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

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

Start by visiting Passetto, a prime spot to begin your journey. This romantic monument is sure to impress. Next on your list is Cathedral Basilica Of St. Cyriacus, another must-visit landmark and worthwhile church renowned for its grand features.

While exploring and sightseeing, take time to savor the culture of Ancona by sampling some local delicacies. When you’re ready for more sightseeing, head to Arch Of Trajan. This breathtaking monument is an essential place to visit for anyone looking for the full Ancona experience. We also recommend visiting Lazzaretto Of Ancona, an often recommended museum. Nearby, you'll also find State Tactile Museum Omero, ready to add charm to your journey. End your self-guided sightseeing tour with a stop at Parco Belvedere Posatora and wrap up your day with its romantic appeal.

Don’t forget to check out all the popular tours and activities you can add to your road trip itinerary. Italy is a beautiful travel destination that offers plenty of unique tours that will enhance your vacation experience. Explore and select your activities below.

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

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.

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!

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.

Today, you'll explore some of the most beautiful places in Ancona, including a castle, a museum, a palace, a church and much more! Start your day with a visit to Fortezza Albornoz. This often recommended castle is a must-visit in the town. When you’re ready for your next discovery, continue to Casa Santi, which may be one of the most photogenic places you will experience today.

One of the best things about exploring Ancona on a self-guided tour is that you set the pace. There’s plenty of time for detours and discovering hidden gems. When you’re ready for your next stop, make your way to Galleria Nazionale Delle Marche, a curiosity-inducing museum in the town. If you’re up for more discoveries, don’t forget to reserve some time for Palazzo Ducale and Oratory Of St John The Baptist, Urbino.

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

As you explore more of Urbino, 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.

Head back to your accommodation in Urbino and get some rest in preparation for another magical 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.

Immerse yourself in Urbino’s rich culture with today's sightseeing itinerary. Start your journey at Chiesa Di Sant'agostino. This photogenic church is sure to ignite your curiosity. Next, dive into the awe-inspiring features of Parco Della Rocca, a must-visit park in the village.

In between sights, stop by local stores, picturesque photo spots, and small eateries. When you’re ready for your next attraction, proceed to Sangimignano1300, a frequently visited museum. For a change of scene, check out Porta San Giovanni, known for its breathtaking features. We also recommend visiting Galleria Continua. This art gallery is a must for anyone looking to experience the village to the fullest. Lastly, end your day with a visit to Piazza Del Duomo, yet another curiosity-inducing attraction in Urbino.

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

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

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

Experience an unparalleled adventure on day 5 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 vibrant destinations - Florence. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Florence. You will spend 2 nights here for some well-deserved relaxation.

Start by visiting The Boboli Gardens, a prime spot to begin your journey. This noteworthy botanical garden is sure to impress. Next on your list is Piazzale Michelangelo, another must-visit landmark and top-rated observation deck renowned for its visually striking features.

While exploring and sightseeing, take time to savor the culture of San Gimignano by sampling some local delicacies. When you’re ready for more sightseeing, head to Basilica Of Santa Croce In Florence. This monumental church is an essential place to visit for anyone looking for the full San Gimignano experience. We also recommend visiting Uffizi Gallery, an impressive art gallery. Nearby, you'll also find Ponte Vecchio, ready to add charm to your journey. End your self-guided sightseeing tour with a stop at Palazzo Vecchio and wrap up your day with its symbolic appeal.

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

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 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.

After your meal, keep the night alive at a bar like Manifattura, known for its lively atmosphere. Se·sto On Arno Rooftop Bar is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Il Vinile offers an excellent atmosphere for those looking to amp up the evening.

Savor another day of unforgettable experiences in Italy!

Wake up to day 6 of your extraordinary road trip in Italy. With 1 night left in Florence, we encourage you to seize the day and discover the unexplored beauty of the city’s surroundings!

