Luxury 11-Day Italy Self-Drive Road Trip With Itinerary from Milan traveling east to Arezzo, Rome, Florence, and Pisa

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

Today’s well-planned self-sightseeing route offers several a picture-perfect, a standout, a charming, an enchanting, a masterful, a symbolic, and a stunning. Whether you decide to explore Milan on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss. Pinacoteca Di Brera is the first of them. Spend some time admiring this visually striking art gallery before continuing your journey. La Scala is your next stop. This popular opera house is one of the best-rated sights in Milan.

Consider grabbing some lunch or a light snack to keep your energy going. Beyond the above-mentioned attractions, today is also the perfect time to visit Galleria Vittorio Emanuele Ii. This visually striking shopping mall is a sight to behold. To round off your sightseeing experience, visit Cathedral Square and Duomo Di Milano Museum.

Italy is the perfect setting for a unique luxury experience. Add an exclusive tour or activity to your plans for the day to enhance your road trip experience.

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

Have a memorable dining experience in Milan by booking a table at Enrico Bartolini al Mudec, renowned as a 3-star Michelin restaurant presenting an exceptional creative menu. For a different culinary experience in Milan, Seta by Antonio Guida shines as one of the top destinations, known for its delicious international and contemporary 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 Luogo Aimo e Nadia is known as a top local spot for its delicious italian contemporary and modern cuisine in Milan. This 1-star Michelin awardee is a highly recommended choice for an unforgettable meal.

Unwind after your meal by stepping into Kilburn Cocktail Bar Milano. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Bar Frida offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook The Friends Pub Milano, another top-rated bar in the area.

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

On day 3 of your luxury holiday in Italy, your road trip route will take you exploring the best of Milan and Bologna. The day's journey will conclude in Arezzo, 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.

Get ready to discover some of the most iconic wonders in Milan, including a castle and a park. Start your day at Sforzesco Castle Art Library. This picture-perfect castle is a widely recognized place to see in Milan. Then, wander over to Parco Sempione. If serene sites excite you, this park will be right up your alley.

When you’ve had your share of Milan, prepare for your next destination. Admire the views and listen to some good music as you drive in the direction of Bologna. Your travel time is around 2 hours 34 min.

Take your self-guided tour to Two Towers, a notable monument that everyone visiting Bologna should see. Enjoy sightseeing at your own pace and allow yourself time to explore the beautiful surroundings. Next, head to Piazza Maggiore. This symbolic public square is one of the most spectacular attractions in the region.

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.

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

Begin your culinary exploration in Arezzo by securing a reservation at Octavin. This renowned restaurant holds 1 Michelin star and offers an exceptional menu of creative cuisine. Or, for a change of pace, La Clandestina boasts a menu that's sure to impress.

If you’re not ready to end the night just yet, Liquid Bar offers a perfect venue to relax and savor a drink.

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

Wake up to day 4 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.

Vatican City’s wonders await as you prepare for another journey on the road, leaving the breathtaking surroundings of Arezzo behind. This drive usually takes around 2 hours 32 min. Vatican City welcomes you with a multitude of unique vacation experiences.

After taking in the atmosphere, continue to Saint Peter's Square, a popular square that is a must-see for anyone visiting the region. Make sure to also explore St. Peter's Basilica, an iconic major basilica that offers a unique experience.

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.

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

Set out on a gastronomic journey in Rome by reserving a table at La Pergola. Renowned for its 3-star Michelin recognition, this restaurant presents an outstanding menu of mediterranean and contemporary cuisine. For a different taste, head over to Il Pagliaccio, renowned for its delectable creative and innovative 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 Enoteca La Torre, a highly rated local gem known for its exquisite mediterranean and creative menu. With a 2-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 Rome.

To truly maximize your evening out, consider visiting La Botticella Of Poggi Giovanni after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Almalu Trastevere, another bar with an inviting ambiance. Similarly, Bar Viminale Di Pepi Maurilio also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

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

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 remaining.

Rome is brimming with adventures. Today’s wonderful stops include a castle, a public square, an archeological site, a monument and much more! Begin your sightseeing adventure at the spectacular Castel Sant'angelo. Just a short distance away is Piazza Navona, a detailed public square that draws visitors from far and near.

Continue your journey to Campo De' Fiori, one of the city’s most impressive spots that you shouldn’t miss. Another great site to visit is the wondrous Roman Forum. Last up on today’s itinerary is an archeological site. Make your way to Colosseum for some final sightseeing. Each attraction will leave you with lasting memories and a deeper appreciation for the rich heritage of Rome.

Italy is the perfect setting for a unique luxury experience. Add an exclusive tour or activity to your plans for the day to enhance your road trip experience.

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

Dine in style at RomAntica, a top recommendation for dinner tonight. Or, for a change of pace, Coso Ristorante boasts a menu that's sure to impress. Also, be sure to check out DEROMA - Farine Romane. Known as a local hotspot, it’s a great choice for tonight in Rome.

Keep the evening going at Sant' Eustachio Caffè, a great choice for enjoying the after-dinner hours with a drink. You could also go to Yellowsquare Rome, 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.

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 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 remaining.

Today's adventure in Rome promises more breathtaking discoveries and enriching experiences! Begin at Piazza Del Popolo. This enchanting public square is a highlight of any visit in the city. Then, enjoy Villa Borghese, another mesmerizing attraction that never fails to captivate visitors. Next, head over to Basilica Di Santa Maria Maggiore, one of the city’s most notable attractions, known for its culturally significant features.

