Two-Week Italy Self-Drive Road Trip With Itinerary from Ancona traveling west to Florence, Siena, Rome, Sorrento, and Perugia

Experience an unparalleled adventure on day 2 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 3 nights here for some well-deserved relaxation.

Get ready for an exciting day in Ancona. Today’s sightseeing agenda includes an observation deck, an art gallery, a food market, a church and much more! Begin your adventure at Piazzale Michelangelo. This is a famous observation deck you should not miss. Another must-see is Galleria Dell'accademia, a locally renowned art gallery in Ancona.

When you’re ready for the next sight, head to Central Market. From there, take a leisurely stroll to Basilica Di Santa Maria Novella, Firenze (fi), another of the city’s captivating attractions.

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.

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

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.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Manifattura stands out as an excellent choice for a post-dinner cocktail. Alternatively, Se·sto On Arno Rooftop Bar offers an ideal atmosphere to enjoy the pleasures of the night. Il Vinile is also a great option that provides a perfect setting for a relaxing evening.

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

On day 3 of your road trip, you will have an entire day to explore Florence. You’ll stay in Florence for 2 nights and discover all the best things to see and do in the area.

A blend of fun adventures, romantic experiences, and breathtaking views await you in Florence on today’s itinerary. First up is the astonishing church, Cathedral Of Santa Maria Del Fiore. Afterward, continue to Ponte Vecchio, a historical landmark every traveler should visit.

As you explore Florence’s charming streets, take in the lively atmosphere and get to know the character of the city. Next, make your way to Uffizi Gallery. This extraordinary art gallery is an essential stop. Following that, head to Palazzo Vecchio, another must-visit site that will enhance your experience. Don’t forget to stop by Piazza Della Signoria, a widely recognized public square in the city. Finally, end your day with a visit to Basilica Of Santa Croce In Florence, a photogenic church that offers the perfect conclusion to your sightseeing of the day.

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 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.

Enjoy a lovely dining experience at Ditta Artigianale, a popular restaurant in Florence. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Florence at Trattoria Da Burde, 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 Casa Toscana. It’s yet another ideal choice to enhance your time in Florence tonight.

Round off your dining experience by visiting Bar 50 Rosso, a prime location for a drink. Alternatively, explore the distinctive characteristics of Bitter Bar, a bar catering to every mood and preference. Archea Brewery likewise offers a unique atmosphere, perfect for a memorable night out.

Raise your glass to another unforgettable day in Italy!

Greet day 4 of your road trip in Italy with a smile and start your day with a hearty breakfast. You will return to Florence for your remaining 1 night in the city 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 Pisa.

Start your day at Piazza Del Duomo, Pisa. This stunning public square is a wondrous place to see in Florence. Then, wander over to Pisa Cathedral. If symbolic sites excite you, this church will be right up your alley. Nearby, you’ll also find Angelo Caduto.

Florence offers plenty to explore, ensuring every moment of your visit is filled with excitement and discovery. If you're up for more, Leaning Tower Of Pisa is a globally renowned spot in the city that will captivate you with its unique charm.

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.

Have a fantastic dining experience at Ristorante Buca Mario, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Agricola Toscana offers an enticing alternative with its varied menu. Additionally, Eataly Firenze is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Florence.

Round off your dining experience by visiting Gosh*, a prime location for a drink. Alternatively, explore the distinctive characteristics of Antico Caffè Del Moro - Art Bar Firenze, a bar catering to every mood and preference. Quelo Bar likewise offers a unique atmosphere, perfect for a memorable night out.

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 Siena, where you'll stay for 1 night more.

Get ready for a day filled with family-friendly attractions, romantic experiences, and breathtaking views in the charming village of Siena. Your adventure starts at Antinori Nel Chianti Classico, a beloved local hot spot. Another notable attraction to explore is Castle Of Verrazzano. This increasingly popular castle is known for its enchanting appeal.

After soaking in the highlights of these sights, take some time to wander Siena's streets and immerse yourself in the local atmosphere. When you're ready to continue your sightseeing adventure, head to Castello Di Brolio. This standout castle offers a fascinating experience that many visitors find memorable.

