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

Your luxury holiday in Italy begins as soon as you reach the city of Florence, where you'll be staying for 2 nights. There, you’ll pick up the luxury rental vehicle of your choice and hit the roads!

Start your sightseeing with a visit to Piazzale Michelangelo. This square is rated an average of 4.8 out of 5 stars from 77,744 visitors.

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

Discover a world of culinary delights in Florence, 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.

Have a fantastic dining experience at Ristorante Oliviero 1962, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Caffe San Firenze offers an enticing alternative with its varied menu. Additionally, Ditta Artigianale is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Florence.

After savoring a delicious meal, step into the vibrant nightlife at Manifattura, where the evening is just getting started. In the same way, Se·sto On Arno Rooftop Bar offers a unique charm perfect for experiencing the local bar scene in Florence. Archea Brewery is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

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

Day 2 of your luxury road trip in Italy begins and concludes in the city of Florence. Set out by car to explore incredible attractions in the nearby area. After a day filled with sightseeing, you'll return to Florence, where you still have 1 night nights remaining.

Drop by the renowned Piazza Della Signoria. This popular square has been rated an average of 4.8 out of 5 stars by 66,956 visitors.

Another unforgettable place to experience is Ponte Vecchio. Rated 4.7 out of 5 stars by 118,099 visitors, this deck arch bridge deserves a spot on today's sightseeing itinerary.

We also recommend a visit to Uffizi Gallery. Hosting around 2,011,219 visitors every year, the fascinating Uffizi Gallery is one of the best places to visit in Florence. This national museum has been rated an average of 4.7 out of 5 stars in 61,794 reviews.

Another favorite attraction in the area is The Boboli Gardens. This park and popular place of interest enjoys a rating of 4.2 out of 5 stars from 25,341 local and international travelers.

If you’re keen to explore even more, then consider a visit to Pitti Palace. This art museum gets around 198,270 annual visitors. With an average rating of 4.6 out of 5 stars from 23,445 travelers, this art museum is an attraction many avid travelers highly recommend visiting while in Florence.

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 Florence for you so you can browse their menus in advance and make a reservation.

Set out on a gastronomic journey in Florence by reserving a table at Enoteca Pinchiorri. Renowned for its 3-star Michelin recognition, this restaurant presents an outstanding menu of italian contemporary cuisine. For a different taste, head over to Santa Elisabetta, renowned for its delectable creative, and mediterranean dishes. This distinguished 2-star Michelin-recipient is a favorite among guests, making it a worthy addition to your holiday plans. Craving more culinary excitement? Explore Gucci Osteria da Massimo Bottura, a highly rated local gem known for its exquisite italian contemporary, and international menu. With a 1-star Michelin acclaim, it promises a dining experience you won't want to miss. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Florence.

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 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.

Make Cathedral Of Santa Maria Del Fiore one of your first sightseeing stops in Florence. Rated an average of 4.8 out of 5 stars by 76,359 travelers, a visit to this local attraction makes for a great introduction to the area.

Galleria Dell'accademia is a worthwhile attraction you can visit next. This national museum is a valued place of interest in the area, with an average rating of 4.6 out of 5 stars from 34,429 reviews. Up to 1,719,645 travelers visit this site every year to make their time in Florence special.

Today is also the perfect opportunity to drop by Central Market. This point of interest has been rated an average of 4.4 out of 5 stars by 43,100 visitors.

If you’re keen to explore more, head to Basilica Di Santa Maria Novella, Firenze (fi). A trip to this popular archives is also your opportunity to see if it lives up to the reputable 4.7 out of 5-star rating as given by 23,075 previous visitors.

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

Treat yourself to a delightful dinner at Antica Trattoria Papei, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Osteria Quattro Venti? It's another excellent option with a diverse menu. Consider reserving a table at Osteria da Divo as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Siena.

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.

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.

On day 4 of your luxury holiday in Italy, your road trip route will take you exploring the best of Vatican City. The day's journey will conclude in Rome, a city that offers you comfort and relaxation for 3 nights. 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. Vatican City, 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 Siena to Vatican City may take around 2 hours 39 min without traffic disruptions. Upon arrival in Vatican City, we highly recommend checking out some of the top attractions.

Journey into the unknown at Saint Peter's Square, a unique attraction awaiting your visit. This remarkable square has an average rating of 4.8 out of 5 stars from 38,954 reviews.

