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 Ancona 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 Ancona on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss. Passetto is the first of them. Spend some time admiring this visually striking monument before continuing your journey. Cathedral Basilica Of St. Cyriacus is your next stop. This worthwhile church is one of the best-rated sights in Ancona.

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 Arch Of Trajan. This breathtaking monument is a sight to behold. To round off your sightseeing experience, visit Lazzaretto Of Ancona and State Tactile Museum Omero. If time allows, end your day with Parco Belvedere Posatora, an idyllic park 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 Ancona. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.

Treat yourself to a delightful dinner at Amarcord, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Bontà delle Marche? It's another excellent option with a diverse menu. Consider reserving a table at Ristorante Pizzeria Da Romano as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Ancona.

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

Say good night to Ancona and look forward to another great day of your road trip 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 underrated museum is known for its eye-catching 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 respected 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.

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.

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 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.

Get ready for an exciting day in Urbino. Today’s sightseeing agenda includes a church, a park, a museum, a monument, an art gallery, a public square and much more! Begin your adventure at Chiesa Di Sant'agostino. This is a worthwhile church you should not miss. Another must-see is Parco Della Rocca, a beloved park in Urbino.

When you’re ready for the next sight, head to Sangimignano1300. From there, take a leisurely stroll to Porta San Giovanni, another of the village’s underrated attractions. We recommend continuing your self-guided tour at Galleria Continua, an eye-catching place of interest in the village. If time allows, add Piazza Del Duomo to your itinerary. This worthwhile public square offers the perfect finishing touch to your day 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 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.

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

On day 5 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, Florence. When you’re not sightseeing, take time to relax at your selected hotel in Florence, where you’ll be staying for 2 nights.

Prepare for a day full of family-friendly attractions, romantic experiences, and breathtaking views. When you’re ready, kick off your sightseeing adventure at The Boboli Gardens. This interesting botanical garden is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Piazzale Michelangelo, one of the city’s best highlights.

Next, check out Basilica Of Santa Croce In Florence, one of the most popular places to see in San Gimignano. This church is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, Uffizi Gallery. Wander around and soak in the romantic atmosphere this art gallery offers. Then, head to Ponte Vecchio, a top-rated historical landmark that adds another dimension to your day. Finally, visit the captivating Palazzo Vecchio, the last of our attraction recommendations for today.

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 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 your delicious meal, get a taste of the vibrant nightlife with a visit to Manifattura, known for its inviting atmosphere. Se·sto On Arno Rooftop Bar is another great option if you’re looking for a place to get the night started. Similarly, Il Vinile provides a great setting to enjoy the night away.

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 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.

Florence is brimming with adventures. Today’s wonderful stops include a public square, a church, a monument, an art gallery and much more! Begin your sightseeing adventure at the world-famous Piazza Del Duomo, Pisa and allow yourself time to explore. Just a short distance away you'll find your next stop, Pisa Cathedral, a historic church that draws visitors from far and near.

Continue your journey to Leaning Tower Of Pisa, one of the city’s most iconic spots that you shouldn’t miss. Another great site to visit is the underrated Knights' Square. When you're finished at the public square, Palazzo Blu awaits your visit. This art gallery is a photogenic highlight on today's itinerary. Last up is a church - the often recommended Santa Maria Della Spina.

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

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

Savor the flavors at Ditta Artigianale, a top pick for dinner tonight. Alternatively, Trattoria Da Burde beckons with its unique menu offerings. Also, consider Casa Toscana. With its consistent customer satisfaction, it’s an excellent option for dining 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.

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

On day 7 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 Siena. In the evening, you’ll end up in Siena, where you will stay for 1 night.

Start by visiting Fortezza Medicea (siena), a prime spot to begin your journey. This historic monument is sure to impress. Next on your list is Basilica Of San Domenico, another must-visit landmark and often recommended church renowned for its historic 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 Siena Cathedral. This romantic church is an essential place to visit for anyone looking for the full Florence experience. We also recommend visiting Pubblico Palace, a frequently visited palace. Nearby, you'll also find Piazza Del Campo, ready to add charm to your journey. End your self-guided sightseeing tour with a stop at Tower Of Mangia and wrap up your day with its picture-perfect appeal.

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 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.

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 your meal, keep the night alive at a bar like Meet Life Cafè, known for its lively atmosphere. Maudit Pub is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Bar Impero Siena offers an excellent atmosphere for those looking to amp up the evening.

Raise your glass to another unforgettable day in Italy!

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 agenda in Siena includes a church, a monastery, a castle, a historical landmark, a public square and much more! Basilica Of Santa Maria Degli Angeli is must-visit church and a great starting point for the day. Next, continue your journey to Eremo Delle Carceri, a worthwhile monastery, located just a leisurely stroll away. Next, head to Rocca Maggiore, a history-steeped castle, also available for your discovery today.

Each stop on today’s itinerary promises to leave you with lasting memories and a deeper appreciation for Siena. When you're ready, let your sightseeing route take you to the notable Basilica Of San Francesco D'assisi. If you’re looking for more, Portico Of Monte Frumentario is also a frequently visited attraction that is worthwhile a visit. Lastly, don’t miss Piazza Del Comune, a place of grand interest in the village.

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.

