Luxury 11-Day Italy Road Trip from Rimini traveling south to Bologna, Florence, Siena, Rome, and Perugia

Your luxury holiday in Italy begins as soon as you reach the city of Rimini, where you'll be staying for 1 night. There, you’ll pick up the luxury rental vehicle of your choice and hit the roads!

Kick off the day at Arch of Augustus, a top pick for today’s sightseeing. This triumphal arch is rated an average of 4.6 out of 5 stars in 12,375 reviews.

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

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

Experience a taste of local culinary excellence while in Rimini by securing a table at Guido. Esteemed as a 1-star Michelin restaurant, it features an exceptional seafood and modern menu. For an alternative taste experience, visit Abocar Due Cucine, famous for its scrumptious creative and international dishes. This 1-star Michelin venue consistently impresses guests, making it a standout addition to your holiday plans. Looking for another choice? Discover Osteria de Börg, a local favorite celebrated for its exquisite from romagna and traditional cuisine in Rimini. Located in the heart of the city, this Bib Gourmand-awardee is an ideal pick for from romagna and traditional cuisine lovers seeking top-notch culinary experiences.

Continue your lively evening at Caffè Il Borgo, a perfect place for winding down or revving up the night, depending on which mood you’re in. Primo Bacio città Lounge Bar is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Hobo's ensures a night out tailored to your taste.

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

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 Rimini to Bologna may take around 1 hour 23 min without traffic disruptions. Upon arrival in Bologna, we highly recommend checking out some of the top attractions.

Start your sightseeing with a visit to Fountain of the four horses. This park is a popular stop on travelers’ itineraries in Rimini, with an average rating of 4.6 out of 5 stars by 2,798 visitors.

Parco Federico Fellini is another popular place of interest you can visit today. The average rating of 4.5 out of 5 stars from 11,076 reviews gives you an idea of other visitors’ experience at this attraction.

When you arrive in Viserbella, it's time to take a break from the road.

Drop by the renowned Italia in miniatura. This popular miniature park has been rated an average of 4.4 out of 5 stars by 20,510 visitors.

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

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

Experience a taste of local culinary excellence while in Bologna by securing a table at I Portici. Esteemed as a 1-star Michelin restaurant, it features an exceptional creative and contemporary menu. For an alternative taste experience, visit Ahimè, famous for its scrumptious country cooking dishes. This Bib Gourmand venue consistently impresses guests, making it a standout addition to your holiday plans. Looking for another choice? Discover Trattoria di Via Serra, a local favorite celebrated for its exquisite emilian cuisine in Bologna. Located in the heart of the city, this Bib Gourmand-awardee is an ideal pick for emilian cuisine lovers seeking top-notch culinary experiences.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Bar Freud e Squisito stands out as an excellent choice for a post-dinner cocktail. Alternatively, Osteria del Sole offers an ideal atmosphere to enjoy the pleasures of the night. Macondo - Cocktail Bar is also a great option that provides a perfect setting for a relaxing 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.

On day 3 of your luxury holiday in Italy, your road trip route will take you exploring the best of Bologna and Pisa. With a day brimming with amazing attractions ahead, fuel up with a hearty breakfast to savor every moment of your luxury vacation in Italy.

Once you're ready to continue your road trip, it's time to buckle up and drive, eagerly anticipating your arrival in Pisa. This drive usually takes around 2 hours 6 min, without any stops or traffic disruptions.

When you’re ready for some sightseeing, make your way to Piazza Maggiore. This much-appreciated square is rated 4.7 out of 5 stars in 64,523 reviews.

Next up is Two Towers. This tower has an average rating of 4.7 out of 5 stars from 25,975 visitors.

Another top sightseeing recommendation is Fountain of Neptune, Bologna. This fountain has been rated 4.7 out of 5 stars in 3,952 reviews.

Embrace the thrill of the open road as you wave goodbye to Bologna and set your GPS to Pisa. 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 6 min. Upon reaching Pisa, unwind, observe, and explore. The best things to do, see, and eat are waiting for you.

Begin your sightseeing with a visit to Leaning Tower of Pisa. This bell tower gets 3,200,000 visitors each year and is rated an average of 4.7 out of 5 stars in 116,882 reviews.

Next up, make your way to Piazza del Duomo, Pisa. This square has an average rating of 4.7 out of 5 stars from 104,550 reviews.

