Spend 10 inspiring days road-tripping around some of the hidden gems of Spain and Italy. Start by seeing the highlights of Madrid from its rooftops before heading to León to marvel at awe-inspiring Gothic cathedrals. Next, turn north for food tours in the famous Basque Country. In Italy, stroll amid Rome's ancient landmarks, then drive north to discover the natural beauty (and local wines) of Lazio and Umbria, with gorgeous hilltop towns and picturesque lakes.


  • Get a bird's-eye view of Madrid's skyline on a rooftop tour
  • Marvel at Gothic architecture in historic cities like León
  • Indulge in delicious Basque Country cuisine while in Bilbao
  • Hit the highlights of Rome, then travel to ancient hill towns

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Madrid (Spain), Rooftops Tour Madrid
Day 2 Pick Up Rental Car, Drive to León, Walking Tour León
Day 3 Drive to Burgos via Atapuerca, Explore Burgos
Day 4 Drive to Bilbao via Vitoria-Gasteiz, Pintxos Tour Bilbao
Day 5 Fly to Rome (Italy), Highlights Tour Rome
Day 6 Pick Up Rental Car, Drive to Viterbo via Calcata Viterbo
Day 7 Drive to Bolsena via Civita di Bagnoregio, Explore Bolsena
Day 8 Lake Bolsena Boat Tour Bolsena
Day 9 Drive to Orvieto, Tour & Wine Tasting Orvieto
Day 10 Drive to Rome, Depart  

Detailed Itinerary

Day 1: Arrive in Madrid (Spain), Rooftops Tour

Bustling, Vibrant Madrid at Night
Start your trip by experiencing some of the best rooftop bars in Madrid

Welcome to Spain! This attractive nation on Europe's Iberian Peninsula offers plenty of culture, fun, and great cuisine. There's no better place to enjoy it all than in the capital of Madrid. A historic city, Madrid reached its heyday during the famous Hapsburg dynasty of the 16th and 17th centuries, and many regal monuments and architecture from this period remain, like the Plaza Mayor and Almudena Cathedral.

Upon arrival, a driver will pick you up and take you to your hotel. Then, you'll get to witness Madrid's famous Habsburg, Art Nouveau, and Art Deco architectural landmarks. After meeting a guide at your hotel, head out on a three-hour excursion to some of the most exclusive sky-high venues in the city.

From the street, the buildings may look nondescript; however, inside, you'll ride elevators up to chic sun terraces and rooftop bars offering panoramic skyline views. Mingle with local Madrileños over wine and tapas while learning about the city's rich history from your guide. He or she can even point out famous landmarks dating to the Hapsburg dynasty of the 17th century. Also, this tour might coincide with sunset, so you can watch the golden glow over the rooftops as the sun disappears behind Madrid.

Day 2: Pick Up Rental Car, Drive to León, Walking Tour

Walk to historic attractions, including the Catedral de León

Time for a road trip! This morning, pick up your rental car and drive 3.5 hours northwest into the province of Léon and the capital city of the same name. What began as a Roman military camp on the Bernesga River in the first century BCE thrived through the centuries, reaching its peak in the Middle Ages.

After checking into your hotel, meet an expert guide for a walking tour. The historic center has many remarkable sites, including the well-preserved Roman Walls, old manor houses, and churches housing Romanesque and Gothic artworks. Also, here is the expansive Plaza Mayor, lined with medieval buildings and long arcades. Plus, you'll visit Casa Botines, another incredible work designed by Gaudí.

The highlight of the walk is undoubtedly the 13th-century Catedral de León (Cathedral of Santa María de Regla), a marvel of Gothic architecture and one of the most beautiful churches anywhere in Spain. It's an enormous place with impressive stained glass mosaics dating from the 13th through 16th centuries. Interestingly, the cathedral was built over the ruins of Roman baths. At the end of the tour, you'll leave your guide and enjoy the evening on your own.

Day 3: Drive to Burgos via Atapuerca, Explore

Finish the day exploring the well-preserved city of Burgos, dating back to Roman times

Get behind the wheel and head east out of León on a two-hour drive to Burgos. This attractive city has played a significant role in Spanish history since its founding as a settlement during Roman times. However, it was in the Middle Ages that it really gained prominence as a major stop on the Camino de Santiago pilgrimage route. Burgos' historic center is remarkably well-preserved, so much so that it's been declared a UNESCO World Heritage Site.

