Relaxed 14-Day Italy Self-Drive Road Trip With Itinerary from Ancona to Bologna, Florence, and Rome

Day 2 of your leisurely self-drive tour in Italy is another opportunity for an in-depth travel experience in the country. On this refreshing new day, you’ll travel from Ancona and continue your laid-back and relaxed road trip adventure in the town of Loreto and the town of Senigallia. You’ll stay in Bologna for 3 nights.

Prepare for a day full of a mesmerizing, a picture-perfect, a history-steeped, a culturally significant, and a stunning. When you’re ready, kick off your sightseeing adventure at Palazzo Degli Anziani. This often recommended palace 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.

After soaking in Ancona’s unique atmosphere, jump into the car with a full heart and drive in the direction of your next destination: Loreto. Expect your car journey to take a minimum of 35 min. When you arrive in Loreto, it's time to take a break from the road.

One of our top recommendations for your sightseeing is Sanctuary Of The Holy House Of Loreto. Spend some time admiring the grand features of the church before you continue to your next stop.

When you’re ready to jump back into the car and say goodbye to Loreto, you’ll hit the road in the direction of Senigallia. This drive usually takes around 41 min. When you arrive, enjoy some sightseeing.

Head to Rocca Roveresca, an increasingly popular castle in Senigallia. Explore its culturally significant features at your own pace before you continue your journey.

Continue your laid-back road trip exploration of the best attractions in Italy at Bologna. Select from top hotels and accommodations in the city to recharge and rejuvenate.

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 Bologna, while looking for a place to eat. Or, check out our top recommendations and treat yourself to a nice meal.

Experience a harmony of flavors at Ahimè in Bologna by securing a reservation in advance. Known for its Bib Gourmand status, Ahimè offers a delightful variety of dishes highlighting its delicious country cooking menu. If you're seeking an alternative culinary experience, be sure to explore I Portici, a highly recommended restaurant known for its enticing creative and contemporary cuisine. This popular 1-star Michelin-awarded venue consistently exceeds expectations, ensuring a memorable holiday experience. Ready for another culinary adventure? Indulge your senses at Trattoria di Via Serra, a highly acclaimed restaurant celebrated for its exceptional emilian menu.

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

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at Bar Al Bricco D'oro, a well-loved spot among locals and tourists. Or, head to Bar Freud E Squisito. This bar boasts a welcoming environment that is perfect for winding down. You could also continue your night at Osteria Del Sole, another top-rated place in the area.

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

Day 3 introduces you to many popular attractions and activities in Bologna, further proving that leisurely self-drive tours in Italy are extraordinary.

Immerse yourself in Bologna’s rich culture with today's sightseeing itinerary. Start your journey at Palazzo D'accursio. This respected palace is sure to ignite your curiosity. Next, dive into the instagrammable features of Porta Maggiore, 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 Piazza Maggiore, a widely recognized public square. For a change of scene, check out Bologna Cathedral, known for its historic features.

Gain a one-of-a-kind experience on your unhurried and relaxed road trip across Italy by joining a traveler-approved tour in Bologna. There are so many fun and eye-opening activities to try out in Bologna 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 Bologna to find the best options for you!

Exploring the food culture in Bologna 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.

Make sure to book a table at Bononia Cafè, a popular restaurant in Bologna. This acclaimed restaurant and its mouthwatering dishes have earned the admiration of countless food lovers. Alternatively, experience a taste of Bologna at Via Con Me, a popular local restaurant. With a menu designed to impress, it promises a journey of flavors that will leave you captivated. Another top-rated restaurant to try is Trattoria Pizzeria La Mela. As a dining spot that gains high praise from guests, it’s an ideal choice to enhance your time to Bologna tonight.

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

Continue your lively evening at Lime Bar, a perfect place for winding down or revving up the night, depending on which mood you’re in. Macondo - Cocktail Bar is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Bar Onda Marina By Night ensures a night out tailored to your taste.

