Luxury Two-Week Relaxed Italy Road Trip Vacation from Pisa to Milan, Bologna, and Florence

On day 2 of your relaxed luxury road trip holiday in Italy, you will have the opportunity to experience Pisa, and Cascine Vecchie; 2 of the most vibrant destinations in the country.

Take the opportunity to see Leaning Tower Of Pisa. This attraction has an average rating of 4.7 out of 5 stars from 116,882 visitors and gets around 3,200,000 visits every year.

Piazza Del Duomo, Pisa is another sightseeing hotspot in the area. This square has been rated an average of 4.7 out of 5 stars by 104,550 travelers.

Pisa is also the home of Pisa Cathedral. Around 8,361 people have rated this cathedral an average of 4.8 out of 5 stars.

Continue your road trip and head to your next destination, Cascine Vecchie. This car ride takes around 9 min.

Start your sightseeing with a visit to Parco Regionale Migliarino, San Rossore, Massaciuccoli. This park is a popular stop on travelers’ itineraries in Cascine Vecchie, with an average rating of 4.4 out of 5 stars by 9,632 visitors.

Tonight, you will stay at one of the best luxury hotels in Milan. We have selected the perfect options for you to have the loveliest experience in Milan.

After a long day of discovering the unique quirks of Italy, it’s an excellent idea to sit down for a lovely meal or enjoy a refreshing drink. We’ve gathered the most recommended dining and drinking spots in Milan so you can check out the menus and make advance reservations.

Discover the culinary delights of Milan by securing a reservation at Enrico Bartolini al Mudec. Esteemed for its 3-star Guide Michelin recognition, this restaurant offers a remarkable selection of creative cuisine. For an alternative dining experience, try Seta by Antonio Guida, renowned for its delicious international, and contemporary 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 Il Luogo Aimo e Nadia, a highly recommended local eatery celebrated for its mouthwatering italian contemporary, and modern menu. With its 1-star Michelin recognition, it offers an unforgettable dining adventure.

Extend your evening after a delightful meal by visiting Nottingham Forest, which offers the perfect atmosphere for a night out. Moreover, Armani/bamboo Bar is another popular option for a drink or two. Likewise, Mag Cafe also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

Raise a toast to another stress-free day of your luxury holiday in Pisa, Italy and seize the opportunity to truly relax.

Day 3 of your luxury holiday in Italy is another opportunity to leisurely explore the spectacular city of Milan. You still have 4 nights in Milan, which gives you enough time to discover some of the most amazing things to see and do in the city. Start your morning with a hearty breakfast and get ready for an entire day of enjoying Milan to the fullest.

Make Royal Palace Of Milan one of your first sightseeing stops in Milan. Rated an average of 4.6 out of 5 stars by 17,538 travelers, a visit to this local attraction makes for a great introduction to the area.

Cathedral Square is a worthwhile attraction you can visit next. This sightseeing destination is a valued place of interest in the area, with an average rating of 4.8 out of 5 stars from 7,539 reviews.

Today is also the perfect opportunity to drop by Duomo Di Milano Museum. This art museum has been rated an average of 4.8 out of 5 stars by 138,554 visitors. Up to 341,609 people travel to this site annually.

If you’re keen to explore more, head to Galleria Vittorio Emanuele Ii. A trip to this popular commercial gallery is also your opportunity to see if it lives up to the reputable 4.7 out of 5-star rating as given by 91,394 previous visitors.

Another top place to visit is La Scala. This opera house enjoys an average rating of 4.7 out of 5 stars from 26,219 local and international travelers.

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

Treat yourself after a day of exploration. Make a reservation at the finest dining and drinking spots in Milan.

Enjoy a delicious meal at Nero 9, a top-rated dining destination in Milan. If you're in the mood to try something new, consider Ristorante la Brisa, another top spot with a mouthwatering menu. You might also want to secure a reservation at UNAHOTELS Cusani Milano. With a reputation for consistently satisfied customers, it’s a perfect choice to enhance your stay in Milan this evening.

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

Raise a glass in celebration of your fantastic luxury holiday in Italy! Head back to your hotel for some much-needed rest in preparation for tomorrow’s easygoing adventures.

Day 4 of your luxury road trip in Italy grants you another day to experience Milan. You will continue your laid-back luxury holiday in the best possible way - by discovering the best sights and most exciting activities. You'll then conclude your adventure at one of finest restaurants in Milan, fully indulging in the 3 nights you have in the city.

