Two-Week Relaxed Italy Self-Drive Road Trip With Itinerary from Ancona to Bologna, Florence, and Rome

Day 2 of your easy, relaxed road trip through Italy lets you travel at your own pace and visit multiple places in a single day. Begin by exploring the best sights in Ancona. By evening, drive toward the Bologna, where you’ll stay at a top-rated hotel of your choice for 1 night.

Palazzo Degli Anziani is an ideal stop early in the day. This underrated palace is a must-visit in the city. When you’re ready for your next discovery, continue to Museo Archeologico Nazionale Delle Marche, which may be one of the most respected 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 Cathedral Basilica Of St. Cyriacus, an up-and-coming church in the city.

After a day of exploration, relax at one of the top hotels or accommodations in Bologna. Staying in the city gives you a comfortable, welcoming place to recharge during your laid-back road trip in Italy.

Exploring new places makes you hungry. Luckily, Bologna has multiple restaurants that offer fantastic dining experiences to continue your laid-back and stress-free discovery of the city.

Set out on a gastronomic journey in Bologna by reserving a table at Ahimè. Renowned for its Bib Gourmand award, this restaurant presents an outstanding menu of country cooking cuisine. For a different taste, head over to I Portici, renowned for its delectable creative and contemporary dishes. This distinguished 1-star Michelin-recipient is a favorite among guests, making it a worthy addition to your holiday plans. Craving more culinary excitement? Explore Trattoria di Via Serra, a highly rated local gem known for its exquisite emilian menu. With a Bib Gourmand acclaim, it promises a dining experience you won't want to miss.

Hang out and unwind at some of the top bars in Bologna.

Let the evening flow smoothly from dinner to drinks at Bar Al Bricco D'oro, a top-rated bar in the area. For other recommendations, Bar Freud E Squisito provides a perfect setting for rounding out your night with style and great drinks. Likewise, Osteria Del Sole offers a memorable night with diverse drink options and excellent service.

Cherish every minute of your relaxed road trip vacation across Italy.

Day 3 of your relaxed road trip in Italy will take you on a self-paced journey to more than one incredible place in one day. See some of the best attractions in Italy, taste the most delectable foods and exquisite drinks, and make incredible memories as you go!

Check out the impressive public square, Piazza Maggiore. Afterward, continue to Piazza Santo Stefano, a public square every traveler should visit. As you explore Bologna’s charming streets, take in the lively atmosphere and get to know the character of the city.

Next, make your way to Two Towers. This captivating monument is an essential stop. Following that, head to Bologna Cathedral, another must-visit site that will enhance your experience. Don’t forget to stop by Fountain Of Neptune, Bologna, an often recommended monument in the city.

When you’re not exploring beautiful places, you can relax in Florence. Here, you can choose from the best hotels and other accommodations as you get to know more about the culture in the city.

When you’re not driving and exploring some of the best places in Italy, it’s time to make your relaxed road trip even more comforting. Sit down for a lovely meal at one of the best restaurants in Florence.

Treat yourself to an extraordinary dining experience at Enoteca Pinchiorri, a 3-star Michelin restaurant offering an incredible italian contemporary menu. Alternatively, if your taste buds call for something different, Santa Elisabetta is one of the best restaurants for creative and mediterranean cuisine in Florence. This 2-star Michelin-awardee earns consistently high praises from guests. We also recommend checking out the menu at Gucci Osteria da Massimo Bottura. As a top-rated establishment with 1 Michelin star, it is an ideal choice for italian contemporary and international cuisine in the city.

As the day is coming to an end, stop at some of Florence’s best bars to celebrate this day of your slow-paced adventure in Italy.

Keep the excitement of the evening going by visiting a bar or two. Manifattura is an excellent place to start. You could also check out Se·sto On Arno Rooftop Bar, offering a different kind of charm. A last recommendation for the day is Il Vinile. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

Grab a drink and enjoy every passing minute of this night of your relaxed road trip experience in Italy!

Day 4 of your relaxed road trip through Italy means 24 hours of making the best memories in Florence. You’ll go sightseeing at famous attractions in Florence. In the evening, you will experience one of the most popular dining spots in the city. So buckle up and prepare to be blown away by Florence!

Look forward to a unique sightseeing adventure at the frequently visited Florence Baptistery and allow yourself time to explore. Just a short distance away you'll find your next stop, Cathedral Of Santa Maria Del Fiore, a history-steeped church that draws visitors from far and near.