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

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

Enjoy an outstanding dining experience at Enoteca Pinchiorri, a 3-star Michelin restaurant offering an exceptional italian contemporary menu. If you are in the mood for trying an alternative dining experience, consider visiting the nearby 2-star Michelin-awardee, Santa Elisabetta, known for its delicious creative and mediterranean cuisine. Another highly-recommended restaurant in Florence is Gucci Osteria da Massimo Bottura, a renowned restaurant , known for its delicious italian contemporary and international menu.

Explore the vibrant nightlife at Manifattura after your meal, a hub for lively evenings and memorable moments. Or, head to SE·STO on Arno Rooftop Bar for a great selection of flavorful drinks and a charming setting. Furthermore, Archea Brewery is perfect for those looking to extend their night with a touch of local flavor.

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 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.

Begin your sightseeing with a visit to Ponte Vecchio. This deck arch bridge is rated an average of 4.7 out of 5 stars in 118,099 reviews.

Next up, make your way to Uffizi Gallery. This national museum has an average rating of 4.7 out of 5 stars from 61,794 reviews. Usually, around 2,011,219 people visit Uffizi Gallery every year.

When you’re ready for your next sight of the day, continue to piazza della Signoria. This square has an average rating of 4.8 out of 5 stars from 66,956 visitors.

Beyond the above-mentioned attractions, you also have the opportunity to visit Basilica of Santa Croce in Florence. This church is rated an average of 4.7 out of 5 stars by 28,544 visitors.

If you’re keen to explore even more, then consider a visit to piazzale Michelangelo. This square is a much-appreciated attraction with an average rating of 4.8 out of 5 stars from 77,744 visitors.

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.

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

Wake up to day 5 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 Siena, where you'll be staying for 1 night. The day's itinerary unfolds with a diverse array of experiences in Florence.

When you’re ready to jump back into the car and say goodbye to Florence, you’ll hit the road in the direction of Siena. This drive usually takes around 1 hour 12 min. When you arrive, enjoy some sightseeing.

Take the opportunity to see Cathedral of Santa Maria del Fiore. This attraction has an average rating of 4.8 out of 5 stars from 76,359 visitors.

Galleria dell'Accademia is another sightseeing hotspot in the area. This national museum has been rated an average of 4.6 out of 5 stars by 34,429 travelers. Up to 1,719,645 people visit Galleria dell'Accademia every year.

Florence is also the home of Central Market. Around 43,100 people have rated this sightseeing destination an average of 4.4 out of 5 stars.

Another place you’ll want to visit is Basilica di Santa Maria Novella, Firenze (FI). With an average rating of 4.7 out of 5 stars from a total of 23,075 reviews, a visit to this archives is a great idea.

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

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

Round off your dining experience by visiting Meet Life Cafè, a prime location for a drink. Alternatively, explore the distinctive characteristics of Maudit Pub, a bar catering to every mood and preference. Bar Impero Siena likewise offers a unique atmosphere, perfect for a memorable night out.

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 6 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.

Upon your arrival in Vatican City, you’ll be greeted with the opportunity to do some sightseeing and exploring.

Begin your sightseeing with a visit to Sistine Chapel. This chapel is rated an average of 4.7 out of 5 stars in 52,083 reviews.

Next up, make your way to St. Peter's Basilica. This major basilica has an average rating of 4.8 out of 5 stars from 131,043 reviews. Usually, around 11,000,000 people visit St. Peter's Basilica every year.

When you’re ready for your next sight of the day, continue to Saint Peter's Square. This square has an average rating of 4.8 out of 5 stars from 38,954 visitors.

Beyond the above-mentioned attractions, you also have the opportunity to visit Vatican Museums. This art museum is rated an average of 4.6 out of 5 stars by 133,310 visitors. Visiting Vatican Museums means you'll be one of 1,612,530 people who do so every year.

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

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

Start your culinary exploration in Rome by securing a reservation at La Pergola. This renowned restaurant holds , 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.

Keep the evening going at La Botticella of Poggi Giovanni, a great choice for enjoying the after-dinner hours with a drink. You could also go to Sant' Eustachio Caffè, which offers a similarly pleasant setting and great drinks. Another option is Caffè Portofino, which provides an inviting environment for unwinding after a busy day out.

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

Day 7 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 Colosseum. This extraordinary roman amphitheatre has an average rating of 4.7 out of 5 stars from 328,821 visitors. Each year, around 7,400,000 people visit this remarkable site to admire its features and learn more about it.

Next, make your way to Roman Forum. This square is rated an average of 4.7 out of 5 stars in 114,450 reviews.

