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

Day 2 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 2 nights.

Bring your curiosity for today’s adventure around Pisa. Some of the city’s most loved attractions await! Leaning Tower Of Pisa is the perfect place to start. This monument is one of the most timeless places to visit in Pisa. Next, head to Piazza Del Duomo, Pisa, a world-famous public square, known for its breathtaking features.

In between the sights, don’t hesitate to take small detours to explore local stores and eateries. When you’re ready to continue your adventure, head to Pisa Cathedral. This historic church is a highly recommended experience. Nearby, you'll also find Parco Regionale Migliarino, San Rossore, Massaciuccoli and Bagno Degli Americani. Visit these for an interesting touch to your journey.

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

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.

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.

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.

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

Today’s itinerary in Florence covers several incredible sights, including an observation deck, a church, a public square, an art gallery, a historical landmark and much more! Start your adventure at Piazzale Michelangelo. This widely recognized observation deck is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the culturally significant wonders of Basilica Of Santa Croce In Florence, a must-see church in the city.

Consider stopping for a small bite to eat or a drink at a local eatery to keep your energy going. When you’re ready, continue your discovery with a visit to Piazza Della Signoria. This extraordinary public square offers an enriching experience. For a change of pace, head to Uffizi Gallery, where you can take in instagrammable features. Conclude your self-guided sightseeing tour with a visit to Ponte Vecchio. These sights offer a fulfilling end to a perfect day.

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, Florence has multiple restaurants that offer fantastic dining experiences to continue your laid-back and stress-free discovery of the city.

Enjoy a delicious meal 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.

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

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at Bar 50 Rosso, a well-loved spot among locals and tourists. Or, head to Bitter Bar. This bar boasts a welcoming environment that is perfect for winding down. You could also continue your night at Archea Brewery, another top-rated place in the area.

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

Day 4 of your relaxed road trip across Italy promises an exciting agenda full of discovery. You’ll start your day in the city of Florence and drive in the direction of the city of Bologna for some laid-back sightseeing. You’ll end your day in the city of Bologna, where you’ll stay for 4 nights.

Florence is brimming with adventures. Today’s wonderful stops include a church, an art gallery, and a food market. Begin your sightseeing adventure at the famous Cathedral Of Santa Maria Del Fiore and allow yourself time to explore. Just a short distance away you'll find your next stop, Galleria Dell'accademia, a respected art gallery that draws visitors from far and near.

Continue your journey to Central Market, one of the city’s most notable spots that you shouldn’t miss. Another great site to visit is the notable Basilica Di Santa Maria Novella, Firenze (fi).

In the city of Bologna, 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.

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.

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

Keep the excitement of the evening going by visiting a bar or two. Bar Al Bricco D'oro is an excellent place to start. You could also check out Bar Freud E Squisito, offering a different kind of charm. A last recommendation for the day is Osteria Del Sole. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

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

On day 5 of your leisurely self-drive tour across Italy, you’ll go deep into Bologna, 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 Bologna, and meet locals along the way!

Today’s well-planned self-sightseeing route offers several fun adventures, romantic experiences, and picturesque spots. 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. Palazzo Pallavicini is the first of them. Spend some time admiring this eye-catching palace before continuing your journey. Bologna Cathedral is your next stop. This underrated church 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 Maggiore. This visually striking public square is a sight to behold. To round off your sightseeing experience, visit Fountain Of Neptune, Bologna and Palazzo Re Enzo.

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.

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 Bononia Cafè, a highly-rated dining destination in Bologna. If you're eager to try something different, consider Via Con Me, another top spot with a tantalizing menu. You might also want to secure a reservation at Trattoria Pizzeria La Mela. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Bologna this evening.

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.

Let the evening flow smoothly from dinner to drinks at Lime Bar, a top-rated bar in the area. For other recommendations, Macondo - Cocktail Bar provides a perfect setting for rounding out your night with style and great drinks. Likewise, Bar Onda Marina By Night offers a memorable night with diverse drink options and excellent service.

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

Day 6 of your relaxed road trip through Italy means 24 hours of making the best memories in Bologna. You’ll go sightseeing at famous attractions in Bologna. 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 Bologna!

