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

Dive into day 2 of your remarkable road trip in Italy. Today you will explore Florence, 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 Florence. You’ll stay here for 3 nights.

Ancona is home to plenty of attractions that offer family-friendly attractions, romantic experiences, and breathtaking views! Start at Piazzale Michelangelo, a top-rated observation deck that is worthwhile a visit in the city. Nearby, you’ll find Galleria Dell'accademia, enchanting visitors with its photogenic appeal. Continue your exploration at Central Market. This food market is one of the city’s most well-known spots.

Enjoy the freedom of exploring Ancona at your own pace and find hidden gems along the way. If you want to see more picture-perfect spots, make sure to visit Basilica Di Santa Maria Novella, Firenze (fi).

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.

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 Ristorante Oliviero 1962, 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 Di Poneta Novoli, 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 Caffe San Firenze. It’s yet another ideal choice to enhance your time in Florence tonight.

To truly maximize your evening out, consider visiting Manifattura after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Se·sto On Arno Rooftop Bar, another bar with an inviting ambiance. Similarly, Il Vinile also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

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

Day 3 of your road trip will take you to the best attractions Florence has to offer. Cherish the 2 nights you have left in Florence by discovering the best things there are to see and do in the city.

Today’s agenda in Florence includes a church, a historical landmark, an art gallery, a palace, a public square and much more! Cathedral Of Santa Maria Del Fiore is must-visit church and a great starting point for the day. Next, continue your journey to Ponte Vecchio, a wondrous historical landmark, located just a leisurely stroll away. Next, head to Uffizi Gallery, a historic art gallery, 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 captivating Palazzo Vecchio. If you’re looking for more, Piazza Della Signoria is also a spectacular attraction that is worthwhile a visit. Lastly, don’t miss Basilica Of Santa Croce In Florence, a place of culturally significant 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 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 delicious dinner at Ditta Artigianale, an excellent option for tonight's dining. Looking for something different? Trattoria Da Burde offers a tantalizing alternative with its diverse menu. And don’t miss Casa Toscana. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Florence.

To truly maximize your evening out, consider visiting Bar 50 Rosso after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Bitter Bar, another bar with an inviting ambiance. Similarly, Archea Brewery also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

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

On day 4 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.

Today's adventure in Florence promises more breathtaking discoveries and enriching experiences! Begin at Piazza Del Duomo, Pisa. This historic public square is a highlight of any visit in the city. Then, enjoy Pisa Cathedral, another stunning attraction that never fails to captivate visitors.

If you’re looking for more, spend time soaking in the atmosphere of Leaning Tower Of Pisa. This breathtaking monument is frequented by locals and tourists alike. To complete your memorable day, make sure to take a stroll around the area.

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

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

Savor the flavors at Ristorante Buca Mario, a top pick for dinner tonight. Alternatively, Agricola Toscana beckons with its unique menu offerings. Also, consider Eataly Firenze. With its consistent customer satisfaction, it’s an excellent option for dining in Florence tonight.

Cap off your dinner by heading to Gosh*, ideal for a leisurely evening with a drink in hand. Antico Caffè Del Moro - Art Bar Firenze is another bar that offers an enjoyable setting. Similarly, Quelo Bar is also a popular place to go on a night out, perfect for relaxing and socializing.

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

Greet day 6 of your road trip in Italy with a smile and start your day with a hearty breakfast. You will return to Siena 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 Bargino, Greve in Chianti, and San Regolo.

Get ready for a day filled with fun adventures, romantic experiences, and breathtaking views in the charming village of Siena. Your adventure starts at Antinori Nel Chianti Classico, a curiosity-inducing local hot spot. Another notable attraction to explore is Castle Of Verrazzano. This beloved 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 romantic castle offers a fascinating experience that many visitors find memorable.

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

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.

Dine in style at Osteria Quattro Venti, a top recommendation for dinner tonight. Or, for a change of pace, Fischi per Fiaschi boasts a menu that's sure to impress. Also, be sure to check out Osteria da Divo. Known as a local hotspot, it’s a great choice for tonight in Siena.

