nazionale Delle Marche, a picture-perfect museum. While you’re nearby, don’t forget to visit Palazzo Ducale, an instagrammable and truly unique palace. End your sightseeing at Oratory Of St John The Baptist, Urbino, an often recommended church that’s highly recommended by travelers passing through the town.

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.

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

Dive into day 4 of your remarkable road trip in Italy. Today you'll explore 1 destination, including San Gimignano. At the end of the day, you’ll unwind at one of the finest accommodations in San Gimignano, where you'll spend 1 night.

Embrace the thrill of the open road as you wave goodbye to Urbino and set your GPS to San Gimignano. While on the road, immerse yourself in your favorite road trip tunes or sample the sounds from a local radio station. This car ride usually takes around 3 hours 20 min. Upon reaching San Gimignano, unwind, observe, and explore. The best things to do, see, and eat are waiting for you.

Our first attraction recommendation in San Gimignano is Chiesa Di Sant'agostino, a worthwhile church that draws attention for its culturally significant features. Spend some time soaking in the atmosphere before continuing to Parco Della Rocca, an enchanting park that stands out in the village.

Time flies when you're having fun! But don't forget to stop for a bit to eat and drink between your adventures. When you're rested and recharged, head to Sangimignano1300, a frequently visited museum that offers a unique experience. Be sure to also explore Porta San Giovanni, a nearby monument, highly recommended by other travelers. End your self-guided tour at Galleria Continua, an instagrammable art gallery and the perfect final attraction in San Gimignano.

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

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

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

Your itinerary for day 5 of your road trip in Italy includes 1 stop and features some of the highlights of Florence. At the end of the day, enjoy the comforts of a top-rated hotel in Florence, where you'll spend 2 nights.

Set your GPS to Florence and hit the road. Expect a journey of approximately 54 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Florence beckons with new experiences!

One of our top recommendations for your sightseeing is The Boboli Gardens. Spend some time admiring the romantic features of the botanical garden before you continue to your next stop. Then, head to Piazzale Michelangelo. This widely recognized observation deck is a traveler-favorite in the city.

If you're keen to see more, continue to Basilica Of Santa Croce In Florence. Feed your curiosity by learning something new about the church. Next, take your journey to Uffizi Gallery, an astonishing art gallery. Conclude your sightseeing at Ponte Vecchio, known for its culturally significant features.

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.

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.

Enjoy a delicious meal at Ristorante Oliviero 1962, a top-rated dining destination in Florence. If you're in the mood to try something new, consider Di Poneta Novoli, another top spot with a mouthwatering menu. You might also want to secure a reservation at Caffe San Firenze. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Florence this evening.

Extend your evening after a delightful meal by visiting Manifattura, which offers the perfect atmosphere for a night out. Moreover, Se·sto On Arno Rooftop Bar is another popular option for a drink or two. Likewise, Il Vinile also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

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 6 of your road trip, you’ll start and end your day in Florence, where you have 1 night left to stay.

Set your GPS to Pisa and hit the road. Expect a journey of approximately 1 hour 16 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Pisa beckons with new experiences!

Enjoy sightseeing at your own pace and allow yourself time to explore the beautiful surroundings. Take your self-guided tour to Piazza Del Duomo, Pisa, a timeless public square that everyone visiting Pisa should see. Next, head to Pisa Cathedral. This majestic church is one of the most worthwhile attractions in the region.

If you're keen to see more, don’t miss out on Leaning Tower Of Pisa, a historic monument popular among locals as well as travelers. Knights' Square is an excellent attraction to visit next. Spend some time learning more about this often recommended public square before you continue your journey. Lastly, visit Palazzo Blu, a respected art gallery and a top attraction in the city.

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

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

Make sure to reserve a table at Ditta Artigianale, 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 Trattoria Da Burde, 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 Casa Toscana, a hidden gem nestled in Florence. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Continue your lively evening at Bar 50 Rosso, a perfect place for winding down or revving up the night, depending on which mood you’re in. Bitter Bar is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Archea Brewery ensures a night out tailored to your taste.

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.

Continue your road trip and head to your next destination, Siena. This car ride takes around 1 hour 10 min.

Set out on a self-guided sightseeing tour at Fortezza Medicea (siena) and explore the stunning features. Next, make your way to Basilica Of San Domenico, another highlight in Siena. When you’re done exploring the church, continue to Siena Cathedral, a history-steeped church.

Nearby, you will also find Pubblico Palace. This beloved palace is a top place to see in the area. Lastly, head to Piazza Del Campo, an enchanting public square that is perfect for some final exploring 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.

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

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

After your delicious meal, get a taste of the vibrant nightlife with a visit to Meet Life Cafè, known for its inviting atmosphere. Maudit Pub is another great option if you’re looking for a place to get the night started. Similarly, Bar Impero Siena provides a great setting to enjoy the night away.

