Luxury 11-Day Italy Road Trip from Pisa to Siena, Rome, Florence, Venice, Verona, and Milan and surrounding area

Your luxury holiday in Italy begins as soon as you reach the city of Pisa. There, you’ll pick up the luxury rental vehicle of your choice and hit the roads!

An excellent attraction to start your day with is Logge dei Banchi. This sightseeing destination is rated an average of 4.2 out of 5 stars in 1,128 reviews.

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 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.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, JEFFER cocktails & friends stands out as an excellent choice for a post-dinner cocktail. Alternatively, Le Parisien Wine Bar offers an ideal atmosphere to enjoy the pleasures of the night. Las Volta cocktailbar is also a great option that provides a perfect setting for a relaxing evening.

Raise a toast to the start of your 11-day luxury vacation in Italy and look forward to more fantastic days to come!

Wake up to day 2 of your luxury holiday in Italy! Remember to have a hearty breakfast because today will be filled with memorable adventures in Pisa. With a flexible itinerary, you're free to adapt and explore additional attractions or enjoy spontaneous discoveries.

Set your GPS to Siena and hit the road. Expect a journey of approximately 1 hour 49 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Siena beckons with new experiences!

When you’re ready for some sightseeing, make your way to Leaning Tower of Pisa. This much-appreciated bell tower is rated 4.7 out of 5 stars in 116,882 reviews. Each year, 3,200,000 people visit this site to admire its unique features.

Next up is Angelo Caduto. This sightseeing destination has an average rating of 4.5 out of 5 stars from 150 visitors.

Another top sightseeing recommendation is Pisa Cathedral. This cathedral has been rated 4.8 out of 5 stars in 8,361 reviews.

Piazza del Duomo, Pisa is another attraction you have the opportunity to visit today. This square has an average rating of 4.7 out of 5 stars from 104,550 reviews.

To continue your sightseeing, head over to Campo santo. This cemetery is rated an average of 4.6 out of 5 stars in 586 reviews.

Relax and unwind in style as you spend the night at one of the top luxury hotels in in Siena.

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

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

Celebrate another great day of your luxury holiday in Italy with a toast! Enjoy a great night’s sleep at your lovely hotel and get ready for another fun day to come.

Wake up to day 3 of your luxury road trip holiday in Italy! Today, you will get the opportunity to visit multiple fantastic bucket-list destinations in the country as you head towards the city of Rome, where you'll be staying for 3 nights. The day's itinerary unfolds with a diverse array of experiences in Vatican City.

Admire the views and listen to some good music as you drive in the direction of Vatican City.

An excellent attraction to start your day with is Sistine Chapel. This chapel is rated an average of 4.7 out of 5 stars in 52,083 reviews.

Continue your journey at St. Peter's Basilica. This major basilica is rated 4.8 out of 5 stars by 131,043 travelers from near and far. Approximately 11,000,000 people come to this place of interest every year to enjoy a unique experience in Vatican City.

Vatican City is also the home of Saint Peter's Square. This square has an average rating of 4.8 out of 5 stars from 38,954 visitors.

You can continue your self-guided sightseeing tour at Vatican Museums. A total of 1,612,530 people explore this attraction every year. Rated 4.6 out of 5 stars by 133,310 visitors, a visit to this top sight is time well spent.

Relax and unwind in style as you spend the night at one of the top luxury hotels in in Rome.

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

Begin your culinary exploration in Rome by securing a reservation at La Pergola. This renowned restaurant offers an exceptional menu of mediterranean and contemporary cuisine. For another dining delight, visit Il Pagliaccio, celebrated for its delectable creative and innovative 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 Enoteca La Torre, a top local spot known for its tantalizing mediterranean and creative menu. With a 2-star Michelin recognition, it guarantees an exceptional dining adventure.

Keep the excitement of the evening going by going to a bar or two. La Botticella of Poggi Giovanni is an excellent place to start. You could also check out Sant' Eustachio Caffè, offering a different kind of charm. A last recommendation for the day is Caffè Portofino. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

Raise your glass and relax after another big day of your luxury holiday in Italy!

Day 4 of your luxury road trip in Italy begins and concludes in the city of Rome. Set out by car to explore incredible attractions in the nearby area. After a day filled with sightseeing, you'll return to Rome, where you still have 2 nights nights remaining.

Seize the day by visiting some of the best attractions in the area, like Spanish Steps. This extraordinary monumental staircase has an average rating of 4.5 out of 5 stars from 57,211 visitors.