Continue your evening by exploring the vibrant nightlife scene at Charlie Mixology Bar Di Aldinucci Riccardo, a prime destination for a thrilling night out. Also, don’t forget to check out Bar Pinacoteca, a bar that offers unique local touches. Likewise, San Paolo Pub provides an excellent alternative for a fun evening.

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

Embark on another extraordinary experience on day 7 of your road trip in Italy. Today, you will make 1 stop and experience some of the highlights of Rome. At the end of the day, you will enjoy the comforts of a top-rated hotel in Rome, which will be your home away from home for 3 nights.

Immerse yourself in Siena’s rich culture with today's sightseeing itinerary. Start your journey at Castel Sant'angelo. This culturally significant castle is sure to ignite your curiosity. Next, dive into the photogenic features of Basilica Di Santa Maria Maggiore, a must-visit church in the city.

In between sights, stop by local stores, picturesque photo spots, and small eateries. When you’re ready for your next attraction, proceed to Trevi Fountain, a globally renowned monument. For a change of scene, check out Pantheon, known for its instagrammable features. We also recommend visiting Piazza Navona. This public square is a must for anyone looking to experience the city to the fullest. Lastly, end your day with a visit to Largo Di Torre Argentina, yet another interesting attraction in Siena.

After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of your accommodation in Rome. Rome 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 Rome. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.

Have a fantastic dining experience at La Bottega Roma, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Pasta In Corso offers an enticing alternative with its varied menu. Additionally, Trattoria Vecchia Roma is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Rome.

Unwind after your meal by stepping into La Botticella Of Poggi Giovanni. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Almalu Trastevere offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Bar Viminale Di Pepi Maurilio, another top-rated bar in the area.

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

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

Trastevere is a neighborhood that stands out as one of the must-see places in Vatican City. Take a moment to explore its distinct atmosphere, and don’t miss the popular sightseeing spots just a short walk away. For another highlight, head to Via del Corso, a street offering its own unique experiences.

Rome is home to plenty of attractions that offer family-friendly attractions, romantic experiences, and scenic views! Start at St. Peter's Basilica, a globally renowned major basilica that is worthwhile a visit in the city. Continue your exploration at Vatican Museums. This art museum is one of the city’s most world-famous spots.

Enjoy the freedom of exploring Rome at your own pace and find hidden gems along the way. If you want to see more picture-perfect spots, make sure to visit Piazza Del Popolo.

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

As dinnertime approaches, it's time to head out for a bite to eat in Rome. 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 RomAntica, a top-rated dining destination in Rome. If you're in the mood to try something new, consider Coso Ristorante, another top spot with a mouthwatering menu. You might also want to secure a reservation at DEROMA - Farine Romane. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Rome this evening.

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

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

Day 9 of your road trip across Italy promises a magnificent time exploring Rome. You have 1 night left in Rome. Take the opportunity to experience more of the best attractions and activities in the city.

A blend of fun adventures, breathtaking views, and photo-friendly spots await you in Rome on today’s itinerary. First up is the world-famous archeological site, Colosseum. Afterward, continue to Arch Of Constantine, a monument every traveler should visit.

As you explore Rome’s charming streets, take in the lively atmosphere and get to know the character of the city. Next, make your way to Roman Forum. This wondrous archeological site is an essential stop. Following that, head to Capitoline Museums, another must-visit site that will enhance your experience. Don’t forget to stop by Piazza Di Spagna, a world-famous public square in the city. Finally, end your day with a visit to Spanish Steps, a romantic public square 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 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 delightful dinner at Hotel de Russie, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try La Taverna Italiana? It's another excellent option with a diverse menu. Consider reserving a table at The Parrot Bar as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Rome.

Unwind after your meal by stepping into The Apartment Bar Roma. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Hotel Hassler Roma offers a dynamic and energetic atmosphere for a glass or two.

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.

Experience an unparalleled adventure on day 10 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 2 vibrant destinations - Alberi and Sorrento. 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.

Brace yourself for today’s incredible lineup of attractions in Rome, featuring fun adventures, romantic experiences, and breathtaking views. Start at Belvedere Sorrento, a beloved observation deck in the village. Then, head to Museo Correale Di Terranova and soak in the ambiance of this picture-perfect museum.