When you’re ready to continue your sightseeing, Sistine Chapel is a recommended place to visit. This chapel is rated an average of 4.7 out of 5 stars in 52,083 reviews.

Another must-see attraction in Vatican City is St. Peter's Basilica. This spectacular major basilica gets over 11,000,000 visitors every year. Rated an average of 4.8 out of 5 stars by 131,043 travelers, this popular tourist destination in Vatican City offers an experience you will remember.

Vatican Museums is another popular stop on travelers' itineraries in Vatican City. This art museum promises memorable moments of exploring. Other travelers have rated this attraction 4.6 out of 5 stars in 133,310 reviews. Each year, approximately 1,612,530 people travel to visit Vatican Museums.

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.

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

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.

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at La Botticella Of Poggi Giovanni, a well-loved spot among locals and tourists. Or, head to Sant' Eustachio Caffè. This bar boasts a welcoming environment that is perfect for winding down. You could also continue your night at Caffè Portofino, another top-rated place 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.

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 2 nights nights remaining.

Seize the day by visiting some of the best attractions in the area, like Campo De' Fiori. This extraordinary square has an average rating of 4.4 out of 5 stars from 51,133 visitors.

Next, make your way to Basilica Di Santa Maria Maggiore. This major basilica is rated an average of 4.8 out of 5 stars in 27,678 reviews.

While in Rome, we also recommend a visit to Pantheon. Hosting around 30,000,000 visitors every year, Pantheon is one of the best places to visit. This roman temple has been rated an average of 4.8 out of 5 stars in 189,682 reviews.

If you’re keen to explore even more, then consider a visit to Piazza Navona. With an average rating of 4.7 out of 5 stars by 158,771 travelers, this square is a highly recommended stop on your sightseeing around Rome.

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

Discover a world of culinary delights in Rome, 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.

Make sure to reserve a table at DEROMA - Farine Romane, an iconic dining spot in Rome. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of La Taverna Italiana, a popular restaurant in Rome. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Centro, a hidden gem nestled in Rome. 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 The Apartment Bar Roma, known for its lively atmosphere. Hotel Hassler Roma is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance.

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.

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.

Begin your sightseeing with a visit to Circus Maximus. This circus is rated an average of 4.4 out of 5 stars in 44,741 reviews.

Next up, make your way to Colosseum. This roman amphitheatre has an average rating of 4.7 out of 5 stars from 328,821 reviews. Usually, around 7,400,000 people visit Colosseum every year.

When you’re ready for your next sight of the day, continue to Roman Forum. This square has an average rating of 4.7 out of 5 stars from 114,450 visitors.

Beyond the above-mentioned attractions, you also have the opportunity to visit Capitoline Hill. This hill is rated an average of 4.7 out of 5 stars by 19,557 visitors.

If you’re keen to explore even more, then consider a visit to Altare Della Patria. This architectural structure is a much-appreciated attraction with an average rating of 4.8 out of 5 stars from 49,843 visitors. Approximately 1,683,070 travelers visit Altare Della Patria 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.

Have a fantastic dining experience at Ristorante Tema, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Maccheroni offers an enticing alternative with its varied menu. Additionally, RoYaL Art Cafè Roma is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Rome.

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

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.

When you’re ready for some sightseeing, make your way to Trevi Fountain. This much-appreciated sculpture is rated 4.8 out of 5 stars in 343,494 reviews.

Next up is Piazza Di Spagna. This square has an average rating of 4.7 out of 5 stars from 113,658 visitors.

Another top sightseeing recommendation is Spanish Steps. This monumental staircase has been rated 4.5 out of 5 stars in 57,211 reviews.

Piazza Del Popolo is another attraction you have the opportunity to visit today. This square has an average rating of 4.6 out of 5 stars from 89,807 reviews.

To continue your sightseeing, head over to Villa Borghese. This urban zone of rome 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 Arezzo. 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 Arezzo. Choose from a selection of excellent restaurants and bars and find the perfect place for your evening.

Treat yourself to an extraordinary dining experience at Octavin, a 1-star Michelin restaurant offering an incredible creative menu. Alternatively, if your taste buds call for something different, La Clandestina is another top choice with a popular menu.

