Two-Week Italy Self-Drive Road Trip With Itinerary from Ancona traveling west to Bologna, Venice, Milan, Genoa, Florence, Siena, and Rome

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 2 vibrant destinations - Ancona and Loreto. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Bologna. You will spend 1 night here for some well-deserved relaxation.

Prepare for a day full of family-friendly attractions, picturesque spots, and history-rich sites. When you’re ready, kick off your sightseeing adventure at Museo Archeologico Nazionale Delle Marche. This frequently visited museum is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Cathedral Basilica Of St. Cyriacus, one of the city’s most promising highlights.

Next, check out Sanctuary Of The Holy House Of Loreto, one of the most locally renowned places to see in Ancona. This church is a favorite among locals and travelers alike.

When you’re done exploring for the day, you’ll drive to your hotel in Bologna. 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 Bologna. 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 an extraordinary dining experience at Ahimè, a Bib Gourmand restaurant offering an incredible country cooking menu. Alternatively, if your taste buds call for something different, I Portici is one of the best restaurants for creative and contemporary cuisine in Bologna. This 1-star Michelin-awardee earns consistently high praises from guests. We also recommend checking out the menu at Trattoria di Via Serra. As a top-rated establishment with a Bib Gourmand status, it is an ideal choice for emilian cuisine in the city.

To truly maximize your evening out, consider visiting Bar Al Bricco D'oro after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Bar Freud E Squisito, another bar with an inviting ambiance. Similarly, Osteria Del Sole also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

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

On day 3 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 2 destinations, Bologna and Padua. When you’re not sightseeing, take time to relax at your selected hotel in Venice, where you’ll be staying for 1 night.

Today’s well-planned self-sightseeing route offers several fun adventures, romantic experiences, and breathtaking views. Whether you decide to explore Bologna on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss. Piazza Maggiore is the first of them. Spend some time admiring this history-steeped public square before continuing your journey. Two Towers is your next stop. This captivating monument is one of the best-rated sights in Bologna.

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 Piazza Santo Stefano. This culturally significant public square is a sight to behold. To round off your sightseeing experience, visit The Basilica Of St. Anthony and Prato Della Valle.

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

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

Enjoy an outstanding dining experience at Local, a 1-star Michelin restaurant offering an exceptional contemporary menu. Alternatively, if you're in the mood for something different, consider the nearby 1-star Michelin-awardee, Wistèria, known for its delicious contemporary and venetian cuisine. Another highly-recommended place to eat in Venice is Quadri, a renowned restaurant with a 1-star Guide Michelin recognition and a delicious modern menu.

Following your dinner, dive into the local bar culture at Al Parlamento. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to The Caffe Rosso, the perfect place for those looking to experience the best of the nightlife. Similarly, Adagio provides excellent drinks and a great atmosphere, ensuring a memorable night out.

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

Embark on another extraordinary experience on day 4 of your road trip in Italy. Today, you will make 2 stops and experience some of the highlights of Venice and Valeggio sul Mincio. At the end of the day, you will enjoy the comforts of a top-rated hotel in Milan, which will be your home away from home for 2 nights.

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Venice allows for both. Start by heading to Rialto Bridge. This wondrous historical landmark provides an insightful glimpse into the city's identity. Next, discover Piazza San Marco, a history-steeped public square, promising a delightful encounter.

Continue your sightseeing with a visit to Doge's Palace, a captivating palace. When you’re done, don’t forget to make a stop at the captivating Parco Giardino Sigurtà.

After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of your accommodation in Milan. Milan offers plenty of top-rated hotels for every travel budget. Take some time to relax before you go out again.

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

Get ready for an unforgettable culinary journey in Milan by reserving a table at Enrico Bartolini al Mudec. Renowned as a 3-star Michelin restaurant, it offers an exceptional creative menu. For a different taste experience, head to Seta by Antonio Guida, recognized for its delicious international and contemporary dishes. This 2-star Michelin restaurant consistently impresses guests, ensuring a memorable addition to your holiday. Looking for another option? Make sure to visit Il Luogo Aimo e Nadia, a local favorite known for its delightful italian contemporary and modern cuisine in Milan. Nestled in the heart of the city, this restaurant with 1 Michelin star is an ideal choice for discerning italian contemporary and modern foodies seeking culinary excellence.