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

On day 8 of your road trip in Italy, your travel plans include 1 stop at the most scenic, wondrous, and interesting places in the region. Santa Maria degli Angeli are on today's agenda. In the evening, you’ll end up in Santa Maria degli Angeli, where you will stay for 1 night.

When you’re ready to jump back into the car and say goodbye to Siena, you’ll hit the road in the direction of Santa Maria degli Angeli. This drive usually takes around 1 hour 32 min.

For a more meaningful self-guided tour of the village's best attractions, visit Basilica Of Santa Maria Degli Angeli, a notable church that is sure to impress. Take in the surroundings and enjoy the freedom of exploring at your own pace before you continue your journey.

Embrace the thrill of the open road as you wave goodbye to Santa Maria degli Angeli and set your GPS to Santa Maria degli Angeli. While on the road, immerse yourself in your favorite road trip tunes or sample the sounds from a local radio station. This car ride usually takes around 19 min. Upon reaching Santa Maria degli Angeli, unwind, observe, and explore. The best things to do, see, and eat are waiting for you.

Our first attraction recommendation in Santa Maria degli Angeli is Eremo Delle Carceri, a frequently visited monastery that draws attention for its enchanting features. Spend some time soaking in the atmosphere before continuing to Rocca Maggiore, an enchanting castle that stands out in the village.

Time flies when you're having fun! But don't forget to stop for a bit to eat and drink between your adventures. When you're rested and recharged, head to Basilica Of San Francesco D'assisi, a locally renowned church that offers a unique experience. Be sure to also explore Portico Of Monte Frumentario, a nearby historical landmark, highly recommended by other travelers. End your self-guided tour at Piazza Del Comune, a romantic public square and the perfect final attraction 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 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 day of adventure, treat yourself to an exquisite dinner at one of Santa Maria degli Angeli's best restaurants.

After your meal, keep the night alive at a bar like Bibenda Assisi Wine Tasting & Gourmet Food, Olive Oil And Chocolate Tastings, known for its lively atmosphere.

Raise your glass to another unforgettable day 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 place, which are Perugia. At the end of the day, you will retreat to the hotel of your choice in Perugia, where will spend 1 night.

When you’ve had your share of Santa Maria degli Angeli, prepare for your next destination. Admire the views and listen to some good music as you drive in the direction of Perugia. Your travel time is around 32 min.

Enjoy sightseeing at your own pace and allow yourself time to explore the beautiful surroundings. Take your self-guided tour to National Archaeological Museum Of Umbria, an increasingly popular museum that everyone visiting Perugia should see. Next, head to Rocca Paolina. This symbolic historical landmark is one of the most underrated attractions in the region.

If you're keen to see more, don’t miss out on Carducci Gardens, a romantic park popular among locals as well as travelers. Perugia Cathedral is an excellent attraction to visit next. Spend some time learning more about this underrated church before you continue your journey. Lastly, visit Piazza Iv Novembre, a romantic public square and a top attraction in the city.

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.

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

Explore the vibrant nightlife at Tommi Bar after your meal, a hub for lively evenings and memorable moments. Or, head to Valentina for a great selection of flavorful drinks and a charming setting. Furthermore, Caffe Dal Perugino is perfect for those looking to extend their night with a touch of local flavor.

Savor another day of unforgettable experiences in Italy!

Dive into day 10 of your remarkable road trip in Italy. Today you'll explore 2 destinations, including Vatican City and Rome. At the end of the day, you’ll unwind at one of the finest accommodations in Rome, where you'll spend 2 nights.

Once you're ready to continue your road trip, it's time to buckle up and drive towards Vatican City, eagerly anticipating your arrival in Vatican City. This drive usually takes around 2 hours 20 min, without any stops or traffic disruptions.

Next, continue your sightseeing at St. Peter's Basilica, a world-famous major basilica.

After soaking in Vatican City’s unique atmosphere, jump into the car with a full heart and drive in the direction of your next destination: Rome, Italy. Expect your car journey to take a minimum of 21 min. When you arrive in Rome, it's time to take a break from the road.

For a more meaningful self-guided tour of the city's best attractions, visit Spanish Steps, a spectacular public square that is sure to impress. Take in the surroundings and enjoy the freedom of exploring at your own pace before you continue your journey.

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.

Treat yourself to a delightful dinner at La Bottega Roma, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Pasta In Corso? It's another excellent option with a diverse menu. Consider reserving a table at Trattoria Vecchia Roma as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Rome.

Keep the evening going at La Botticella Of Poggi Giovanni, a great choice for enjoying the after-dinner hours with a drink. You could also go to Almalu Trastevere, which offers a similarly pleasant setting and great drinks. Another option is Bar Viminale Di Pepi Maurilio, which provides an inviting environment for unwinding after a busy day out.