Be one of the day’s first visitors at Arch Of Peace. This monument is rated an average of 4.6 out of 5 stars by 27,502 visitors.

When you’re finished at Arch Of Peace, head to Triennale Di Milano. This one-of-a-kind art museum is rated an average of 4.5 out of 5 stars in 6,956 reviews. Every year, approximately 180,067 travelers come here to experience the art museum for themselves.

Beyond the above-mentioned attractions, you also have the opportunity to visit Parco Sempione. This park is rated an average of 4.6 out of 5 stars by 72,914 visitors.

If you’re keen to explore more, then consider a visit to Sforzesco Castle Art Library. This library is a much-appreciated attraction with an average rating of 4.6 out of 5 stars from 68,714 visitors.

To round off your sightseeing experience, make your way to Pinacoteca Di Brera. This famous art museum welcomes around 417 visitors annually and is rated an average of 4.7 out of 5 stars by 26,077 travelers.

One of the most unique ways of discovering what else Milan has to offer is by going on a top-rated tour. Be sure to check out all the experiences Milan offers and add your favorites to your Italy travel package below.

After a long day of discovering the unique quirks of Italy, it’s an excellent idea to sit down for a lovely meal or enjoy a refreshing drink. We’ve gathered the most recommended dining and drinking spots in Milan so you can check out the menus and make advance reservations.

Enjoy a lovely meal at Vento di Sardegna, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Palazzo Parigi Hotel & Grand Spa Milano is another top choice with a popular menu. You could also check for a table at Galleria Restaurant. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Milan tonight.

Round off your dining experience by visiting Bhangrabar, a prime location for a drink. Alternatively, explore the distinctive characteristics of Rufus Cocktail Bar, a bar catering to every mood and preference. Ostello Bello Grande likewise offers a unique atmosphere, perfect for a memorable night out.

Enjoy an amazing evening in Milan, and get ready for more fantastic days to come on your relaxed luxury vacation in Italy!

On day 5 of your relaxed luxury holiday across Italy, you'll continue your adventures in the city of Milan. You'll explore Milan, taking breaks from the road for some sightseeing. At the end of day, you'll dine at some of Milan's best restaurants and bars conveniently located close to your accommodation, making the most of your remaining 2 nights in the area.

Journey into the unknown at Basilica Di Sant'ambrogio, a unique attraction awaiting your visit. This remarkable church has an average rating of 4.7 out of 5 stars from 12,883 reviews.

When you’re ready to continue your sightseeing, Museo Della Scienza E Della Tecnologia "leonardo Da Vinci" is a recommended place to visit. This technology museum is rated an average of 4.5 out of 5 stars in 22,235 reviews. Based on recent data, the attraction hosts 532,084 visitors per year.

Another must-see attraction in Milan is Santa Maria Delle Grazie Church. Rated an average of 4.5 out of 5 stars by 13,490 travelers, this popular tourist destination in Milan offers an experience you will remember.

Mudec - Museum Of Cultures is another popular stop on travelers' itineraries in Milan. This ethnographic museum promises memorable moments of exploring. Other travelers have rated this attraction 4.4 out of 5 stars in 14,355 reviews. Each year, approximately 626,650 people travel to visit Mudec - Museum Of Cultures.

You can learn more about Milan today by going on a tour. Milan offers many top-rated tours and unique experiences that will inspire you. You can browse and select your favorites below.

After exploring the unique sights of Italy, savor a delicious meal or get refreshed with a drink. We’ve gathered the most recommended restaurants and bars in the city of Milan for you so you can browse their menus in advance and make a reservation.

Have a fantastic dining experience at Tommasi Milano, a highly recommended choice for tonight's dinner. If you're looking to mix things up, da Vic offers an enticing alternative with its varied menu. Additionally, G. B. Bar is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Milan.

Continue your evening by exploring the vibrant nightlife scene at Qc Termemilano, a prime destination for a thrilling night out. Also, don’t forget to check out Yguana Cafè, a bar that offers unique local touches.

Relax and enjoy an amazing evening in Milan, and get ready for more fantastic days to come on your relaxed luxury vacation in Italy!

Day 6 of your luxury road trip in Italy brings you another chance to explore the wonders of Milan. Immerse yourself in the best sights and most thrilling activities as you continue your laid-back holiday in style. End your day at one of the top restaurants in Milan, making the most of your 1 night in this exquisite city.

