Luxury 14-Day Relaxed Italy Road Trip Vacation from Rimini to Venice, Bologna, and Arezzo

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Glide effortlessly through Italy on a luxurious 14-day relaxed road trip to Rimini, Viserbella, Venice, Lido, Bologna, Arezzo, Sansepolcro, Pocaia, Pratovecchio, Badia Prataglia, Terranuova Bracciolini, Cortona, Urbino, Pesaro, and Gradara. Italy is the perfect backdrop for a lavish getaway, where the essence of luxury travel meets the ease of a laid-back journey.

Italy offers the ultimate luxury holiday experience for anyone up for an unforgettable adventure, including couples, families, solo travelers, and friends.

Your exclusive luxury holiday package will bring you to the country's most popular attractions and restaurants in the best destinations in Italy. With this perfectly planned itinerary, you will stay 2 nights in Rimini, 4 nights in Venice, 2 nights in Bologna, and 5 nights in Arezzo, experiencing a stress-free luxury vacation in Italy.

Finding the perfect luxury lodging is going to make your vacation in Italy feel truly special. The home for your 14-day luxury holiday will be only the most exclusive 5-star hotels in Italy. You will choose from the best selection of luxury hotels and places to stay, all conveniently located along your carefully planned self-drive route.

Upon arriving in Italy, you will collect the luxury rental vehicle of your choice. We will provide you with the best car rental for the entirety of your 14-day luxury self-drive holiday, including CDW insurance. From there, you will drive off at a relaxed pace to discover some of the best travel destinations in Italy.

Throughout your exclusive vacation in Italy, you will get to experience some of the best attractions and activities offered in the country. Each moment promises to be filled with unforgettable memories and unique experiences.

Between attractions and activities, you will have plenty of time to stroll along the best shopping streets and markets in Italy. We recommend you take the opportunity to explore the shopping experiences available to you in Rimini. Here you can find unique souvenirs to preserve the memory of your relaxed luxury holiday in Italy.

This exclusive travel plan is designed to include everything you need to have the best vacation in Italy. By booking this luxury holiday package, you can avoid spending hours researching and planning your 14-day road trip in Italy. Let the experts figure out the details, so you can focus on enjoying.

To deliver the best experience possible, we make it easy for you to customize each day of your luxury holiday in Italy before and after booking. Our flexible trip planning means you will be able to explore Rimini, Viserbella, Venice, Lido, Bologna, Arezzo, Sansepolcro, Pocaia, Pratovecchio, Badia Prataglia, Terranuova Bracciolini, Cortona, Urbino, Pesaro, and Gradara at your own pace.

Book with us to get access to 24/7 personal travel support throughout your entire journey. Enjoy a step-by-step guide in our easy-to-use mobile app, including all travel documents for your exclusive getaway to Italy.

The best services in Italy fill up quickly, so book your luxury vacation package in advance. Select a date and start planning your relaxing luxury holiday in Italy today!

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Day 1

Day 1 – Rimini - arrival day

  • Rimini - Arrival day
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  • Arco di Augusto
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Your relaxed luxury holiday in Italy begins as soon as you reach the city of Rimini, your home for 1 night. There, you’ll pick up the luxury rental vehicle of your choice and set off on a relaxed drive to discover Italy.

When you’re ready for some sightseeing, make your way to Arch Of Augustus. This much-appreciated triumphal arch is rated 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.

Don’t miss out on dining at Bar Lento, a top-rated dining destination in Rimini. If you're in the mood to try something new, consider Ristorante Lo Zodiaco Rimini, another top spot with a mouthwatering menu. You might also want to secure a reservation at Amarina. With a reputation for consistently satisfied customers, it’s a perfect choice to enhance your stay in Rimini this evening.

Following your dinner, dive into the local bar culture at Caffè Il Borgo. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Primo Bacio Città Lounge Bar, the perfect place for those looking to experience the best of the nightlife. Similarly, Hobo's provides excellent drinks and a great atmosphere, ensuring a memorable night out.

Raise a toast to the start of your relaxed 14-day luxury vacation in Italy and look forward to more fantastic days to come!

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Day 2

Day 2 – Rimini, Viserbella, and Venice

  • Venice
  • Rimini
  • Viserbella
  • More

Drive 265 km, 3 hours 4 min

  • Parco Federico Fellini
  • Fountain of the four horses
  • Italia in Miniatura
  • More

On day 2 of your relaxed luxury holiday in Italy, wonderful attractions await. Today you have the opportunity to discover 2 remarkable destinations — Rimini, and Viserbella.