Next, make your way to Piazza di Spagna. This square is rated an average of 4.7 out of 5 stars in 113,658 reviews.

While in Rome, we also recommend a visit to Altare della Patria. Hosting around 1,683,070 visitors every year, Altare della Patria is one of the best places to visit. This architectural structure has been rated an average of 4.8 out of 5 stars in 49,843 reviews.

If you’re keen to explore even more, then consider a visit to Roman Forum. With an average rating of 4.7 out of 5 stars by 114,450 travelers, this square is a highly recommended stop on your sightseeing around Rome.

Make your way to Colosseum, perhaps the most famous roman amphitheatre in Rome. This attraction welcomes around 7,400,000 visitors annually and is rated an average of 4.7 out of 5 stars in 328,821 reviews.

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

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

Celebrate another great day of your luxury holiday in Italy with a toast! Enjoy a great night’s sleep at your lovely hotel and get ready for another fun day to come.

Day 5 of your luxury road trip in Italy begins and concludes in the city of Rome. Set out by car to explore incredible attractions in the nearby area. After a day filled with sightseeing, you'll return to Rome, where you still have 1 night nights remaining.

Begin your sightseeing with a visit to Piazza Navona. This square is rated an average of 4.7 out of 5 stars in 158,771 reviews.

Next up, make your way to Campo de' Fiori. This square has an average rating of 4.4 out of 5 stars from 51,133 reviews.

When you’re ready for your next sight of the day, continue to Foro Italico. This sightseeing destination has an average rating of 4.6 out of 5 stars from 25,438 visitors.

Beyond the above-mentioned attractions, you also have the opportunity to visit Circus Maximus. This circus is rated an average of 4.4 out of 5 stars by 44,741 visitors.

If you’re keen to explore even more, then consider a visit to Castel Sant'Angelo. This museum is a much-appreciated attraction with an average rating of 4.7 out of 5 stars from 72,431 visitors. Approximately 918,591 travelers visit Castel Sant'Angelo every year.

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 Rome. Savor the local cuisine and relax as you recount the day's experiences.

Raise a toast to another amazing day of your luxury holiday in Rome, Italy and seize the opportunity to celebrate.

On day 6 of your luxury holiday in Italy, your road trip route will take you exploring the best of Rome. With a day brimming with amazing attractions ahead, fuel up with a hearty breakfast to savor every moment of your luxury vacation in Italy.

Continue your road trip and head to your next destination, Florence. This car ride takes around 3 hours 4 min.

Seize the day by visiting some of the best attractions in the area, like largo di Torre Argentina. This extraordinary square has an average rating of 4.5 out of 5 stars from 30,433 visitors.

Next, make your way to Pantheon. This roman temple welcomes around 30,000,000 visitors yearly and is rated an average of 4.8 out of 5 stars in 189,682 reviews.

While in Rome, we also recommend a visit to Trevi Fountain. This sculpture has been rated an average of 4.8 out of 5 stars in 343,494 reviews.

If you’re keen to explore even more, then consider a visit to piazza del Popolo. With an average rating of 4.6 out of 5 stars by 89,807 travelers, this square is a highly recommended stop on your sightseeing around Rome.

Make your way to Villa Borghese, perhaps the most famous urban zone of rome in Rome. This attraction is rated an average of 4.6 out of 5 stars in 69,749 reviews.

Relax and unwind in style as you spend the night at one of the top luxury hotels in in Florence.

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 Florence so you can check out the menus and make advance reservations.

Experience a symphony of flavors at Enoteca Pinchiorri in Florence by securing a reservation in advance. Renowned for its 3-star Michelin distinction, Enoteca Pinchiorri delights its guests with its exceptional variety of meals showcasing delicious italian contemporary cuisine. For a palate-pleasing alternative, make sure to dine at Santa Elisabetta, acclaimed for its delectable creative and mediterranean specialties. This local 2-star Michelin establishment consistently satisfies guests, ensuring an unforgettable holiday experience. Want to go on another culinary journey? Delight your senses at Gucci Osteria da Massimo Bottura, a top-rated restaurant known for its outstanding menu. Known as a top-rated , it's a top choice for italian contemporary and international cuisine in the city.

Keep the evening going at Manifattura, a great choice for enjoying the after-dinner hours with a drink. You could also go to SE·STO on Arno Rooftop Bar, which offers a similarly pleasant setting and great drinks. Another option is Archea Brewery, which provides an inviting environment for unwinding after a busy day out.

Reminisce about your day, look through photos, and prepare for another great day to come! Your stress-free luxury holiday in Italy has plenty more in store for you.

