Luxury 6-Day Italy Road Trip from Florence traveling south to Perugia, Rome, and Siena

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

A top pick for your self-guided sightseeing tour today is Central Market. Previous visitors have rated this point of interest an average of 4.4 out of 5 stars in 43,100 reviews.

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

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.

Enjoy a delicious meal at Ristorante Oliviero 1962, a highly-rated dining destination in Florence. If you're eager to try something different, consider Caffe San Firenze, another top spot with a tantalizing menu. You might also want to secure a reservation at Ditta Artigianale. With a reputation for consistently satisfied customers, it’s an excellent choice to enhance your stay in Florence this evening.

After savoring a delicious meal, step into the vibrant nightlife at Manifattura, where the evening is just getting started. In the same way, Se·sto On Arno Rooftop Bar offers a unique charm perfect for experiencing the local bar scene in Florence. Archea Brewery is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

Raise a toast to the start of your 6-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 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 Cathedral Of Santa Maria Del Fiore. This church is rated 4.8 out of 5 stars by 76,359 travelers from near and far.

Florence is also the home of Piazza Della Repubblica. This square has an average rating of 4.6 out of 5 stars from 22,356 visitors.

You can continue your self-guided sightseeing tour at Ponte Vecchio. Rated 4.7 out of 5 stars by 118,099 visitors, a visit to this top sight is time well spent.

Lastly, don't miss out on Uffizi Gallery. With an average rating of 4.7 out of 5 stars from 61,794 reviews, it’s hard to refuse the opportunity to see this national museum. Approximately 2,011,219 people visit this attraction every year.

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.

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

Treat yourself to a delightful dinner at Ristorante Settimo Sigillo, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Bar Pellas? It's another excellent option with a diverse menu. Consider reserving a table at La Taverna as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Perugia.

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 Florence, 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 Vatican City. The day's journey will conclude in Rome, 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.

Continue your road trip and head to your next destination, Vatican City, Vatican City. This car ride takes around 2 hours 17 min.

When you’re ready for some sightseeing, make your way to Vatican Museums. This much-appreciated art museum is rated 4.6 out of 5 stars in 133,310 reviews. Each year, 1,612,530 people visit this site to admire its unique features.

Next up is Saint Peter's Square. This square has an average rating of 4.8 out of 5 stars from 38,954 visitors.

Another top sightseeing recommendation is Sistine Chapel. This chapel has been rated 4.7 out of 5 stars in 52,083 reviews.

St. Peter's Basilica is another attraction you have the opportunity to visit today. This major basilica has an average rating of 4.8 out of 5 stars from 131,043 reviews. This popular attraction gets 11,000,000 visits every year.

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

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

After your meal, keep the night alive at a bar like La Botticella Of Poggi Giovanni, known for its lively atmosphere. Sant' Eustachio Caffè is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Caffè Portofino offers an excellent atmosphere for those looking to amp up the evening.

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

Wake up to day 4 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 Rome.

Make Roman Forum your first stop of the day. Previous visitors have rated this square an average of 4.7 out of 5 stars in 114,450 reviews.

Next up, make a stop at Colosseum. With an average rating of 4.7 out of 5 stars by 328,821 visitors, it's easy to understand why so many people visit this roman amphitheatre every year. In fact, this attraction welcomes 7,400,000 annual visitors.

Piazza Navona is another attraction you can visit on this day of your vacation. This square has an average rating of 4.7 out of 5 stars by 158,771 visitors.

When you’re finished at Piazza Navona, the perfect next stop is Pantheon. This roman temple is rated an average of 4.8 out of 5 stars in 189,682 reviews. Pantheon attracts approximately 30,000,000 visitors annually.

If you’re keen to explore even more, then consider a visit to Trevi Fountain. This sculpture is a top place to visit, with a rating of 4.8 out of 5 stars from 343,494 reviews.

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

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

Make sure to reserve a table at Antica Trattoria Papei, an iconic dining spot in Siena. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Osteria Quattro Venti, a popular restaurant in Siena. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Osteria da Divo, a hidden gem nestled in Siena. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Following your dinner, dive into the local bar culture at Meet Life Cafè. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Maudit Pub, the perfect place for those looking to experience the best of the nightlife. Similarly, Bar Impero Siena provides excellent drinks and a great atmosphere, ensuring a memorable night 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.

Wake up to day 5 of your luxury holiday in Italy! Remember to have a hearty breakfast because today will be filled with memorable adventures in Siena, and Pisa. With a flexible itinerary, you're free to adapt and explore additional attractions or enjoy spontaneous discoveries.

Start your sightseeing with a visit to Piazza Del Campo. This square is rated an average of 4.8 out of 5 stars from 64,175 visitors.

Siena Cathedral is another popular attraction you could visit today. This domus has a rating of 4.8 out of 5 stars from 21,656 visitors.

Fontebranda is also highly recommended by travelers. This fountain has a rating of 4.6 out of 5 stars from 1,441 visitors.

As you’ve unraveled the marvels of Siena, it’s time to gear up for the next part of your road trip adventure. Under favorable conditions, your drive to Pisa may take around 1 hour 43 min. Upon your arrival in Pisa, you’ll be greeted with the opportunity to do some sightseeing and exploring.

Seize the day by visiting some of the best attractions in the area, like Piazza Del Duomo, Pisa. This extraordinary square has an average rating of 4.7 out of 5 stars from 104,550 visitors.

Next, make your way to Leaning Tower Of Pisa. This bell tower welcomes around 3,200,000 visitors yearly and is rated an average of 4.7 out of 5 stars in 116,882 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 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 Florence so you can check out the menus and make advance reservations.

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

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 6-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 Florence before saying goodbye.

Explore local shops for souvenirs to remember your trip or find unique gifts for loved ones.

Make the most of what's left of your luxury vacation and head out to the stunning Piazzale Michelangelo. This extraordinary square and attraction is rated an average of 4.8 out of 5 stars in 77,744 reviews, and is an excellent choice for your last sightseeing in Florence.

Treat yourself to a final feast. Savor the unique flavors of Florence one last time before you head to the airport.

You will then say farewell to Florence 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!