Continue your journey to Brunelleschi's Dome, one of the city’s most curiosity-inducing spots that you shouldn’t miss. Another great site to visit is the frequently visited Museo Dell'opera Del Duomo.

Gain a one-of-a-kind experience on your unhurried and relaxed road trip across Italy by joining a traveler-approved tour in Ancona. There are so many fun and eye-opening activities to try out in Ancona that will make your slow-paced self-drive tour in Italy more memorable. Check out all the most recommended and top-rated tour options in the city of Florence to find the best options for you!

Exploring new places makes you hungry. Luckily, Florence has multiple restaurants that offer fantastic dining experiences to continue your laid-back and stress-free discovery of the city.

Dine in style at Ditta Artigianale, a top recommendation for dinner tonight. Or, for a change of pace, Trattoria Da Burde boasts a menu that's sure to impress. Also, be sure to check out Casa Toscana. Known as a local hotspot, it’s a great choice for tonight in Florence.

Experience the amazing nightlife in Florence and unwind at the coolest bars in the city.

Continue the enjoyment post-dinner at Bar 50 Rosso, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Bitter Bar offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out Archea Brewery. This bar is a favorite among both locals and visitors looking for a delightful evening out filled with laughter and fun.

Raise your glass to celebrate another day of your laid-back and relaxed road trip experience in Italy!

On day 5 of your leisurely self-drive tour across Italy, you’ll go deep into Florence, where you'll stay for 3 nights, and see some of the city’s unforgettable attractions. To learn more of the city's culture, you'll also dine at the most popular restaurants in Florence, and meet locals along the way!

Oltrarno is one of the highlights of today. Take your time exploring this iconic neighborhood in Florence, which offers a perfect blend of history and culture. Plus, it's close to many must-see landmarks in the city.

Enjoy all that Strozzi Palace Mantua has to offer. This is a curiosity-inducing palace you should not miss. Another must-see is Pitti Palace, a locally renowned palace in Florence.

When you’re ready for the next sight, head to The Boboli Gardens. From there, take a leisurely stroll to Porta Romana, another of the city’s up-and-coming attractions.

Italy makes the perfect setting for a calming but fun road trip experience. Aside from amazing sights, Italy also offers plenty of tours to enhance your relaxed road trip experience.

When it’s time to eat, the city has a variety of restaurants and cuisines to suit your palate and complement your relaxed road trip experience. Take a leisurely walk around Florence, while looking for a place to eat. Or, check out our top recommendations and treat yourself to a nice meal.

Enjoy a lovely meal at Ristorante Buca Mario, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Agricola Toscana is another top choice with a popular menu. You could also check for a table at Eataly Firenze. As an establishment that consistently gains high praises from customers, it’s an ideal choice in Florence tonight.

As the day is coming to an end, stop at some of Florence’s best bars to celebrate this day of your slow-paced adventure in Italy.

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.

Free your mind of worries as you enjoy the taste of freedom on your laid-back road trip adventure across Italy.

Day 6 introduces you to many popular attractions and activities in Florence, further proving that leisurely self-drive tours in Italy are extraordinary.

Check out the captivating statue, David. Afterward, continue to Galleria Dell'accademia, an art gallery 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 Central Market. This captivating food market is an essential stop. Following that, head to Basilica Di Santa Maria Novella, Firenze (fi), another must-visit site that will enhance your experience.

Make the most of your time in the country by joining activities that let you discover more about Italy. Check out all of the tours you can join this day of your leisurely self-drive holiday in Italy and ensure the experience of a lifetime.

Mealtimes are the perfect opportunities to immerse yourself in the local culture of Italy. When you're not appreciating the best places to visit in Florence, explore the city like a local by trying out the best restaurants in the area.

Make sure to reserve a table at Tijuana, 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 Djària - American Bar, 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 The Florence Irish Pub, a hidden gem nestled in Florence. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

A visit to a top-rated local bar is one of the most refreshing ways to cap off a beautiful night in Florence.

Soak in the unique atmosphere of Florence as you commemorate this day of your relaxed road trip with a toast. Cheers to a memorable, leisurely self-drive holiday in Italy!

Day 7 of your relaxed road trip through Italy means 24 hours of making the best memories in Florence. You’ll go sightseeing at famous attractions in Florence. In the evening, you will experience one of the most popular dining spots in the city. So buckle up and prepare to be blown away by Florence!

Florence is brimming with adventures.