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at Bibenda Assisi Wine Tasting & Gourmet Food, Olive Oil And Chocolate Tastings, a well-loved spot among locals and tourists.

Savor another day of unforgettable experiences 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.

Today's adventure in Santa Maria degli Angeli promises more breathtaking discoveries and enriching experiences! Begin at National Archaeological Museum Of Umbria. This respected museum is a highlight of any visit in the city. Then, enjoy Rocca Paolina, another symbolic attraction that never fails to captivate visitors. Next, head over to Carducci Gardens, one of the city’s most up-and-coming attractions, known for its gorgeous features.

If you’re looking for more, spend time soaking in the atmosphere of Perugia Cathedral. This heritage-rich church is frequented by locals and tourists alike. To complete your memorable day, make sure to visit Piazza Iv Novembre, an increasingly popular public square, and take a stroll around the area. If you want to extend your self-guided sightseeing tour, go check out The Fontana Maggiore before you head back to your hotel.

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.

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

Cap off your dinner by heading to Tommi Bar, ideal for a leisurely evening with a drink in hand. Valentina is another bar that offers an enjoyable setting. Similarly, Caffe Dal Perugino is also a popular place to go on a night out, perfect for relaxing and socializing.

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

A blend of family-friendly attractions, romantic experiences, and breathtaking views await you in Perugia on today’s itinerary. First up is the widely recognized chapel, Sistine Chapel. Afterward, continue to St. Peter's Basilica, a major basilica every traveler should visit.

As you explore Perugia’s charming streets, take in the lively atmosphere and get to know the character of the city. Next, make your way to Vatican Museums. This timeless art museum is an essential stop. Following that, head to Spanish Steps, another must-visit site that will enhance your experience.

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.

Dine in style at La Bottega Roma, a top recommendation for dinner tonight. Or, for a change of pace, Pasta In Corso boasts a menu that's sure to impress. Also, be sure to check out Trattoria Vecchia Roma. Known as a local hotspot, it’s a great choice for tonight in Rome.

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.

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

Day 11 offers a multitude of experiences. You will stay in Rome for 1 night more, offering you enough time to explore at a relaxed pace.

Today’s agenda in Rome includes a museum, an archeological site, a monument, a castle and much more! Villa Borghese Pinciana is must-visit museum and a great starting point for the day. Next, continue your journey to Colosseum, a world-famous archeological site, located just a leisurely stroll away. Next, head to Roman Forum, a culturally significant archeological site, also available for your discovery today.

Each stop on today’s itinerary promises to leave you with lasting memories and a deeper appreciation for Rome. When you're ready, let your sightseeing route take you to the iconic Trevi Fountain. If you’re looking for more, Pantheon is also a timeless attraction that is worthwhile a visit. Lastly, don’t miss Castel Sant'angelo, a place of respected interest 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 you explore more of Rome, 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 RomAntica, an iconic dining spot in Rome. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Coso Ristorante, a popular restaurant in Rome. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of DEROMA - Farine Romane, a hidden gem nestled in Rome. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

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.

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

On day 12 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, Naples. When you’re not sightseeing, take time to relax at your selected hotel in Sorrento, where you’ll be staying for 2 nights.

Rome is home to plenty of attractions that offer fun adventures, breathtaking views, and photo-friendly spots! Start at Castel Sant'elmo, a well-known castle that is worthwhile a visit in the city. Nearby, you’ll find Naples National Archaeological Museum, enchanting visitors with its heritage-rich appeal. Continue your exploration at Spaccanapoli. This street is one of the city’s most increasingly popular spots.

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 delicious dinner at Frankie's Pizza Bar Sorrento Brunch & Vegan, an excellent option for tonight's dining. Looking for something different? Bougainvillea offers a tantalizing alternative with its diverse menu. And don’t miss Banana Split. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Sorrento.

Unwind after your meal by stepping into Leone Rosso Café. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Hotel Antiche Mura Sorrento offers a dynamic and energetic atmosphere for a glass or two.

Relax and reminisce about your day in Italy 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 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.

A blend of fun adventures, romantic experiences, and breathtaking views await you in Sorrento on today’s itinerary. First up is the underrated cultural center, Fondazione Ravello. Afterward, continue to Costiera Amalfitana Positano, a beach every traveler should visit.

As you explore Sorrento’s charming streets, take in the lively atmosphere and get to know the character of the village. Next, make your way to Amalfi Coast. This famous coast is an essential stop. Following that, head to Collegiate Santa Maria Maddalena, another must-visit site that will enhance your experience. Don’t forget to stop by Villa Rufolo, a well-known historical landmark 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 and reflect on the day'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 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 Pompei. In the evening, you’ll end up in Ancona, where you will stay for 1 night.

Start your day with a visit to Archaeological Park Of Pompeii. This captivating archeological site is a must-visit in the town. When you’re ready for your next discovery, continue to Amphitheatre Of Pompeii, which may be one of the most UNESCO world heritage-designated places you will experience today.

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

Enjoy a delicious meal at Pizzeria Pulcinella, a highly-rated dining destination in Ancona. If you're eager to try something different, consider Donegal Irish Pub, another top spot with a tantalizing menu. You might also want to secure a reservation at Vino E Cucina Miscia. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Ancona this evening.

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