Enjoy the perfect balance of relaxation and exploration in Bologna today. One of the most underrated attractions included on the itinerary is Arco Del Meloncello. This culturally significant monument will help you start your sightseeing on top. Then, take a leisurely stroll to Basilica Of San Domenico and learn what makes this detailed church unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the notable Two Towers. After exploring the monument, head to Piazza Santo Stefano. This increasingly popular public square is a highlight in Bologna. As your day continues, stop by Porta Santo Stefano, known for its standout 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.

Enjoy a lovely meal at Va Mo Là, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Trattoria dal Biassanot is another top choice with a popular menu. You could also check for a table at Ristorante Enoteca da Lucia. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Bologna tonight.

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 your delicious meal, get a taste of the vibrant nightlife with a visit to Aurum, known for its inviting atmosphere. Bar Senza Nome is another great option if you’re looking for a place to get the night started. Similarly, Caffè Ristretto provides a great setting to enjoy the night away.

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

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

Bring your curiosity for today’s adventure around Bologna. Some of the city’s most loved attractions await! Ducati Museum is the perfect place to start. This museum is one of the most frequently visited places to visit in Bologna. Next, head to Porta Galliera, an intriguing monument, known for its photogenic features.

In between the sights, don’t hesitate to take small detours to explore local stores and eateries. When you’re ready to continue your adventure, head to Botanical Garden And Herbarium. This romantic botanical garden is a highly recommended experience. Nearby, you'll also find Pinacoteca Nazionale Di Bologna. Visit these for an interesting touch to your journey.

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 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 Bologna.

Dine in style at Pappare' - Bologna, a top recommendation for dinner tonight. Or, for a change of pace, Mister Coffee Bistrò boasts a menu that's sure to impress. Also, be sure to check out All'Osteria Bottega. Known as a local hotspot, it’s a great choice for tonight in Bologna.

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.

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

Soak in the unique atmosphere of Bologna 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 8 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.

Get ready for an exciting day in Bologna. Today’s sightseeing agenda includes a museum, a monument, a stadium, a public square and much more! Begin your adventure at Castelvecchio Museum. This is a well-known museum you should not miss. Another must-see is Castelvecchio Bridge, a popular monument in Bologna.

When you’re ready for the next sight, head to Verona Arena. From there, take a leisurely stroll to Piazza Delle Erbe, another of the city’s captivating attractions.

You’ll be staying at the incredible city of Milan in this laid-back road trip in Italy. You'll stay here for 5 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 Milan.

Start your culinary exploration in Milan by securing a reservation at Enrico Bartolini al Mudec. This renowned restaurant holds 3 Michelin star and offers an exceptional menu of creative cuisine. For another dining delight, visit Seta by Antonio Guida, celebrated for its delectable international and contemporary 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 Il Luogo Aimo e Nadia, a top local spot known for its tantalizing italian contemporary and modern menu. With a 1-star Michelin recognition, it guarantees an exceptional dining adventure.

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

Continue your evening by exploring the vibrant nightlife scene at Nottingham Forest, a prime destination for a thrilling night out. Also, don’t forget to check out Armani/bamboo Bar, a bar that offers unique local touches. Likewise, Mag Cafe provides an excellent alternative for a fun evening.

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

On day 9 of your leisurely self-drive tour across Italy, you’ll go deep into Milan, where you'll stay for 4 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 Milan, and meet locals along the way!

Prepare for a day full of family-friendly attractions, romantic experiences, and photo-friendly spots. When you’re ready, kick off your sightseeing adventure at La Scala. This captivating opera house is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Galleria Vittorio Emanuele Ii, one of the city’s best highlights.

Next, check out Duomo Di Milano Museum, one of the most globally renowned places to see in Milan. This church is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, Cathedral Square. Wander around and soak in the majestic atmosphere this public square offers. Then, head to Royal Palace Of Milan, a top-rated palace that adds another dimension to your day.

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.

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 Milan, 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 Dessert Bar Milano, an excellent option for tonight's dining. Looking for something different? Radisson Blu Hotel Milan offers a tantalizing alternative with its diverse menu. And don’t miss Ristorante Qui Si Mangia. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Milan.

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

Continue your lively evening at Kilburn Cocktail Bar Milano, a perfect place for winding down or revving up the night, depending on which mood you’re in. Bar Frida is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, The Friends Pub Milano ensures a night out tailored to your taste.