Begin your sightseeing with a visit to Parco Federico Fellini. This park is rated an average of 4.5 out of 5 stars in 11,076 reviews.

Next up, make your way to Fountain Of The Four Horses. This park has an average rating of 4.6 out of 5 stars from 2,798 reviews.

When you’ve had your share of Rimini, prepare for your next destination. Admire the views and listen to some good music as you drive in the direction of Viserbella. Your travel time is around 14 min.

Make Italia In Miniatura your first stop of the day. Previous visitors have rated this miniature park an average of 4.4 out of 5 stars in 20,510 reviews.

Tonight, you will stay at one of the best luxury hotels in Venice. We have selected the perfect options for you to have the loveliest experience in Venice.

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

Have a memorable dining experience in Venice by booking a table at Local, renowned as a 1-star Michelin restaurant presenting an exceptional contemporary menu. For a different culinary experience in Venice, Wistèria shines as one of the top destinations, known for its delicious contemporary, and venetian cuisine. This 1-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, Quadri is known as a top local spot for its delicious modern cuisine in Venice. This 1-star Michelin awardee is a highly recommended choice for an unforgettable meal.

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 your glass and toast to another unforgettable day of your relaxed luxury holiday in Italy!

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Day 3

Day 3 – Venice

  • Venice
  • More

Drive 2 km, 32 min

  • St. Mark's Square
  • St Mark's Campanile
  • Saint Mark's Basilica
  • Doge's Palace
  • Bridge of Sighs
  • More

Day 3 of your luxury road trip in Italy grants you another day to experience Venice. You will continue your laid-back luxury holiday in the best possible way - by discovering the best sights and most exciting activities. You'll then conclude your adventure at one of finest restaurants in Venice, fully indulging in the 3 nights you have in the city.

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 Campanile. Rated 4.7 out of 5 stars by 3,884 visitors, this bell tower deserves a spot on today's sightseeing itinerary.

We also recommend a visit to St Mark's Basilica. This cathedral has been rated an average of 4.7 out of 5 stars in 18,439 reviews.

Another favorite attraction in the area is Doge's Palace, drawing over 318,104 yearly visitors. This palace and popular place of interest enjoys a rating of 4.7 out of 5 stars from 24,775 local and international travelers.

If you’re keen to explore even more, then consider a visit to Bridge Of Sighs. With an average rating of 4.6 out of 5 stars from 18,223 travelers, this footbridge is an attraction many avid travelers highly recommend visiting while in Venice.

Your discoveries in Venice do not have to stop there. Check out the fantastic selection of tours and tickets offered in Venice on this day of your trip. You can select your tours below.

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

Enjoy a delicious meal at Cantina Do Spade, a top-rated dining destination in Venice. If you're in the mood to try something new, consider Trattoria Al Gazzettino, another top spot with a mouthwatering menu. You might also want to secure a reservation at Trattoria Bar Pontini. With a reputation for consistently satisfied customers, it’s a perfect choice to enhance your stay in Venice this evening.

After savoring a delicious meal, step into the vibrant nightlife at The Irish Pub Venezia, where the evening is just getting started. In the same way, Dolce Vita Venezia offers a unique charm perfect for experiencing the local bar scene in Venice. Devils Forest Pub 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 relaxing luxury vacation in Italy still has more in store for you.

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Day 4

Day 4 – Venice, and Lido

  • Venice
  • Lido
  • More

Drive 6 km, 1 hour 24 min

  • Giardini della Biennale
  • Venetian Arsenal
  • Rialto Bridge
  • More

Day 4 of your luxury holiday in Italy is another opportunity to leisurely explore the spectacular town of Lido. You still have 2 nights in Venice, which gives you enough time to discover some of the most amazing things to see and do in the town. Start your morning with a hearty breakfast and get ready for an entire day of enjoying Lido to the fullest.

Make Venetian Arsenal your first stop of the day. Previous visitors have rated this naval arsenal an average of 4.6 out of 5 stars in 8,749 reviews.

Next up, make a stop at Rialto Bridge. With an average rating of 4.7 out of 5 stars by 141,666 visitors, it's easy to understand why so many people visit this stone bridge every year.