While in Rome, we also recommend a visit to largo di Torre Argentina. This square has been rated an average of 4.5 out of 5 stars in 30,433 reviews.

If you’re keen to explore even more, then consider a visit to Basilica di Santa Maria Maggiore. With an average rating of 4.8 out of 5 stars by 27,678 travelers, this major basilica is a highly recommended stop on your sightseeing around Rome.

Make your way to piazza del Popolo, perhaps the most famous square in Rome. This attraction is rated an average of 4.6 out of 5 stars in 89,807 reviews.

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.

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at The Apartment Bar Roma, a well-loved spot among locals and tourists. Or, head to Hotel Hassler Roma. This bar boasts a welcoming environment that is perfect for winding down.

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 8 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.

Your sightseeing of the day begins at Circus Maximus, a remarkable circus where it’s easy to get lost in exploration. This top attraction is rated an average of 4.4 out of 5 stars in 44,741 reviews.

Next, satisfy your wanderlust at Pantheon. This roman temple has an average rating of 4.8 out of 5 stars from 189,682 travelers. Given the site's popularity, it’s easy to understand why more than 30,000,000 people visit it every year.

Piazza Navona is another must-visit attraction. This renowned square offers a memorable experience, well worth a stop on your self-guided sightseeing tour. Rated 4.7 out of 5 stars by 158,771 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 Campo de' Fiori. This well-loved square boasts a 4.4 out of 5-star rating from 51,133 reviews.

When there’s still energy left for exploring, Castel Sant'Angelo awaits. If you’ve been interested in experiencing a museum, this is a top pick rated 4.7 out of 5 stars by 72,431 previous visitors. Each year, approximately 918,591 people travel to Rome to experience it.

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

Esteemed as a restaurant, it features an exceptional menu.

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 9 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, Perugia. This car ride takes around 2 hours 12 min.

A top pick for your self-guided sightseeing tour today is Altare della Patria. Over 1,683,070 travelers visit this attraction every year. Previous visitors have rated this architectural structure an average of 4.8 out of 5 stars in 49,843 reviews.

Trevi Fountain is a local recommendation that you also can pay a visit today. This sculpture is rated an average of 4.8 out of 5 stars in 343,494 reviews.

Another attraction you won't want to miss is Piazza di Spagna. This square is rated an average of 4.7 out of 5 stars in 113,658 reviews.

Spanish Steps is another outstanding experience in Rome. Around 57,211 travelers have rated this monumental staircase an average of 4.5 out of 5 stars.

If you long for more, Villa Borghese is not far away. This urban zone of rome is a lovely addition to your itinerary. Previous visitors have rated it 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 Perugia.

Discover a world of culinary delights in Perugia, 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.

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

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

Wake up to day 10 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 Rimini, where you'll be staying for 1 night. The day's itinerary unfolds with a diverse array of experiences in Santa Maria degli Angeli, San Vittore, and Cesano.

Embrace the thrill of the open road as you wave goodbye to Santa Maria degli Angeli and set your GPS to Santa Maria degli Angeli. 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 9 min. Upon reaching Santa Maria degli Angeli, unwind, observe, and explore. The best things to do, see, and eat are waiting for you.

Make Basilica of San Francesco d'Assisi your first stop of the day. Previous visitors have rated this papal basilica an average of 4.9 out of 5 stars in 33,258 reviews.

Continue your road trip and head to your next destination, San Vittore. This car ride takes around 1 hour 6 min.

An excellent attraction to start your day with is Frasassi Caves. This show cave is rated an average of 4.8 out of 5 stars in 20,728 reviews.

Set your GPS to Santa Maria degli Angeli and hit the road. Expect a journey of approximately 25 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Santa Maria degli Angeli beckons with new experiences!

Start your sightseeing with a visit to Basilica of Santa Maria degli Angeli. This papal basilica is a popular stop on travelers’ itineraries in Santa Maria degli Angeli, with an average rating of 4.8 out of 5 stars by 19,258 visitors.

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

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

As a top-rated it is an ideal choice in the city.

After savoring a delicious meal, step into the vibrant nightlife at Bar Capogiro, where the evening is just getting started. In the same way, Caffè Cavour offers a unique charm perfect for experiencing the local bar scene in Rimini. Bar Ilde - Il Baretto della Buona Piadina is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

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.

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 Rimini before saying goodbye.

As you approach the end of your journey in Italy, take a moment for some retail therapy in Rimini’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 Rimini one last time before you head to the airport.

You will then say farewell to Rimini 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!