Before arriving in Burgos, you'll stop just west of the city in Atapuerca. This town has also earned UNESCO status due to its wealth of paleontological and archaeological discoveries. The greatest came in 2007 when archaeologists uncovered teeth and a jawbone dating back 1.2 million years, which are believed to be the remains of the oldest-known European human. On a two-hour tour, you'll visit some of the sites and exhibits to learn more about the area's prehistoric wonders. Afterward, you'll continue to Burgos and check into your hotel. 

Day 4: Drive to Bilbao via Vitoria-Gasteiz, Pintxos Tour

Sample pintxos, the go-to snack in every city in the Spanish Basque Country

Eat a light breakfast today because this morning, you're headed north into the famed Spanish Basque Country, where incredible cuisine awaits. From Burgos, it's a two-hour drive north to Bilbao, the largest city in the province of Biscay and the de facto capital of the Basque Country. Sitting on the River Nervíon and surrounded by lush green mountains, this metropolis offers innovative architecture, world-class art museums, and a venerable dining scene.

On the way to Bilbao, you can stop in the city of Vitoria-Gasteiz, the official capital of the Basque region. Though a bit off the beaten path, Vitoria, as it's commonly known, offers a rich history, a well-preserved medieval quarter, and a vibrant cultural scene. You can discover some historical landmarks on a self-guided tour. Your first stop might be the 17th-century Plaza de la Virgen Blanca, which features an impressive monument to the 1813 Battle of Vitoria. Also, don't miss the Gothic-style Cathedral of Santa María, which dates to the 13th century.

After checking into your hotel in Bilbao, you'll finish the day by indulging in the city's finest pintxos (pronounced "peen-chos"). This type of tapas is prevalent in the Basque region and is served in most bars, cafés, and restaurants. An expert guide will take you on a private, gourmet walking tour, stopping at the city's top food spots and teaching you about the local cuisine. Over three hours, you'll taste everything from lamb skewers to oxtail croquettes and cheese and mushroom pancakes.

Day 5: Fly to Rome (Italy), Highlights Tour

Stop at Trevi Fountain and toss in a coin to ensure a return trip
Plan your trip to Spain
Chat with a local specialist who can help organize your trip.

Drive to the airport in the morning and drop off your rental car. Then, catch a connecting flight via Barcelona to Rome, Italy's fashionable and historic capital. Upon arrival, a driver will transfer you to your hotel. There's no time to waste because after checking in, you'll meet a local guide for a highlights tour of the city. Start by hiking up the Spanish Steps and entering Rome's maze of charming cobblestone streets. As you go, your guide will recount stories and historical anecdotes of the many fountains, buildings, and hidden piazzas tucked away in the corners of this magnificent city.

You'll eventually wind up outside of the Pantheon, the only intact pagan temple left in Rome. The tour continues to the ornate Trevi Fountain, arguably the most famous fountain in the world. Toss a coin in to ensure this isn't your last visit to Rome! Next, stop for gelato at an authentic Roman gelateria, where you'll get a tasty lesson in the difference between gelato and ice cream. The tour concludes at Piazza Navona, home to Bernini's Four Rivers Fountain.

Later, meet up with a historian guide for a private tour of the world's largest amphitheater: the Colosseum. At its prime, it held 50,000 spectators and was the central venue for gladiator fights. Learn about some of ancient Rome's most famous and illustrious citizens, such as Julius Caesar, Emperors Augustus and Nero, and the Flavian emperors who built the Colosseum. From here, continue to the Forum and Palatine Hill, which were built between 46 BCE and 113 CEC. Afterward, you'll say goodbye to your guide and enjoy the rest of the day on your own.

Day 6: Pick Up Rental Car, Drive to Viterbo via Calcata

Wander the cobbled streets of ancient Italian towns like Viterbo and Calcata

Pick up your rental car in the morning and drive from the capital north to Viterbo. This historic city is located in the Lazio region of central Italy and enjoys a fairy-tale location perched atop a hill. The city is known for its well-preserved medieval quarter, thermal baths, and impressive architectural landmarks.

The drive to Viterbo takes about two hours, but you can break up the trip with a stop at Calcata. Also in Lazio, this ancient town sits on a volcanic rock formation rising out of the surrounding forests of the Treja River Valley. Experience its medieval charm as you stroll Calcata's narrow cobbled streets around the historic center, which abounds with colorful houses and artisan shops. Also here is San Michele Arcangelo, a humble church whose small size betrays an interior adorned with beautiful frescoes. You'll quickly discover that the entire town of Calcata is itself a work of art.