Your adventure in Florence is only getting started when you visit Piazza Della Signoria, a spectacular local hot spot. Another notable attraction to explore is Loggia Dei Lanzi. This locally appreciated public square is known for its grand appeal.

After soaking in the highlights of these sights, take some time to wander Florence's streets and immerse yourself in the local atmosphere. When you're ready to continue your sightseeing adventure, head to Palazzo Vecchio. This enchanting palace offers a fascinating experience that many visitors find memorable. Uffizi Gallery is also worth visiting, along with Ponte Vecchio. These standout landmarks offer unique experiences that add to the day’s enjoyment.

Another way to make your easygoing and relaxed road trip in Italy more special is by joining unique tours and activities. Florence offers a wide selection of experiences for every traveler.

When you’re not driving and exploring some of the best places in Italy, it’s time to make your relaxed road trip even more comforting. Sit down for a lovely meal at one of the best restaurants in Florence.

Don’t miss out on dining at Ristorante Buca Niccolini, a top-rated dining destination in Florence. If you're in the mood to try something new, consider Essenziale, another top spot with a mouthwatering menu. You might also want to secure a reservation at Ristorante La Grotta Toscana. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Florence this evening.

After dinner, it’s time to fall in love with the amazing nightlife in Florence and unwind at some of the best bars in the city.

Toast to another unforgettable and relaxing road trip adventure in Italy!

Day 8 of your leisurely self-drive tour in Italy offers another chance for an in-depth travel experience. You’ll stay in Rome for 6 nights.

Experience Basilica Of Santa Croce In Florence, a captivating church in the city. Then, head to Piazzale Michelangelo and soak in the ambiance of this visually striking observation deck.

There are many interesting places to see in Florence, and when you are ready for more, go to Tower Of San Niccolò. This is one of the city’s most often recommended visually striking spots of interest.

In Rome, you’ll find plenty of places to unwind after a day on the road. Our top recommendations go perfectly with your laid-back road trip in Italy.

After a laid-back day of exploring top attractions in the area, it’s an excellent idea to sit down for a lovely and peaceful dinner. We’ve collected the most recommended restaurants in the city for you, so you can check out the menus and make your reservation in advance.

Experience a harmony of flavors at La Pergola in Rome by securing a reservation in advance. Known for its 3-star Michelin status, La Pergola offers a delightful variety of dishes highlighting its delicious mediterranean and contemporary menu. If you're seeking an alternative culinary experience, be sure to explore Il Pagliaccio, a highly recommended restaurant known for its enticing creative and innovative 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 Enoteca La Torre, a highly acclaimed restaurant celebrated for its exceptional mediterranean and creative menu.

As the day is coming to an end, retreat to your hotel for some rest, or head out to a bar to celebrate your time in Rome. The bars in Rome make the perfect setting for a laid-back drink and chilled hangout with your travel companions.

Explore the vibrant nightlife at La Botticella Of Poggi Giovanni after your meal, a hub for lively evenings and memorable moments. Or, head to Almalu Trastevere for a great selection of flavorful drinks and a charming setting. Furthermore, Bar Viminale Di Pepi Maurilio is perfect for those looking to extend their night with a touch of local flavor.

Raise your glass in celebration of your freedom and relaxed road trip adventure in Italy!

On day 9 of your leisurely self-drive tour across Italy, you’ll go deep into Rome, where you'll stay for 5 nights, and see some of the city’s unforgettable attractions. To learn more of the city's culture, you'll also dine at the most popular restaurants in Rome, and meet locals along the way!

Set aside time today to explore Via del Corso, a standout street that reflects the essence of the city. While you're there, you'll also be within reach of some of the city's top landmarks, making it easy to maximize your day. You might also want to visit Via dei Condotti, a street offering another perspective on the city.

One of the most timeless attractions included on the itinerary is Trevi Fountain. This visually striking monument will help you start your sightseeing on top. Then, take a leisurely stroll to Piazza Di Spagna and learn what makes this visually striking public square unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the famous Spanish Steps.

Gain a one-of-a-kind experience on your unhurried and relaxed road trip across Italy by joining a traveler-approved tour in Ancona. There are so many fun and eye-opening activities to try out in Ancona that will make your slow-paced self-drive tour in Italy more memorable. Check out all the most recommended and top-rated tour options in the city of Rome to find the best options for you!

