Luxury 9-Day Italy Road Trip from Florence traveling south to Siena, and Rome

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

Take the opportunity to see Central Market. This attraction has an average rating of 4.4 out of 5 stars from 43,100 visitors.

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.

Discover a world of culinary delights in Florence, 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.

Savor the flavors at Ristorante Oliviero 1962, a top pick for dinner tonight. Alternatively, Caffe San Firenze beckons with its unique menu offerings. Also, consider Ditta Artigianale. With its consistent customer satisfaction, it’s an excellent option for dining in Florence tonight.

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. Archea Brewery likewise offers a unique atmosphere, perfect for a memorable night out.

Raise a toast to the start of your 9-day luxury vacation in Italy and look forward to more fantastic days to come!

Day 2 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.

Seize the day by visiting some of the best attractions in the area, like Uffizi Gallery. This extraordinary national museum has an average rating of 4.7 out of 5 stars from 61,794 visitors. Each year, around 2,011,219 people visit this remarkable site to admire its features and learn more about it.

Next, make your way to Ponte Vecchio. This deck arch bridge is rated an average of 4.7 out of 5 stars in 118,099 reviews.

While in Florence, we also recommend a visit to Piazza Della Signoria. This square has been rated an average of 4.8 out of 5 stars in 66,956 reviews.

If you’re keen to explore even more, then consider a visit to Piazza Della Repubblica. With an average rating of 4.6 out of 5 stars by 22,356 travelers, this square is a highly recommended stop on your sightseeing around Florence.

Make your way to Cathedral Of Santa Maria Del Fiore, perhaps the most famous church in Florence. This attraction is rated an average of 4.8 out of 5 stars in 76,359 reviews.

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.

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 with a 1-star Guide Michelin recognition, known for its delicious italian contemporary, and international menu.

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 Florence, and Pisa. The day's journey will conclude in Siena, 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.

Begin your sightseeing with a visit to Galleria Dell'accademia. This national museum gets 1,719,645 visitors each year and is rated an average of 4.6 out of 5 stars in 34,429 reviews.

Next up, make your way to Basilica Di Santa Maria Novella, Firenze (fi). This archives has an average rating of 4.7 out of 5 stars from 23,075 reviews.

Pisa’s wonders await as you prepare for another journey on the road, leaving the breathtaking surroundings of Florence behind. This drive usually takes around 1 hour 12 min. Pisa welcomes you with a multitude of unique vacation experiences.

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

Enjoy a delicious meal at Antica Trattoria Papei, a top-rated dining destination in Siena. If you're in the mood to try something new, consider Osteria Quattro Venti, another top spot with a mouthwatering menu. You might also want to secure a reservation at Osteria da Divo. With a reputation for consistently satisfied customers, it’s a perfect choice to enhance your stay in Siena this evening.

Cap off your dinner by heading to Meet Life Cafè, ideal for a leisurely evening with a drink in hand. Maudit Pub is another bar that offers an enjoyable setting. Similarly, Bar Impero Siena is also a popular place to go on a night out, perfect for relaxing and socializing.

Raise a toast to another amazing day of your luxury holiday in Florence, 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 Siena. With a flexible itinerary, you're free to adapt and explore additional attractions or enjoy spontaneous discoveries.

Drop by the renowned Siena Cathedral. This popular domus has been rated an average of 4.8 out of 5 stars by 21,656 visitors.

Another unforgettable place to experience is Piazza Del Campo. Rated 4.8 out of 5 stars by 64,175 visitors, this square deserves a spot on today's sightseeing itinerary.

We also recommend a visit to Tower Of Mangia. This sightseeing destination has been rated an average of 4.6 out of 5 stars in 673 reviews.

Another favorite attraction in the area is Fortezza Medicea (siena). This fortress and popular place of interest enjoys a rating of 4.5 out of 5 stars from 9,835 local and international travelers.

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.

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.

Have a memorable dining experience in Rome by booking a table at La Pergola, renowned as a 3-star Michelin restaurant presenting an exceptional mediterranean, and contemporary menu. For a different culinary experience in Rome, Il Pagliaccio shines as one of the top destinations, known for its delicious creative, and innovative 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, Enoteca La Torre is known as a top local spot for its delicious mediterranean, and creative cuisine in Rome. This 2-star Michelin awardee is a highly recommended choice for an unforgettable meal.

Keep the excitement of the evening going by visiting a bar or two. La Botticella Of Poggi Giovanni is an excellent place to start. You could also check out Sant' Eustachio Caffè, offering a different kind of charm. A last recommendation for the day is Caffè Portofino. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

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

When you’re ready for some sightseeing, make your way to Castel Sant'angelo. This much-appreciated museum is rated 4.7 out of 5 stars in 72,431 reviews. Each year, 918,591 people visit this site to admire its unique features.

Embrace the thrill of the open road as you wave goodbye to Rome and set your GPS to Vatican City, Vatican City. 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 12 min. Upon reaching Vatican City, unwind, observe, and explore. The best things to do, see, and eat are waiting for you.

