Luxury 5-Day Italy Road Trip from Pisa traveling east to Florence and Bologna

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

Begin your sightseeing with a visit to “Tuttomondo” (Keith Haring). This extraordinary point of interest is rated an average of 4.6 out of 5 stars by 1,937 visitors.

Tonight, you will be treated to a stay at one of the best luxury hotels in Pisa. 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 Pisa.

Continue your lively evening at JEFFER cocktails & friends, a perfect place for winding down or revving up the night, depending on which mood you’re in. Le Parisien Wine Bar is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Las Volta cocktailbar ensures a night out tailored to your taste.

Raise a toast to the start of your 5-day luxury vacation in Italy and look forward to more fantastic days to come!

On day 2 of your luxury holiday in Italy, your road trip route will take you exploring the best of Pisa and Cascine Vecchie. 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 Palazzo Blu. This art museum gets 37,457 visitors each year and is rated an average of 4.5 out of 5 stars in 4,244 reviews.

Next up, make your way to Leaning Tower of Pisa. This bell tower has an average rating of 4.7 out of 5 stars from 116,882 reviews. Usually, around 3,200,000 people visit Leaning Tower of Pisa every year.

When you’re ready for your next sight of the day, continue to Piazza del Duomo, Pisa. This square has an average rating of 4.7 out of 5 stars from 104,550 visitors.

Beyond the above-mentioned attractions, you also have the opportunity to visit Pisa Cathedral. This cathedral is rated an average of 4.8 out of 5 stars by 8,361 visitors.

Set your GPS to Cascine Vecchie and hit the road. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Cascine Vecchie beckons with new experiences!

Make Parco Regionale Migliarino, San Rossore, Massaciuccoli your first stop of the day. Previous visitors have rated this park an average of 4.4 out of 5 stars in 9,632 reviews.

Relax and unwind in style as you spend the night at one of the top luxury hotels in in Florence.

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.

Prepare for an extraordinary culinary adventure in Florence by booking a table at Enoteca Pinchiorri, a 3-star Michelin restaurant that boasts an exceptional italian contemporary menu. For a different flavor experience, head to Santa Elisabetta, renowned for its delectable creative and mediterranean dishes. This 2-star Michelin restaurant consistently wows guests, making it a memorable stop during your holiday. Looking for another option? Visit Gucci Osteria da Massimo Bottura, a local gem known for its delightful italian contemporary and international cuisine in Florence. Nestled in the city's heart, this 1-star Michelin restaurant is a perfect choice for discerning restaurant-goers seeking a new experience.

Keep the evening going at Manifattura, a great choice for enjoying the after-dinner hours with a drink. You could also go to SE·STO on Arno Rooftop Bar, which offers a similarly pleasant setting and great drinks. Another option is Archea Brewery, which provides an inviting environment for unwinding after a busy day out.

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

Wake up to day 3 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 Bologna, where you'll be staying for 1 night. The day's itinerary unfolds with a diverse array of experiences in Florence.

Drop by the renowned piazza della Signoria. This popular square has been rated an average of 4.8 out of 5 stars by 66,956 visitors.

Another unforgettable place to experience is Cathedral of Santa Maria del Fiore. Rated 4.8 out of 5 stars by 76,359 visitors, this church deserves a spot on today's sightseeing itinerary.

We also recommend a visit to Ponte Vecchio. This deck arch bridge has been rated an average of 4.7 out of 5 stars in 118,099 reviews.

Another favorite attraction in the area is Uffizi Gallery, drawing over 2,011,219 yearly visitors. This national museum and popular place of interest enjoys a rating of 4.7 out of 5 stars from 61,794 local and international travelers.

If you’re keen to explore even more, then consider a visit to piazzale Michelangelo. With an average rating of 4.8 out of 5 stars from 77,744 travelers, this square is an attraction many avid travelers highly recommend visiting while in Florence.

Relax and unwind in style as you spend the night at one of the top luxury hotels in in Bologna.

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

Set out on a gastronomic journey in Bologna by reserving a table at I Portici. Renowned for its , this restaurant presents an outstanding menu of creative and contemporary cuisine. For a different taste, head over to Ahimè, renowned for its delectable country cooking dishes. This distinguished Bib Gourmand-recipient is a favorite among guests, making it a worthy addition to your holiday plans. Craving more culinary excitement? Explore Trattoria di Via Serra, a highly rated local gem known for its exquisite emilian menu. With a Bib Gourmand 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 Bologna.

If you’re not ready to end the night just yet, Bar Freud e Squisito offers a perfect venue to relax and savor a drink. Similarly, Osteria del Sole is well-suited for those looking to unwind in a social setting. Macondo - Cocktail Bar is another excellent spot to enjoy a nightcap after a delightful meal.

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.

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

Kick off the day at Piazza Maggiore, a top pick for today’s sightseeing. This square is rated an average of 4.7 out of 5 stars in 64,523 reviews.

Today is also your chance to visit Piazza Santo Stefano. Piazza Santo Stefano is a square with an average rating of 4.8 out of 5 stars from 7,617 reviews.

Two Towers is another top attraction we highly recommend you visit today. This tower is rated an average of 4.7 out of 5 stars by 25,975 visitors.

Beyond the attractions mentioned above, you also have the opportunity to visit Bologna Cathedral. This catholic cathedral is rated an average of 4.6 out of 5 stars by 3,852 visitors.

Lastly, don’t miss out on Fountain of Neptune, Bologna, a famous fountain in Bologna. This attraction is rated an average of 4.7 out of 5 stars by 3,952 travelers.

Relax and unwind in style as you spend the night at one of the top luxury hotels in in Pisa.

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

Cap off your dinner by heading to Bar Mocambo, ideal for a leisurely evening with a drink in hand. Tree is another bar that offers an enjoyable setting. Similarly, Chupiteria is also a popular place to go on a night out, perfect for relaxing and socializing.

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 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 Pisa before saying goodbye.

Make the most of your final day in Italy by visiting Pisa’s iconic markets and shopping establishments. Your stay’s proximity to the city’s retail haven invites an unhurried and unforgettable exploration of its variety of stores and establishments. Secure the perfect souvenirs for your family and friends back home or buy yourself a remembrance of your amazing experience in Italy. Take home a piece of Italy with these souvenirs, keeping your adventures close.

Make the most of what's left of your luxury vacation and head out to the stunning Knights' Square. This extraordinary square and attraction is rated an average of 4.5 out of 5 stars in 9,051 reviews, and is an excellent choice for your last sightseeing in Pisa.

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

Have a fantastic dining experience at Sud, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Kiste' - La Pizza Artigianale. It's the second restaurant coming from the tower. Offers an enticing alternative with its varied menu.

You will then say farewell to Pisa 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!