Don’t forget to check out all the popular tours and activities you can add to your travel plan. Italy is a beautiful travel destination that offers plenty of unique tours that will enhance your vacation experience. Explore and select your activities below.

Discover a world of culinary delights in Venice, 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 a lovely meal at La Palanca, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Farini is another top choice with a popular menu. You could also check for a table at Trattoria Dona Onesta. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Venice tonight.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Bar Al Vecio Calice stands out as an excellent choice for a post-dinner cocktail.

Relax and enjoy an amazing evening in Venice, and get ready for more fantastic days to come on your relaxed luxury vacation in Italy!

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Day 5

Day 5 – Venice

  • Venice
  • More

Drive 4 km, 1 hour 4 min

  • Ca' Pesaro International Gallery of Modern Art
  • Grand Canal
  • Palazzo Contarini del Bovolo
  • Teatro La Fenice
  • Grassi Palace
  • More

Day 5 of your luxury road trip in Italy brings you another chance to explore the wonders of Venice. Immerse yourself in the best sights and most thrilling activities as you continue your laid-back holiday in style. End your day at one of the top restaurants in Venice, making the most of your 1 night in this exquisite city.

When you’re ready for some sightseeing, make your way to Ca' Pesaro International Gallery Of Modern Art. This much-appreciated museum is rated 4.5 out of 5 stars in 2,185 reviews.

Next up is Grand Canal. This sightseeing destination has an average rating of 4.8 out of 5 stars from 3,806 visitors.

Another top sightseeing recommendation is Palazzo Contarini Del Bovolo. This sightseeing destination has been rated 4.5 out of 5 stars in 11,745 reviews.

Teatro La Fenice is another attraction you have the opportunity to visit today. This opera house has an average rating of 4.7 out of 5 stars from 10,677 reviews.

To continue your sightseeing, head over to Grassi Palace. This museum is rated an average of 4.5 out of 5 stars in 2,160 reviews.

Immerse yourself in the local scene through top-rated tours and activities. You can choose from a wide variety of easy to challenging tours and easily add them to your travel package below.

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

Make sure to reserve a table at Pizzeria Birreria Barbanera, 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 Irish Pub Santa Lucia, 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 Rio Novo, a hidden gem nestled in Venice. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Raise a glass in celebration of your fantastic luxury holiday in Italy! Head back to your hotel for some much-needed rest in preparation for tomorrow’s easygoing adventures.

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Day 6

Day 6 – Venice, and Bologna

  • Bologna
  • Venice
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Drive 161 km, 2 hours 29 min

  • Gallerie dell'Accademia
  • Peggy Guggenheim Collection
  • Basilica di Santa Maria della Salute
  • Punta della Dogana - Pinault Collection
  • More

On day 6 of your relaxed luxury road trip holiday in Italy, you will have the opportunity to experience Venice; 1 of the most vibrant destinations in the country.

Journey into the unknown at Gallerie Dell'accademia, a unique attraction awaiting your visit. This remarkable art museum has an average rating of 4.5 out of 5 stars from 7,950 reviews. Every year, Gallerie Dell'accademia welcomes more than 210,149 curious visitors.

When you’re ready to continue your sightseeing, Peggy Guggenheim Collection is a recommended place to visit. This art museum is rated an average of 4.6 out of 5 stars in 10,128 reviews. Based on recent data, the attraction hosts 92,922 visitors per year.

Another must-see attraction in Venice is Santa Maria Della Salute. Rated an average of 4.7 out of 5 stars by 8,681 travelers, this popular tourist destination in Venice offers an experience you will remember.

Punta Della Dogana - Pinault Collection is another popular stop on travelers' itineraries in Venice. This museum promises memorable moments of exploring. Other travelers have rated this attraction 4.6 out of 5 stars in 2,371 reviews.

In Bologna, you will be treated to a stay at one of the most exclusive 5-star luxury hotels the destination has to offer. From the moment you arrive in Bologna, prepare to be pampered with exceptional service, luxurious accommodations, and top-notch amenities that promise to make your stay truly unforgettable.

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.

Start your culinary exploration in Bologna by securing a reservation at I Portici. This renowned restaurant holds 1 Michelin star and offers an exceptional menu of creative, and contemporary cuisine. For another dining delight, visit Ahimè, celebrated for its delectable country cooking menu. This acclaimed Bib Gourmand-recipient consistently leaves guests satisfied, making it a must-visit during your holiday. Looking for a different experience? Discover Trattoria di Via Serra, a top local spot known for its tantalizing emilian menu. With a Bib Gourmand recognition, it guarantees an exceptional dining adventure.