Your sightseeing of the day begins at Vatican Museums, a remarkable art museum where it’s easy to get lost in exploration. This top attraction is rated an average of 4.6 out of 5 stars in 133,310 reviews. Each year, this popular place of interest welcomes approximately 1,612,530 visitors.

Next, satisfy your wanderlust at Sistine Chapel. This chapel has an average rating of 4.7 out of 5 stars from 52,083 travelers.

St. Peter's Basilica is another must-visit attraction. This renowned major basilica offers a memorable experience, well worth a stop on your self-guided sightseeing tour. Rated 4.8 out of 5 stars by 131,043 travelers and attracting 11,000,000 annual visitors, it's one of the more popular places to see in the area.

When you’re done exploring the best attractions, you’ll drive back to your luxury accommodation near the city of Rome.

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

Make sure to book a table at DEROMA - Farine Romane, a popular restaurant in Rome. This acclaimed restaurant and its mouthwatering dishes have earned the admiration of countless food lovers. Alternatively, experience a taste of Rome at La Taverna Italiana, 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 Centro. As a dining spot that gains high praise from guests, it’s an ideal choice to enhance your time to Rome tonight.

If you’re not ready to end the night just yet, The Apartment Bar Roma offers a perfect venue to relax and savor a drink. Similarly, Hotel Hassler Roma is well-suited for those looking to unwind in a social setting.

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 2 nights nights remaining.

Make Colosseum one of your first sightseeing stops in Rome. Rated an average of 4.7 out of 5 stars by 328,821 travelers, a visit to this local attraction makes for a great introduction to the area. This roman amphitheatre attracts 7,400,000 visitors every year.

Roman Forum is a worthwhile attraction you can visit next. This square is a valued place of interest in the area, with an average rating of 4.7 out of 5 stars from 114,450 reviews.

Today is also the perfect opportunity to drop by Pantheon. This roman temple has been rated an average of 4.8 out of 5 stars by 189,682 visitors. Up to 30,000,000 people travel to this site annually.

If you’re keen to explore more, head to Piazza Navona. A trip to this popular square is also your opportunity to see if it lives up to the reputable 4.7 out of 5-star rating as given by 158,771 previous visitors.

Another top place to visit is Altare Della Patria. This architectural structure enjoys an average rating of 4.8 out of 5 stars from 49,843 local and international travelers. Approximately 1,683,070 people visit this attraction every year.

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.

Savor the flavors at Ristorante Tema, a top pick for dinner tonight. Alternatively, Maccheroni beckons with its unique menu offerings. Also, consider RoYaL Art Cafè Roma. With its consistent customer satisfaction, it’s an excellent option for dining in Rome tonight.

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 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 1 night nights remaining.

Make Trevi Fountain your first stop of the day. Previous visitors have rated this sculpture an average of 4.8 out of 5 stars in 343,494 reviews.

Next up, make a stop at Piazza Di Spagna. With an average rating of 4.7 out of 5 stars by 113,658 visitors, it's easy to understand why so many people visit this square every year.

Spanish Steps is another attraction you can visit on this day of your vacation. This monumental staircase has an average rating of 4.5 out of 5 stars by 57,211 visitors.

When you’re finished at Spanish Steps, the perfect next stop is Piazza Del Popolo. This square is rated an average of 4.6 out of 5 stars in 89,807 reviews.

If you’re keen to explore even more, then consider a visit to Villa Borghese. This urban zone of rome is a top place to visit, with a rating of 4.6 out of 5 stars from 69,749 reviews.

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

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

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

Wake up to day 8 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 1 night. The day's itinerary unfolds with a diverse array of experiences in Nera Montoro, and Orvieto.

Continue your road trip and head to your next destination, Nera Montoro. This car ride takes around 1 hour 15 min.

Take the opportunity to see The Mole Di Narni. This attraction has an average rating of 4.2 out of 5 stars from 1,394 visitors.

Embrace the thrill of the open road as you wave goodbye to Nera Montoro and set your GPS to Orvieto. 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 48 min. Upon reaching Orvieto, unwind, observe, and explore. The best things to do, see, and eat are waiting for you.

Make Orvieto Cathedral your first stop of the day. Previous visitors have rated this catholic cathedral an average of 4.8 out of 5 stars in 15,057 reviews.

Next up, make a stop at Orvieto Underground. With an average rating of 4.6 out of 5 stars by 1,517 visitors, it's easy to understand why so many people visit this archaeological site every year. In fact, this attraction welcomes 37,000 annual visitors.

Orvieto’s wonders await as you prepare for another journey on the road, leaving the breathtaking surroundings of Nera Montoro behind. This drive usually takes around 48 min. Orvieto welcomes you with a multitude of unique vacation experiences.

Start your sightseeing with a visit to Well Of St. Patrick. This point of interest is rated an average of 4.5 out of 5 stars from 14,274 visitors.

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.

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

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

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.

Today is the last day of your 9-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.

If you're in the mood to try something new, consider Ristorante Le Volte Firenze, another top spot with a mouthwatering menu.

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!