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

On day 2 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.

Begin your adventure at Leaning Tower Of Pisa. This is a wondrous monument you should not miss. Another must-see is Piazza Del Duomo, Pisa, a world-famous public square in Pisa.

When you’re ready for the next sight, head to Pisa Cathedral. From there, take a leisurely stroll to Parco Regionale Migliarino, San Rossore, Massaciuccoli, another of the city’s underrated attractions.

Continue your laid-back road trip exploration of the best attractions in Italy at Florence. 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 Florence, while looking for a place to eat. Or, check out our top recommendations and treat yourself to a nice meal.

Enjoy an outstanding dining experience at Enoteca Pinchiorri, a 3-star Michelin restaurant offering an exceptional italian contemporary menu. Alternatively, if you're in the mood for something different, consider the nearby 2-star Michelin-awardee, Santa Elisabetta, known for its delicious creative and mediterranean cuisine. Another highly-recommended place to eat in Florence is Gucci Osteria da Massimo Bottura, a renowned restaurant with a 1-star Guide Michelin recognition and a delicious italian contemporary and international menu.

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 fulfilling meal, continue your evening at Manifattura, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Se·sto On Arno Rooftop Bar offers a welcoming atmosphere for easing into the nightlife. Similarly, Il Vinile provides an excellent environment for a relaxed and enjoyable evening.

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

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

Set out on a day brimming with family-friendly attractions, romantic experiences, and breathtaking views. Start at the impressive Piazzale Michelangelo, a majestic observation deck in Florence. Next, go to Basilica Of Santa Croce In Florence.

After visiting Piazzale Michelangelo and Basilica Of Santa Croce In Florence, have a stroll along Florence's streets and take in the local charm. Continue your sightseeing by heading to Piazza Della Signoria. This visually striking public square offers a unique experience. Uffizi Gallery is another noteworthy attraction worthwhile a visit. End your self-guided sightseeing tour on top with a visit to Ponte Vecchio, one of the most majestic places to visit in Florence.

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.

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.

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

If you’re not ready to end the night just yet, Bar 50 Rosso offers a perfect venue to relax and savor a drink. Similarly, Bitter Bar is well-suited for those looking to unwind in a social setting. Archea Brewery is another excellent spot to enjoy a nightcap after a delightful meal.

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

Day 4 of your self-drive tour in Italy is your opportunity to see and experience the diversity of the country. You’ll stay in Bologna for 4 nights. 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.

Today’s itinerary in Florence covers several incredible sights, including a church, an art gallery, and a food market. Start your adventure at Cathedral Of Santa Maria Del Fiore. This widely recognized church is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the standout wonders of Galleria Dell'accademia, a must-see art gallery 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 Central Market. This interesting food market offers an enriching experience. For a change of pace, head to Basilica Di Santa Maria Novella, Firenze (fi), where you can take in romantic features. These sights offer a fulfilling end to a perfect day.

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.

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

Extend your evening after a delightful meal by visiting Bar Al Bricco D'oro, which offers the perfect atmosphere for a night out. Moreover, Bar Freud E Squisito is another popular option for a drink or two. Likewise, Osteria Del Sole also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

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

Day 5 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!

Get ready for an exciting day in Bologna. Today’s sightseeing agenda includes a palace, a church, a public square, a monument and much more! Begin your adventure at Palazzo Pallavicini. This is an intriguing palace you should not miss. Another must-see is Bologna Cathedral, a beloved church in Bologna.

When you’re ready for the next sight, head to Piazza Maggiore. From there, take a leisurely stroll to Fountain Of Neptune, Bologna, another of the city’s locally appreciated attractions. We recommend continuing your self-guided tour at Palazzo Re Enzo, an instagrammable place of interest in the city.

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.

Have a fantastic dining experience at Bononia Cafè, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Via Con Me offers an enticing alternative with its varied menu. Additionally, Trattoria Pizzeria La Mela is worth considering. Renowned for satisfying diners, it’s an ideal option 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.

Explore the vibrant nightlife at Lime Bar after your meal, a hub for lively evenings and memorable moments. Or, head to Macondo - Cocktail Bar for a great selection of flavorful drinks and a charming setting. Furthermore, Bar Onda Marina By Night is perfect for those looking to extend their night with a touch of local flavor.

