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

Wake up to day 2 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 Bologna.

When you're ready to see some sights, Piazza Maggiore is a great place to start. This square is rated an average of 4.7 out of 5 stars by 64,523 visitors.

Another popular attraction you can visit today is Piazza Santo Stefano. This square has an average rating of 4.8 out of 5 stars from 7,617 travelers.

We also recommend a stop at Two Towers. The tower has been rated an average of 4.7 out of 5 stars by 25,975 visitors.

If you're keen to explore more, consider visiting Bologna Cathedral. This catholic cathedral is a popular attraction with an average rating of 4.6 out of 5 stars from 3,852 reviews.

Fountain Of Neptune, Bologna is another easily accessible place to visit on this day of your trip. Stop by this fountain, rated 4.7 out of 5 stars in 3,952 reviews, to discover more of what makes it unique.

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

Prepare for an extraordinary culinary adventure in Arezzo by booking a table at Octavin, a 1-star Michelin restaurant that boasts an exceptional creative menu. If you're eager to try something different, consider La Clandestina, another top spot with a tantalizing menu.

Let the evening flow smoothly from dinner to drinks at Liquid Bar, a top-rated bar in the area.

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

On day 3 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 2 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 Arezzo to Vatican City may take around 2 hours 32 min without traffic disruptions. Upon arrival in Vatican City, we highly recommend checking out some of the top attractions.

Begin your sightseeing with a visit to Vatican Museums. This art museum gets 1,612,530 visitors each year and is rated an average of 4.6 out of 5 stars in 133,310 reviews.

Next up, make your way to Saint Peter's Square. This square has an average rating of 4.8 out of 5 stars from 38,954 reviews.

When you’re ready for your next sight of the day, continue to Sistine Chapel. This chapel has an average rating of 4.7 out of 5 stars from 52,083 visitors.

Beyond the above-mentioned attractions, you also have the opportunity to visit St. Peter's Basilica. This major basilica is rated an average of 4.8 out of 5 stars by 131,043 visitors. Visiting St. Peter's Basilica means you'll be one of 11,000,000 people who do so every year.

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.

Enjoy an outstanding dining experience at La Pergola, a 3-star Michelin restaurant offering an exceptional mediterranean, and contemporary menu. If you are in the mood for trying an alternative dining experience, consider visiting the nearby 2-star Michelin-awardee, Il Pagliaccio, known for its delicious creative, and innovative cuisine. Another highly-recommended restaurant in Rome is Enoteca La Torre, a renowned restaurant with a 2-star Guide Michelin recognition, known for its delicious mediterranean, and creative menu.

Continue your evening by exploring the vibrant nightlife scene at La Botticella Of Poggi Giovanni, a prime destination for a thrilling night out. Also, don’t forget to check out Sant' Eustachio Caffè, a bar that offers unique local touches. Likewise, Caffè Portofino provides an excellent alternative for a fun evening.

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.

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 1 night nights remaining.

Begin your sightseeing with a visit to Colosseum. This roman amphitheatre gets 7,400,000 visitors each year and is rated an average of 4.7 out of 5 stars in 328,821 reviews.

Next up, make your way to Roman Forum. This square has an average rating of 4.7 out of 5 stars from 114,450 reviews.

When you’re ready for your next sight of the day, continue to Pantheon. This roman temple has an average rating of 4.8 out of 5 stars from 189,682 visitors. Up to 30,000,000 people visit this place of interest annually.

Beyond the above-mentioned attractions, you also have the opportunity to visit Piazza Navona. This square is rated an average of 4.7 out of 5 stars by 158,771 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.

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

Enjoy a delicious meal at DEROMA - Farine Romane, a top-rated dining destination in Rome. If you're in the mood to try something new, consider La Taverna Italiana, another top spot with a mouthwatering menu. You might also want to secure a reservation at Centro. With a reputation for consistently satisfied customers, it’s a perfect choice to enhance your stay in Rome this evening.

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.

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

Make Altare Della Patria one of your first sightseeing stops in Rome. Rated an average of 4.8 out of 5 stars by 49,843 travelers, a visit to this local attraction makes for a great introduction to the area. This architectural structure attracts 1,683,070 visitors every year.

Trevi Fountain is a worthwhile attraction you can visit next. This sculpture is a valued place of interest in the area, with an average rating of 4.8 out of 5 stars from 343,494 reviews.

Today is also the perfect opportunity to drop by Piazza Di Spagna. This square has been rated an average of 4.7 out of 5 stars by 113,658 visitors.

If you’re keen to explore more, head to Piazza Del Popolo. A trip to this popular square is also your opportunity to see if it lives up to the reputable 4.6 out of 5-star rating as given by 89,807 previous visitors.

Another top place to visit is Villa Borghese. This urban zone of rome enjoys an average rating of 4.6 out of 5 stars from 69,749 local and international 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.

Discover a world of culinary delights in Siena, 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.

