Luxury 5-Day Italy Road Trip from Pisa traveling south to Siena and Viterbo

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

An excellent attraction to start your day with is Knights' Square. This square is rated an average of 4.5 out of 5 stars in 9,051 reviews.

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.

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

This renowned restaurant holds , and offers an exceptional menu of cuisine. Make sure to reserve a table at Ristorante Capodimonte Pisa, an iconic dining spot in Pisa. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Baribaldi Pisa, a popular restaurant in Pisa. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Restaurant -Pizzeria Il Mio Capriccio, a hidden gem nestled in Pisa. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Continue the enjoyment post-dinner at JEFFER cocktails & friends, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Le Parisien Wine Bar offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out Las Volta cocktailbar. This bar is a favorite among both locals and visitors looking for a delightful evening out filled with laughter and fun.

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

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 Siena, where you'll be staying for 1 night. The day's itinerary unfolds with a diverse array of experiences in Pisa and Cascine Vecchie.

Start your sightseeing with a visit to Palazzo Blu. This art museum is a popular stop on travelers’ itineraries in Pisa, with an average rating of 4.5 out of 5 stars by 4,244 visitors. Around 37,457 people visit this attraction every year.

Leaning Tower of Pisa is another popular place of interest you can visit today. The average rating of 4.7 out of 5 stars from 116,882 reviews gives you an idea of other visitors’ experience at this attraction. It’s estimated that around 3,200,000 people visit this bell tower every year.

If it’s still bright and early, make your way to Piazza del Duomo, Pisa. Visitors have rated this square an average of 4.7 out of 5 stars in 104,550 reviews.

Pisa Cathedral is another unique site you can experience today. This attraction is a cathedral rated an average of 4.8 out of 5 stars in 8,361 reviews.

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

When you’re ready for some sightseeing, make your way to Parco Regionale Migliarino, San Rossore, Massaciuccoli. This much-appreciated park is rated 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 Siena.

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 Siena for you so you can browse their menus in advance and make a reservation.

Savor the flavors at Antica Trattoria Papei, a top pick for dinner tonight. Alternatively, Osteria Quattro Venti beckons with its unique menu offerings. Also, consider Osteria da Divo. With its consistent customer satisfaction, it’s an excellent option for dining in Siena tonight.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Meet Life Cafè, known for its inviting atmosphere. Maudit Pub is another great option if you’re looking for a place to get the night started. Similarly, Bar Impero Siena provides a great setting to enjoy the night away.

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.

Wake up to day 3 of your luxury holiday in Italy! Remember to have a hearty breakfast because today will be filled with memorable adventures in Siena and Orvieto. With a flexible itinerary, you're free to adapt and explore additional attractions or enjoy spontaneous discoveries.

Begin your sightseeing with a visit to piazza del Campo. This extraordinary square is rated an average of 4.8 out of 5 stars by 64,175 visitors.

Next, make your way to Siena Cathedral. This top attraction is a domus with an average rating of 4.8 out of 5 stars by 21,656 visitors.

We also recommend a visit to Fortezza Medicea (Siena). This fortress is rated 4.5 out of 5 stars by 9,835 travelers.

Orvieto’s wonders await as you prepare for another journey on the road, leaving the breathtaking surroundings of Siena behind. This drive usually takes around 1 hour 32 min. Orvieto welcomes you with a multitude of unique vacation experiences.

An excellent attraction to start your day with is Orvieto Cathedral. This catholic cathedral is rated an average of 4.8 out of 5 stars in 15,057 reviews.

Fasten your seatbelt and make your way to your next stop. Orvieto, 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 Siena to Orvieto may take around 1 hour 32 min without traffic disruptions. Upon arrival in Orvieto, we highly recommend checking out some of the top attractions.

Begin 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 in 14,274 reviews.

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

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

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

On day 4 of your luxury holiday in Italy, your road trip route will take you exploring the best of Viterbo. With a day brimming with amazing attractions ahead, fuel up with a hearty breakfast to savor every moment of your luxury vacation in Italy.

Be one of the day’s first visitors at Piazza del Plebiscito. This sightseeing destination is rated an average of 4.3 out of 5 stars by 3,004 visitors.

When you’re finished at Piazza del Plebiscito, head to Palazzo dei Papi di Viterbo. This one-of-a-kind palace is rated an average of 4.5 out of 5 stars in 6,905 reviews.

Beyond the above-mentioned attractions, you also have the opportunity to visit Terme dei papi. This spa is rated an average of 4.3 out of 5 stars by 6,981 visitors.

If you’re keen to explore more, then consider a visit to Therma Oasi. This spa is a much-appreciated attraction with an average rating of 4.3 out of 5 stars from 1,518 visitors.

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

Discover a world of culinary delights in Pisa, 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.

Esteemed as a restaurant, it features an exceptional menu. Treat yourself to a wonderful meal at Ristorante alle Bandierine, a top-rated dining spot in Pisa. If you're in the mood for something new, try Barrique Cocktail And Bistrot, another premier location with a delectable menu. You might also want to book a table at Filter Coffee Lab. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Pisa.

Explore the vibrant nightlife at Bar Mocambo after your meal, a hub for lively evenings and memorable moments. Or, head to Tree for a great selection of flavorful drinks and a charming setting. Furthermore, Chupiteria is perfect for those looking to extend their night with a touch of local flavor.

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

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 “Tuttomondo” (Keith Haring). This extraordinary sightseeing destination and attraction is rated an average of 4.6 out of 5 stars in 1,937 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.

Dine in style at Sud, a top recommendation for dinner tonight. Or, for a change of pace, Kiste' - La Pizza Artigianale. It's the second restaurant coming from the tower. Boasts a menu that's sure to impress.

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!