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

On day 6 of your leisurely self-drive tour across Italy, you’ll go deep into Bologna, 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 Bologna, and meet locals along the way!

Bring your curiosity for today’s adventure around Bologna. Some of the city’s most loved attractions await! Arco Del Meloncello is the perfect place to start. This monument is one of the most intriguing places to visit in Bologna. Next, head to Basilica Of San Domenico, a frequently visited church, known for its heritage-rich 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 Two Towers. This picture-perfect monument is a highly recommended experience. Nearby, you'll also find Piazza Santo Stefano and Porta Santo Stefano. 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.

Savor the flavors at Va Mo Là, a top pick for dinner tonight. Alternatively, Trattoria dal Biassanot beckons with its unique menu offerings. Also, consider Ristorante Enoteca da Lucia. With its consistent customer satisfaction, it’s an excellent option for dining in Bologna 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.

Cap off your dinner by heading to Aurum, ideal for a leisurely evening with a drink in hand. Bar Senza Nome is another bar that offers an enjoyable setting. Similarly, Caffè Ristretto is also a popular place to go on a night out, perfect for relaxing and socializing.

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!

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

Start by visiting Ducati Museum, a prime spot to begin your journey. This eye-catching museum is sure to impress. Next on your list is Porta Galliera, another must-visit landmark and up-and-coming monument renowned for its instagrammable features.

While exploring and sightseeing, take time to savor the culture of Bologna by sampling some local delicacies. When you’re ready for more sightseeing, head to Botanical Garden And Herbarium. This standout botanical garden is an essential place to visit for anyone looking for the full Bologna experience. We also recommend visiting Pinacoteca Nazionale Di Bologna, an up-and-coming art gallery.

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.

Treat yourself to a wonderful meal at Pappare' - Bologna, a top-rated dining spot in Bologna. If you're in the mood for something new, try Mister Coffee Bistrò, another premier location with a delectable menu. You might also want to book a table at All'Osteria Bottega. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Bologna.

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

Keep the evening going at Bar Piratello, a great choice for enjoying the after-dinner hours with a drink. You could also go to Bar Carlo, which offers a similarly pleasant setting and great drinks. Another option is Bar Maurizio, which provides an inviting environment for unwinding after a busy day out.

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

Day 8 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 Verona. By the end of the day, you’ll drive in the direction of the city of Milan, where you’ll stay at a top-rated hotel of your choice for 5 nights.

Discover a day packed with fun adventures, scenic views, and photo-friendly spots in Bologna. Begin your sightseeing with Castelvecchio Museum. This interesting museum is one of the top attractions in the city. Proceed to Castelvecchio Bridge, another must-visit attraction.

As you wander through the inviting streets of Bologna, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to Verona Arena. This world-famous stadium is a traveler-favorite. Not far away, you’ll find Piazza Delle Erbe, another key site on your sightseeing itinerary.

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.

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.

Set out on a gastronomic journey in Milan by reserving a table at Enrico Bartolini al Mudec. Renowned for its 3-star Michelin recognition, this restaurant presents an outstanding menu of creative cuisine. For a different taste, head over to Seta by Antonio Guida, renowned for its delectable international and contemporary dishes. This distinguished 2-star Michelin-recipient is a favorite among guests, making it a worthy addition to your holiday plans. Craving more culinary excitement? Explore Il Luogo Aimo e Nadia, a highly rated local gem known for its exquisite italian contemporary and modern menu. With a 1-star Michelin acclaim, it promises a dining experience you won't want to miss. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Milan.

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

After your delicious meal, get a taste of the vibrant nightlife with a visit to Nottingham Forest, known for its inviting atmosphere. Armani/bamboo Bar is another great option if you’re looking for a place to get the night started. Similarly, Mag Cafe provides a great setting to enjoy the night away.

Soak in the unique atmosphere of Milan 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 9 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!

Brace yourself for today’s incredible lineup of attractions in Milan, featuring fun adventures, romantic experiences, and photo-friendly spots. Start at La Scala, an interesting opera house in the city. Then, head to Galleria Vittorio Emanuele Ii and soak in the ambiance of this romantic shopping mall.