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

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

Enjoy a delicious meal at Osteria Quattro Venti, a highly-rated dining destination in Siena. If you're eager to try something different, consider Fischi per Fiaschi, another top spot with a tantalizing menu. You might also want to secure a reservation at Osteria da Divo. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Siena this evening.

After savoring a delicious meal, step into the vibrant nightlife at Charlie Mixology Bar Di Aldinucci Riccardo, where the evening is just getting started. In the same way, Bar Pinacoteca offers a unique charm perfect for experiencing the local bar scene in Siena. San Paolo Pub is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

Raise your glass and celebrate another amazing day of your road trip 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 Rome. In the evening, you’ll end up in Rome, where you will stay for 3 nights.

Today’s well-planned self-sightseeing route offers several family-friendly attractions, romantic experiences, and breathtaking views. Whether you decide to explore Siena on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss. Castel Sant'angelo is the first of them. Spend some time admiring this enchanting castle before continuing your journey. Basilica Di Santa Maria Maggiore is your next stop. This captivating church is one of the best-rated sights in Siena.

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 Trevi Fountain. This enchanting monument is a sight to behold. To round off your sightseeing experience, visit Pantheon and Piazza Navona. If time allows, end your day with Largo Di Torre Argentina, a standout archeological site that offers a memorable conclusion to your exploration.

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.

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

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.

Cap off your dinner by heading to La Botticella Of Poggi Giovanni, ideal for a leisurely evening with a drink in hand. Almalu Trastevere is another bar that offers an enjoyable setting. Similarly, Bar Viminale Di Pepi Maurilio is also a popular place to go on a night out, perfect for relaxing and socializing.

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

At the end of the day, you'll drive back to Rome, where you'll stay for 2 nights more.

One of the most iconic places you can visit today in Vatican City is Trastevere. Allow yourself some time to explore this neighborhood and discover its unique quirks. You'll also find many of the best sightseeing spots nearby. You can also explore Via del Corso, a street that offers a glimpse into local life and culture.

Today’s route brings fun adventures, romantic experiences, and breathtaking views. The first attraction of today is St. Peter's Basilica.

As you stroll around Rome, take in the distinct atmosphere and learn what makes this city so unique. Maximize your sightseeing with a visit to Vatican Museums. Next, make your way to Piazza Del Popolo to add another highlight to your day. Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day in Rome.

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

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.

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.

Extend your evening after a delightful meal by visiting Sant' Eustachio Caffè, which offers the perfect atmosphere for a night out. Moreover, Yellowsquare Rome is another popular option for a drink or two. Likewise, Caffè Portofino also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

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

Day 9 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, you'll explore some of the most beautiful places in Rome, including an archeological site, a monument, a museum, a public square and much more! Start your day with a visit to Colosseum. This globally renowned archeological site is a must-visit in the city. When you’re ready for your next discovery, continue to Arch Of Constantine, which may be one of the most UNESCO world heritage-listed places you will experience today.

One of the best things about exploring Rome 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 Roman Forum, a timeless archeological site in the city. If you’re up for more discoveries, don’t forget to reserve some time for Capitoline Museums and Piazza Di Spagna. End your day with a visit to Spanish Steps, a top-rated public square that’s sure to leave a lasting impression.

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.

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

Treat yourself to a wonderful meal at Hotel de Russie, a top-rated dining spot in Rome. If you're in the mood for something new, try La Taverna Italiana, another premier location with a delectable menu. You might also want to book a table at The Parrot Bar. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Rome.

To truly maximize your evening out, consider visiting The Apartment Bar Roma after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Hotel Hassler Roma, another bar with an inviting ambiance.

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

On day 10 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 2 destinations, Alberi and Sorrento. 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 family-friendly attractions, romantic experiences, and scenic views! Start at Belvedere Sorrento, an increasingly popular observation deck that is worthwhile a visit in the village. Nearby, you’ll find Museo Correale Di Terranova, enchanting visitors with its eye-catching appeal. Continue your exploration at Cathedral Of Saints Philip And James. This church is one of the village’s most beloved 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.

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 wonderful meal at Frankie's Pizza Bar Sorrento Brunch & Vegan, a top-rated dining spot in Sorrento. If you're in the mood for something new, try Bougainvillea, another premier location with a delectable menu. You might also want to book a table at Banana Split. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Sorrento.

