Luxury 9-Day Italy Road Trip from Venice traveling south to Milan, Florence, Siena, Rome, and Arezzo

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 Venice. With a flexible itinerary, you're free to adapt and explore additional attractions or enjoy spontaneous discoveries.

Drop by the renowned Piazza San Marco. This popular square has been rated an average of 4.7 out of 5 stars by 152,982 visitors.

Another unforgettable place to experience is St Mark's Basilica. Rated 4.7 out of 5 stars by 18,439 visitors, this cathedral deserves a spot on today's sightseeing itinerary.

We also recommend a visit to Doge's Palace. Hosting around 318,104 visitors every year, the fascinating Doge's Palace is one of the best places to visit in Venice. This palace has been rated an average of 4.7 out of 5 stars in 24,775 reviews.

Another favorite attraction in the area is Bridge Of Sighs. This footbridge and popular place of interest enjoys a rating of 4.6 out of 5 stars from 18,223 local and international travelers.

Relax and unwind in style as you spend the night at one of the top luxury hotels in Milan. Recharge after a day of exploring, enjoying luxurious comfort and serene surroundings.

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.

Begin your culinary exploration in Milan by securing a reservation at Enrico Bartolini al Mudec. This renowned restaurant holds 3 Michelin star and offers an exceptional menu of creative cuisine. For another dining delight, visit Seta by Antonio Guida, celebrated for its delectable international, and contemporary menu. This acclaimed 2-star Michelin-recipient consistently leaves guests satisfied, making it a must-visit during your holiday. Looking for a different experience? Discover Il Luogo Aimo e Nadia, a top local spot known for its tantalizing italian contemporary, and modern menu. With a 1-star Michelin recognition, it guarantees an exceptional dining adventure.

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

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

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 Florence, where you'll be staying for 1 night. The day's itinerary unfolds with a diverse array of experiences in Milan, and Modena.

Make La Scala your first stop of the day. Previous visitors have rated this opera house an average of 4.7 out of 5 stars in 26,219 reviews.

Next up, make a stop at Galleria Vittorio Emanuele Ii. With an average rating of 4.7 out of 5 stars by 91,394 visitors, it's easy to understand why so many people visit this commercial gallery every year.

Duomo Di Milano Museum is another attraction you can visit on this day of your vacation. This art museum has an average rating of 4.8 out of 5 stars by 138,554 visitors. Up to 341,609 travelers come to Milan every year to see Duomo Di Milano Museum with their own eyes.

Embrace the thrill of the open road as you wave goodbye to Milan and set your GPS to Modena. 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 2 hours 2 min. Upon reaching Modena, unwind, observe, and explore. The best things to do, see, and eat are waiting for you.

Seize the day by visiting some of the best attractions in the area, like Enzo Ferrari Museum. This extraordinary museum has an average rating of 4.5 out of 5 stars from 13,416 visitors.

Relax and unwind in style as you spend the night at one of the top luxury hotels in Florence. Recharge after a day of exploring, enjoying luxurious comfort and serene surroundings.

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.

Have a memorable dining experience in Florence by booking a table at Enoteca Pinchiorri, renowned as a 3-star Michelin restaurant presenting an exceptional italian contemporary menu. For a different culinary experience in Florence, Santa Elisabetta shines as one of the top destinations, known for its delicious creative, and mediterranean cuisine. This 2-star Michelin-awardee earns consistently high praises from previous guests, making it a must-visit addition to your holiday experience. If you're looking for an alternative, Il Palagio is known as a top local spot for its delicious italian contemporary cuisine in Florence. This 1-star Michelin awardee is a highly recommended choice for an unforgettable meal.

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.

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.

On day 4 of your luxury holiday in Italy, your road trip route will take you exploring the best of Florence, and Pisa. The day's journey will conclude in Siena, a city that offers you comfort and relaxation for 1 night. With a day brimming with amazing attractions ahead, fuel up with a hearty breakfast to savor every moment of your luxury vacation in Italy.

Start your sightseeing with a visit to Piazza Della Signoria. This square is a popular stop on travelers’ itineraries in Florence, with an average rating of 4.8 out of 5 stars by 66,956 visitors.