After savoring a delicious meal, step into the vibrant nightlife at Nottingham Forest, where the evening is just getting started. In the same way, Armani/bamboo Bar offers a unique charm perfect for experiencing the local bar scene in Milan. Mag Cafe 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.

At the end of the day, you'll drive back to Milan, where you'll stay for 1 night more.

Get ready for a day filled with fun adventures, romantic experiences, and scenic views in the charming city of Milan. Your adventure starts at Verona Arena, an iconic local hot spot. Another notable attraction to explore is Piazza Gae Aulenti. This well-known public square is known for its majestic appeal.

After soaking in the highlights of these sights, take some time to wander Milan's streets and immerse yourself in the local atmosphere. When you're ready to continue your sightseeing adventure, head to Arch Of Peace. This historic monument offers a fascinating experience that many visitors find memorable. Milan Natural History Museum is also worth visiting.

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

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

Enjoy a delicious meal at Dessert Bar Milano, a highly-rated dining destination in Milan. If you're eager to try something different, consider Radisson Blu Hotel Milan, another top spot with a tantalizing menu. You might also want to secure a reservation at Ristorante Qui Si Mangia. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Milan this evening.

Continue your evening by exploring the vibrant nightlife scene at Kilburn Cocktail Bar Milano, a prime destination for a thrilling night out. Also, don’t forget to check out Bar Frida, a bar that offers unique local touches. Likewise, The Friends Pub Milano provides an excellent alternative for a fun evening.

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

Dive into day 6 of your remarkable road trip in Italy. Today you will explore Milan, 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 Genoa. You’ll stay here for 1 night.

A blend of family-friendly attractions, romantic experiences, and scenic views await you in Milan on today’s itinerary. First up is the timeless church, Duomo Di Milano Museum. Afterward, continue to Galleria Vittorio Emanuele Ii.

As you explore Milan’s charming streets, take in the lively atmosphere and get to know the character of the city. Next, make your way to La Scala. This interesting opera house is an essential stop that should not be missed. Following that, head to Sforzesco Castle Art Library, another must-visit site that will enhance your experience. Lastly, visit Parco Sempione and learn why this park is renowned as one of the city's most astonishing attractions.

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

As you explore more of Genoa, 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.

Prepare for an extraordinary culinary adventure in Genoa by booking a table at San Giorgio, a 1-star Michelin restaurant that boasts an exceptional modern and ligurian menu. For a different flavor experience, head to The Cook, renowned for its delectable modern dishes. This 1-star Michelin restaurant consistently wows guests, making it a memorable stop during your holiday. Looking for another option? Visit Il Marin, a local gem known for its delightful seafood and contemporary cuisine in Genoa. Nestled in the city's heart, this 1-star Michelin restaurant is a perfect choice for discerning restaurant-goers seeking a new experience.

Let the evening flow smoothly from dinner to drinks at Scurreria Beer & Bagel, a top-rated bar in the area. For other recommendations, La Lepre provides a perfect setting for rounding out your night with style and great drinks. Likewise, Bar Pisacane Iii 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 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 Genoa and Pisa. In the evening, you’ll end up in Florence, where you will stay for 2 nights.

Brace yourself for today’s incredible lineup of attractions in Genoa, featuring family-friendly attractions, romantic experiences, and breathtaking views. Start at Piazza De Ferrari, a captivating public square in the city. Then, head to Aquarium Of Genoa and soak in the ambiance of this mesmerizing aquarium.

There are many interesting places to see in Genoa and when you are ready for more, go to Leaning Tower Of Pisa. This is one of the city’s most world-famous spots. After exploring the monument, visit the wondrous Piazza Del Duomo, Pisa.

