Madrid to Lisbon by Road Bike

Begin your adventure in the heart of Madrid at Plaza del Sol, where we meet at a central location near the iconic km 0 marker where all roads of Spain begin. We transfer north out of the city a short distance to avoid traffic, then begin our epic point-to-point cycling journey across Spain and Portugal. You'll skirt the verdant Anillo Verde range, but the real challenge begins just a few kilometers in, as the road gets closer to the sharp climbs of the majestic Guadarrama Mountains. Conquering these climbs will be the exhilarating highlight of your day, setting the stage for a triumphant arrival at your first accommodation in the village of Miraflores de La Sierra.

Today, wake up in the charming mountain town of Miraflores de la Sierra, nestled in the foothills of the Guadarrama Mountains. After breakfast and coffee, start with a gentle warm-up through pine-scented roads and rolling terrain, heading toward the peaceful village of Rascafría, surrounded by alpine meadows and rivers and catching glimpses of high peaks and sweeping valleys. The subsequent descent is exhilarating, bringing you through the ski town of Navacerrada, where mountain energy and crisp air set the tone. Ride into the elegant San Ildefonso, home to the royal palace and beautifully-manicured gardens inspired by Versailles — a perfect place to pause and take in the history and grandeur of the Spanish monarchy. Your final stretch leads through San Cristóbal de Segovia, with panoramic views of the Castilian plains, before you arrive in the historic city of Segovia. A UNESCO World Heritage Site, Segovia welcomes you with its magnificent Roman aqueduct, fairy-tale Alcázar, and charming cobbled streets — the perfect ending to a spectacular day of mountain and heritage on the bike.

Covering around 80 kilometers of captivating terrain, today’s stage introduces you to the beautiful Guadarrama Mountains, home to wildlife including ibex, wild cats, and foxes, as well as gigantic Eurasian Black Vultures and eagles. The gentle climbs and smooth descents make the route both scenic and manageable. Starting in Segovia, perhaps with a walk around town to take in its beauty, you'll soon find yourself cycling a picturesque path through rolling hills and lush forests. The gradients are kind, offering a pleasant challenge without overwhelming your legs. The stage concludes with a smooth descent towards Ávila. Yet another UNESCO World Heritage Site, Ávila stands as one of the most fascinating stops on our route, making it a true highlight of this cycling and cultural adventure. Explore the many sights within its medieval walls, then gather once more for dinner!

Leaving Ávila along the city walls, we embark on another exhilarating day of cycling on high mountain roads. The breathtaking views along the Tormes River, with its Roman bridges, and the charming villages of the Zapatero massif will make the grueling 100 km ride seem almost effortless. This challenging stage offers a perfect blend of natural beauty and historical charm. Later in the day, the route will take us to the town of Barco d'Ávila, steeped in history and cultural depth, with the landscape dominated by its 12th century castle and city walls, as well as a medieval bridge across the Tormes. Enjoy the sweeping views over the surrounding mountains from the hotel terrace and pool.

This stage of our adventure begins with a daunting climb over the Puerto del Tremedal, a favourite pass on the Vuelta a España race. Taking us up to 1,600 meters, this is the opening to a day of intense climbs and remote roads. Along the way, you'll pedal through tranquil oak forests and the quaint village of Candelário. After crossing the valley into the Hurdes region, prepare for another grueling climb of over an hour. This climb will take us to La Alberca, within the stunning Sierra de Francia Natural Park. The day is both challenging and exhilarating, combining the thrill of rugged terrain with the awe-inspiring beauty of the natural landscape. This ancient town is also rich in history and spirituality, the perfect place to linger a while; tomorrow will be a well-deserved day off the bike. Settle into our inviting hotel, with its spa and thermal baths, and make the most of your time in this gorgeous setting.

Today, we set our bikes aside to explore the town, relax at our hotel’s spa and thermal baths, or both! A day in La Alberca offers an enchanting blend of tradition, nature, and flavor—an authentic Castilian village experience that lingers long after you leave. Wander narrow cobbled streets lined with centuries-old half-timbered and granite houses, with wooden balconies and colorful flowers. Relax in the Plaza Mayor, framed by arcade galleries and dotted with cafés—ideal for sipping coffee, people-watching, or enjoying local artisans’ markets. Visit the Baroque Church of Nuestra Señora de la Asunción with its beautiful sacred art, or venture beyond the village on easy nature walks, such as the Chestnut Grove loop or trails through the Las Batuecas valley—and perhaps visit the serene Monastery of Las Batuecas hidden in the forest. Tonight, you are free to choose from the many dining options in the town, including succulent Jamón ibérico, hornazo meat pies, honey, turrón sweets, and hearty tapas in rustic taverns.

Refreshed after our time in La Alberca, we begin with an epic climb up Peña de Francia, one of the most iconic and challenging ascents in western Spain, featuring a summit at over 1700 metres crowned by a monastery known for its wide-open mountain views. Your route will then wind gently downhill through the natural park, offering breathtaking panoramas as you descend into the village of Monsagro, known for its fossil-marked stone walls and peaceful mountain charm. Continue through Serradilla del Arroyo and La Atalaya across rolling hills and quiet farmlands dotted with sheep and fig trees — an idyllic slice of rural Spain. The road carries you west through Zamarra, then northward as you follow the meandering Río Águeda, riding alongside shimmering waters, lush meadows, and golden countryside. A stop in picturesque Sanjuanejo provides a rest before your final stretch, culminating in Ciudad Rodrigo, a magnificent walled town rich in medieval and Renaissance architecture. Enter through one of its historic gates and roll into a plaza where you can toast the day’s adventure, replete with nature, culture, and the freedom of the open road!

