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 across Italy promises a magnificent time exploring Ancona. You have 1 night left in Ancona. Take the opportunity to experience more of the best attractions and activities in the city.

Brace yourself for today’s incredible lineup of attractions in Ancona, featuring fun adventures, romantic experiences, and breathtaking views. Start at Passetto, a beloved 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 increasingly popular culturally significant spots of interest. After exploring the monument, visit the beloved Lazzaretto Of Ancona. Not far away, you'll also find State Tactile Museum Omero. This museum is a remarkable highlight in Ancona. Before wrapping up your self-guided sightseeing tour, head to Parco Belvedere Posatora, a frequently visited park in the city.

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 Ancona. 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.

Have a fantastic dining experience at Amarcord, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Bontà delle Marche offers an enticing alternative with its varied menu. Additionally, Ristorante Pizzeria Da Romano is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Ancona.

Unwind after your meal by stepping into Alla Tazza D'oro. This venue is celebrated for its extensive drink selections and cozy vibes.

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

Dive into day 3 of your remarkable road trip in Italy. Today you will explore Urbino, 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 Urbino. You’ll stay here for 1 night.

Brace yourself for today’s incredible lineup of attractions in Ancona, featuring fun adventures, scenic views, and photo-friendly spots. Start at Fortezza Albornoz, an up-and-coming castle in the town. Then, head to Casa Santi and soak in the ambiance of this visually striking museum.

There are many interesting places to see in Ancona, and when you are ready for more, go to Galleria Nazionale Delle Marche. This is one of the town’s most intriguing historic spots of interest. After exploring the museum, visit the interesting Palazzo Ducale. Not far away, you'll also find Oratory Of St John The Baptist, Urbino. This church is a stunning highlight in Ancona.

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

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

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

On day 4 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 San Gimignano. In the evening, you’ll end up in San Gimignano, where you will stay for 1 night.

Today's adventure in Urbino promises more breathtaking discoveries and enriching experiences! Begin at Chiesa Di Sant'agostino. This heritage-rich church is a highlight of any visit in the village. Then, enjoy Parco Della Rocca, another stunning attraction that never fails to captivate visitors. Next, head over to Sangimignano1300, one of the village’s most intriguing attractions, known for its eye-catching features.

If you’re looking for more, spend time soaking in the atmosphere of Porta San Giovanni. This culturally significant monument is frequented by locals and tourists alike. To complete your memorable day, make sure to visit Galleria Continua, an underrated art gallery, and take a stroll around the area. If you want to extend your self-guided sightseeing tour, go check out Piazza Del Duomo before you head back to your hotel.

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

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 5 of your road trip in Italy. Today, you will make 1 stop and experience some of the highlights of Florence. At the end of the day, you will enjoy the comforts of a top-rated hotel in Florence, which will be your home away from home for 2 nights.

Today’s itinerary in San Gimignano covers several incredible sights, including a botanical garden, an observation deck, a church, an art gallery, a historical landmark, a palace and much more! Start your adventure at The Boboli Gardens. This interesting botanical garden is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the visually striking wonders of Piazzale Michelangelo, a must-see observation deck in the city.

Consider stopping for a small bite to eat or a drink at a local eatery to keep your energy going. When you’re ready, continue your discovery with a visit to Basilica Of Santa Croce In Florence. This popular church offers an enriching experience. For a change of pace, head to Uffizi Gallery, where you can take in eye-catching features. Conclude your self-guided sightseeing tour with a visit to Ponte Vecchio and Palazzo Vecchio. These sights offer a fulfilling end to a perfect day.

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.

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.

Don’t miss out on dining 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.

Following your dinner, dive into the local bar culture at Manifattura. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Se·sto On Arno Rooftop Bar, the perfect place for those looking to experience the best of the nightlife. Similarly, Il Vinile provides excellent drinks and a great atmosphere, ensuring a memorable night out.

