Off-the-Beaten-Path Road Trip in Spain & Italy - 21 Days

Highlights

• Get a bird's-eye view of Madrid's skyline on a rooftop tour
• Discover the joys of Galician cuisine in Santiago de Compostela
• Marvel at Gothic architecture in less-visited cities like León
• Immerse yourself in art and culture in the Basque capital of Bilbao
• Hit the highlights of Rome, then visit ancient towns in Umbria

Brief Itinerary

Detailed Itinerary

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

Welcome to Spain! The next couple of weeks will be anything but ordinary, and you'll see it right away with your arrival in Madrid. This city has a long history dating back to when it was the site of a Roman conquest in the third century BCE. It was officially founded in the ninth century by the Moors and became the nation's capital in the 16th century under King Phillip II, a member of the famous Habsburg dynasty of Europe. The Habsburg influence is seen in architectural landmarks throughout the city, particularly in the historic center, El Madrid de Los Austrias.

Upon arrival at the airport, a driver will pick you up and transfer you to your hotel. After check-in, you'll meet a local guide and head out for a city tour of an altogether different kind. This three-hour excursion will take you not only on Madrid's streets but also on its rooftops.

Your guide will lead you to a few buildings, many of which appear unremarkable from the outside. Enter a nondescript office building, for example, and ride the elevator up to an expansive sun terrace for panoramic views of the city skyline. Some stops even include rooftop bars and restaurants, where you can mingle with local Madrileños while sharing a glass of wine and some tapas. Depending on your arrival time, this tour will coincide with sunset, so you can watch the golden glow over the rooftops as the sun disappears behind Madrid.

Day 2: Train to Santiago de Compostela, Food Tour

Transfer to Atocha station in the morning and catch a train for the three-hour ride northwest into the region of Galicia. You'll arrive in the capital of Santiago de Compostela, which isn't only a historic city but also the terminus of the Camino de Santiago. This famed pilgrimage route begins in France and spans 500 miles (800 km) across Spain, ending at the Cathedral of Santiago de Compostela, a Romanesque/Gothic/Baroque church that's the most iconic landmark in the city. Upon arrival, you'll check into your hotel and then head right back out for a tour.

After meeting a local guide, you'll embark on a walk to discover what makes Galician cuisine world-famous. It's a half-day excursion, during which your guide will lead you to some of the city's food markets, where you can browse fresh produce and sample some of the region's legendary seafood, regarded as some of the best in the world. Traditional dishes you can try include pulpo a la Gallego (Galician octopus) and gambas al ajillo (garlic shrimp). Pair these delicious morsels with the region's famed white wine or, if you're feeling adventurous, the local queimada, a type of flaming brandy. 

Day 3: Guided City Tour of Santiago de Compostela

This morning, meet your guide and discover Santiago through its architectural heritage. Your two-hour walking tour begins in Obradoiro Square, at the east end of which sits the Cathedral of Santiago de Compostela. Construction on this church began in the 11th century over what is believed to be the burial place of the apostle Saint James the Great. It's been a religious pilgrimage site ever since.

Other stops include Colexio de San Xerome (San Jerónimo College), dating to 1501; the 16th-century Hospital de los Reyes Católicos, a hospital built to treat weary pilgrims after their arduous journey; the Pazo de Raxoi (Raxoi Palace), an 18th-century neoclassical palace that's now Santiago's City Hall; and the 18th-century San Fructuoso Church. Here, you can witness pilgrim rituals and see the Botafumeiro, the largest silver-plated censer (ceremonial incense container) in the world.

After the tour, you'll bid farewell to your guide and have the evening free. There's a lot of fun to be had in Santiago, such as splurging on dinner at one of the city's fine-dining restaurants. Or, there are any number of casual eateries where you can enjoy everything from traditional Galician dishes to fusion plates to snackable tapas and more. 

Day 4: Day Trip to Pontevedra & Cambados

After breakfast, meet your driver for a full-day tour of Galicia's gorgeous coast and historic cities. About 45 minutes south of Santiago is your first stop: Pontevedra. Sitting at the mouth of the Lérez River, a historic city dating to Roman times known for its well-preserved historic center.

While here, you'll wander the maze of cobblestone streets and secluded plazas that are abuzz with activity. As you go, marvel at medieval landmarks like the Gothic-style Basilica of Santa María, the Pilgrims' Chapel, and the San Francisco Monastery. Cap the visit with a stop at the Mercado de Abastos, a famous riverfront market and meetup spot where you can browse vendor stalls while enjoying views of the 12th-century Burgo Bridge.

About 30 minutes up the coast is the seaside resort of Cambados. Besides its scenic coastal location, excellent seafood, and 17th-century palace, Cambados is famous in the Galician wine industry. It's the capital of Albariño, a delicious white grape variety grown in the region. Be sure to enjoy a glass before strolling the picturesque seaside promenade. Afterward, transfer back to Santiago with your guide.