Wake up to day 7 of your luxury holiday in Italy! Remember to have a hearty breakfast because today will be filled with memorable adventures in Florence. With a flexible itinerary, you're free to adapt and explore additional attractions or enjoy spontaneous discoveries.

As you’ve unraveled the marvels of Florence, it’s time to gear up for the next part of your road trip adventure. Under favorable conditions, your drive to Venice may take around 2 hours 54 min. Upon your arrival in Venice, you’ll be greeted with the opportunity to do some sightseeing and exploring.

Start your sightseeing with a visit to piazza della Signoria. This square is rated an average of 4.8 out of 5 stars from 66,956 visitors.

Cathedral of Santa Maria del Fiore is another popular attraction you could visit today. This church has a rating of 4.8 out of 5 stars from 76,359 visitors.

Piazza della Repubblica is also highly recommended by travelers. This square has a rating of 4.6 out of 5 stars from 22,356 visitors.

Ponte Vecchio is an attraction you won’t want to miss. This deck arch bridge is rated an average of 4.7 out of 5 stars in 118,099 reviews.

Another attraction you have the opportunity to visit today is piazzale Michelangelo. This square has received an average rating of 4.8 out of 5 stars from 77,744 travelers.

Relax and unwind in style as you spend the night at one of the top luxury hotels in in Venice.

In Venice, 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 Venice by booking a table at Local, a 1-star Michelin restaurant that boasts an exceptional contemporary menu. For a different flavor experience, head to Wistèria, renowned for its delectable contemporary and venetian dishes. This 1-star Michelin restaurant consistently wows guests, making it a memorable stop during your holiday. Looking for another option? Visit Quadri, a local gem known for its delightful modern cuisine in Venice. Nestled in the city's heart, this 1-star Michelin restaurant is a perfect choice for discerning restaurant-goers seeking a new experience.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Al Parlamento, known for its inviting atmosphere. Adagio is another great option if you’re looking for a place to get the night started. Similarly, Il Mercante provides a great setting to enjoy the night away.

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

Wake up to day 8 of your luxury road trip holiday in Italy! Today, you will get the opportunity to visit multiple fantastic bucket-list destinations in the country as you head towards the city of Verona, where you'll be staying for 1 night. The day's itinerary unfolds with a diverse array of experiences in Venice.

After soaking in Venice’s unique atmosphere, jump into the car with a full heart and drive in the direction of your next destination: Verona. Expect your car journey to take a minimum of 1 hour 23 min. When you arrive in Verona, it's time to take a break from the road.

Begin your sightseeing with a visit to Rialto Bridge. This stone bridge is rated an average of 4.7 out of 5 stars in 141,666 reviews.

Next up, make your way to Piazza San Marco. This square has an average rating of 4.7 out of 5 stars from 152,982 reviews.

When you’re ready for your next sight of the day, continue to St Mark's Basilica. This cathedral has an average rating of 4.7 out of 5 stars from 18,439 visitors.

Beyond the above-mentioned attractions, you also have the opportunity to visit Doge's Palace. This palace is rated an average of 4.7 out of 5 stars by 24,775 visitors. Visiting Doge's Palace means you'll be one of 318,104 people who do so every year.

If you’re keen to explore even more, then consider a visit to Bridge of Sighs. This footbridge is a much-appreciated attraction with an average rating of 4.6 out of 5 stars from 18,223 visitors.

Relax and unwind in style as you spend the night at one of the top luxury hotels in in Verona.

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 Verona. Savor the local cuisine and relax as you recount the day's experiences.

Set out on a gastronomic journey in Verona by reserving a table at Casa Perbellini 12 Apostoli. Renowned for its , this restaurant presents an outstanding menu of creative and contemporary cuisine. For a different taste, head over to Il Desco, renowned for its delectable italian contemporary dishes. This distinguished 1-star Michelin-recipient is a favorite among guests, making it a worthy addition to your holiday plans. Craving more culinary excitement? Explore Osteria Mondo d'Oro, a highly rated local gem known for its exquisite italian and seasonal menu. With a Bib Gourmand 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 Verona.

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

Raise a toast to another amazing day of your luxury holiday in Venice, Italy and seize the opportunity to celebrate.

On day 9 of your luxury holiday in Italy, your road trip route will take you exploring the best of Verona and Ronchi. With a day brimming with amazing attractions ahead, fuel up with a hearty breakfast to savor every moment of your luxury vacation in Italy.