When you’re ready for some sightseeing, make your way to Monumental Cemetery. This much-appreciated cemetery is rated 4.8 out of 5 stars in 1,929 reviews.

Next up is Piazza Gae Aulenti. This square has an average rating of 4.6 out of 5 stars from 30,398 visitors.

Another top sightseeing recommendation is Milan Natural History Museum. This museum has been rated 4.4 out of 5 stars in 8,412 reviews.

Villa Necchi Campiglio is another attraction you have the opportunity to visit today. This museum has an average rating of 4.7 out of 5 stars from 5,298 reviews.

If you have an appetite for more adventure, check out the fantastic selection of tours and tickets offered in Milan on this day of your trip. You'll find the most recommended ones below.

After a day filled with travel and exploration, we recommend you treat yourself to a meal or a drink at the finest restaurants and bars in Milan. Savor the local cuisine and relax as you recount the day's experiences.

Dine in style at Ribot Restaurant, a top recommendation for dinner tonight. Or, for a change of pace, Pizza And Food boasts a menu that's sure to impress. Also, be sure to check out Primè. Known as a local hotspot, it’s a great choice for tonight in Milan.

Raise your glass and toast to another unforgettable day of your relaxed luxury holiday in Italy!

On day 7 of your relaxed luxury holiday in Italy, wonderful attractions await. Today you have the opportunity to discover 2 remarkable destinations — Monza, and Verona.

When you’ve had your share of Milan, prepare for your next destination. Admire the views and listen to some good music as you drive in the direction of Monza. Your travel time is around 46 min.

When you’re ready for some sightseeing, make your way to Monza Circuit. This much-appreciated motorsport racing track is rated 4.6 out of 5 stars in 14,877 reviews.

Next up is Monza Park. This park has an average rating of 4.7 out of 5 stars from 34,629 visitors.

As you’ve unraveled the marvels of Monza, it’s time to gear up for the next part of your road trip adventure. Under favorable conditions, your drive to Verona may take around 1 hour 47 min. Upon your arrival in Verona, you’ll be greeted with the opportunity to do some sightseeing and exploring.

Make Castelvecchio Museum your first stop of the day. Previous visitors have rated this art museum an average of 4.6 out of 5 stars in 13,854 reviews. More than 35,031 people visit this place of interest every year.

Next up, make a stop at Verona Arena. With an average rating of 4.7 out of 5 stars by 123,818 visitors, it's easy to understand why so many people visit this opera house every year. In fact, this attraction welcomes 195,540 annual visitors.

Tonight, you will stay at one of the best luxury hotels in Bologna. Renowned for their impeccable facilities and delightful rooms, luxury hotels in Bologna promise an unparalleled experience. With a team of dedicated staff eager to assist and provide recommendations, your stay promises to be nothing short of extraordinary. Relax and unwind in the lap of luxury, where every moment is crafted to exceed your expectations.

Treat yourself after a day of exploration. Make a reservation at the finest dining and drinking spots in Bologna.

Begin your culinary exploration in Bologna by securing a reservation at I Portici. This renowned restaurant holds 1 Michelin star and offers an exceptional menu of creative, and contemporary cuisine. For another dining delight, visit Ahimè, celebrated for its delectable country cooking menu. This acclaimed Bib Gourmand-recipient consistently leaves guests satisfied, making it a must-visit during your holiday. Looking for a different experience? Discover Trattoria di Via Serra, a top local spot known for its tantalizing emilian menu. With a Bib Gourmand recognition, it guarantees an exceptional dining adventure.

Following your dinner, dive into the local bar culture at Bar Freud E Squisito. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Osteria Del Sole, the perfect place for those looking to experience the best of the nightlife. Similarly, Macondo - Cocktail Bar provides excellent drinks and a great atmosphere, ensuring a memorable night out.

Raise a glass in celebration of your fantastic luxury holiday in Italy! Head back to your hotel for some much-needed rest in preparation for tomorrow’s easygoing adventures.

Day 9 of your luxury holiday in Italy is another opportunity to leisurely explore the spectacular city of Bologna. You still have 3 nights in Bologna, which gives you enough time to discover some of the most amazing things to see and do in the city. Start your morning with a hearty breakfast and get ready for an entire day of enjoying Bologna to the fullest.

Kick off the day at Devotional Portico Of St. Luke, a top pick for today’s sightseeing. This point of interest is rated an average of 4.8 out of 5 stars in 626 reviews.

