A Unique Northern Spain Itinerary: Medieval Towns to Captivating Culture

Madrid is a delightful city when you’re on two feet. Compact and charming, it’s full of angled lanes and maze-like walkways, which open out onto elegant plazas consumed by the smells of hot chocolate and coffee. Today, you are greeted at the airport and transferred to a five-star hotel in the heart of the old city where you are surrounded by ornate architecture from across the centuries. The Plaza Mayor is one place to start, perhaps for a glass of red wine beneath the rustic ochre hues of the townhouses. Down at Plaza de la Villa, the atmosphere is even more laid-back and is perfect for settling into the Spanish rhythm after the international flight.

Colorful townhouses rise around you as a private Madrid walking tour begins. Soft yellows, rustic reds, pleasant hues of blue and green are all juxtaposed on narrow city lanes. There is little traffic or noise, just the tip-tap of your shoes and the chatter from al fresco cafe terraces. History is etched into these walls, from tales of royalty and the conquistadors to those left behind by legendary artists. On today’s walking tour, you spend one to two hours taking these back lanes, listening to the city’s narratives. After a break for chocolate and churros, there is a range of options of where to go, from the royal palace to the Prado Museum, where your guide provides additional insight into the art and design. On this relaxed private tour, you finish up with lunch at one of Madrid’s local haunts, savoring a fusion of tastes that come from all around the country.

A magnificent Roman aqueduct guides you into Segovia, marking the landscape for miles around. It lures you forward, with two stories of scorched red brick and evocative design, a memoir to a very distant time. Earlier today, a luxury hire car is dropped off at your hotel. It does not take long to leave the city behind and be amongst the rural landscapes of Castile, where rolling plains are punctuated by fairy tale villages from the Middle Ages. Park and settle into a handpicked hotel within Segovia’s old town, where a private guide greets you for a two-hour walking tour. You ascend steep streets of gothic architecture, toward the castle where Queen Isabella was crowned. Centuries merge in this city, and you need a guide to piece together such contrasting narratives. For the evening, you have a dinner reservation at an old restaurant close to the Alcazar, the best place to taste the roast suckling pig that Segovia is famous for.

Mystical names dominate the discovery in Avila, where Santa Teresa de Jesus and San Juan de la Cruz are written into the city walls. Lost on the plains of Castile, seemingly unconnected from the world, the city has stood still for hundreds of years, enclosed by some of the world’s finest medieval walls. Nothing appears to have changed, and a local guide narrates the tales of conquistadors, who returned with treasures to fund what was one of the continent’s most prosperous cities. Church bells reverberate here, ringing out from gothic spires and Roman-inspired bells. This World Heritage city immerses you in the 16th century until you wander beneath the city walls and also find a legacy to the 11th century.

Salamanca is the third of the World Heritage cities on your route. Its vibrant atmosphere is ideal for an arrival in the late afternoon. Your hotel overlooks the Plaza Mayor, perfectly situated for a festive evening in the old city. A local guide leads you on a one-hour tour of the major highlights: houses painted with shells, cathedrals and university buildings that redefine old-world elegance, and palaces that shimmer white in the afternoon sun. Like Castile’s other cities, there is a real enchantment to walking without a map and following the maze of alleyways into the past. Every angle is a photo, every cafe is a place to embrace local culture, and each street an immersion into a city that was almost completely forgotten after the 16th century.

The road to La Rioja is a dreamy one, twisting out of the plains then crossing the mountains with landscapes of red and green all around. Stop at Burgos en route, home to a magnificent World Heritage cathedral that is surrounded by typical cafes. Laguardia is your base for the next three nights, so park the car and explore on two legs, wandering randomly through this medieval village obsessed with wine. Almost every house has its own large cellar, carved into the rock below. Local bars have huge menus with hundreds of Rioja wines and vintages available. You will quickly come to appreciate the local style with subtle blends dominated by the Tempranillo grape. Look out specifically for 2005 and 2001 vintages which have gone down in local folklore. Your hotel is within this tiny village, and for the next three nights you will soak up the languid atmosphere, one that is dictated by a bottle of red at lunchtime.

