Luxury 5-Day Italy Road Trip from Rimini traveling west to Perugia, and Florence

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Set off on the ultimate travel extravagance with this 5-day luxury road trip across Italy. Every aspect of your journey is crafted to provide a sophisticated and comfortable experience. Enjoy a holiday where luxury unfolds at every turn in each stop of your adventure in Italy.

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 vacation itinerary, you will stay 2 nights in Rimini, 1 night in Perugia, and 1 night in Florence, experiencing the ultimate luxury vacation in Italy.

Finding the perfect luxury lodging is going to make your vacation in Italy feel truly special. The home for your 5-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 5-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. Here you can find unique souvenirs to preserve the memory of your 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 5-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, Perugia, Santa Maria degli Angeli, Siena, and Florence 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 flights, activities, tours, and hotels in Italy fill up quickly, so book your luxury vacation package in advance. Select a date and start planning your 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 luxury holiday in Italy begins as soon as you reach the city of Rimini. There, you’ll pick up the luxury rental vehicle of your choice and hit the roads!

Start your sightseeing with a visit to Arch Of Augustus. This triumphal arch is rated an average of 4.6 out of 5 stars from 12,375 visitors.

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.

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

Treat yourself to a delicious dinner at Bar Lento, an excellent option for tonight's dining. Looking for something different? Ristorante Lo Zodiaco Rimini offers a tantalizing alternative with its diverse menu. And don’t miss Amarina. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Rimini.

If you’re not ready to end the night just yet, Caffè Il Borgo offers a perfect venue to relax and savor a drink. Similarly, Primo Bacio Città Lounge Bar is well-suited for those looking to unwind in a social setting. Hobo's is another excellent spot to enjoy a nightcap after a delightful meal.

Raise a toast to the start of your 5-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 Perugia

  • Perugia
  • Rimini
  • Viserbella
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Drive 223 km, 3 hours 1 min

  • Parco Federico Fellini
  • Spiaggia libera
  • Italia in Miniatura
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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 Perugia, where you'll be staying for 1 night. The day's itinerary unfolds with a diverse array of experiences in Rimini, and Viserbella.

When you're ready to see some sights, Parco Federico Fellini is a great place to start. This park is rated an average of 4.5 out of 5 stars by 11,076 visitors.

Another popular attraction you can visit today is Spiaggia Libera. This sightseeing destination has an average rating of 4.3 out of 5 stars from 4,793 travelers.

Embrace the thrill of the open road as you wave goodbye to Rimini and set your GPS to Viserbella. 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 13 min. Upon reaching Viserbella, unwind, observe, and explore. The best things to do, see, and eat are waiting for you.

Start your sightseeing with a visit to Italia In Miniatura. This miniature park is a popular stop on travelers’ itineraries in Viserbella, with an average rating 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 Perugia. 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 Perugia for you, so you can check out the menus and make your reservation in advance.

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

Keep the evening going at Tommi Bar, a great choice for enjoying the after-dinner hours with a drink. You could also go to Valentina, which offers a similarly pleasant setting and great drinks. Another option is Caffe Dal Perugino, which provides an inviting environment for unwinding after a busy day out.

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

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Day 3

Day 3 – Perugia, Santa Maria degli Angeli, Siena, and Florence

  • Florence
  • Assisi
  • Siena
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Drive 226 km, 3 hours 49 min

  • Basilica of San Francesco d'Assisi
  • Piazza del Campo
  • Duomo di Siena
  • Fortezza Medicea
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On day 3 of your luxury holiday in Italy, your road trip route will take you exploring the best of Santa Maria degli Angeli, and Siena. The day's journey will conclude in Florence, a city that offers you comfort and relaxation for 1 night. With a day brimming with amazing attractions ahead, fuel up with a hearty breakfast to savor every moment of your luxury vacation in Italy.

Embrace the thrill of the open road as you wave goodbye to Perugia 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 32 min. Upon reaching Santa Maria degli Angeli, unwind, observe, and explore. The best things to do, see, and eat are waiting for you.

Take the opportunity to see Basilica Of San Francesco D'assisi. This attraction has an average rating of 4.9 out of 5 stars from 33,258 visitors.

When you’re ready to jump back into the car and say goodbye to Santa Maria degli Angeli, you’ll hit the road in the direction of Siena. This drive usually takes around 1 hour 38 min. When you arrive, enjoy some sightseeing.

A top pick for your self-guided sightseeing tour today is Piazza Del Campo. Previous visitors have rated this square an average of 4.8 out of 5 stars in 64,175 reviews.

Siena Cathedral is a local recommendation that you also can pay a visit today. This domus is rated an average of 4.8 out of 5 stars in 21,656 reviews.

Another attraction you won't want to miss is Fortezza Medicea (siena). This fortress is rated an average of 4.5 out of 5 stars in 9,835 reviews.

Relax and unwind in style as you spend the night at one of the top luxury hotels in Florence. Recharge after a day of exploring, enjoying luxurious comfort and serene surroundings.

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

Discover the culinary delights of Florence by securing a reservation at Enoteca Pinchiorri. Esteemed for its 3-star Guide Michelin recognition, this restaurant offers a remarkable selection of italian contemporary cuisine. For an alternative dining experience, try Santa Elisabetta, renowned for its delicious creative, and mediterranean dishes. This esteemed 2-star Michelin-recipient consistently impresses guests, making it a must-visit spot during your holiday. Craving more culinary excitement? Head to Gucci Osteria da Massimo Bottura, a highly recommended local eatery celebrated for its mouthwatering italian contemporary, and international menu. With its 1-star Michelin recognition, it offers an unforgettable dining adventure.

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at Manifattura, a well-loved spot among locals and tourists. Or, head to Se·sto On Arno Rooftop Bar. This bar boasts a welcoming environment that is perfect for winding down. You could also continue your night at Archea Brewery, another top-rated place in the area.

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.

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Day 4

Day 4 – Florence, and Rimini

  • Rimini
  • Florence
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Drive 233 km, 3 hours 2 min

  • Piazza della Signoria
  • Uffizi Gallery
  • Ponte Vecchio
  • Cathedral of Santa Maria del Fiore
  • Piazzale Michelangelo
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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 Florence. With a flexible itinerary, you're free to adapt and explore additional attractions or enjoy spontaneous discoveries.

An excellent attraction to start your day with is Piazza Della Signoria. This square is rated an average of 4.8 out of 5 stars in 66,956 reviews.

Continue your journey at Uffizi Gallery. This national museum is rated 4.7 out of 5 stars by 61,794 travelers from near and far. Approximately 2,011,219 people come to this place of interest every year to enjoy a unique experience in Florence.

Florence is also the home of Ponte Vecchio. This deck arch bridge has an average rating of 4.7 out of 5 stars from 118,099 visitors.

You can continue your self-guided sightseeing tour at Cathedral Of Santa Maria Del Fiore. Rated 4.8 out of 5 stars by 76,359 visitors, a visit to this top sight is time well spent.

Lastly, don't miss out on Piazzale Michelangelo. With an average rating of 4.8 out of 5 stars from 77,744 reviews, it’s hard to refuse the opportunity to see this square.

Relax and unwind in style as you spend the night at one of the top luxury hotels in Rimini. 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 Rimini. Savor the local cuisine and relax as you recount the day's experiences.

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.

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

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Day 5

Day 5 – Rimini - departure day

  • Rimini - Departure day
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  • Cavour Square
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Today is the last day of your 5-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 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.

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!

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