Today is also your chance to visit Arco Del Meloncello. Arco Del Meloncello is an arch with an average rating of 4.6 out of 5 stars from 3,755 reviews.

Palazzo Pallavicini is another top attraction we highly recommend you visit today. This museum is rated an average of 4.5 out of 5 stars by 2,173 visitors.

Beyond the attractions mentioned above, you also have the opportunity to visit Chiesa Del Santissimo Salvatore. This church building is rated an average of 4.6 out of 5 stars by 328 visitors.

Lastly, don’t miss out on Porta Galliera, a famous city gate in Bologna. This attraction is rated an average of 4.3 out of 5 stars by 1,185 travelers.

To immerse yourself in more memorable moments in Bologna, check out the best-rated tours the region offers. You can discover and choose from all of the top-rated activities you can do on this day in Bologna below.

Exploring new destinations can leave you craving great food and drinks. Satisfy your cravings and unwind by visiting the finest restaurants and bars in Bologna.

Make sure to reserve a table at Trattoria del Tempo Buono, an iconic dining spot in Bologna. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Cantina Bentivoglio, a popular restaurant in Bologna. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Ristorante San Pietro, a hidden gem nestled in Bologna. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

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

Raise your glass and toast to another relaxing day of your luxury holiday in Italy!

On day 11 of your relaxed luxury holiday across Italy, you'll continue your adventures in the city of Bologna. You'll explore Bologna, taking breaks from the road for some sightseeing. At the end of day, you'll dine at some of Bologna's best restaurants and bars conveniently located close to your accommodation, making the most of your remaining 1 night in the area.

Begin your sightseeing with a visit to Palazzo D'accursio. This palazzo is rated an average of 4.6 out of 5 stars in 969 reviews.

Next up, make your way to Bologna Cathedral. This catholic cathedral has an average rating of 4.6 out of 5 stars from 3,852 reviews.

When you’re ready for your next sight of the day, continue to Piazza Maggiore. This square has an average rating of 4.7 out of 5 stars from 64,523 visitors.

Beyond the above-mentioned attractions, you also have the opportunity to visit Fountain Of Neptune, Bologna. This fountain is rated an average of 4.7 out of 5 stars by 3,952 visitors.

If you’re keen to explore even more, then consider a visit to Palazzo Re Enzo. This palazzo is a much-appreciated attraction with an average rating of 4.6 out of 5 stars from 2,072 visitors.

There are plenty of experiences you can choose from in Italy that will add excitement to your vacation. When you’re keen to discover what else Bologna has in store for you, use this day to go on a tour. Scroll down and select tours and activities to include on your itinerary for the day.

After a long day of exploring, it’s a great idea to relax with a lovely dinner or a refreshing drink. We’ve gathered the most recommended dining and drinking spots in Bologna for you, so you can check out the menus and make your reservation in advance.

Don’t miss out on dining at Ca' Pelletti - Altabella, a top-rated dining destination in Bologna. If you're in the mood to try something new, consider Corner Bar, another top spot with a mouthwatering menu. You might also want to secure a reservation at Ristorante I Portici. With a reputation for consistently satisfied customers, it’s a perfect choice to enhance your stay in Bologna this evening.

Enjoy an amazing evening in Bologna, and get ready for more fantastic days to come on your relaxed luxury vacation in Italy!

On day 12 of your relaxed luxury road trip holiday in Italy, you will have the opportunity to experience Bologna; 1 of the most vibrant destinations in the country.

Start your sightseeing with a visit to San Martino. This minor basilica is a popular stop on travelers’ itineraries in Bologna, with an average rating of 4.6 out of 5 stars by 320 visitors.

La Piccola Venezia is another popular place of interest you can visit today. The average rating of 4.2 out of 5 stars from 1,491 reviews gives you an idea of other visitors’ experience at this attraction.

If it’s still bright and early, make your way to Faizan-e-madina Bologna. Visitors have rated this mosque an average of 4.8 out of 5 stars in 344 reviews.

Ducati Museum, boasting an annual visitor count of up to 7,600 people, is another unique site you can experience today. This attraction is an industry museum rated an average of 4.5 out of 5 stars in 4,028 reviews.

As the day is coming to an end, it's time to make your way to your home for the night. On this day of your exclusive holiday, you will stay at a luxury hotel in Florence. With a variety of popular luxury lodging options available in the city, you'll have the opportunity to select the perfect retreat to unwind and pamper yourself in style.

In Florence, delicious dining experiences are never far from reach. Take your pick and consider whether you need to book a table in advance.