Dine in style at Antica Trattoria Papei, a top recommendation for dinner tonight. Or, for a change of pace, Osteria Quattro Venti boasts a menu that's sure to impress. Also, be sure to check out Osteria da Divo. Known as a local hotspot, it’s a great choice for tonight in Siena.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Meet Life Cafè stands out as an excellent choice for a post-dinner cocktail. Alternatively, Maudit Pub offers an ideal atmosphere to enjoy the pleasures of the night. Bar Impero Siena is also a great option that provides a perfect setting for a relaxing evening.

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

Wake up to day 6 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 2 nights. The day's itinerary unfolds with a diverse array of experiences in Siena, and Pisa.

Take the opportunity to see Tower Of Mangia. This attraction has an average rating of 4.6 out of 5 stars from 673 visitors.

Piazza Del Campo is another sightseeing hotspot in the area. This square has been rated an average of 4.8 out of 5 stars by 64,175 travelers.

Siena is also the home of Siena Cathedral. Around 21,656 people have rated this domus an average of 4.8 out of 5 stars.

Pisa’s wonders await as you prepare for another journey on the road, leaving the breathtaking surroundings of Siena behind. This drive usually takes around 1 hour 48 min. Pisa welcomes you with a multitude of unique vacation experiences.

Make Piazza Del Duomo, Pisa one of your first sightseeing stops in Pisa. Rated an average of 4.7 out of 5 stars by 104,550 travelers, a visit to this local attraction makes for a great introduction to the area.

Leaning Tower Of Pisa is a worthwhile attraction you can visit next. This bell tower is a valued place of interest in the area, with an average rating of 4.7 out of 5 stars from 116,882 reviews. Up to 3,200,000 travelers visit this site every year to make their time in Pisa special.

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

Get ready for an unforgettable culinary journey in Florence by reserving a table at Enoteca Pinchiorri. Renowned as a 3-star Michelin restaurant, it offers an exceptional italian contemporary menu. For a different taste experience, head to Santa Elisabetta, recognized for its delicious creative, and mediterranean dishes. This 2-star Michelin restaurant consistently impresses guests, ensuring a memorable addition to your holiday. Looking for another option? Make sure to visit Il Palagio, a local favorite known for its delightful italian contemporary cuisine in Florence. Nestled in the heart of the city, this restaurant with 1 Michelin star is an ideal choice for discerning italian contemporary foodies seeking culinary excellence.

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.

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 7 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.

Be one of the day’s first visitors at Basilica Of Santa Croce In Florence. This church is rated an average of 4.7 out of 5 stars by 28,544 visitors.

When you’re finished at Basilica Of Santa Croce In Florence, head to Piazza Della Signoria. This one-of-a-kind square is rated an average of 4.8 out of 5 stars in 66,956 reviews.

Beyond the above-mentioned attractions, you also have the opportunity to visit Ponte Vecchio. This deck arch bridge is rated an average of 4.7 out of 5 stars by 118,099 visitors.

If you’re keen to explore more, then consider a visit to Uffizi Gallery. This national museum is a much-appreciated attraction with an average rating of 4.7 out of 5 stars from 61,794 visitors. Around 2,011,219 travelers visit Uffizi Gallery every year.

To round off your sightseeing experience, make your way to Piazzale Michelangelo. This famous square is rated an average of 4.8 out of 5 stars by 77,744 travelers.

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

Don’t miss out on dining at Trattoria Da Burde, a top-rated dining destination in Florence. If you're in the mood to try something new, consider Ristorante Buca Mario, another top spot with a mouthwatering menu. You might also want to secure a reservation at Eataly Firenze. With a reputation for consistently satisfied customers, it’s a perfect choice to enhance your stay in Florence this evening.

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 Florence. The day's journey will conclude in Bologna, 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.

Seize the day by visiting some of the best attractions in the area, like Cathedral Of Santa Maria Del Fiore. This extraordinary church has an average rating of 4.8 out of 5 stars from 76,359 visitors.

Next, make your way to Galleria Dell'accademia. This national museum welcomes around 1,719,645 visitors yearly and is rated an average of 4.6 out of 5 stars in 34,429 reviews.

While in Florence, we also recommend a visit to Central Market. This sightseeing destination has been rated an average of 4.4 out of 5 stars in 43,100 reviews.

If you’re keen to explore even more, then consider a visit to Basilica Di Santa Maria Novella, Firenze (fi). With an average rating of 4.7 out of 5 stars by 23,075 travelers, this archives is a highly recommended stop on your sightseeing around Florence.

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

Treat yourself to an extraordinary dining experience at I Portici, a 1-star Michelin restaurant offering an incredible creative, and contemporary menu. Alternatively, if your taste buds call for something different, Ahimè is one of the best restaurants for country cooking cuisine in Bologna. This Bib Gourmand-awardee earns consistently high praises from guests. We also recommend checking out the menu at Trattoria di Via Serra. As a top-rated establishment with a Bib Gourmand status, it is an ideal choice for emilian cuisine in the city.

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at Bar Senza Nome, a well-loved spot among locals and tourists. Or, head to Bar Maurizio. This bar boasts a welcoming environment that is perfect for winding down. You could also continue your night at Brewdog Bar Bologna, 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.