If you’re looking for more, spend time soaking in the atmosphere of Circus Maximus. This awe-inspiring archeological site is frequented by locals and tourists alike. To complete your memorable day, make sure to visit Altare Della Patria, a popular monument, and take a stroll around the area.

Italy is the perfect setting for a unique luxury experience. Add an exclusive tour or activity to your plans for the day to enhance your road trip experience.

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

Make sure to reserve a table at Hotel de Russie, 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 The Parrot Bar, 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 savoring a delicious meal, step into the vibrant nightlife at The Apartment Bar Roma, where the evening is just getting started. In the same way, Hotel Hassler Roma offers a unique charm perfect for experiencing the local bar scene in Rome.

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 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 Florence, where you'll be staying for 2 nights. The day's itinerary unfolds with a diverse array of experiences in Rome.

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Rome allows for both. Start by heading to Largo Di Torre Argentina. This locally renowned archeological site provides an insightful glimpse into the city's identity. Next, discover Pantheon, a culturally significant monument, promising a delightful encounter.

Continue your sightseeing with a visit to Piazza Di Spagna, a wondrous public square. When you’re done, don’t forget to make a stop at the astonishing Spanish Steps.

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.

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

Experience a taste of local culinary excellence while in Florence by securing a table at Enoteca Pinchiorri. An esteemed 3-star Michelin restaurant, it features an exceptional italian contemporary menu. For an alternative taste experience, visit Santa Elisabetta, famous for its scrumptious creative and mediterranean dishes. This 2-star Michelin venue consistently impresses guests, making it a standout addition to your holiday plans. Looking for another choice? Discover Gucci Osteria da Massimo Bottura, a local favorite celebrated for its exquisite italian contemporary and international cuisine in Florence. Located in the heart of the city, this 1-star Michelin restaurant is an ideal pick for italian contemporary and international cuisine lovers seeking top-notch culinary experiences.

Round off your dining experience by visiting Manifattura, a prime location for a drink. Alternatively, explore the distinctive characteristics of Se·sto On Arno Rooftop Bar, a bar catering to every mood and preference. Il Vinile 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.

Day 8 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 remaining.

Immerse yourself in Florence’s rich culture with today's sightseeing itinerary. Start your journey at Piazzale Michelangelo. This visually striking observation deck is sure to ignite your curiosity. Next, dive into the enchanting features of Ponte Vecchio, a must-visit historical landmark in the city.

In between sights, stop by local stores, picturesque photo spots, and small eateries. When you’re ready for your next attraction, proceed to Uffizi Gallery, a spectacular art gallery. For a change of scene, check out Palazzo Vecchio, known for its enchanting features.

Italy is the perfect setting for a unique luxury experience. Add an exclusive tour or activity to your plans for the day to enhance your road trip experience.

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.

Treat yourself to a delicious dinner at Ditta Artigianale, an excellent option for tonight's dining. Looking for something different? Trattoria Da Burde offers a tantalizing alternative with its diverse menu. And don’t miss Casa Toscana. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Florence.

Let the evening flow smoothly from dinner to drinks at Bar 50 Rosso, a top-rated bar in the area. For other recommendations, Bitter Bar provides a perfect setting for rounding out your night with style and great drinks. Likewise, Archea Brewery 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.

On day 9 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 Pisa, 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.

Immerse yourself in Florence’s rich culture with today's sightseeing itinerary. Start your journey at Basilica Of Santa Croce In Florence. This culturally significant church is sure to ignite your curiosity. Next, dive into the romantic features of Cathedral Of Santa Maria Del Fiore, a must-visit church in the city.

In between sights, stop by local stores, picturesque photo spots, and small eateries. When you’re ready for your next attraction, proceed to Galleria Dell'accademia, a popular art gallery. For a change of scene, check out Central Market, known for its visually striking features.

Relax and unwind in style as you spend the night at one of the top luxury hotels in Pisa. 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 Pisa so you can check out the menus and make advance reservations.

Treat yourself to a delightful dinner at Anima di Grano Pizzeria Napoletana Pisa Italy, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try il Mercante? It's another excellent option with a diverse menu. Consider reserving a table at La Ghiotteria as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Pisa.

Let the evening flow smoothly from dinner to drinks at Jeffer Cocktails & Friends, a top-rated bar in the area. For other recommendations, Le Parisien Wine Bar provides a perfect setting for rounding out your night with style and great drinks. Likewise, Las Volta Cocktailbar offers a memorable night with diverse drink options and excellent service.

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

Savor the day by visiting some of the best places to see in Pisa, including a monument and a public square. Start your adventure at Leaning Tower Of Pisa. This world-famous monument is a must-visit for travelers looking for a unique holiday experience. Make your way to Piazza Del Duomo, Pisa located in Pisa for an enchanting atmosphere.

After soaking in Pisa’s unique atmosphere, jump into the car with a full heart and drive in the direction of your next destination: Corniglia. Expect your car journey to take a minimum of 1 hour 30 min. When you arrive in Corniglia, it's time to take a break from the road.

Your self-guided tour starts at Cinque Terre National Park, a captivating national park that is sure to impress. Take in the surroundings and enjoy the freedom of exploring before you continue your journey.

Set your GPS to La Spezia and hit the road. Expect a journey of approximately 35 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. La Spezia beckons with new experiences!

One of our top recommendations for your sightseeing is Giardini Pubblici. Spend some time admiring the mesmerizing features of the park before you continue to your next stop.

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.

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

Enjoy a lovely meal at Bice Restaurant, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Alto Ristorante is another top choice with a popular menu. You could also check for a table at Nero 9. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Milan tonight.

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

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.