Today’s agenda in Florence includes a public square, a church, a monument, an art gallery and much more! Piazza Del Duomo, Pisa is must-visit public square and a great starting point for the day. Next, continue your journey to Pisa Cathedral, an increasingly popular church, located just a leisurely stroll away. Next, head to Leaning Tower Of Pisa, a breathtaking monument, also available for your discovery today.

Each stop on today’s itinerary promises to leave you with lasting memories and a deeper appreciation for Florence. When you're ready, let your sightseeing route take you to the beloved Knights' Square. If you’re looking for more, Palazzo Blu is also an up-and-coming attraction that is worthwhile a visit. Lastly, don’t miss Santa Maria Della Spina, a place of visually striking interest in the city.

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.

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.

Explore the vibrant nightlife at Bar 50 Rosso after your meal, a hub for lively evenings and memorable moments. Or, head to Bitter Bar for a great selection of flavorful drinks and a charming setting. Furthermore, Archea Brewery is perfect for those looking to extend their night with a touch of local flavor.

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.

Get ready for an exciting day in Florence. Today’s sightseeing agenda includes a monument, a church, a palace, a public square and much more! Begin your adventure at Fortezza Medicea (siena). This is a beloved monument you should not miss. Another must-see is Basilica Of San Domenico, a curiosity-inducing church in Florence.

When you’re ready for the next sight, head to Siena Cathedral. From there, take a leisurely stroll to Pubblico Palace, another of the city’s beloved attractions. We recommend continuing your self-guided tour at Piazza Del Campo, an UNESCO world heritage-listed place of interest in the city. If time allows, add Tower Of Mangia to your itinerary. This locally appreciated monument offers the perfect finishing touch to your day in Florence.

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

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

Enjoy a lovely meal at Enoteca I Terzi, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Ristorante Tar-Tufo is another top choice with a popular menu. You could also check for a table at Antica Trattoria Papei. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Siena tonight.

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.

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

A blend of family-friendly attractions, scenic views, and picturesque spots await you in Siena on today’s itinerary. First up is the locally renowned 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, a curiosity-inducing historical landmark in the village. Finally, end your day with a visit to Piazza Del Comune, an UNESCO world heritage-listed public square that offers the perfect conclusion to your sightseeing of the day.

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

As dinnertime approaches, it's time to head out for a bite to eat in Santa Maria degli Angeli. 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.

Cap off your dinner by heading to Bibenda Assisi Wine Tasting & Gourmet Food, Olive Oil And Chocolate Tastings, ideal for a leisurely evening with a drink in hand.

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

Brace yourself for today’s incredible lineup of attractions in Santa Maria degli Angeli, featuring fun adventures, photo-friendly spots, and history-rich sites. Start at National Archaeological Museum Of Umbria, an often recommended museum in the city. Then, head to Rocca Paolina and soak in the ambiance of this heritage-rich historical landmark.

There are many interesting places to see in Santa Maria degli Angeli, and when you are ready for more, go to Carducci Gardens. This is one of the city’s most intriguing enchanting spots of interest. After exploring the park, visit the up-and-coming Perugia Cathedral. Not far away, you'll also find Piazza Iv Novembre. This public square is a history-steeped highlight in Santa Maria degli Angeli. Before wrapping up your self-guided sightseeing tour, head to The Fontana Maggiore, an intriguing monument in the city.

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

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 and reflect on the day's adventures.

Treat yourself to a delicious dinner at Ristorante Settimo Sigillo, an excellent option for tonight's dining. Looking for something different? Caffè Baglioni offers a tantalizing alternative with its diverse menu. And don’t miss Bar Pellas. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Perugia.

Continue your evening by exploring the vibrant nightlife scene at Tommi Bar, a prime destination for a thrilling night out. Also, don’t forget to check out Valentina, a bar that offers unique local touches. Likewise, Caffe Dal Perugino provides an excellent alternative for a fun evening.

Raise your glass to another unforgettable day 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.

Prepare for a day full of fun adventures, romantic experiences, and breathtaking views. When you’re ready, kick off your sightseeing adventure at Sistine Chapel. This impressive chapel is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is St. Peter's Basilica, one of the city’s best highlights.