There are many interesting places to see in Milan, and when you are ready for more, go to Duomo Di Milano Museum. This is one of the city’s most iconic inviting spots of interest. After exploring the church, visit the up-and-coming Cathedral Square. Not far away, you'll also find Royal Palace Of Milan. This palace is a photogenic highlight in Milan.

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.

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.

Enjoy a lovely meal at Dessert Bar Milano, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Radisson Blu Hotel Milan is another top choice with a popular menu. You could also check for a table at Ristorante Qui Si Mangia. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Milan tonight.

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.

To truly maximize your evening out, consider visiting Kilburn Cocktail Bar Milano after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Bar Frida, another bar with an inviting ambiance. Similarly, The Friends Pub Milano also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

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

On day 10 of your leisurely self-drive tour across Italy, you’ll go deep into Milan, 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 Milan, and meet locals along the way!

Savor the day by visiting some of the best places to see in Milan, including a monument, a museum, a park, a castle, a public square and much more! Start your adventure at Arch Of Peace. This well-known monument is a must-visit for travelers looking for a unique holiday experience. Make your way to Triennale Di Milano located in Milan for another exciting encounter.

Next, immerse yourself in the setting of Parco Sempione. Its romantic features will captivate you. After the park, continue your tour of the city with a visit to Sforzesco Castle Art Library. Visitors usually appreciate the picture-perfect features of this castle. Next up is Piazza Castello Fountain, a highly recommended public square.

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!

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.

Enjoy a lovely dining experience at Bice Restaurant, 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 Alto Ristorante, 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 Nero 9. It’s yet another ideal choice to enhance your time in Milan tonight.

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 Bhangrabar, a perfect place for winding down or revving up the night, depending on which mood you’re in. Rufus Cocktail Bar is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Ostello Bello Grande ensures a night out tailored to your taste.

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 Milan, further proving that leisurely self-drive tours in Italy are extraordinary.

Today, you'll explore some of the most beautiful places in Milan, including a public square, an art gallery, and a museum. Start your day with a visit to Piazza Gae Aulenti. This popular public square is a must-visit in the city. When you’re ready for your next discovery, continue to Pinacoteca Di Brera, which may be one of the most heritage-rich places you will experience today.

One of the best things about exploring Milan 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 Milan Natural History Museum, an underrated museum in the city. If you’re up for more discoveries, don’t forget to reserve some time for Villa Necchi Campiglio.

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

Make sure to reserve a table at Ristorante la Brisa, an iconic dining spot in Milan. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Pasticceria San Carlo, a popular restaurant in Milan. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of UNAHOTELS Cusani Milano, a hidden gem nestled in Milan. 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 Milan.

After enjoying a fulfilling meal, continue your evening at Qc Termemilano, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Yguana Cafè offers a welcoming atmosphere for easing into the nightlife.

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.

Day 12 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!

Today’s agenda in Milan includes a church and a museum. Basilica Di Sant'ambrogio is must-visit church and a great starting point for the day. Next, continue your journey to Museo Della Scienza E Della Tecnologia "leonardo Da Vinci", an interesting museum, located just a leisurely stroll away. Next, head to Santa Maria Delle Grazie Church, an UNESCO world heritage-listed church, also available for your discovery today.

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 Milan 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 Vento di Sardegna, an iconic dining spot in Milan. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Palazzo Parigi Hotel & Grand Spa Milano, a popular restaurant in Milan. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Galleria Restaurant, a hidden gem nestled in Milan. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

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

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

Day 13 of your relaxed road trip across the beautiful country of 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!

A blend of fun adventures, scenic views, and photo-friendly spots await you in Milan on today’s itinerary. First up is the locally appreciated castle, Castello San Giorgio. Afterward, continue to Giardini Pubblici, a park every traveler should visit.

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 Technical Naval Museum Of Spezia. This intriguing museum is an essential stop.

When you’re not exploring beautiful places, you’ll have a relaxed time at Pisa. 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 the food culture in Pisa 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.

Dine in style at Ristorante Capodimonte Pisa, a top recommendation for dinner tonight. Or, for a change of pace, La Locanda Dei Pisani Doc Pisa boasts a menu that's sure to impress. Also, be sure to check out Baribaldi Pisa. Known as a local hotspot, it’s a great choice for tonight in Pisa.

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

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

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.