Cap off your dinner by heading to Bar Freud E Squisito, ideal for a leisurely evening with a drink in hand. Osteria Del Sole is another bar that offers an enjoyable setting. Similarly, Macondo - Cocktail Bar is also a popular place to go on a night out, perfect for relaxing and socializing.

Go over your photos from the day, raise a toast, and rest your tired legs. A new adventurous day of your relaxed luxury road trip in Italy awaits!

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Day 7

Day 7 – Bologna

  • Bologna
  • More

Drive 1 km, 21 min

  • Cattedrale Metropolitana di San Pietro
  • Palazzo Re Enzo
  • Fontana del Nettuno
  • Piazza Maggiore
  • More

On day 7 of your relaxed luxury holiday across Italy, you'll continue your adventures in the city of Bologna. You'll explore Bologna, taking breaks from the road for some sightseeing. At the end of day, you'll dine at some of Bologna's best restaurants and bars conveniently located close to your accommodation, making the most of your remaining 1 night in the area.

Start your sightseeing with a visit to Bologna Cathedral. This catholic cathedral is a popular stop on travelers’ itineraries in Bologna, with an average rating of 4.6 out of 5 stars by 3,852 visitors.

Palazzo Re Enzo is another popular place of interest you can visit today. The average rating of 4.6 out of 5 stars from 2,072 reviews gives you an idea of other visitors’ experience at this attraction.

If it’s still bright and early, make your way to Fountain Of Neptune, Bologna. Visitors have rated this fountain an average of 4.7 out of 5 stars in 3,952 reviews.

Piazza Maggiore is another unique site you can experience today. This attraction is a square rated an average of 4.7 out of 5 stars in 64,523 reviews.

Make your way to the fantastic Basilica Of San Domenico, perhaps the most famous church in Bologna. This attraction is rated 4.7 out of 5 stars by 3,380 travelers.

You can learn more about Bologna today by going on a tour. Bologna offers many top-rated tours and unique experiences that will inspire you. You can browse and select your favorites below.

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.

Dine in style at Ristorante Enoteca da Lucia, a top recommendation for dinner tonight. Or, for a change of pace, Victoria Station boasts a menu that's sure to impress. Also, be sure to check out Trattoria da Me. Known as a local hotspot, it’s a great choice for tonight in Bologna.

After enjoying a fulfilling meal, continue your evening at Bar Senza Nome, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Bar Maurizio offers a welcoming atmosphere for easing into the nightlife. Similarly, Brewdog Bar Bologna provides an excellent environment for a relaxed and enjoyable evening.

Go over your photos from the day, raise a toast, and rest your tired legs. A new adventurous day of your relaxed luxury road trip in Italy awaits!

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Day 8

Day 8 – Bologna, and Arezzo

  • Arezzo
  • Bologna
  • More

Drive 188 km, 2 hours 35 min

  • Two Towers
  • Piazza Santo Stefano
  • Arco Del Meloncello
  • Museo Ducati
  • More

On day 8 of your relaxed luxury holiday in Italy, wonderful attractions await. Today you have the opportunity to discover 1 remarkable destinations — Bologna.

Drop by the renowned Two Towers. This popular tower has been rated an average of 4.7 out of 5 stars by 25,975 visitors.

Another unforgettable place to experience is Piazza Santo Stefano. Rated 4.8 out of 5 stars by 7,617 visitors, this square deserves a spot on today's sightseeing itinerary.

We also recommend a visit to Villa Ghigi. This park has been rated an average of 4.7 out of 5 stars in 2,035 reviews.

Another favorite attraction in the area is Arco Del Meloncello. This arch and popular place of interest enjoys a rating of 4.6 out of 5 stars from 3,755 local and international travelers.

If you’re keen to explore even more, then consider a visit to Ducati Museum. This industry museum gets around 7,600 annual visitors. With an average rating of 4.5 out of 5 stars from 4,028 travelers, this industry museum is an attraction many avid travelers highly recommend visiting while in Bologna.

Tonight, you will stay at one of the best luxury hotels in Arezzo. Renowned for their impeccable facilities and delightful rooms, luxury hotels in Arezzo promise an unparalleled experience. With a team of dedicated staff eager to assist and provide recommendations, your stay promises to be nothing short of extraordinary. Relax and unwind in the lap of luxury, where every moment is crafted to exceed your expectations.

