Luxury 9-Day Relaxed Italy Road Trip Vacation from Pisa to Milan

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Set off on a luxurious, relaxed road trip across Italy for 9 days. Italy invites you to an unmatched holiday experience in Pisa, Tirrenia, Collecchio, Priorato, Milan, and La Spezia, where a unique mix of relaxation and luxury is yours to enjoy.

Italy offers the ultimate luxury holiday experience for anyone up for an unforgettable adventure, including couples, families, solo travelers, and friends.

Your exclusive luxury holiday package will bring you to the country's most popular attractions and restaurants in the best destinations in Italy. With this perfectly planned itinerary, you will stay 4 nights in Pisa, and 4 nights in Milan, experiencing a stress-free luxury vacation in Italy.

Finding the perfect luxury lodging is going to make your vacation in Italy feel truly special. The home for your 9-day luxury holiday will be only the most exclusive 5-star hotels in Italy. You will choose from the best selection of luxury hotels and places to stay, all conveniently located along your carefully planned self-drive route.

Upon arriving in Italy, you will collect the luxury rental vehicle of your choice. We will provide you with the best car rental for the entirety of your 9-day luxury self-drive holiday, including CDW insurance. From there, you will drive off at a relaxed pace to discover some of the best travel destinations in Italy.

Throughout your exclusive vacation in Italy, you will get to experience some of the best attractions and activities offered in the country. Each moment promises to be filled with unforgettable memories and unique experiences.

Between attractions and activities, you will have plenty of time to stroll along the best shopping streets and markets in Italy. We recommend you take the opportunity to explore the shopping experiences available to you in Pisa. Here you can find unique souvenirs to preserve the memory of your relaxed luxury holiday in Italy.

This exclusive travel plan is designed to include everything you need to have the best vacation in Italy. By booking this luxury holiday package, you can avoid spending hours researching and planning your 9-day road trip in Italy. Let the experts figure out the details, so you can focus on enjoying.

To deliver the best experience possible, we make it easy for you to customize each day of your luxury holiday in Italy before and after booking. Our flexible trip planning means you will be able to explore Pisa, Tirrenia, Collecchio, Priorato, Milan, and La Spezia at your own pace.

Book with us to get access to 24/7 personal travel support throughout your entire journey. Enjoy a step-by-step guide in our easy-to-use mobile app, including all travel documents for your exclusive getaway to Italy.

The best services in Italy fill up quickly, so book your luxury vacation package in advance. Select a date and start planning your relaxing luxury holiday in Italy today!

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Day 1

Day 1 – Pisa - arrival day

  • Pisa - Arrival day
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  • Piazza dei Cavalieri
  • More

Your relaxed luxury holiday in Italy begins as soon as you reach the city of Pisa, your home for 3 nights. There, you’ll pick up the luxury rental vehicle of your choice and set off on a relaxed drive to discover Italy.

Make Knights' Square one of your first sightseeing stops in Pisa. Rated an average of 4.5 out of 5 stars by 9,051 travelers, a visit to this local attraction makes for a great introduction to the area.

Tonight, you will be treated to a stay at one of the best luxury hotels in Pisa. We have picked out three of the most exclusive luxury lodging and hotel options for you to choose from.

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 Pisa for you, so you can check out the menus and make your reservation in advance.

Enjoy a lovely meal at Ristorante Capodimonte Pisa, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Baribaldi Pisa is another top choice with a popular menu. You could also check for a table at Restaurant -Pizzeria Il Mio Capriccio. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Pisa tonight.

Let the evening flow smoothly from dinner to drinks at Jeffer Cocktails & Friends, a top-rated bar in the area. For other recommendations, Le Parisien Wine Bar provides a perfect setting for rounding out your night with style and great drinks. Likewise, Las Volta Cocktailbar offers a memorable night with diverse drink options and excellent service.

Raise a toast to the start of your relaxed 9-day luxury vacation in Italy and look forward to more fantastic days to come!

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Day 2

Day 2 – Pisa, Tirrenia, and Cascine Vecchie

  • Pisa
  • Tirrenia
  • More

Drive 44 km, 1 hour 13 min

  • Leaning Tower of Pisa
  • Piazza del Duomo
  • Cattedrale di Pisa
  • Parco Regionale Migliarino, San Rossore, Massaciuccoli
  • More

Day 2 of your luxury road trip means another day to soak in the splendor of Italy. At the village of Tirrenia, you will continue your laid-back luxury holiday in the best possible way. Enjoy the best sights, the most exciting activities, and the finest restaurants in the village. You have ample opportunities to make your 2 nights in the village more special.