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

Experience a harmony of flavors at Enoteca Pinchiorri in Florence by securing a reservation in advance. Known for its 3-star Michelin status, Enoteca Pinchiorri offers a delightful variety of dishes highlighting its delicious italian contemporary menu. If you're seeking an alternative culinary experience, be sure to explore Santa Elisabetta, a highly recommended restaurant known for its enticing creative and mediterranean cuisine. This popular 2-star Michelin-awarded venue consistently exceeds expectations, ensuring a memorable holiday experience. Ready for another culinary adventure? Indulge your senses at Gucci Osteria da Massimo Bottura, a highly acclaimed restaurant celebrated for its exceptional italian contemporary and international menu.

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.

Savor another day of unforgettable experiences in Italy!

Day 8 offers a multitude of experiences. You will stay in Florence for 1 night more, offering you enough time to explore at a relaxed pace.

Begin your adventure at David. This is a captivating statue you should not miss. Another must-see is Galleria Dell'accademia, a locally renowned art gallery in Florence.

When you’re ready for the next sight, head to Central Market. From there, take a leisurely stroll to Cathedral Of Santa Maria Del Fiore, another of the city’s famous attractions. We recommend ending your self-guided tour of the city with an enchanting observation deck. Piazzale Michelangelo is a truly remarkable place to visit in Florence.

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

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.

Cap off your dinner by heading to Bar 50 Rosso, ideal for a leisurely evening with a drink in hand. Bitter Bar is another bar that offers an enjoyable setting. Similarly, Archea Brewery is also a popular place to go on a night out, perfect for relaxing and socializing.

Take some time to reflect on your day and savor another beautiful night 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 - Florence. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Siena. You will spend 1 night here for some well-deserved relaxation.

Today’s agenda in Florence includes a public square, a church, an art gallery, a historical landmark, a botanical garden and much more! Piazza Della Signoria is must-visit public square and a great starting point for the day. Next, continue your journey to Basilica Of Santa Croce In Florence, a captivating church, located just a leisurely stroll away. Next, head to Uffizi Gallery, a standout 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. If you’re looking for more, Ponte Vecchio is also a globally renowned attraction that is worthwhile a visit. Lastly, don’t miss The Boboli Gardens, a well-known gem to see 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 Siena. Siena 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 Siena's most popular restaurants, and connect with friendly locals for an authentic adventure.

Make sure to reserve a table at Enoteca I Terzi, an iconic dining spot in Siena. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Ristorante Tar-Tufo, a popular restaurant in Siena. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Antica Trattoria Papei, a hidden gem nestled in Siena. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Explore the vibrant nightlife at Meet Life Cafè after your meal, a hub for lively evenings and memorable moments. Or, head to Maudit Pub for a great selection of flavorful drinks and a charming setting. Furthermore, Bar Impero Siena 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 10 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 2 destinations, Siena and Vatican City. When you’re not sightseeing, take time to relax at your selected hotel in Rome, where you’ll be staying for 4 nights.

Start your adventure at Piazza Del Campo. This widely recognized public square is a must-visit for travelers looking for a unique holiday experience. Make your way to Siena Cathedral located in Siena for an enchanting atmosphere.

Next, immerse yourself in the setting of Saint Peter's Square. After the square, continue your tour of the city with a visit to St. Peter's Basilica.

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 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.

Begin your culinary exploration in Rome by securing a reservation at La Pergola. This renowned restaurant holds 3 Michelin star and offers an exceptional menu of mediterranean and contemporary cuisine. For another dining delight, visit Il Pagliaccio, celebrated for its delectable creative and innovative menu. This acclaimed 2-star Michelin-recipient consistently leaves guests satisfied, making it a must-visit during your holiday. Looking for a different experience? Discover Enoteca La Torre, a top local spot known for its tantalizing mediterranean and creative menu. With a 2-star Michelin recognition, it guarantees an exceptional dining adventure.

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at La Botticella Of Poggi Giovanni, a well-loved spot among locals and tourists. Or, head to Almalu Trastevere. This bar boasts a welcoming environment that is perfect for winding down. You could also continue your night at Bar Viminale Di Pepi Maurilio, another top-rated place in the area.

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

On day 11 of your road trip, you will have an entire day to explore Rome. You’ll stay in Rome for 3 nights and discover all the best things to see and do in the area.