Ponte Vecchio is another popular place of interest you can visit today. The average rating of 4.7 out of 5 stars from 118,099 reviews gives you an idea of other visitors’ experience at this attraction.

If it’s still bright and early, make your way to Piazzale Michelangelo. Visitors have rated this square an average of 4.8 out of 5 stars in 77,744 reviews.

When you’ve had your share of Florence, prepare for your next destination. Admire the views and listen to some good music as you drive in the direction of Pisa. Your travel time is around 1 hour 19 min.

Your sightseeing of the day begins at Leaning Tower Of Pisa, a remarkable bell tower where it’s easy to get lost in exploration. This top attraction is rated an average of 4.7 out of 5 stars in 116,882 reviews. Each year, this popular place of interest welcomes approximately 3,200,000 visitors.

Next, satisfy your wanderlust at Piazza Del Duomo, Pisa. This square has an average rating of 4.7 out of 5 stars from 104,550 travelers.

Relax and unwind in style as you spend the night at one of the top luxury hotels in Siena. Recharge after a day of exploring, enjoying luxurious comfort and serene surroundings.

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

Enjoy a delicious meal at Antica Trattoria Papei, a highly-rated dining destination in Siena. If you're eager to try something different, consider Osteria Quattro Venti, another top spot with a tantalizing menu. You might also want to secure a reservation at Osteria da Divo. With a reputation for consistently satisfied customers, it’s an excellent choice to enhance your stay in Siena this evening.

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

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

Once you're ready to continue your road trip, it's time to buckle up and drive towards Vatican City, eagerly anticipating your arrival in Vatican City. This drive usually takes around 2 hours 40 min, without any stops or traffic disruptions.

Your sightseeing of the day begins at Sistine Chapel, a remarkable chapel where it’s easy to get lost in exploration. This top attraction is rated an average of 4.7 out of 5 stars in 52,083 reviews.

Next, satisfy your wanderlust at St. Peter's Basilica. This major basilica has an average rating of 4.8 out of 5 stars from 131,043 travelers. Given the site's popularity, it’s easy to understand why more than 11,000,000 people visit it every year.

Saint Peter's Square is another must-visit attraction. This renowned square offers a memorable experience, well worth a stop on your self-guided sightseeing tour. Rated 4.8 out of 5 stars by 38,954 travelers, 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 Vatican Museums. This well-loved art museum boasts a 4.6 out of 5-star rating from 133,310 reviews. In a single year, approximately 1,612,530 visitors add this sightseeing spot to their travel itineraries.

Relax and unwind in style as you spend the night at one of the top luxury hotels in Rome. Recharge after a day of exploring, enjoying luxurious comfort and serene surroundings.

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.

Start your culinary exploration in Rome by securing a reservation at La Pergola. This renowned restaurant holds 3 Michelin star and 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.

Following your dinner, dive into the local bar culture at La Botticella Of Poggi Giovanni. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Sant' Eustachio Caffè, the perfect place for those looking to experience the best of the nightlife. Similarly, Caffè Portofino provides excellent drinks and a great atmosphere, ensuring a memorable night out.

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

Day 6 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.

Start your sightseeing with a visit to Colosseum. This roman amphitheatre is a popular stop on travelers’ itineraries in Rome, with an average rating of 4.7 out of 5 stars by 328,821 visitors. Around 7,400,000 people visit this attraction every year.

Roman Forum is another popular place of interest you can visit today. The average rating of 4.7 out of 5 stars from 114,450 reviews gives you an idea of other visitors’ experience at this attraction.

If it’s still bright and early, make your way to Pantheon. Visitors have rated this roman temple an average of 4.8 out of 5 stars in 189,682 reviews. Pantheon receives around 30,000,000 visitors every year.

Piazza Navona is another unique site you can experience today. This attraction is a square rated an average of 4.7 out of 5 stars in 158,771 reviews.

Make your way to the fantastic Castel Sant'angelo, perhaps the most famous museum in Rome. This attraction welcomes around 918,591 visitors annually and is rated 4.7 out of 5 stars by 72,431 travelers.