Make Leaning Tower Of Pisa your first stop of the day. Previous visitors have rated this bell tower an average of 4.7 out of 5 stars in 116,882 reviews. More than 3,200,000 people visit this place of interest every year.

Next up, make a stop at Piazza Del Duomo, Pisa. With an average rating of 4.7 out of 5 stars by 104,550 visitors, it's easy to understand why so many people visit this square every year.

Pisa Cathedral is another attraction you can visit on this day of your vacation. This cathedral has an average rating of 4.8 out of 5 stars by 8,361 visitors.

To immerse yourself in more memorable moments in Tirrenia, 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 Tirrenia 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 Pisa for you so you can browse their menus in advance and make a reservation.

Treat yourself to a wonderful meal at Ristorante alle Bandierine, a top-rated dining spot in Pisa. If you're in the mood for something new, try Barrique Cocktail And Bistrot, another premier location with a delectable menu. You might also want to book a table at Filter Coffee Lab. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Pisa.

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

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

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Day 3

Day 3 – Pisa

  • Pisa
  • More

Drive 3 km, 43 min

  • Giardino Scotto
  • Logge dei Banchi
  • Palazzo Blu
  • Chiesa di Santa Maria della Spina
  • More

Day 3 of your luxury road trip in Italy brings you another chance to explore the wonders of Pisa. 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 Pisa, making the most of your 1 night in this exquisite city.

Your sightseeing of the day begins at Cittadella Nuova, a remarkable fortress where it’s easy to get lost in exploration. This top attraction is rated an average of 4.4 out of 5 stars in 3,114 reviews.

Next, satisfy your wanderlust at Logge Dei Banchi. This point of interest has an average rating of 4.2 out of 5 stars from 1,128 travelers.

Palazzo Blu is another must-visit attraction. This renowned art museum offers a memorable experience, well worth a stop on your self-guided sightseeing tour. Rated 4.5 out of 5 stars by 4,244 travelers and attracting 37,457 annual visitors, it's one of the more popular places to see in the area.

Beyond the above-mentioned sites, you also have the opportunity to visit Santa Maria Della Spina. This well-loved church building boasts a 4.5 out of 5-star rating from 3,092 reviews.

When there’s still energy left for exploring, “tuttomondo” (keith Haring) awaits. If you’ve been interested in experiencing a point of interest, this is a top pick rated 4.6 out of 5 stars by 1,937 previous visitors.

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

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 Pisa for you, so you can check out the menus and make your reservation in advance.

Dine in style at Sud, a top recommendation for dinner tonight. Or, for a change of pace, Kiste' - La Pizza Artigianale. It's the second restaurant coming from the tower. Boasts a menu that's sure to impress. Also, be sure to check out Osteria dei Cavalieri. Known as a local hotspot, it’s a great choice for tonight in Pisa.

Following your dinner, dive into the local bar culture at Bar Livorno. Enjoy this evening's relaxed ambiance with delightful drinks.

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.

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Day 4

Day 4 – Pisa, Collecchio, Priorato II, Priorato, and Milan

  • Milan
  • Collecchio
  • Priorato
  • More

Drive 298 km, 3 hours 51 min

  • Labirinto della Masone
  • More

On day 4 of your relaxed luxury road trip holiday in Italy, you will have the opportunity to experience Collecchio, Priorato II, and Priorato; 3 of the most vibrant destinations in the country.

Collecchio’s wonders await as you prepare for another journey on the road, leaving the breathtaking surroundings of Pisa behind. This drive usually takes around 1 hour 55 min. Collecchio welcomes you with a multitude of unique vacation experiences.

Seize the day by visiting some of the best attractions in the area, like Parco Nevicati. This extraordinary park has an average rating of 4.5 out of 5 stars from 2,089 visitors.

When you’re ready to jump back into the car and say goodbye to Collecchio, you’ll hit the road in the direction of Priorato II. This drive usually takes around 22 min. When you arrive, enjoy some sightseeing.

An excellent attraction to start your day with is Labirinto Della Masone. This art museum typically receives around 63,000 visitors every year and is rated an average of 4.3 out of 5 stars in 5,266 reviews.