Day 5: Drive to León, Self-Guided Tour

It's time for a road trip! This morning, you'll pick up your rental car and leave Santiago for the province of Léon and the capital city of the same name. The scenic drive takes about 3.5 hours, but you can stop at regional highlights along the way. Las Médulas is known for its ancient Roman gold mines; Templar Castle, in the city of Ponderrada, is a 12th-century fortress built by the Knights Templar; and the historic town of Astorga sits at the crossroads of the Camino de Santiago. It's famous for its iconic Episcopal Palace, built in the 19th century by renowned Catalan architect Antoni Gaudí. 

Eventually, you'll arrive in León. What began as a Roman military camp on the Bernesga River in the first century BCE then 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 6: Drive to Burgos, Visit Atapuerca

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 a jawbone and teeth 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 7: Guided Tour of Burgos

Meet a local guide in the morning for a stroll around the cobbled streets of Burgos' medieval Old Town. Your guide will lead you to all the historic architectural marvels, including old monasteries and convents. You'll also visit the Cathedral of Santa María de Burgos, a jaw-dropping 13th-century church inspired by Paris' Notre Dame. It enjoys the distinction of being the first Gothic church ever built on the Iberian Peninsula and thus has earned UNESCO World Heritage status. Other landmarks you'll visit include the 12th-century Castle of Burgos (known as the Alcázar) and the Monastery of San Juan.

After the tour, you'll have the rest of the afternoon free. If you like, take a scenic stroll on the banks of the Arlanzón River. You can also pop in at some local museums. The Fedrique de Basilea Book, in Old Town, recounts the history of books, while the Burgos Museum, which occupies a historic 16th-century palace, features exhibits on prehistory and archaeology. Also, Burgos is known for its delicious cuisine, so in the evening, head to a local eatery and try local dishes like morcilla (blood sausage), cochinillo asado (roast suckling pig), or lechazo (roast lamb).

Day 8: Drive to Bilbao, Pintxos Tour

Eat a light breakfast 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 Nervíon River 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, has 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. 

Day 9: Bilbao Self-Guided Tour

The day is yours to discover the highlights of Bilbao at your own pace. You can begin a walking tour in the Casco Viejo (Old Town) and Plaza Moyua, which was established in 1876 and features a beautiful fountain and gardens. Other major sites include the 18th-century Church of San Nicolás and the Flemish Chavarri Palace, built in the early 20th century. Also, don't miss the 14th-century Cathedral of Santiago and the Mercado de la Ribera, the largest covered marketplace in Europe.

A visit to Bilbao isn't complete without stopping in at the Guggenheim Museum, a masterpiece of contemporary architecture by the legendary Frank Gehry. This glimmering titanium structure looks more like a sculpture than a building, with its sleek lines curving in virtual defiance of physics. Inside is a treasure trove of works from great artists such as Andy Warhol, Anish Kapoor, Jeff Koons, Louise Bourgeois, and Eduardo Chillida.

Day 10: Fly to Rome (Italy), Highlights Tour

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 to enter 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 CE. Afterward, you'll say goodbye to your guide and enjoy the rest of the day on your own.

Day 11: Drive to Viterbo, Stop in 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 12: Viterbo Walking Tour & the "Park of Monsters"

After breakfast, you'll meet your guide for a private walking tour. Over two hours, you'll discover the remarkable architecture of this medieval city as your guide recounts the Viterbo's fascinating history. Begin in the well-preserved Old Town and visit famous landmarks, including the Palazzo dei Papi (Palace of the Popes), a medieval palace that served as a residence for several popes during the 13th century. Throughout the excursion, you'll hike around cobbled streets, passing ancient fountains and famous squares, like Piazza del Plebiscito, known for its looming bell tower.

You'll also travel east of Viterbo to the town of Bomarzo and visit the Sacro Bosco (Sacred Grove). Also known as the "Parco dei Mostri" (Park of Monsters), this Renaissance-era garden is aptly named, as it's filled with massive stone sculptures of mythological creatures, monsters, and other fantastical figures. They were created in the 16th century by artist Pirro Ligorio, and macabre highlights include the "Leaning House," "Turtle Fountain," the colossal "Orcus' (a monstrous figure with gaping jaws), and the famous "Mouth of Hell," as foreboding as the name implies.

Day 13: Drive to Bolsena, Stop at Civita di Bagnoregio

This morning, you'll leave Viterbo 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 14: Lake Bolsena Boat Tour

Trade the car for a boat, as this morning, you'll head to the harbor for a full-day tour of the azure waters on 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 15: Drive to Orvieto, Tour & Wine Tasting

After breakfast, leave Lake 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/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 off your time here 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, which features black truffles and olive oil. One tasty specialty is strangozzi, a handmade pasta with truffle sauce.

Day 16: Drive to Perugia, Tunnels & Highlights Tour

Leave Orvieto today and continue driving about 1.5 hours north to Perugia, the capital of the Umbria region. There's a lot to recommend here, from its idyllic hilltop location and well-preserved Etruscan/medieval architecture to its historic university and annual chocolate and jazz festivals. After checking into your hotel, you'll dive deep into Perugia's ancient history on a tour.