Savor the rest of the night and celebrate another incredible relaxed road trip adventure in the magical Bologna!

On day 4 of your leisurely self-drive tour across Italy, you’ll go deep into Bologna, where you'll stay for 1 night, 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 Bologna, and meet locals along the way!

Today’s well-planned self-sightseeing route offers several an awe-inspiring, a photogenic, a heritage-rich, a grand, a charming, and a profound. 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. Two Towers is the first of them. Spend some time admiring this historic monument before continuing your journey. International Museum And Library Of Music is your next stop. This increasingly popular museum 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 history-steeped public square is a sight to behold.

Another way to make your easygoing and relaxed road trip in Italy more special is by joining unique tours and activities. Bologna 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 Bologna, while looking for a place to eat. Or, check out our top recommendations and treat yourself to a nice meal.

Dine in style at Va Mo Là, a top recommendation for dinner tonight. Or, for a change of pace, Trattoria dal Biassanot boasts a menu that's sure to impress. Also, be sure to check out Ristorante Enoteca da Lucia. Known as a local hotspot, it’s a great choice for tonight in Bologna.

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.

Let the evening flow smoothly from dinner to drinks at Aurum, a top-rated bar in the area. For other recommendations, Bar Senza Nome provides a perfect setting for rounding out your night with style and great drinks. Likewise, Caffè Ristretto offers a memorable night with diverse drink options and excellent service.

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

Day 5 of your easy and relaxed road trip through Italy gives you the opportunity to travel leisurely and experience more than one place in one day. You will start your day by exploring some of the best sights in the city of Pisa. By the end of the day, you’ll drive in the direction of the city of Florence, where you’ll stay at a top-rated hotel of your choice for 4 nights.

Fasten your seatbelt and make your way to your next stop. Pisa, home to many well-known sights in the region, is a lovely destination on today’s itinerary. Keep in mind that your travel time from Bologna to Pisa may take around 2 hours 12 min without traffic disruptions. Upon arrival in Pisa, we highly recommend checking out some of the top attractions.

Spend your afternoon discovering Leaning Tower Of Pisa, an iconic monument known for its detailed features. After taking in the atmosphere, continue to Pisa Cathedral, an often recommended church that is a must-see for anyone visiting the region. Next, stop by Piazza Del Duomo, Pisa and uncover the details of this UNESCO world heritage-listed public square. Make sure to also explore Campo Santo, a locally appreciated cemetery that offers a unique experience.

You’ll be staying at the incredible city of Florence in this laid-back road trip in Italy. You'll stay here for 4 nights.

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.

Discover the culinary delights of Florence by securing a reservation at Enoteca Pinchiorri. Esteemed for its 3-star Guide Michelin recognition, this restaurant offers a remarkable selection of italian contemporary cuisine. For an alternative dining experience, try Santa Elisabetta, renowned for its delicious creative and mediterranean dishes. This esteemed 2-star Michelin-recipient consistently impresses guests, making it a must-visit spot during your holiday. Craving more culinary excitement? Head to Gucci Osteria da Massimo Bottura, a highly recommended local eatery celebrated for its mouthwatering italian contemporary and international menu. With its 1-star Michelin recognition, it offers an unforgettable dining adventure.

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.

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 the rest of the night and celebrate another incredible relaxed road trip adventure in the magical Florence!

Day 6 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!

Today’s agenda in Florence includes a public square, a palace, an art gallery, a historical landmark, an observation deck and much more! Piazza Della Signoria is must-visit public square and a great starting point for the day. Next, continue your journey to Palazzo Vecchio, a well-known palace, located just a leisurely stroll away. Next, head to Uffizi Gallery, a romantic 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 timeless attraction that is worthwhile a visit. Lastly, don’t miss Piazzale Michelangelo, a top-rated gem to see in the city.

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.

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.

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

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.