When you’ve had your share of Priorato II, prepare for your next destination. Admire the views and listen to some good music as you drive in the direction of Priorato. Your travel time is around 7 min.

A top pick for your self-guided sightseeing tour today is Rocca Sanvitale. Previous visitors have rated this castle an average of 4.5 out of 5 stars in 8,032 reviews.

In Milan, 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 Milan, prepare to be pampered with exceptional service, luxurious accommodations, and top-notch amenities that promise to make your stay truly unforgettable.

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

Prepare for an extraordinary culinary adventure in Milan by booking a table at Enrico Bartolini al Mudec, a 3-star Michelin restaurant that boasts an exceptional creative menu. For a different flavor experience, head to Seta by Antonio Guida, renowned for its delectable international, and contemporary dishes. This 2-star Michelin restaurant consistently wows guests, making it a memorable stop during your holiday. Looking for another option? Visit Il Luogo Aimo e Nadia, a local gem known for its delightful italian contemporary, and modern cuisine in Milan. Nestled in the city's heart, this 1-star Michelin restaurant is a perfect choice for discerning restaurant-goers seeking a new experience.

Cap off your dinner by heading to Nottingham Forest, ideal for a leisurely evening with a drink in hand. Armani/bamboo Bar is another bar that offers an enjoyable setting. Similarly, Mag Cafe is also a popular place to go on a night out, perfect for relaxing and socializing.

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

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Day 5

Day 5 – Milan

  • Milan
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Drive 1 km, 20 min

  • Palazzo Reale di Milano
  • Cathedral Square
  • Duomo di Milano
  • Galleria Vittorio Emanuele II
  • Teatro alla Scala
  • More

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 3 nights in the area.

Take the opportunity to see Royal Palace Of Milan. This attraction has an average rating of 4.6 out of 5 stars from 17,538 visitors.

Cathedral Square is another sightseeing hotspot in the area. This point of interest has been rated an average of 4.8 out of 5 stars by 7,539 travelers.

Milan is also the home of Duomo Di Milano Museum. This art museum gets more than 341,609 visitors on an annual basis. Around 138,554 people have rated this art museum an average of 4.8 out of 5 stars.

Another place you’ll want to visit is Galleria Vittorio Emanuele Ii. With an average rating of 4.7 out of 5 stars from a total of 91,394 reviews, a visit to this commercial gallery is a great idea.

This day of your vacation in Milan is also your chance to admire La Scala. This must-visit opera house enjoys an average rating of 4.7 out of 5 stars from 26,219 reviews.

Your discoveries in Milan do not have to stop there. Check out the fantastic selection of tours and tickets offered in Milan on this day of your trip. You can select your tours below.

After a full day of exploring, treat yourself to a delightful dinner or a refreshing drink at the best spots in Milan. Choose from a selection of excellent restaurants and bars and find the perfect place for your evening.

Don’t miss out on dining 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.

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.

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.

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Day 6

Day 6 – Milan

  • Milan
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Drive 11 km, 1 hour 16 min

  • Arco della Pace
  • Sempione Park
  • Sforzesco Castle
  • Pinacoteca di Brera
  • Piazza Gae Aulenti
  • More

Day 6 of your luxury holiday in Italy is another opportunity to leisurely explore the spectacular city of Milan. You still have 2 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.

When you're ready to see some sights, Arch Of Peace is a great place to start. This monument is rated an average of 4.6 out of 5 stars by 27,502 visitors.

Another popular attraction you can visit today is Parco Sempione. This park has an average rating of 4.6 out of 5 stars from 72,914 travelers.

We also recommend a stop at Sforzesco Castle Art Library. The library has been rated an average of 4.6 out of 5 stars by 68,714 visitors.

If you're keen to explore more, consider visiting Pinacoteca Di Brera. This art museum is a popular attraction with an average rating of 4.7 out of 5 stars from 26,077 reviews. As a top-rated attraction, it's no surprise that 417 people visit Pinacoteca Di Brera every year.

Piazza Gae Aulenti is another easily accessible place to visit on this day of your trip. Stop by this square, rated 4.6 out of 5 stars in 30,398 reviews, to discover more of what makes it unique.

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.

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.

Treat yourself to a delightful dinner at Vento di Sardegna, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Palazzo Parigi Hotel & Grand Spa Milano? It's another excellent option with a diverse menu. Consider reserving a table at Galleria Restaurant as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Milan.