There are many interesting places to see in Rome, and when you are ready for more, go to Cathedral Of Saints Philip And James. This is one of the village’s most increasingly popular culturally significant spots of interest.

At the end of the day, you will drive to Sorrento, 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 Sorrento's best restaurants.

Savor the flavors at Frankie's Pizza Bar Sorrento Brunch & Vegan, a top pick for dinner tonight. Alternatively, Bougainvillea beckons with its unique menu offerings. Also, consider Banana Split. With its consistent customer satisfaction, it’s an excellent option for dining in Sorrento tonight.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Leone Rosso Café, known for its inviting atmosphere. Hotel Antiche Mura Sorrento is another great option if you’re looking for a place to get the night started.

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

Wake up to day 11 of your extraordinary road trip in Italy. With 1 night left in Sorrento, we encourage you to seize the day and discover the unexplored beauty of the town’s surroundings!

Savor the day by visiting some of the best places to see in Sorrento, including a beach, a park, and a historical landmark. Start your adventure at Costiera Amalfitana Positano. This frequently visited beach is a must-visit for travelers looking for a unique holiday experience. Make your way to Giardini Principessa Di Piemonte located in Sorrento for another exciting encounter.

Next, immerse yourself in the setting of Villa Rufolo. Its visually striking features will captivate you.

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

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.

Enjoy a lovely meal at Fuoro51, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Hotel Bellevue Syrene is another top choice with a popular menu. You could also check for a table at Hotel Villa Fiorita. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Sorrento tonight.

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

Today, you'll explore some of the most beautiful places in Sorrento, including a historical landmark, a church, a public square, a monument and much more! Start your day with a visit to Etruscan Arch. This curiosity-inducing historical landmark is a must-visit in the city. When you’re ready for your next discovery, continue to Perugia Cathedral, which may be one of the most photogenic places you will experience today.

One of the best things about exploring Sorrento 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 Piazza Iv Novembre, a curiosity-inducing public square in the city. If you’re up for more discoveries, don’t forget to reserve some time for The Fontana Maggiore.

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

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.

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.

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.

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

On day 13 of your road trip, you’ll start and end your day in Perugia, where you'll stay for 1 night more.

Discover a day packed with fun adventures, picturesque spots, and historic treasures in Perugia. Begin your sightseeing with Rocca Paolina. This intriguing historical landmark is one of the top attractions in the city. Proceed to Basilica Of San Francesco D'assisi, 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 Piazza Del Comune. This intriguing public square is a traveler-favorite. Not far away, you’ll find Basilica Di Santa Chiara, another key site on your sightseeing itinerary. Rocca Maggiore is yet another highly recommended place to visit nearby, offering plenty to discover for curious travelers.

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

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

Make sure to reserve a table at La Taverna, 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 Ristorante del Sole, 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 Al Mangiar Bene, a hidden gem nestled in Perugia. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Caffè Fortebraccio, known for its inviting atmosphere. Caffe Del Banco is another great option if you’re looking for a place to get the night started. Similarly, Dempsey's Perugia provides a great setting to enjoy the night away.

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

Dive into day 14 of your remarkable road trip in Italy. Today you will explore Recanati, 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 Ancona. You’ll stay here for 1 night.

Prepare for a day full of fun adventures, photo-friendly spots, and history-rich sites. When you’re ready, kick off your sightseeing adventure at Villa Colloredo Mels Museum. This frequently visited museum is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Basilica Cattedrale Di San Flaviano, one of the town’s best highlights.

Next, check out Leopardi's House, one of the most up-and-coming places to see in Perugia. This museum is a favorite among locals and travelers alike.

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 wonderful meal at Amarcord, a top-rated dining spot in Ancona. If you're in the mood for something new, try Bontà delle Marche, another premier location with a delectable menu. You might also want to book a table at Ristorante Pizzeria Da Romano. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Ancona.

Following your dinner, dive into the local bar culture at Alla Tazza D'oro. Enjoy this evening's relaxed ambiance with delightful drinks.

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