Afterward, continue to Viterbo. Founded by the Etruscans and later taken over by the Romans, Viterbo developed into an important medieval center and, in the 13th century, was briefly the seat of the papacy. It was heavily bombed in World War II, but much of its historic core survived, and its attractive tangle of grey-stone buildings remains in excellent shape. Upon arrival, you'll check into your hotel and have the rest of the day free.

Day 7: Drive to Bolsena via Civita di Bagnoregio, Explore

Walk on a pedestrian bridge to get to Civita di Bagnoregio

This morning, you'll leave Viertbo on a quick 19-mile (31 km) drive north to Bolsena. Located on the shores of Lake Bolsena (Europe's largest volcanic lake), this medieval gem of a town is famous for its well-preserved historic center. This part of town is characterized by narrow cobblestone streets, Romanesque/Gothic cathedrals, and charming piazzas.

You can stop at Civita di Bagnoregio, located just east of Bolsena, for a walking tour. Known as the "Dying Town" (La Città che Muore), this remarkable and ancient village (it was founded over 2,500 years ago by the Etruscans) is perched atop a narrow pinnacle of volcanic rock. Adding to its uniqueness, the town is only accessible by a pedestrian bridge.

Over time, parts of Civita di Bagnoregio have collapsed into the valleys below (hence the nickname). However, the town's ancient main square, Piazza Donato Bramante, remains. Around it are historic churches, such as the Church of San Donato, a Romanesque gem believed to date to the ninth century. After the walk around Civita di Bagnoregio, you'll drive to Bolsena and check into your hotel.

Day 8: Lake Bolsena Boat Tour

Visit the islands and medieval towns in and around Lake Bolsena

Trade the car for a boat this morning, as you'll head to the harbor for a full-day tour on the azure waters of Lake Bolsena. The lake was formed in the crater of a now-extinct volcano, and a couple of historic islands—Martana and Bisentina—were also the result of past eruptions.

On a stop at Bisentina, you'll hike to its beautiful Renaissance-era Farnese Palace, the summer home of an aristocratic family in the 16th century. Another famous landmark here is the Gothic/Renaissance Church of St. James, which dates to the 13th century. You'll also stroll the island's famous gardens and enjoy panoramic lake views.

The tour continues with visits to the charming towns and villages dotting the lakeshore. At midday, you'll stop for lunch at a restaurant overlooking the water. Be sure to try the local pasta and fresh lake fish like carp and perch. At the end of the afternoon, you'll return to the harbor in Bolsena.

Day 9: Drive to Orvieto, Tour & Wine Tasting

Drive to the "Green Heart of Italy" and take a wine tour

After breakfast, leave Bolsena on a 30-minute drive northeast to Orvieto, located in the Umbria region of central Italy. Known as the "Green Heart of Italy," Umbria remains off the radar to many tourists but rewards those who do make the journey with its rolling green hills, vineyards, and rich artistic and religious heritage. Orvieto is a fine example of all that Umbria has to offer: an attractive medieval town perched on a hill in the scenic green countryside.

Upon arrival, you'll check into your hotel and kick things off with a wine tour. Meet a local guide who will lead you to a winery in the area. Here, you'll enjoy a private tour of the estate as well as a sampling of some of the famous wines produced in the area, like Orvieto Clasico, a semi-dry white.

After the tasting, you'll return to town for a walk around its many highlight landmarks. The star is the Duomo di Orvieto, a Gothic masterpiece dating to 1290 and one of Italy's most awe-inspiring churches. The tour also includes lunch in a restaurant in town where you can enjoy some traditional dishes. Umbria is famous for its rustic cuisine that often features black truffles and olive oil. One tasty specialty is strangozzi, a handmade pasta with truffle sauce.

Day 10: Drive to Rome, Depart

If time allows, take a morning stroll in Orvieto before departure
Alas, it's time to say arrivederci! In the morning, you'll hit the road one last time on a 1.5-hour drive back to Rome. At the airport, you'll drop off your rental car and board your flight home. Safe travels!

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Map of Off-the-Beaten-Path Road Trip in Spain & Italy - 10 Days
Map of Off-the-Beaten-Path Road Trip in Spain & Italy - 10 Days