Next, check out Vatican Museums, one of the most timeless places to see in Perugia. This art museum is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, Spanish Steps. Wander around and soak in the history-steeped atmosphere this public square offers.

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

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.

Enjoy a delicious meal at La Bottega Roma, a highly-rated dining destination in Rome. If you're eager to try something different, consider Pasta In Corso, another top spot with a tantalizing menu. You might also want to secure a reservation at Trattoria Vecchia Roma. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Rome this evening.

After enjoying a fulfilling meal, continue your evening at La Botticella Of Poggi Giovanni, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Almalu Trastevere offers a welcoming atmosphere for easing into the nightlife. Similarly, Bar Viminale Di Pepi Maurilio provides an excellent environment for a relaxed and enjoyable evening.

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

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

Bring your curiosity for today’s adventure around Rome. Some of the city’s most loved attractions await! Villa Borghese Pinciana is the perfect place to start. This museum is one of the most well-known places to visit in Rome. Next, head to Colosseum, a globally renowned archeological site, known for its picture-perfect features.

In between the sights, don’t hesitate to take small detours to explore local stores and eateries. When you’re ready to continue your adventure, head to Roman Forum. This UNESCO world heritage-designated archeological site is a highly recommended experience. Nearby, you'll also find Trevi Fountain and Pantheon. Visit these for an interesting touch to your journey. Finish the day with a visit to Castel Sant'angelo, a majestic castle in Rome.

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.

Treat yourself to a delightful dinner at RomAntica, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Coso Ristorante? It's another excellent option with a diverse menu. Consider reserving a table at DEROMA - Farine Romane as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Rome.

If you’re not ready to end the night just yet, Sant' Eustachio Caffè offers a perfect venue to relax and savor a drink. Similarly, Yellowsquare Rome is well-suited for those looking to unwind in a social setting. Caffè Portofino is another excellent spot to enjoy a nightcap after a delightful meal.

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

Experience an unparalleled adventure on day 12 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 vibrant destinations - Naples. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Sorrento. You will spend 2 nights here for some well-deserved relaxation.

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Rome allows for both. Start by heading to Castel Sant'elmo. This notable castle provides an insightful glimpse into the city's identity. Next, discover Naples National Archaeological Museum, a detailed museum, promising a delightful encounter.

Continue your sightseeing with a visit to Spaccanapoli, a locally appreciated street.

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

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

Have a fantastic dining experience at Frankie's Pizza Bar Sorrento Brunch & Vegan, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Bougainvillea offers an enticing alternative with its varied menu. Additionally, Banana Split is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Sorrento.

Round off your dining experience by visiting Leone Rosso Café, a prime location for a drink. Alternatively, explore the distinctive characteristics of Hotel Antiche Mura Sorrento, a bar catering to every mood and preference.

Raise your glass and celebrate another amazing day of your road trip 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 will return to Sorrento for 1 night more, there’s no need to rush. Experience Ravello, Positano, Amalfi, and Atrani to the fullest today with this curated day itinerary!

A blend of fun adventures, romantic experiences, and breathtaking views await you in Sorrento on today’s itinerary. First up is the up-and-coming 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 astonishing 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 notable 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 explore more of Sorrento, 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 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.

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

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

Today’s well-planned self-sightseeing route offers several fun adventures, scenic views, and photo-friendly spots. Whether you decide to explore Sorrento on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss. Archaeological Park Of Pompeii is the first of them. Spend some time admiring this UNESCO world heritage-designated archeological site before continuing your journey. Amphitheatre Of Pompeii is your next stop. This interesting archeological site is one of the best-rated sights in Sorrento.

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

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.

Treat yourself to a delightful dinner at Pizzeria Pulcinella, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Donegal Irish Pub? It's another excellent option with a diverse menu. Consider reserving a table at Vino E Cucina Miscia as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Ancona.

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.