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

On day 11 of your road trip, you will have an entire day to discover what to see in Rome. You’ll stay in Rome for 1 night.

Start your day at Villa Borghese Pinciana. This enchanting museum is a popular place to see in Rome. Then, wander over to Colosseum. If picture-perfect sites excite you, this archeological site will be right up your alley. Nearby, you’ll also find Roman Forum. This historic archeological site is a favorite among visitors.

Rome offers plenty to explore, ensuring every moment of your visit is filled with excitement and discovery. If you're up for more, Trevi Fountain is a wondrous spot in the city that will captivate you with its unique charm. When you’re done at the monument, don’t forget to check out the heritage-rich Pantheon. Take a moment to appreciate the fascinating details of this globally renowned monument. Wrap up your self-guided tour of Rome's top attractions with a visit to Castel Sant'angelo.

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 Rome, it's often a good idea to reserve a table in advance.

Enjoy a lovely dining experience at RomAntica, a popular restaurant in Rome. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Rome at Coso Ristorante, 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 DEROMA - Farine Romane. It’s yet another ideal choice to enhance your time in Rome tonight.

Unwind after your meal by stepping into Sant' Eustachio Caffè. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Yellowsquare Rome offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Caffè Portofino, another top-rated bar in the area.

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

Your itinerary for day 12 of your road trip in Italy includes 1 stop and features some of the highlights of Naples. At the end of the day, enjoy the comforts of a top-rated hotel in Sorrento, where you'll spend 2 nights.

Throughout the day, make sure to take breaks to appreciate the surroundings.

Naples’s wonders await as you prepare for another journey on the road, leaving the breathtaking surroundings of Rome behind. This drive usually takes around 2 hours 32 min. Naples welcomes you with a multitude of unique vacation experiences.

Savor the day by heading to Castel Sant'elmo, a notable castle that draws visitors from near and far. When you're done, continue to Naples National Archaeological Museum, where you can soak in the heritage-rich surroundings.

Next, explore Spaccanapoli, yet another worthwhile place to see in the area.

After soaking up all the sights on today's itinerary, you'll be ready to head to 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 long day of exploring, sit down for a delicious dinner at a top-rated restaurant in Sorrento. Enjoy a satisfying meal that will recharge you for tonight's adventures.

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

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

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

On day 13 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 still have 1 night to spend in Sorrento, there’s no need to rush. Experience Ravello, Positano, Amalfi, and Atrani to the fullest today with this curated day itinerary.

Ravello is brimming with adventures.

Throughout the day, make sure to take breaks to appreciate the surroundings.

After soaking in Sorrento’s unique atmosphere, jump into the car with a full heart and drive in the direction of your next destination: Ravello. Expect your car journey to take a minimum of 1 hour 30 min. When you arrive in Ravello, it's time to take a break from the road.

One of our top recommendations for your sightseeing is Fondazione Ravello. Spend some time admiring the instagrammable features of the cultural center before you continue to your next stop. Then, head to Villa Rufolo. This well-known historical landmark is a traveler-favorite in the village.

Continue your road trip and head to your next destination, Positano. This car ride takes around 1 hour 5 min.

Spend your afternoon discovering Costiera Amalfitana Positano, an often recommended beach known for its mesmerizing features.

Embrace the thrill of the open road as you wave goodbye to Positano and set your GPS to Amalfi. While on the road, immerse yourself in your favorite road trip tunes or sample the sounds from a local radio station. This car ride usually takes around 41 min. Upon reaching Amalfi, unwind, observe, and explore. The best things to do, see, and eat are waiting for you.

Amalfi Coast is an astonishing coast we recommend visiting today.

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. If you are looking to dine at a popular restaurant in Sorrento, 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.

Celebrate another amazing day of your road trip adventure 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.

Fasten your seatbelt and make your way to your next stop — Pompei, home to many well-known sights in the region. Keep in mind that your travel time from Sorrento to Pompei may take around 48 min without traffic disruptions. Upon arrival in Pompei, we highly recommend checking out some of the top attractions.

When you're ready for some sights, head to Archaeological Park Of Pompeii, a well-known archeological site in Pompei. Explore its breathtaking features at your own pace before you continue your journey to your next attraction, Amphitheatre Of Pompeii. This well-known archeological site is a top recommendation in the area.

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

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.

Savor the flavors at Pizzeria Pulcinella, a top pick for dinner tonight. Alternatively, Donegal Irish Pub beckons with its unique menu offerings. Also, consider Vino E Cucina Miscia. With its consistent customer satisfaction, it’s an excellent option for dining in Ancona tonight.

Say good night to Ancona and look forward to another great day of your road trip in Italy!