Enjoy an outstanding dining experience at Enoteca Pinchiorri, a 3-star Michelin restaurant offering an exceptional italian contemporary menu. If you are in the mood for trying an alternative dining experience, consider visiting the nearby 2-star Michelin-awardee, Santa Elisabetta, known for its delicious creative, and mediterranean cuisine. Another highly-recommended restaurant in Florence is Gucci Osteria da Massimo Bottura, a renowned restaurant with a 1-star Guide Michelin recognition, known for its delicious italian contemporary, and international menu.

Unwind after your meal by stepping into Manifattura. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Se·sto On Arno Rooftop Bar offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Archea Brewery, another top-rated bar in the area.

Go over your photos from the day, raise a toast, and rest your tired legs. A new adventurous day of your relaxed luxury road trip in Italy awaits!

Day 13 of your luxury road trip in Italy brings you another chance to explore the wonders of Florence. Immerse yourself in the best sights and most thrilling activities as you continue your laid-back holiday in style. End your day at one of the top restaurants in Florence, making the most of your 1 night in this exquisite city.

Seize the day by visiting some of the best attractions in the area, like Piazzale Michelangelo. This extraordinary square has an average rating of 4.8 out of 5 stars from 77,744 visitors.

Next, make your way to Basilica Of Santa Croce In Florence. This church is rated an average of 4.7 out of 5 stars in 28,544 reviews.

While in Florence, we also recommend a visit to Piazza Della Signoria. This square has been rated an average of 4.8 out of 5 stars in 66,956 reviews.

If you’re keen to explore even more, then consider a visit to Uffizi Gallery. This attraction gets around 2,011,219 yearly visitors. With an average rating of 4.7 out of 5 stars by 61,794 travelers, this national museum is a highly recommended stop on your sightseeing around Florence.

Make your way to Ponte Vecchio, perhaps the most famous deck arch bridge in Florence. This attraction is rated an average of 4.7 out of 5 stars in 118,099 reviews.

Immerse yourself in the local scene through top-rated tours and activities. You can choose from a wide variety of easy to challenging tours and easily add them to your travel package below.

In Florence, delicious dining experiences are never far from reach. Take your pick and consider whether you need to book a table in advance.

Savor the flavors at Trattoria Da Burde, a top pick for dinner tonight. Alternatively, Ristorante Buca Mario 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.

Reminisce about your day, look through photos, and prepare for another great day to come! Your relaxing luxury vacation in Italy still has more in store for you.

On day 14 of your relaxed luxury holiday in Italy, wonderful attractions await. Today you have the opportunity to discover 1 remarkable destinations — Florence.

Kick off the day at Cathedral Of Santa Maria Del Fiore, a top pick for today’s sightseeing. This church is rated an average of 4.8 out of 5 stars in 76,359 reviews.

Today is also your chance to visit Galleria Dell'accademia. Galleria Dell'accademia is a national museum with an average rating of 4.6 out of 5 stars from 34,429 reviews. Attracting more than 1,719,645 yearly visitors, this place of interest is an attraction you don’t want to miss out on.

Central Market is another top attraction we highly recommend you visit today. This sightseeing destination is rated an average of 4.4 out of 5 stars by 43,100 visitors.

Beyond the attractions mentioned above, you also have the opportunity to visit Basilica Di Santa Maria Novella, Firenze (fi). This archives is rated an average of 4.7 out of 5 stars by 23,075 visitors.

In Pisa, you will be treated to a stay at one of the most exclusive 5-star luxury hotels the destination has to offer. From the moment you arrive in Pisa, prepare to be pampered with exceptional service, luxurious accommodations, and top-notch amenities that promise to make your stay truly unforgettable.

After exploring the unique sights of Italy, savor a delicious meal or get refreshed with a drink. We’ve gathered the most recommended restaurants and bars in the city of Pisa for you so you can browse their menus in advance and make a reservation.

Enjoy a delicious meal at Ristorante alle Bandierine, a top-rated dining destination in Pisa. If you're in the mood to try something new, consider Barrique Cocktail And Bistrot, another top spot with a mouthwatering menu. You might also want to secure a reservation at Filter Coffee Lab. With a reputation for consistently satisfied customers, it’s a perfect choice to enhance your stay in Pisa this evening.

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

Go over your photos from the day, raise a toast, and rest your tired legs. A new adventurous day of your relaxed luxury road trip in Italy awaits!