Extend your evening after a delightful meal by visiting Leone Rosso Café, which offers the perfect atmosphere for a night out. Moreover, Hotel Antiche Mura Sorrento is another popular option for a drink or two.

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

On day 11 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 Positano and Ravello to the fullest today with this curated day itinerary!

Enjoy the perfect balance of relaxation and exploration in Sorrento today. One of the most locally appreciated attractions included on the itinerary is Costiera Amalfitana Positano. This romantic beach will help you start your sightseeing on top. Then, take a leisurely stroll to Giardini Principessa Di Piemonte and learn what makes this enchanting park unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the well-known Villa Rufolo.

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.

Savor the flavors at Fuoro51, a top pick for dinner tonight. Alternatively, Hotel Bellevue Syrene beckons with its unique menu offerings. Also, consider Hotel Villa Fiorita. With its consistent customer satisfaction, it’s an excellent option for dining in Sorrento tonight.

Raise your glass to another unforgettable day 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 Perugia. At the end of the day, you will enjoy the comforts of a top-rated hotel in Perugia, which will be your home away from home for 2 nights.

Today’s agenda in Sorrento includes a historical landmark, a church, a public square, a monument and much more! Etruscan Arch is must-visit historical landmark and a great starting point for the day. Next, continue your journey to Perugia Cathedral, a curiosity-inducing church, located just a leisurely stroll away. Next, head to Piazza Iv Novembre, a romantic public square, also available for your discovery today.

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 dinnertime approaches, it's time to head out for a bite to eat in Perugia. 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.

Enjoy a delicious meal 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.

After savoring a delicious meal, step into the vibrant nightlife at Tommi Bar, where the evening is just getting started. In the same way, Valentina offers a unique charm perfect for experiencing the local bar scene in Perugia. Caffe Dal Perugino is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

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

On day 13 of your road trip, you’ll start and end your day in Perugia, but spend part of the day exploring places of interest outside the immediate city. On today's itinerary, you'll find attractions in Perugia and Santa Maria degli Angeli. You still have 1 night left in Perugia.

Today's adventure in Perugia promises more breathtaking discoveries and enriching experiences! Begin at Rocca Paolina. This heritage-rich historical landmark is a highlight of any visit in the city. Then, enjoy Basilica Of San Francesco D'assisi, another UNESCO world heritage-listed attraction that never fails to captivate visitors. Next, head over to Piazza Del Comune, one of the city’s most up-and-coming attractions, known for its UNESCO world heritage-listed features.

If you’re looking for more, spend time soaking in the atmosphere of Basilica Di Santa Chiara. This stunning church is frequented by locals and tourists alike. To complete your memorable day, make sure to visit Rocca Maggiore, an up-and-coming castle, and take a stroll around the area.

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

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

Enjoy a lovely dining experience at La Taverna, a popular restaurant in Perugia. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Perugia at Ristorante del Sole, 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 Al Mangiar Bene. It’s yet another ideal choice to enhance your time in Perugia tonight.

If you’re not ready to end the night just yet, Caffè Fortebraccio offers a perfect venue to relax and savor a drink. Similarly, Caffe Del Banco is well-suited for those looking to unwind in a social setting. Dempsey's Perugia is another excellent spot to enjoy a nightcap after a delightful meal.

Savor another day of unforgettable experiences in Italy!

Experience an unparalleled adventure on day 14 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 vibrant destinations - Recanati. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Ancona. You will spend 1 night here for some well-deserved relaxation.

Discover a day packed with fun adventures, photo-friendly spots, and history-rich sites in Perugia. Begin your sightseeing with Villa Colloredo Mels Museum. This frequently visited museum is one of the top attractions in the town. Proceed to Basilica Cattedrale Di San Flaviano, another must-visit attraction.

As you wander through the inviting streets of Perugia, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to Leopardi's House. This frequently visited museum is a traveler-favorite.

When you’re done exploring for the day, you’ll drive to your hotel in Ancona. 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 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.

Keep the excitement of the evening going by visiting a bar or two. Alla Tazza D'oro is an excellent place to start.

Savor another day of unforgettable experiences in Italy!