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

Experience a taste of local culinary excellence while in Arezzo by securing a table at Octavin. An esteemed 1-star Michelin restaurant, it features an exceptional creative menu. If you're in the mood for something new, try La Clandestina, another premier location with a delectable menu.

Round off your dining experience by visiting Liquid Bar, a prime location for a drink.

Raise a glass in celebration of your fantastic luxury holiday in Italy! Head back to your hotel for some much-needed rest in preparation for tomorrow’s easygoing adventures.

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Day 9

Day 9 – Arezzo, Sansepolcro, and Pocaia

  • Arezzo
  • Sansepolcro
  • Pocaia
  • More

Drive 82 km, 1 hour 58 min

  • Roman Amphitheatre of Arezzo
  • Piazza Grande
  • The Medici Fortress Park
  • More

Day 9 of your luxury road trip in Italy is another opportunity to explore what this region has to offer. Start your day with a drive to visit the amazing attractions in the surrounding area of Arezzo. After a day of sightseeing, return to the city, where you still have 4 nights left to enjoy. End your evening with a fulfilling dinner at one of the finest restaurants in Arezzo, savoring the local culinary delights.

Seize the day by visiting some of the best attractions in the area, like Roman Amphitheatre Of Arezzo. This extraordinary archaeological site has an average rating of 4.4 out of 5 stars from 518 visitors.

Next, make your way to Piazza Grande. This square is rated an average of 4.6 out of 5 stars in 14,465 reviews.

While in Arezzo, we also recommend a visit to The Medici Fortress Park. This park has been rated an average of 4.5 out of 5 stars in 1,117 reviews.

Embrace the thrill of the open road as you wave goodbye to Arezzo and set your GPS to Sansepolcro. 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 39 min. Upon reaching Sansepolcro, unwind, observe, and explore. The best things to do, see, and eat are waiting for you.

When you're ready to see some sights, Aboca Museum is a great place to start. This museum is rated an average of 4.7 out of 5 stars by 1,068 visitors.

Embrace the thrill of the open road as you wave goodbye to Sansepolcro and set your GPS to Pocaia. 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 19 min. Upon reaching Pocaia, unwind, observe, and explore. The best things to do, see, and eat are waiting for you.

Begin your sightseeing with a visit to Civic Museum Madonna Del Parto. This extraordinary museum is rated an average of 4.5 out of 5 stars by 789 visitors.

When you’re done exploring for the day, you’ll return to Arezzo and your accommodation.

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

Have a fantastic dining experience at La Nuova Tagliatella, a highly recommended choice for tonight's dinner. If you're looking to mix things up, i 3 bicchieri offers an enticing alternative with its varied menu. Additionally, Il Cantuccio is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Arezzo.

Enjoy an amazing evening in Arezzo, and get ready for more fantastic days to come on your relaxed luxury vacation in Italy!

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Day 10

Day 10 – Arezzo, Pratovecchio, Badia Prataglia, and La Verna

  • Arezzo
  • Pratovecchio
  • Badia Prataglia
  • More

Drive 150 km, 3 hours 37 min

  • La Verna - Franciscan Sanctuary
  • More

On day 10 of your luxurious vacation in Italy, you’ll start and end your day in Arezzo, but spend most of the day exploring attractions outside of the city. After a long day of sightseeing, you'll drive back to Arezzo, where you'll stay for 3 nights more.

After soaking in Arezzo’s unique atmosphere, jump into the car with a full heart and drive in the direction of your next destination: Pratovecchio. Expect your car journey to take a minimum of 58 min. When you arrive in Pratovecchio, it's time to take a break from the road.

Take the opportunity to see Romena Castle. This attraction has an average rating of 4.4 out of 5 stars from 965 visitors.

San Pietro A Romena is another sightseeing hotspot in the area. This church has been rated an average of 4.8 out of 5 stars by 1,089 travelers.

Continue your road trip and head to your next destination, Badia Prataglia. This car ride takes around 33 min.

Start your sightseeing with a visit to Parco Nazionale Foreste Casentinesi, Centro Visite. This park is rated an average of 4.7 out of 5 stars from 838 visitors.

Fasten your seatbelt and make your way to your next stop. La Verna, 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 Badia Prataglia to La Verna may take around 42 min without traffic disruptions. Upon arrival in La Verna, we highly recommend checking out some of the top attractions.