Exploring the food culture in Rome offers you an exciting chance to connect with locals and experience diversity along your relaxed road trip. When you’re ready to eat, we recommend you visit one of the best dining spots in the city.

Have a fantastic dining experience at RomAntica, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Coso Ristorante offers an enticing alternative with its varied menu. Additionally, DEROMA - Farine Romane is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Rome.

Before calling it a day, visit one of the best bars in Rome. There, you can look back on the highlights of today’s pleasant and invigorating travel experiences, have friendly conversations with locals, and unwind.

After enjoying a fulfilling meal, continue your evening at Sant' Eustachio Caffè, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Yellowsquare Rome offers a welcoming atmosphere for easing into the nightlife. Similarly, Caffè Portofino provides an excellent environment for a relaxed and enjoyable evening.

Cherish every minute of your relaxed road trip vacation across Italy.

Day 10 introduces you to many popular attractions and activities in Rome, further proving that leisurely self-drive tours in Italy are extraordinary.

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.

Catch Foro Italico before the crowds roll in. This heritage-rich sports complex is sure to ignite your curiosity. Next, dive into the culturally significant features of Altare Della Patria, a must-visit monument 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 Capitoline Hill, an interesting public square. For a change of scene, check out Roman Forum, known for its UNESCO world heritage-designated features. We also recommend visiting Colosseum. This archeological site is a must for anyone looking to experience the city to the fullest.

Italy makes the perfect setting for a calming but fun road trip experience. Aside from amazing sights, Italy also offers plenty of tours to enhance your relaxed road trip experience.

After a laid-back day of exploring top attractions in the area, it’s an excellent idea to sit down for a lovely and peaceful dinner. We’ve collected the most recommended restaurants in the city for you, so you can check out the menus and make your reservation in advance.

Enjoy a delicious meal at Hotel de Russie, a highly-rated dining destination in Rome. If you're eager to try something different, consider La Taverna Italiana, another top spot with a tantalizing menu. You might also want to secure a reservation at The Parrot Bar. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Rome this evening.

Hang out and unwind at some of the top bars in Rome.

Round off your dining experience by visiting The Apartment Bar Roma, a prime location for a drink. Alternatively, explore the distinctive characteristics of Hotel Hassler Roma, a bar catering to every mood and preference.

Grab a drink and enjoy every passing minute of this night of your relaxed road trip experience in Italy!

Day 11 of your relaxed road trip through Italy means 24 hours of making the best memories in Rome. You’ll go sightseeing at famous attractions in Rome. In the evening, you will experience one of the most popular dining spots in the city. So buckle up and prepare to be blown away by Rome!

Experience Campo De' Fiori, an impressive public square in the city. Then, head to Largo Di Torre Argentina and soak in the ambiance of this standout archeological site.

There are many interesting places to see in Rome, and when you are ready for more, go to Pantheon. This is one of the city’s most world-famous photogenic spots of interest. After exploring the monument, visit the timeless Piazza Navona. Not far away, you'll also find Castel Sant'angelo. This castle is a history-steeped highlight in Rome.

Make the most of your time in the country by joining activities that let you discover more about Italy. Check out all of the tours you can join this day of your leisurely self-drive holiday in Italy and ensure the experience of a lifetime.

Exploring new places makes you hungry. Luckily, Rome has multiple restaurants that offer fantastic dining experiences to continue your laid-back and stress-free discovery of the city.

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

Take a stroll around the area, head back to your accommodation for the night, or continue your evening at one of the best-rated bars in the city.

A leisurely self-drive holiday in Rome can’t get any better than this! Toast to another amazing day in Italy!

On day 12 of your leisurely self-drive tour across Italy, you’ll go deep into Rome, where you'll stay for 2 nights, and see some of the city’s unforgettable attractions. To learn more of the city's culture, you'll also dine at the most popular restaurants in Rome, and meet locals along the way!

A top thing to do today is to explore Monti, a must-see neighborhood in Rome. It's the perfect starting point for touring the top attractions in the area.

Start your day at Piazza Del Popolo. This visually striking public square is a top-rated place to see in Rome. Then, wander over to Villa Borghese. If serene sites excite you, this park will be right up your alley. Nearby, you’ll also find Villa Borghese Pinciana. This romantic museum is a favorite among visitors.

Rome offers plenty to explore, ensuring every moment of your visit is filled with excitement and discovery. If you're up for more, Basilica Di Santa Maria Maggiore is a well-known spot in the city that will captivate you with its unique charm.