So many wineries deserve attention in Spain’s most famous wine region. Marques de Riscal, where a cathedral of vintage wine bottles dates back some 150 years. Muga is the producer of so much fine wine that they have four specialist staff solely dedicated to making oak barrels. Most of the vineyards are open by appointment only, and your guide takes you to a selection, encompassing the nuances of tradition. There is little variety in the grapes, although the wines are aged differently, up to two years in French oak for the Gran Reservas. Each vineyard has a youngish Crianza, along with a Reserva and Gran Reserva. When locals guide you, all manner of vintages may be opened, enabling you to taste and compare Gran Reservas from the last three decades. Included on the tour is an opulent lunch at one of the vineyards, the strong meat flavors pairing perfectly with the region’s wine.

Vineyards are clustered around the La Rioja towns, and there is a lot to taste within a short distance. Today, you get a new perspective on the region, first soaring across the vineyards in a hot air balloon, watching how the lines of grapes bake in the sun. Touch down to a glass of sparkling rose and a platter of snacks, then continue the tasting on horseback, clip-clopping through the vines to three different wineries. It is an elegant journey, the rounded scents of Tempranillo going perfectly with this style of discovery. Like yesterday, a long Spanish-style lunch complements the wine, enjoyed over two to three hours.

San Sebastian is the city of regal tastes and ornate townhouses. Europe’s gentry has been visiting here since the 19th century, lured by fine dining restaurants and an atmosphere of grandeur. Elaborate balconies gaze down on narrow cobbled streets, 19th-century hotels overlook broad curved beaches, and it is impossible to find anything out of place. This has long been Spain’s most glamorous city, perfectly perched on the ocean, backdropped by rugged cliffs. Your hotel is legendary, recently renovated to celebrate its century-old history, boasting a haven of chandeliers and decadent dining rooms. After checking in, you go on a one-hour walking tour of the old city, taking in the major monuments before an afternoon at leisure. You may consider walking the promenade past the beaches and marina. San Sebastian has numerous entries in the World’s Top 50 Restaurants, and this evening you have a reservation at one of them, where 12 small courses showcase the best of Basque fine dining.

Spain’s northern coastline is rural and full of charm. You will cross green mountains and rivers to neighboring France, barely an hour away, where chic Biarritz is a meeting place of French art, Basque culture, and Spanish influence. Uncover the aristocratic buildings of Hondarribia, wandering behind the medieval walls to artistic cathedrals and churches. Stop for lunch in Getaria, a quiet fishing town with iconic seafood. Then continue down the coast to Bilbao, the largest city in Basque. Leave your car at the hotel, and it will be picked up by a representative. Then set off on a pintxo tour. These are small dishes, similar but distinct from tapas, that line the bar area in dozens of establishments. Each bar has its specialty. Test your sense of adventure by trying their roasted pulpo (octopus), Iberian hams, creamed sea urchin, and find that everywhere encourages indulgence. Try a couple in each bar, piecing together the street food flavors of Basque, a great contrast to the local gastronomy of yesterday’s evening. Your guide knows which bar is famous for what, helping lead your discovery of Bilbao’s pleasures.

Bilbao lounges along the river, colorful apartments of red and green reflected in a meandering waterway. On one side of the river is a legacy to the past, a labyrinth of lanes leading to cathedrals and squares from the 17th century. On the other side is the glamour of the late 19th century, where art deco apartments stand on broad tree-lined boulevards. Along the riverfront is 21st-century Basque, where the cityscape is dominated by Frank Gehry’s Guggenheim, a masterpiece of design and contemporary art. In particular, you will have the opportunity to see the 1950s Jackson Pollock commissioned by Peggy Guggenheim. It is worth visiting for the building alone, an extravagant titanium structure that has become an icon of modern Europe. Bilbao is a relaxed city, and you can see various highlights on foot, before joining the locals in the pintxo bars, sipping on wine that comes from La Rioja. You will find that Bilbao is proudly Basque, but they will happily cede that their neighbor’s wine is better.

You depart from Bilbao’s small airport after a chauffeured airport transfer. There is time for a typically laid-back breakfast at the hotel and a short walk through Bilbao’s old town before departure.