Seize the day by visiting some of the best attractions in the area, like La Verna - Franciscan Sanctuary. This extraordinary church has an average rating of 4.8 out of 5 stars from 7,374 visitors.

When you’re done exploring the area’s best attractions, you’ll drive back to your accommodation in Arezzo.

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.

Dine in style at Emilio, a top recommendation for dinner tonight. Or, for a change of pace, Trattoria Il Saraceno boasts a menu that's sure to impress. Also, be sure to check out Ristorante La Lancia D'Oro Arezzo. Known as a local hotspot, it’s a great choice for tonight in Arezzo.

Relax and enjoy an amazing evening in Arezzo, and get ready for more fantastic days to come on your relaxed luxury vacation in Italy!

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Day 11

Day 11 – Arezzo

  • Arezzo
  • More

Drive 2 km, 30 min

  • Casa Vasari
  • Arezzo Cathedral
  • Basilica di San Francesco
  • More

Day 11 of your luxury road trip means another day to soak in the splendor of Italy. At the city of Arezzo, you will continue your laid-back luxury holiday in the best possible way. Enjoy the best sights, the most exciting activities, and the finest restaurants in the city. You have ample opportunities to make your 2 nights in the city more special.

Begin your sightseeing with a visit to Casa Vasari. This building is rated an average of 4.5 out of 5 stars in 871 reviews.

Next up, make your way to San Domenico. This church has an average rating of 4.6 out of 5 stars from 704 reviews.

When you’re ready for your next sight of the day, continue to Arezzo Cathedral. This cathedral has an average rating of 4.6 out of 5 stars from 2,450 visitors.

Beyond the above-mentioned attractions, you also have the opportunity to visit San Francesco, Arezzo. This minor basilica is rated an average of 4.6 out of 5 stars by 2,377 visitors. Visiting San Francesco, Arezzo means you'll be one of 20,939 people who do so every year.

To do something one-of-a-kind on this day of your trip, you can join a tour. You can discover all of the most fun and eye-opening experiences in your destination below and secure your spot here.

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

Treat yourself to a delightful dinner at Antica Osteria l'Agania, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Ristorante LaPieve? It's another excellent option with a diverse menu. Consider reserving a table at Teorema del Gusto as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Arezzo.

Enjoy an amazing evening in Arezzo, and get ready for more fantastic days to come on your relaxed luxury vacation in Italy!

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Day 12

Day 12 – Arezzo, Terranuova Bracciolini, and Cortona

  • Arezzo
  • Terranuova Bracciolini
  • Cortona
  • More

Drive 109 km, 2 hours 45 min

On day 12 of your luxury road trip in Italy, you’ll start and end your day in the city of Arezzo, but jump in the car to visit amazing attractions in the nearby area. After a day of sightseeing, you'll drive back to Arezzo, where you still have 1 night left.

Set your GPS to Terranuova Bracciolini and hit the road. Expect a journey of approximately 32 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Terranuova Bracciolini beckons with new experiences!

A top pick for your self-guided sightseeing tour today is Valle Dell'inferno E Bandella. Previous visitors have rated this park an average of 4.2 out of 5 stars in 1,137 reviews.

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

Your sightseeing of the day begins at Parterre, a remarkable park where it’s easy to get lost in exploration. This top attraction is rated an average of 4.5 out of 5 stars in 793 reviews.

Next, satisfy your wanderlust at Basilica Of Saint Margaret Of Cortona. This church has an average rating of 4.6 out of 5 stars from 985 travelers.

Hermitage "le Celle" is another must-visit attraction. This renowned place of worship offers a memorable experience, well worth a stop on your self-guided sightseeing tour. Rated 4.8 out of 5 stars by 2,292 travelers, it's one of the more popular places to see in the area.

When you’re done exploring for the day, you’ll return to Arezzo and your accommodation.

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

Make sure to book a table at Le Cattive Abitudini Home made food, a popular restaurant in Arezzo. This acclaimed restaurant and its mouthwatering dishes have earned the admiration of countless food lovers. Alternatively, experience a taste of Arezzo at Brasserie Del Vicolo, 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 Trattoria Cavour 42. As a dining spot that gains high praise from guests, it’s an ideal choice to enhance your time to Arezzo tonight.

Raise your glass and toast to another unforgettable day of your relaxed luxury holiday in Italy!