Ronchi’s wonders await as you prepare for another journey on the road, leaving the breathtaking surroundings of Verona behind. This drive usually takes around 35 min. Ronchi welcomes you with a multitude of unique vacation experiences.

Make Gran Guardia one of your first sightseeing stops in Verona. Rated an average of 4.5 out of 5 stars by 1,551 travelers, a visit to this local attraction makes for a great introduction to the area.

Verona Arena is a worthwhile attraction you can visit next. This opera house is a valued place of interest in the area, with an average rating of 4.7 out of 5 stars from 123,818 reviews. Up to 195,540 travelers visit this site every year to make their time in Verona special.

Ronchi’s wonders await as you prepare for another journey on the road, leaving the breathtaking surroundings of Verona behind. This drive usually takes around 35 min. Ronchi welcomes you with a multitude of unique vacation experiences.

Kick off the day at Gardaland Resort, a top pick for today’s sightseeing. This amusement park is rated an average of 4.4 out of 5 stars in 99,291 reviews.

Relax and unwind in style as you spend the night at one of the top luxury hotels in in Milan.

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

Treat yourself to an extraordinary dining experience at Enrico Bartolini al Mudec, a 3-star Michelin restaurant offering an incredible creative menu. Alternatively, if your taste buds call for something different, Seta by Antonio Guida is one of the best restaurants for international and contemporary cuisine in Milan. This 2-star Michelin-awardee earns consistently high praises from guests. We also recommend checking out the menu at Il Luogo Aimo e Nadia. As a top-rated it is an ideal choice for italian contemporary and modern cuisine in the city.

After enjoying a fulfilling meal, continue your evening at Nottingham Forest, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Armani/Bamboo Bar offers a welcoming atmosphere for easing into the nightlife. Similarly, Mag Cafe provides an excellent environment for a relaxed and enjoyable evening.

Celebrate another great day of your luxury holiday in Italy with a toast! Enjoy a great night’s sleep at your lovely hotel and get ready for another fun day to come.

Wake up to day 10 of your luxury holiday in Italy! Remember to have a hearty breakfast because today will be filled with memorable adventures in Genoa and Milan. With a flexible itinerary, you're free to adapt and explore additional attractions or enjoy spontaneous discoveries.

Embrace the thrill of the open road as you wave goodbye to Milan and set your GPS to Genoa. While on the road, immerse yourself in your favorite road trip tunes or sample the sounds from a local radio station. This car ride usually takes around 1 hour 58 min. Upon reaching Genoa, unwind, observe, and explore. The best things to do, see, and eat are waiting for you.

Be one of the day’s first visitors at Aquarium of Genoa. This public aquarium is rated an average of 4.5 out of 5 stars by 62,259 visitors. Attracting more than 1,200,000 yearly visitors, it’s a top sight you don’t want to miss.

Once you're ready to continue your road trip, it's time to buckle up and drive, eagerly anticipating your arrival in Genoa. This drive usually takes around 1 hour 58 min, without any stops or traffic disruptions.

Make Galleria Vittorio Emanuele II your first stop of the day. Previous visitors have rated this commercial gallery an average of 4.7 out of 5 stars in 91,394 reviews.

Next up, make a stop at Duomo di Milano Museum. With an average rating of 4.8 out of 5 stars by 138,554 visitors, it's easy to understand why so many people visit this art museum every year. In fact, this attraction welcomes 341,609 annual visitors.

Relax and unwind in style as you spend the night at one of the top luxury hotels in in Pisa.

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.

After savoring a delicious meal, step into the vibrant nightlife at Bar Mocambo, where the evening is just getting started. In the same way, Tree offers a unique charm perfect for experiencing the local bar scene in Pisa. Chupiteria is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

Raise your glass and relax after another big day of your luxury holiday in Italy!

Today is the last day of your 11-day 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.

As you approach the end of your journey in Italy, take a moment for some retail therapy in Pisa’s celebrated shopping district. Thanks to your stay’s premier location, you can easily visit the city’s commercial hubs and wander through its diverse range of local shops without rushing.

Whether you’re on a hunt for an ideal present to give to your friends or family or looking for a personal memento to remind you of Italy, a variety of items are waiting for you. Hold onto the magic of Italy with these wonderful souvenirs, ensuring your memories never fade.

Treat yourself to a final feast. Savor the unique flavors of Pisa one last time before you head to the airport.

If you're eager to try something different, consider Kiste' - La Pizza Artigianale. It's the second restaurant coming from the tower. , another top spot with a tantalizing menu.

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 luxury holiday in Italy in your luggage!