After your meal, keep the night alive at a bar like Bar 50 Rosso, known for its lively atmosphere. Bitter Bar is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Archea Brewery offers an excellent atmosphere for those looking to amp up the evening.

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

Day 7 introduces you to many popular attractions and activities in Florence, further proving that leisurely self-drive tours in Italy are extraordinary.

Get ready for an exciting day in Florence. Today’s sightseeing agenda includes a food market, a church, and a botanical garden. Begin your adventure at Central Market. This is a locally renowned food market you should not miss. Another must-see is Basilica Di Santa Maria Novella, Firenze (fi), a locally renowned church in Florence.

When you’re ready for the next sight, head to The Boboli Gardens. From there, take a leisurely stroll to Basilica Of Santa Croce In Florence, another of the city’s notable attractions.

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

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.

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.

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.

Keep the excitement of the evening going by visiting a bar or two. Gosh* is an excellent place to start. You could also check out Antico Caffè Del Moro - Art Bar Firenze, offering a different kind of charm. A last recommendation for the day is Quelo Bar. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

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

On day 8 of your leisurely self-drive tour across Italy, you’ll go deep into Florence, where you'll stay for 1 night, 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!

Today, you'll explore some of the most beautiful places in Florence, including an art gallery, a church, and a palace. Start your day with a visit to Galleria Dell'accademia. This captivating art gallery is a must-visit in the city. When you’re ready for your next discovery, continue to Cathedral Of Santa Maria Del Fiore, which may be one of the most UNESCO world heritage-listed places you will experience today.

One of the best things about exploring Florence 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 Pitti Palace, one of the city’s most popular palace.

Gain a one-of-a-kind experience on your unhurried and relaxed road trip across Italy by joining a traveler-approved tour in Florence. There are so many fun and eye-opening activities to try out in Florence 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!

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.

Enjoy a lovely meal at Tijuana, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Djària - American Bar is another top choice with a popular menu. You could also check for a table at The Florence Irish Pub. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Florence tonight.

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 through Italy with a toast. Cheers to a memorable leisurely self-drive holiday in Italy!

On day 9 of your laid-back and relaxed road trip adventure, you’ll have the chance to visit more than one remarkable area in Italy. Since this self-drive tour offers freedom and flexibility, you can decide how much time you want to spend in each place to enjoy the memorable travel destinations in Italy.

When you’re ready to jump back into the car and say goodbye to Florence, you’ll hit the road in the direction of Orvieto. This drive usually takes around 1 hour 54 min. When you arrive, enjoy some sightseeing.

Head to Well Of St. Patrick, a notable monument in Orvieto. Explore its culturally significant features at your own pace before you continue your journey.

Vatican City’s wonders await as you prepare for another journey on the road, leaving the breathtaking surroundings of Orvieto behind. This drive usually takes around 1 hour 34 min. Vatican City welcomes you with a multitude of unique vacation experiences.

Sistine Chapel is an impressive chapel we recommend making time to visit today.

In the city of Rome, you’ll find plenty of stay options that will accommodate your need for rest and relaxation after spending your day on the road. Our top recommendations perfectly complement your relaxed road trip vacation 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.

Treat yourself to an extraordinary dining experience at La Pergola, a 3-star Michelin restaurant offering an incredible mediterranean and contemporary menu. Alternatively, if your taste buds call for something different, Il Pagliaccio is one of the best restaurants for creative and innovative cuisine in Rome. This 2-star Michelin-awardee earns consistently high praises from guests. We also recommend checking out the menu at Enoteca La Torre. As a top-rated establishment with 2 Michelin star, it is an ideal choice for mediterranean and creative cuisine in the city.

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

Following your dinner, dive into the local bar culture at La Botticella Of Poggi Giovanni. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Almalu Trastevere, the perfect place for those looking to experience the best of the nightlife. Similarly, Bar Viminale Di Pepi Maurilio provides excellent drinks and a great atmosphere, ensuring a memorable night out.