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

On day 6 of your road trip, you’ll start and end your day in Florence, where you'll stay for 1 night more.

Start by visiting Piazza Del Duomo, Pisa, a prime spot to begin your journey. This culturally significant public square is sure to impress. Next on your list is Pisa Cathedral, another must-visit landmark and locally appreciated church renowned for its breathtaking features.

While exploring and sightseeing, take time to savor the culture of Florence by sampling some local delicacies. When you’re ready for more sightseeing, head to Leaning Tower Of Pisa. This breathtaking monument is an essential place to visit for anyone looking for the full Florence experience. We also recommend visiting Knights' Square, a beloved public square. Nearby, you'll also find Palazzo Blu, ready to add charm to your journey. End your self-guided sightseeing tour with a stop at Santa Maria Della Spina and wrap up your day with its majestic appeal.

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

As you explore more of Florence, you'll discover that its culinary landscape is as diverse as its attractions. Whether you're craving traditional dishes bursting with local flavors or innovative creations that push the boundaries of taste, you're sure to find a dining experience that satisfies your cravings.

Treat yourself to a wonderful meal at Ditta Artigianale, a top-rated dining spot in Florence. If you're in the mood for something new, try Trattoria Da Burde, another premier location with a delectable menu. You might also want to book a table at Casa Toscana. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Florence.

After savoring a delicious meal, step into the vibrant nightlife at Bar 50 Rosso, where the evening is just getting started. In the same way, Bitter Bar offers a unique charm perfect for experiencing the local bar scene in Florence. Archea Brewery is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

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

On day 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 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. Fortezza Medicea (siena) is the first of them. Spend some time admiring this standout monument before continuing your journey. Basilica Of San Domenico is your next stop. This frequently visited 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 Siena Cathedral. This grand church is a sight to behold. To round off your sightseeing experience, visit Pubblico Palace and Piazza Del Campo. If time allows, end your day with Tower Of Mangia, an UNESCO world heritage-designated monument that offers a memorable conclusion to your exploration.

When you’re done exploring for the day, you’ll drive to your hotel in Siena. 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 Siena's best restaurants.

Enjoy a delicious meal at Enoteca I Terzi, a top-rated dining destination in Siena. If you're in the mood to try something new, consider Ristorante Tar-Tufo, another top spot with a mouthwatering menu. You might also want to secure a reservation at Antica Trattoria Papei. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Siena this evening.

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

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

Experience an unparalleled adventure on day 8 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 vibrant destinations - Santa Maria degli Angeli. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Santa Maria degli Angeli. You will spend 1 night here for some well-deserved relaxation.

A blend of fun adventures, scenic views, and picturesque spots await you in Siena on today’s itinerary. First up is the captivating church, Basilica Of Santa Maria Degli Angeli. Afterward, continue to Eremo Delle Carceri, a monastery every traveler should visit.

As you explore Siena’s charming streets, take in the lively atmosphere and get to know the character of the village. Next, make your way to Rocca Maggiore. This frequently visited castle is an essential stop. Following that, head to Basilica Of San Francesco D'assisi, another must-visit site that will enhance your experience. Don’t forget to stop by Portico Of Monte Frumentario, an intriguing historical landmark in the village. Finally, end your day with a visit to Piazza Del Comune, a romantic public square that offers the perfect conclusion to your sightseeing of the day.

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.

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

Extend your evening after a delightful meal by visiting Bibenda Assisi Wine Tasting & Gourmet Food, Olive Oil And Chocolate Tastings, which offers the perfect atmosphere for a night out.

Raise your glass to another unforgettable day in Italy!

Dive into day 9 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 1 night.

Get ready for an exciting day in Santa Maria degli Angeli. Today’s sightseeing agenda includes a museum, a historical landmark, a park, a church, a public square, a monument and much more! Begin your adventure at National Archaeological Museum Of Umbria. This is a curiosity-inducing museum you should not miss. Another must-see is Rocca Paolina, a frequently visited 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 increasingly popular attractions. We recommend continuing your self-guided tour at Piazza Iv Novembre, a majestic place of interest in the city. If time allows, add The Fontana Maggiore to your itinerary. This locally appreciated monument offers the perfect finishing touch to your day in Santa Maria degli Angeli.