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Day 13

Day 13 – Arezzo, Urbino, Pesaro, Fiorenzuola di Focara, Gradara, and Rimini

  • Rimini
  • Urbino
  • Pesaro
  • Gradara
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Drive 191 km, 3 hours 58 min

  • Palazzo Ducale di Urbino
  • Big Sphere A Pomodoro
  • Parco Naturale Monte San Bartolo
  • Castello di Gradara
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On day 13 of your relaxed luxury road trip holiday in Italy, you will have the opportunity to experience Urbino, Pesaro, Fiorenzuola di Focara, and Gradara; 4 of the most vibrant destinations in the country.

After soaking in Arezzo’s unique atmosphere, jump into the car with a full heart and drive in the direction of your next destination: Urbino. Expect your car journey to take a minimum of 2 hours 1 min. When you arrive in Urbino, it's time to take a break from the road.

Make Palazzo Ducale one of your first sightseeing stops in Urbino. Rated an average of 4.6 out of 5 stars by 10,806 travelers, a visit to this local attraction makes for a great introduction to the area.

Fasten your seatbelt and make your way to your next stop. Pesaro, 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 Urbino to Pesaro may take around 48 min without traffic disruptions. Upon arrival in Pesaro, we highly recommend checking out some of the top attractions.

Start your sightseeing with a visit to Big Sphere A. Pomodoro. This point of interest is a popular stop on travelers’ itineraries in Pesaro, with an average rating of 4.5 out of 5 stars by 5,652 visitors.

Parco Naturale Monte San Bartolo is another popular place of interest you can visit today. The average rating of 4.6 out of 5 stars from 12,733 reviews gives you an idea of other visitors’ experience at this attraction.

Once you're ready to continue your road trip, it's time to buckle up and drive, eagerly anticipating your arrival in Fiorenzuola di Focara.

Begin your sightseeing with a visit to Fiorenzuola Di Focara. This extraordinary sightseeing destination is rated an average of 4.7 out of 5 stars by 1,374 visitors.

For the night, you’ll have the choice of the best luxury hotels and places to stay in the city of Rimini. Whether you prefer the grandeur of a luxury hotel or the charm of a boutique stay, you'll find an array of exquisite options to suit your tastes and preferences. Indulge in world-class amenities, impeccable service, and unforgettable experiences as you unwind and create memories in Rimini.

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

Experience a symphony of flavors at Guido in Rimini by securing a reservation in advance. Renowned for its 1-star Michelin distinction, Guido delights its guests with its exceptional variety of meals showcasing delicious seafood, and modern cuisine. For a palate-pleasing alternative, make sure to dine at Abocar Due Cucine, acclaimed for its delectable creative, and international specialties. This local 1-star Michelin establishment consistently satisfies guests, ensuring an unforgettable holiday experience. Want to go on another culinary journey? Delight your senses at Osteria de Börg, a top-rated restaurant known for its outstanding menu. Known as a top-rated Bib Gourmand-establishment, it's a top choice for from romagna, and traditional cuisine in the city.

Continue the enjoyment post-dinner at Bar Capogiro, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Caffè Cavour offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out Bar Ilde - Il Baretto Della Buona Piadina. This bar is a favorite among both locals and visitors looking for a delightful evening out filled with laughter and fun.

Relax and enjoy an amazing evening in Rimini, and get ready for more fantastic days to come on your relaxed luxury vacation in Italy!

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Day 14

Day 14 – Rimini - departure day

  • Rimini - Departure day
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  • Cavour Square
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Today is the last day of your 14-day relaxed 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 your final day in Italy unfolds, enjoy a last-minute shopping spree in Rimini's best shopping area. Enjoy finding the perfect gift or keepsake to remind you of your wonderful trip to Italy.

Make the most of what's left of your luxury vacation and head out to the stunning Piazza Cavour. This extraordinary point of interest and attraction is rated an average of 4.5 out of 5 stars in 11,447 reviews, and is an excellent choice for your last sightseeing in Rimini.

Unwind and look back at the past 14 days of your relaxed road trip over a bite to eat. This is your chance to enjoy one last traditional meal in Rimini or just grab something light to keep you going.

Savor the flavors at Sabbioni Pizza & Restaurant, a top pick for dinner tonight. Alternatively, In The Courtyard Center Gourmet Pizza beckons with its unique menu offerings.

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 relaxed luxury holiday in Italy in your luggage!

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