Brace yourself for today’s incredible lineup of attractions in Rome, featuring family-friendly attractions, romantic experiences, and scenic views. Start at Piazza Del Popolo, an extraordinary public square in the city. Then, head to Spanish Steps and soak in the ambiance of this enchanting public square.

There are many interesting places to see in Rome and when you are ready for more, go to Piazza Di Spagna. This is one of the city’s most timeless spots. After exploring the public square, visit the globally renowned Pantheon. Before wrapping up your self-guided sightseeing tour, head to the notable Largo Di Torre Argentina, a notable archeological site 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.

Treat yourself to a wonderful meal at RomAntica, a top-rated dining spot in Rome. If you're in the mood for something new, try Coso Ristorante, another premier location with a delectable menu. You might also want to book a table at DEROMA - Farine Romane. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Rome.

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at Sant' Eustachio Caffè, a well-loved spot among locals and tourists. Or, head to Yellowsquare Rome. This bar boasts a welcoming environment that is perfect for winding down. You could also continue your night at Caffè Portofino, another top-rated place in the area.

Savor another day of unforgettable experiences in Italy!

Day 12 of your road trip will take you to the best attractions Rome has to offer. Cherish the 2 nights you have left in Rome by discovering the best things there are to see and do in the city.

Set out on a day brimming with family-friendly attractions, breathtaking views, and photo-friendly spots. Start at the locally renowned Circus Maximus, a historic archeological site in Rome. Next, go to Colosseum.

After visiting Circus Maximus and Colosseum, take time to explore Rome's streets and absorb its charm. Continue your sightseeing by heading to Roman Forum. This UNESCO world heritage-listed archeological site offers a unique experience. Altare Della Patria is another noteworthy stop. End your self-guided sightseeing tour on top with a visit to Trevi Fountain, one of the most majestic places to visit 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.

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.

Don’t miss out on dining at Hotel de Russie, a top-rated dining destination in Rome. If you're in the mood to try something new, consider La Taverna Italiana, another top spot with a mouthwatering menu. You might also want to secure a reservation at The Parrot Bar. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Rome this evening.

Continue your evening by exploring the vibrant nightlife scene at The Apartment Bar Roma, a prime destination for a thrilling night out. Also, don’t forget to check out Hotel Hassler Roma, a bar that offers unique local touches.

Raise your glass to another unforgettable day in Italy!

Day 13 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.

Today’s well-planned self-sightseeing route offers several fun adventures, romantic experiences, and natural wonders. Whether you decide to explore Rome on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss. Villa Borghese is the first of them. Spend some time admiring this romantic park before continuing your journey. Castel Sant'angelo is your next stop. This widely recognized castle is one of the best-rated sights in Rome.

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 Piazza Navona. This enchanting public square is a sight to behold. To round off your sightseeing experience, visit Campo De' Fiori and Basilica Di Santa Maria Maggiore.

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

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

Dine in style at Sofitel Roma Villa Borghese, a top recommendation for dinner tonight. Or, for a change of pace, Centro boasts a menu that's sure to impress. Also, be sure to check out Ristorante Tema. Known as a local hotspot, it’s a great choice for tonight in Rome.

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

Embark on another extraordinary experience on day 14 of your road trip in Italy. Today, you will make 2 stops and experience some of the highlights of Tivoli and Teramo. At the end of the day, you will enjoy the comforts of a top-rated hotel in Ancona, which will be your home away from home for 1 night.

Today's adventure in Rome promises more breathtaking discoveries and enriching experiences! Begin at Villa D'este. This visually striking palace is a highlight of any visit in the town. Then, enjoy Gregorian Bridge, another standout attraction that never fails to captivate visitors. Next, head over to Villa Gregoriana, one of the town’s most frequently visited attractions, known for its serene features.

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

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

Discover the culinary delights of Ancona by securing a reservation at Sot'Ajarchi. Esteemed for its a Bib Gourmand award, this restaurant offers a remarkable selection of seafood and from the marches cuisine. Alternatively, Bontà delle Marche beckons with its unique menu offerings.

Continue your lively evening at Alla Tazza D'oro, a perfect place for winding down or revving up the night, depending on which mood you’re in.

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