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

Savor the flavors at DEROMA - Farine Romane, a top pick for dinner tonight. Alternatively, La Taverna Italiana beckons with its unique menu offerings. Also, consider Centro. With its consistent customer satisfaction, it’s an excellent option for dining in Rome tonight.

Explore the vibrant nightlife at The Apartment Bar Roma after your meal, a hub for lively evenings and memorable moments. Or, head to Hotel Hassler Roma for a great selection of flavorful drinks and a charming setting.

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 7 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 Arezzo, where you'll be staying for 1 night. The day's itinerary unfolds with a diverse array of experiences in Rome.

An excellent attraction to start your day with is Altare Della Patria. This architectural structure typically receives around 1,683,070 visitors every year and is rated an average of 4.8 out of 5 stars in 49,843 reviews.

Continue your journey at Trevi Fountain. This sculpture is rated 4.8 out of 5 stars by 343,494 travelers from near and far.

Rome is also the home of Piazza Di Spagna. This square has an average rating of 4.7 out of 5 stars from 113,658 visitors.

You can continue your self-guided sightseeing tour at Piazza Del Popolo. Rated 4.6 out of 5 stars by 89,807 visitors, a visit to this top sight is time well spent.

Lastly, don't miss out on Villa Borghese. With an average rating of 4.6 out of 5 stars from 69,749 reviews, it’s hard to refuse the opportunity to see this urban zone of rome.

Relax and unwind in style as you spend the night at one of the top luxury hotels in Arezzo. Recharge after a day of exploring, enjoying luxurious comfort and serene surroundings.

Discover a world of culinary delights in Arezzo, where top-notch dining experiences await at every corner. Consider whether you need to make a reservation in advance to secure a table at your preferred restaurant.

Enjoy an outstanding dining experience at Octavin, a 1-star Michelin restaurant offering an exceptional creative menu. Alternatively, experience a taste of Arezzo at La Clandestina, a popular local restaurant. With a menu designed to impress, it promises a journey of flavors that will leave you captivated.

Keep the excitement of the evening going by visiting a bar or two. Liquid Bar is an excellent place to start.

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.

On day 8 of your luxury holiday in Italy, your road trip route will take you exploring the best of Bologna. The day's journey will conclude in Venice, a city that offers you comfort and relaxation for 1 night. With a day brimming with amazing attractions ahead, fuel up with a hearty breakfast to savor every moment of your luxury vacation in Italy.

Fasten your seatbelt and make your way to your next stop. Bologna, home to many well-known sights in the region, is a lovely destination on today’s itinerary. Keep in mind that your travel time from Arezzo to Bologna may take around 2 hours 9 min without traffic disruptions. Upon arrival in Bologna, we highly recommend checking out some of the top attractions.

Make Palazzo D'accursio one of your first sightseeing stops in Bologna. Rated an average of 4.6 out of 5 stars by 969 travelers, a visit to this local attraction makes for a great introduction to the area.

Piazza Maggiore is a worthwhile attraction you can visit next. This square is a valued place of interest in the area, with an average rating of 4.7 out of 5 stars from 64,523 reviews.

Today is also the perfect opportunity to drop by Two Towers. This tower has been rated an average of 4.7 out of 5 stars by 25,975 visitors.

If you’re keen to explore more, head to Piazza Santo Stefano. A trip to this popular square is also your opportunity to see if it lives up to the reputable 4.8 out of 5-star rating as given by 7,617 previous visitors.

Relax and unwind in style as you spend the night at one of the top luxury hotels in Venice. Recharge after a day of exploring, enjoying luxurious comfort and serene surroundings.

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

Experience a harmony of flavors at Local in Venice by securing a reservation in advance. Known for its 1-star Michelin status, Local offers a delightful variety of dishes highlighting its delicious contemporary menu. If you're seeking an alternative culinary experience, be sure to explore Wistèria, a highly recommended restaurant known for its enticing contemporary, and venetian 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 Quadri, a highly acclaimed restaurant celebrated for its exceptional modern menu.

Extend your evening after a delightful meal by visiting The Irish Pub Venezia, which offers the perfect atmosphere for a night out. Moreover, Dolce Vita Venezia is another popular option for a drink or two. Likewise, Devils Forest Pub also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

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