Another way to make your easygoing and relaxed road trip in Italy more special is by joining unique tours and activities. Rome offers a wide selection of experiences for every traveler.

When it’s time to eat, the city has a variety of restaurants and cuisines to suit your palate and complement your relaxed road trip experience. Take a leisurely walk around Rome, while looking for a place to eat. Or, check out our top recommendations and treat yourself to a nice meal.

Treat yourself to a delicious dinner at Ristorante Va. Do. , an excellent option for tonight's dining. Looking for something different? Giulia Restaurant offers a tantalizing alternative with its diverse menu. And don’t miss L'Archeologia. Known for great service, it’s a fantastic choice for tonight in Rome.

After dinner, you can choose between heading back to your hotel to recharge, taking a leisurely stroll, or going out to a bar for a relaxed drink in great company.

Grab a drink and enjoy every passing minute of this night of your relaxed road trip experience in Italy!

Day 13 introduces you to many popular attractions and activities in Rome, further proving that leisurely self-drive tours in Italy are extraordinary.

At the top of the list of things to do today is to explore Trastevere, a neighborhood that captures the true essence of Rome. Take your time to uncover its best sides and enjoy its proximity to many of the area’s best attractions.

Awaiting your discovery is the locally renowned Orange Garden, a visually striking park in Rome. Next, go to Circus Maximus.

After visiting Orange Garden and Circus Maximus, have a stroll along Rome's streets and take in the local charm. Continue your sightseeing by heading to Fontana Dell'acqua Paola. This visually striking monument offers a unique experience. Belvedere Del Gianicolo is another noteworthy attraction worthwhile a visit.

Gain a one-of-a-kind experience on your unhurried and relaxed road trip across Italy by joining a traveler-approved tour in Ancona. There are so many fun and eye-opening activities to try out in Ancona that will make your slow-paced self-drive tour in Italy more memorable. Check out all the most recommended and top-rated tour options in the city of Rome to find the best options for you!

Mealtimes are the perfect opportunities to immerse yourself in the local culture of Italy. When you're not appreciating the best places to visit in Rome, explore the city like a local by trying out the best restaurants in the area.

Make sure to reserve a table at Caffè Antica Roma, 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 Maccheroni, 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 In Roma - since 1917, a hidden gem nestled in Rome. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

If you feel like it, head out to a bar to celebrate another fantastic day in Rome and take the pulse of the city’s nightlife. Enjoy the night without rushing to fully appreciate it.

Raise your glass and toast to another unforgettable, laid-back road trip adventure in Italy!

Day 14 of your relaxed road trip across Italy offers a day of exciting discoveries. You’ll start your day in Teramo and drive in the direction of Ancona for some laid-back sightseeing. You’ll end your day in Ancona, where you’ll stay for 1 night.

Embrace the thrill of the open road as you wave goodbye to Rome and set your GPS to Teramo. While on the road, immerse yourself in your favorite road trip tunes or sample the sounds from a local radio station. This car ride usually takes around 2 hours 7 min. Upon reaching Teramo, unwind, observe, and explore. The best things to do, see, and eat are waiting for you.

When you're ready for some sights, head to Santuario Madonna Delle Grazie, a frequently visited church in Teramo. Explore its heritage-rich features at your own pace before you continue your journey to your next attraction, Roman Theatre Of Teramo. This beloved archeological site is a top recommendation in the area.

When you’re ready to explore more, Fontana Dei Due Leoni is an excellent choice. Spend some time discovering what some claim to be the most noteworthy monument in the region.

You'll be staying in Ancona on this laid-back road trip through Italy. You'll stay here for 1 night.

When it’s time to eat, the city has a variety of restaurants and cuisines to suit your palate and complement your relaxed road trip experience. Take a leisurely walk around Ancona, while looking for a place to eat. Or, check out our top recommendations and treat yourself to a nice meal.

Dive into a culinary adventure like no other in Ancona by booking a table at Sot'Ajarchi. This popular restaurant holds a Bib Gourmand award and offers an exceptional menu of seafood and from the marches cuisine. If you're in the mood to try something new, consider Bontà delle Marche, another top spot with a mouthwatering menu.

After dinner, it’s time to fall in love with the amazing nightlife in Ancona and unwind at some of the best bars in the city.

If you’re not ready to end the night just yet, Alla Tazza D'oro offers a perfect venue to relax and savor a drink.

Raise your glass and toast to another unforgettable, laid-back road trip adventure in Italy!