Meet your guide and embark on a three-hour walk to discover one of Italy's most interesting pre-Roman civilizations. Perugia was settled by the Etruscans around 2,500 years ago, and as you stroll through its ancient tunnels, you'll pass landmarks spanning the ages. Highlights include Porta Marzia (the southern entrance to the Etruscan historic center), the 16th-century Rocca Paolina fortress, and the 13th-century San Domenico Convent. That last one is home to the National Archaeological Museum of Umbria, whose fine collection of artifacts ranges from the Paleolithic to the Roman period.

As you go, you'll pass ancient Etruscan wells, arches, and gates and hike up to viewpoints offering splendid views of the Umbrian countryside. Continue along Perugia's famous travertine walls until you reach the expansive Piazza IV Novembre (Fourth of November Square). The tour ends here, but feel free to stick around and mingle with locals at a café near the plaza's historic fountains and cathedral.

Day 17: Day Trip to Assisi & Spello

Leave early on a day trip to a couple of jewels in Umbria's crown. First, you'll drive east about 30 minutes to the hilltop village of Assisi. Birthplace of St. Francis and home to the 13th-century Basilica di San Francesco, this UNESCO World Heritage Site will surely charm you. Once there, you can visit the basilica and other medieval landmarks like Rocca Maggiore, a 14th-century castle high above the town. 

While Assisi is primarily known for its medieval and religious heritage, there are some Roman ruins and archaeological sites in the town that reflect its earlier history. Restored ruins you can visit include the Roman Amphitheater and the Temple of Minerva. The latter is one of the most well-preserved Roman structures in Assisi. It was originally constructed in the first century BCE and was later converted into a church, though the interior still displays its Roman origins.

After a lunch break, you'll drive about 15 minutes south to Spello. This little ancient gem is home to a yearly flower festival that fills the place with incredible color. Take a couple of hours to explore its narrow cobbled streets and charming plaza. Culture buffs will want to visit the 11th-century Church of St. Maria Maggiore, which houses a chapel frescoed by Renaissance artist Pinturicchio in 1500. At the end of the day, drive back to your hotel in Perugia.

Day 18: Drive to Spoleto, Stop in Foligno

Bid farewell to Perugia this morning and hit the road on an hour's drive to Spoleto. At the halfway point, you can stop to stretch your legs in Foligno. This is another dazzling town that exudes medieval charm. It has a well-preserved Old Town with winding medieval streets, elegant squares, and historic buildings. One highlight is the 12th-century Cathedral of San Feliciano, an example of Gothic architecture.

The historic center is a great spot to begin a self-guided walking tour, particularly the Piazza della Repubblica. Located in the heart of the town, it's surrounded by historic buildings like the 12th-century Cathedral of San Feliciano, a great example of Gothic architecture. Also, there's no shortage of shops, cafés, and boutiques to visit in the area. Another must-visit landmark in the historic center is Casa Cava, an underground house of the kind that was common during medieval times. You can take guided tours to explore its underground rooms.

When you get hungry, stop at a trattoria and try some local specialties, like porchetta (roast pork). Umbria's famous truffles often complement these dishes, which are best enjoyed with local wines. At the end of the afternoon, continue to Spoleto and check into your hotel. 

Day 19: Spoleto Walking Tour

Spoleto is another of Umbria's ancient towns dating to the Roman period. Over the centuries, the Etruscans, Romans, Goths, Lombards, and the Papal States have influenced Spoleto's history. You'll see all these cultural influences and more on a guided tour.

Meet your guide in the morning and head out on a two-hour walk around town. Along the way, you'll see the famous historical landmarks spanning the ages. These include the ruins of Roman temples, forums, arches, and even pre-Roman fortifications that still stand today. One of the more recent highlights you'll visit is the Duomo (Cathedral of Santa Maria Assunta). This Romanesque/Gothic masterpiece dates to the 12th century, and inside are frescoes painted by Florentine Renaissance artist Filippo Lippi. 

After the tour, you can continue exploring on your own. Another icon you shouldn't miss is the Rocca Albornoziana. This 14th-century castle is perched on a hill overlooking the town and is an impressive example of medieval military architecture characterized by its massive stone walls, towers, and battlements. Hike up its towers and enjoy sweeping views of the rolling green hills, vineyards, and olive groves surrounding Spoleto.

Day 20: Day Trip to Piediluco & Marmore Waterfalls

Buckle up for another day trip! This time, you'll forgo cities and towns and focus on Umbria's unspoiled nature. It begins with a 45-minute drive from Spoleto to Piediluco. This idyllic little town sits on the shores of Lake Piediluco at the base of a pyramid-shaped hill blanketed in lush forest. 

A short drive away is Marmore Waterfall (Cascata delle Marmore), one of Italy's tallest waterfalls. The largest of its three-tiered cascades plunges an impressive 165 feet (50 m). Even more interesting, this marvel is human-made, created by the Romans in the third century BCE. You can experience the falls' raw power and sheer beauty from viewing platforms and snap plenty of photos. Afterward, you'll transfer back to your hotel in Spoleto.

Day 21: Drive to Rome, Depart

It's time to embark on the last leg of this grand self-drive adventure. Enjoy an early breakfast, then hit the road on a two-hour drive south back to Rome. At the airport, you'll drop off your rental car and catch your flight home. Safe travels!

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