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 explore more of Perugia, 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.

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!

On day 10 of your road trip in Italy, you will get a true taste of the freedom a self-drive vacation in Europe entails. Today’s travel plans include stops at the most scenic, wondrous, and interesting places in Vatican City and Rome. In the evening, you’ll end up in Rome, where you will stay for 2 nights.

Bring your curiosity for today’s adventure around Perugia. Some of the city’s most loved attractions await! Sistine Chapel is the perfect place to start. This chapel is one of the most top-rated places to visit in Perugia.

Nearby, you'll also find Spanish Steps. Visit these for an interesting touch to your journey.

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

As you 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.

Treat yourself to a delicious dinner at La Bottega Roma, an excellent option for tonight's dining. Looking for something different? Pasta In Corso offers a tantalizing alternative with its diverse menu. And don’t miss Trattoria Vecchia Roma. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Rome.

Continue your evening by exploring the vibrant nightlife scene at La Botticella Of Poggi Giovanni, a prime destination for a thrilling night out. Also, don’t forget to check out Almalu Trastevere, a bar that offers unique local touches. Likewise, Bar Viminale Di Pepi Maurilio provides an excellent alternative for a fun 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 in Italy.

On day 11 of your road trip, you will have an entire day to explore Rome. You’ll stay in Rome for 1 night and discover all the best things to see and do in the area.

Savor the day by visiting some of the best places to see in Rome, including a museum, an archeological site, a monument, a castle and much more! Start your adventure at Villa Borghese Pinciana. This interesting museum is a must-visit for travelers looking for a unique holiday experience. Make your way to Colosseum located in Rome for another exciting encounter.

Next, immerse yourself in the setting of Roman Forum. Its awe-inspiring features will captivate you. After the archeological site, continue your tour of the city with a visit to Trevi Fountain. Visitors usually appreciate the detailed features of this monument. Next up is Pantheon, a highly recommended monument. For a change of pace, head to Castel Sant'angelo. As one of the most spectacular attractions in Rome, this castle is the perfect place to end your self-guided sightseeing tour.

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.

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.

Following your dinner, dive into the local bar culture at Sant' Eustachio Caffè. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Yellowsquare Rome, the perfect place for those looking to experience the best of the nightlife. Similarly, Caffè Portofino provides excellent drinks and a great atmosphere, ensuring a memorable night out.

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

Embark on another extraordinary experience on day 12 of your road trip in Italy. Today, you will make 1 stop and experience some of the highlights of Naples. 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.

Savor the day by visiting some of the best places to see in Rome, including a castle, a museum, and a street. Start your adventure at Castel Sant'elmo. This interesting castle is a must-visit for travelers looking for a unique holiday experience. Make your way to Naples National Archaeological Museum located in Rome for another exciting encounter.

Next, immerse yourself in the setting of Spaccanapoli. Its romantic features will captivate you.

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 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.

Continue the enjoyment post-dinner at Leone Rosso Café, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Hotel Antiche Mura Sorrento offers a vibrant space for indulging in well-crafted drinks and engaging conversation.

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.

Begin your adventure at Fondazione Ravello. This is a curiosity-inducing 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 increasingly popular attractions. We recommend continuing your self-guided tour at Villa Rufolo, a history-steeped 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.

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.

Treat yourself to a delightful dinner at Fuoro51, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Hotel Bellevue Syrene? It's another excellent option with a diverse menu. Consider reserving a table at Fauno Bar as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Sorrento.

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

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.

Just a short distance away you'll find your next stop, Amphitheatre Of Pompeii, a picture-perfect archeological site that draws visitors from far and near.

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.

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.

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.

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