Continue your evening by exploring the vibrant nightlife scene at Bhangrabar, a prime destination for a thrilling night out. Also, don’t forget to check out Rufus Cocktail Bar, a bar that offers unique local touches. Likewise, Ostello Bello Grande provides an excellent alternative for a fun evening.

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

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Day 7

Day 7 – Milan

  • Milan
  • More

Drive 9 km, 59 min

  • Basilica di Sant'Ambrogio
  • Leonardo da Vinci Museum of Science and Technology
  • Santa Maria delle Grazie
  • Mudec
  • More

Day 7 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 1 night you have in the city.

An excellent attraction to start your day with is Basilica Di Sant'ambrogio. This church is rated an average of 4.7 out of 5 stars in 12,883 reviews.

Continue your journey at Museo Della Scienza E Della Tecnologia "leonardo Da Vinci". This technology museum is rated 4.5 out of 5 stars by 22,235 travelers from near and far. Approximately 532,084 people come to this place of interest every year to enjoy a unique experience in Milan.

Milan is also the home of Santa Maria Delle Grazie Church. This convent has an average rating of 4.5 out of 5 stars from 13,490 visitors.

You can continue your self-guided sightseeing tour at Mudec - Museum Of Cultures. A total of 626,650 people explore this attraction every year. Rated 4.4 out of 5 stars by 14,355 visitors, a visit to this top sight is time well spent.

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.

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

Make sure to reserve a table at Tommasi Milano, 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 da Vic, 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 G. B. Bar, a hidden gem nestled in Milan. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

After your meal, keep the night alive at a bar like Qc Termemilano, known for its lively atmosphere. Yguana Cafè is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance.

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

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Day 8

Day 8 – Milan, La Spezia, and Pisa

  • Pisa
  • La Spezia
  • More

Drive 312 km, 4 hours 8 min

  • Castello San Giorgio
  • Giardini Pubblici
  • More

On day 8 of your relaxed luxury holiday in Italy, wonderful attractions await. Today you have the opportunity to discover 1 remarkable destinations — La Spezia.

Set your GPS to La Spezia and hit the road. Expect a journey of approximately 2 hours 41 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. La Spezia beckons with new experiences!

Journey into the unknown at Parco Giochi La Maggiolina, a unique attraction awaiting your visit. This remarkable bar has an average rating of 4.2 out of 5 stars from 785 reviews.

When you’re ready to continue your sightseeing, Castello San Giorgio is a recommended place to visit. This castle is rated an average of 4.4 out of 5 stars in 2,452 reviews.

Another must-see attraction in La Spezia is Giardini Pubblici. Rated an average of 4.1 out of 5 stars by 2,364 travelers, this popular tourist destination in La Spezia offers an experience you will remember.

Technical Naval Museum Of Spezia is another popular stop on travelers' itineraries in La Spezia. This museum promises memorable moments of exploring. Other travelers have rated this attraction 4.5 out of 5 stars in 1,561 reviews.

For the night, you’ll have the choice of the best luxury hotels and places to stay in the city of Pisa. Whether you prefer the grandeur of a luxury hotel or the charm of a boutique stay, you'll find an array of exquisite options to suit your tastes and preferences. Indulge in world-class amenities, impeccable service, and unforgettable experiences as you unwind and create memories in Pisa.

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

Treat yourself to a delicious dinner at We Love Pasta - Pisa, an excellent option for tonight's dining. Looking for something different? Il Peperoncino offers a tantalizing alternative with its diverse menu. And don’t miss La Taverna Del Grillo. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Pisa.

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!

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Day 9

Day 9 – Pisa - departure day

  • Pisa - Departure day
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Today is the last day of your 9-day relaxed luxury holiday in Italy and it’s soon time to start your journey home. This is your chance to get one last glimpse of Pisa before saying goodbye.

Explore local shops for souvenirs to remember your trip or find unique gifts for loved ones.

Make the most of what's left of your luxury vacation and head out to the stunning Baths Of Nero. This extraordinary point of interest and attraction is rated an average of 4.1 out of 5 stars in 775 reviews, and is an excellent choice for your last sightseeing in Pisa.

Unwind and look back at the past 9 days of your relaxed road trip over a bite to eat. This is your chance to enjoy one last traditional meal in Pisa or just grab something light to keep you going.

You will then say farewell to Pisa and begin your journey home. We wish you safe travels and a warm welcome home, with unforgettable memories and incredible photos from your relaxed luxury holiday in Italy in your luggage!

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