After savoring a delicious meal, step into the vibrant nightlife at Liquid Bar, where the evening is just getting started.

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

Wake up to day 8 of your luxury holiday in Italy! Remember to have a hearty breakfast because today will be filled with memorable adventures in Bologna. With a flexible itinerary, you're free to adapt and explore additional attractions or enjoy spontaneous discoveries.

As you’ve unraveled the marvels of Arezzo, it’s time to gear up for the next part of your road trip adventure. Under favorable conditions, your drive to Bologna may take around 2 hours 5 min. Upon your arrival in Bologna, you’ll be greeted with the opportunity to do some sightseeing and exploring.

Make Piazza Maggiore one of your first sightseeing stops in Bologna. Rated an average of 4.7 out of 5 stars by 64,523 travelers, a visit to this local attraction makes for a great introduction to the area.

Two Towers is a worthwhile attraction you can visit next. This tower is a valued place of interest in the area, with an average rating of 4.7 out of 5 stars from 25,975 reviews.

Today is also the perfect opportunity to drop by Piazza Santo Stefano. This square has been rated an average of 4.8 out of 5 stars by 7,617 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.

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

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.

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

Day 9 of your luxury road trip in Italy begins and concludes in the city of Venice. Set out by car to explore incredible attractions in the nearby area. After a day filled with sightseeing, you'll return to Venice, where you still have 1 night nights remaining.

Begin your sightseeing with a visit to Piazza San Marco. This extraordinary square is rated an average of 4.7 out of 5 stars by 152,982 visitors.

Next, make your way to St Mark's Campanile. This top attraction is a bell tower with an average rating of 4.7 out of 5 stars by 3,884 visitors.

We also recommend a visit to St Mark's Basilica. This cathedral is rated 4.7 out of 5 stars by 18,439 travelers.

If you’re keen to keep exploring, visit Doge's Palace. This highly recommended sightseeing destination has received an average rating of 4.7 out of 5 stars from 24,775 travelers. Around 318,104 people come to experience this place of interest every year.

Today is also your chance to spend some time at Bridge Of Sighs. This footbridge is rated an average of 4.6 out of 5 stars by 18,223 travelers.

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

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

If you’re not ready to end the night just yet, The Irish Pub Venezia offers a perfect venue to relax and savor a drink. Similarly, Dolce Vita Venezia is well-suited for those looking to unwind in a social setting. Devils Forest Pub is another excellent spot to enjoy a nightcap after a delightful meal.

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 10 of your luxury holiday in Italy, your road trip route will take you exploring the best of Venice. The day's journey will conclude in Florence, 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.

Your sightseeing of the day begins at Rialto Bridge, a remarkable stone bridge where it’s easy to get lost in exploration. This top attraction is rated an average of 4.7 out of 5 stars in 141,666 reviews.

Next, satisfy your wanderlust at Palazzo Contarini Del Bovolo. This point of interest has an average rating of 4.5 out of 5 stars from 11,745 travelers.

Gallerie Dell'accademia 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 7,950 travelers and attracting 210,149 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 Teatro La Fenice. This well-loved opera house boasts a 4.7 out of 5-star rating from 10,677 reviews.

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.

Discover a world of culinary delights in Florence, 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.

Make sure to book a table at Tijuana, a popular restaurant in Florence. This acclaimed restaurant and its mouthwatering dishes have earned the admiration of countless food lovers. Alternatively, experience a taste of Florence at Djària - American Bar, a popular local restaurant. With a menu designed to impress, it promises a journey of flavors that will leave you captivated. Another top-rated restaurant to try is Ristorante Buca Niccolini. As a dining spot that gains high praise from guests, it’s an ideal choice to enhance your time to Florence tonight.

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.

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 Florence before saying goodbye.

On your last day in Italy, take time to indulge in shopping at Florence’s popular marketplace. Look for keepsakes or souvenirs to remind you of your trip.

Make the most of what's left of your luxury vacation and head out to the stunning Piazza Della Libertà. This extraordinary sightseeing destination and attraction is rated an average of 4.1 out of 5 stars in 4,139 reviews, and is an excellent choice for your last sightseeing in Florence.

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

Have a fantastic dining experience at Cibrèo Caffè, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Ristorante Le Volte Firenze offers an enticing alternative with its varied menu.

You will then say farewell to Florence 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!