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

Day 10 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!

Enjoy the perfect balance of relaxation and exploration in Rome today. One of the most astonishing attractions included on the itinerary is Villa Borghese. This eye-catching park will help you start your sightseeing on top. Then, take a leisurely stroll to Pantheon and learn what makes this instagrammable monument unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the globally renowned Trevi Fountain. After exploring the monument, head to Roman Forum. This world-famous archeological site is a highlight in Rome. Lastly, don’t forget to check out the wondrous Colosseum. Enjoy exploring this incredible archeological site at your own pace.

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 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 Rome.

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.

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.

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.

Raise your glass and relax after another big day of your leisurely paced road trip in Italy!

Day 11 introduces you to many popular attractions and activities in Rome, further proving that leisurely self-drive tours in Italy are extraordinary.

A blend of a stunning, an eye-catching, a history-steeped, a symbolic, a romantic, and a noteworthy await you in Rome on today’s itinerary. First up is the notable archeological site, Circus Maximus. It's a standout spot that offers a memorable visit. Afterward, continue to Campo De' Fiori. A visit to this public square is an enriching experience for all.

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 Piazza Navona. This wondrous public square is an essential stop that should not be missed. Following that, head to Castel Sant'angelo, 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.

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.

Make sure to reserve a table at Hotel de Russie, 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 La Taverna Italiana, 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 The Parrot Bar, a hidden gem nestled in Rome. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

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.

Continue the enjoyment post-dinner at The Apartment Bar Roma, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Hotel Hassler Roma offers a vibrant space for indulging in well-crafted drinks and engaging conversation.

Look back at an amazing day filled with adventure in Italy. And don’t forget to get some rest so you can continue your relaxed holiday in Italy tomorrow with new energy.

On day 12 of your leisurely self-drive tour across Italy, you’ll go deep into Rome, where you'll stay for 1 night, 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!

Start your adventure at Piazza Del Popolo. This astonishing public square is a must-visit for travelers looking for a unique holiday experience. Make your way to Piazza Di Spagna located in Rome for an enchanting atmosphere.

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

Italy makes the perfect setting for a calming but fun exploration. 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 Rome, while looking for a place to eat. Or, check out our top recommendations and treat yourself to a nice meal.

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

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

Grab yourself a drink and savor every moment of your relaxed road trip experience in Italy!

Day 13 of your self-drive tour in Italy is your opportunity to see and experience the diversity of the country. You’ll stay in Ancona for 1 night. Along the route of your relaxed road trip, you can get a glimpse of the locals’ way of life and visit some of the most amazing locations in Italy.

Get ready to discover some of the most iconic wonders in Rome, including a monument and a church. Start your day at Altare Della Patria. This historic monument is a locally renowned place to see in Rome. Then, wander over to Basilica Di Santa Maria Maggiore. If photogenic sites excite you, this church will be right up your alley.

Continue your road trip and head to your next destination, Teramo. This car ride takes around 2 hours 1 min.

Your self-guided tour starts at Santuario Madonna Delle Grazie, an intriguing church that is sure to impress. Take in the surroundings and enjoy the freedom of exploring before you continue your journey.

When you’re not exploring beautiful places, you’ll have a relaxed time at Ancona. Here, you can choose from the best selection of hotels and places to stay as you get to know more about this spectacular city.

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

Enjoy an outstanding dining experience at Sot'Ajarchi, a Bib Gourmand restaurant offering an exceptional seafood and from the marches menu. Alternatively, experience a taste of Ancona at Bontà delle Marche, a popular local restaurant. With a menu designed to impress, it promises a journey of flavors that will leave you captivated.

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.

To truly maximize your evening out, consider visiting Alla Tazza D'oro after dinner. This bar is known for offering some of the best drinks and vibes in the city.

Grab yourself a drink and savor every moment of your relaxed road trip experience in Italy!