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

Day 10 of your relaxed road trip through Italy means 24 hours of making the best memories in Milan. You’ll go sightseeing at famous attractions in Milan. 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 Milan!

Start by visiting Arch Of Peace, a prime spot to begin your journey. This picture-perfect monument is sure to impress. Next on your list is Triennale Di Milano, another must-visit landmark and increasingly popular museum renowned for its eye-catching features.

While exploring and sightseeing, take time to savor the culture of Milan by sampling some local delicacies. When you’re ready for more sightseeing, head to Parco Sempione. This stunning park is an essential place to visit for anyone looking for the full Milan experience. We also recommend visiting Sforzesco Castle Art Library, a widely recognized castle. Nearby, you'll also find Piazza Castello Fountain, ready to add charm to your journey.

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

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 Milan, explore the city like a local by trying out the best restaurants in the area.

Treat yourself to a delightful dinner at Bice Restaurant, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Alto Ristorante? It's another excellent option with a diverse menu. Consider reserving a table at Nero 9 as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Milan.

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 Milan. The bars in Milan make the perfect setting for a laid-back drink and chilled hangout with your travel companions.

Unwind after your meal by stepping into Bhangrabar. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Rufus Cocktail Bar offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Ostello Bello Grande, another top-rated bar in the area.

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

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

Today’s agenda in Milan includes a public square, an art gallery, and a museum. Piazza Gae Aulenti is must-visit public square and a great starting point for the day. Next, continue your journey to Pinacoteca Di Brera, a popular art gallery, located just a leisurely stroll away. Next, head to Milan Natural History Museum, a picture-perfect museum, also available for your discovery today.

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

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

Enjoy a lovely dining experience at Ristorante la Brisa, a popular restaurant in Milan. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Milan at Pasticceria San Carlo, 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 UNAHOTELS Cusani Milano. It’s yet another ideal choice to enhance your time in Milan tonight.

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

Keep the excitement of the evening going by visiting a bar or two. Qc Termemilano is an excellent place to start. You could also check out Yguana Cafè, offering a different kind of charm.

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 Milan, 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 Milan, and meet locals along the way!

Set out on a day brimming with family-friendly attractions, photo-friendly spots, and history-rich sites. Start at the notable Basilica Di Sant'ambrogio, a culturally significant church in Milan. Next, go to Museo Della Scienza E Della Tecnologia "leonardo Da Vinci".

After visiting Basilica Di Sant'ambrogio and Museo Della Scienza E Della Tecnologia "leonardo Da Vinci", have a stroll along Milan's streets and take in the local charm. Continue your sightseeing by heading to Santa Maria Delle Grazie Church. This heritage-rich church offers a unique experience. Mudec - Museum Of Cultures is another noteworthy attraction worthwhile a visit.

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.

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.

Savor the flavors at Vento di Sardegna, a top pick for dinner tonight. Alternatively, Palazzo Parigi Hotel & Grand Spa Milano beckons with its unique menu offerings. Also, consider Galleria Restaurant. With its consistent customer satisfaction, it’s an excellent option for dining in Milan tonight.

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

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

Day 13 of your leisurely self-drive tour in Italy is another opportunity for an in-depth travel experience in the country. You’ll stay in Pisa for 1 night.

Today’s itinerary in Milan covers several incredible sights, including a castle, a park, and a museum. Start your adventure at Castello San Giorgio. This curiosity-inducing castle is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the serene wonders of Giardini Pubblici, a must-see park in the city.

Consider stopping for a small bite to eat or a drink at a local eatery to keep your energy going. When you’re ready, continue your discovery with a visit to Technical Naval Museum Of Spezia. This frequently visited museum offers an enriching experience. These sights offer a fulfilling end to a perfect day.

After a day of exploration, relax at one of the top hotels or accommodations in Pisa. Staying in the city enhances your laid-back road trip experience in Italy by offering a comfortable and welcoming environment to recharge in this charming destination.

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 a delightful dinner at Ristorante Capodimonte Pisa, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try La Locanda Dei Pisani Doc Pisa? It's another excellent option with a diverse menu. Consider reserving a table at Baribaldi Pisa as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Pisa.

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

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

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