This morning, you’ll roll out into the golden Castilian countryside, pedaling through quiet roads and gently-rolling farmland toward Ituero de Azaba and Puebla de Azaba. As you head south, the landscape shifts from green hills and oak groves to a more arid terrain with expansive horizons and the first glimpses of the distant Serra da Malcata. Crossing into Portugal, you’ll enter a new world of granite villages and wild beauty, passing through Aldeia da Ribeira and Bismula, where cobbled streets and stone houses seem to hold stories spanning centuries. The ride continues through Vale das Éguas and Rapoula do Côa, offering peaceful river views and lush valleys that invite you to slow down and breathe it in. Climb gently through traditional villages where rural life continues at an unhurried pace, and every turn offers a postcard-perfect view. Your final stretch leads you through the scenic foothills of the Serra da Estrela and then into Belmonte, a picturesque town perched on a hillside. Here, Jewish heritage, medieval castles, and dynamic vistas of the Cova da Beira valley greet you at the end of an unforgettable day in the saddle. This is also the birthplace of Pedro Álvares Cabral, who claimed Brazil for Portugal in the year 1500.

After breakfast, leave these stone-paved streets behind as you descend toward the lush valley of the Zêzere River, tracing its winding course through central Portugal’s most captivating landscapes. Pass through Valhelhas and Vale de Amoreira, riverside villages surrounded by chestnut forests and granite cliffs, with quiet roads offering gentle undulations and soothing views. As you continue, the route leads into Manteigas, nestled in the heart of the Serra da Estrela Natural Park, where the mountain air becomes crisper. From here, the climb begins — a long, steady ascent along the Zêzere Glacier Valley, one of the most striking glacial valleys in Europe. The road meanders past alpine meadows and granite formations, eventually reaching the Nascente do Rio Zêzere, the river’s stunning mountain source. The highlight of your ride awaits at Torre, the highest point in mainland Portugal (1,993 m), offering panoramic views across the Serra da Estrela range — a true cyclist’s milestone. The descent is pure joy: smooth, sweeping turns take you past the Miradouro do Vale de Loriga, where panoramic views of the picturesque glacial valley unfold below. You’ll ride through terraced hillsides and schist hamlets before reaching the fairy-tale village of Piódão, a hidden gem nestled into the mountainside with its slate-roofed houses and cobbled lanes.

Today’s ride is a bit more relaxed, while still offering some challenges along the way., We ride through the soul of central Portugal, starting from the storybook village of Piódão, nestled in the Serra do Açor mountains, a picture-perfect starting point. As you start you will have a challenging ascent, then you will enjoy pedaling on the top of the mountains where breathtaking views unfold. From here, enjoy the fast descent, another demanding climb, then enjoy a smooth road descent until reaching Lousa. This town greets you with its historical charm, mountain air, and views of ancient castles tucked into the hills. Nearby, Miranda do Corvo brings a mix of culture and countryside, where you can pause for a break in a lively town square or a local café. Your ride finishes in Penela, crowned by a medieval castle and offering sweeping views of the rolling landscape you’ve just conquered.

Begin your cycling journey in Penela, a charming hilltop town crowned by a medieval castle and surrounded by peaceful countryside. As you set off, the road winds through the quiet beauty of central Portugal, passing through the ancient Roman ruins of Rabaçal, where olive groves and vineyards frame the landscape. You’ll continue through the quaint villages of Degracias and Mogadouro, where traditional stone houses and sleepy town squares reflect a timeless rural rhythm. The ride then rolls toward Almagreira, offering open views of forested hills and wide valleys, perfect for a tranquil and scenic pedal. Approaching Pedrógão, the terrain gently shifts as you get closer to the Atlantic coast. You’ll feel the fresh sea breeze as you ride toward the dramatic cliffs of Farol do Penedo da Saudade, a lighthouse perched above the ocean with stunning panoramic views — a perfect photo stop and rest point. From there, the road hugs the rugged coastline through São Pedro de Moel, a beautiful beach town framed by pine forests and crashing waves. This final stretch offers a mix of coastal vistas and forest-lined paths as you cruise into Nazaré, one of Portugal’s most iconic seaside towns, known for its golden beaches, cliff-top views, and legendary waves.

This morning, set off along the coast, taking in the golden sands of Praia da Nazaré’s and the vibrant energy of this historic fishing village turned surfer’s paradise. Your journey continues south to the serene bay of São Martinho do Porto, a natural shell-shaped haven perfect for a short break. Just across the river lies Salir do Porto, where a gentle climb rewards you with expansive views over the ocean and the green hinterlands. From here, follow the scenic road to Foz do Arelho, where the calm waters of the Óbidos Lagoon meet the sea — a surreal landscape of shimmering water, dunes, and wind-blown trees. Ride along the lagoon’s edge, surrounded by the peaceful rhythm of nature. Continue through quiet countryside roads to Vimeiro, where rolling hills and eucalyptus-scented air lead you into Porto Novo, a wild and untamed stretch of coastline with dramatic cliffs and crashing waves— a perfect backdrop for a quick photo or snack break. The final leg of our ride descends into the port villages of Santa Cruz and Ericeira with their cobbled streets, whitewashed houses, and breathtaking sunset views over the Atlantic.

Our last day of riding offers an unforgettable mix of inland and coastal cycling adventure from Ericaira to Cascais. Trace the coastline past Praia de São Julião, where cliffs tumble into wild waves, then climb gently toward the fairy-tale village of Azenhas do Mar — a cliff-perched gem with stunning views and iconic seaside pools. Next comes Praia das Maçãs, perfect for a relaxed pause to soak in the Atlantic air. The route then ascends toward Cabo da Roca, the westernmost point of mainland Europe. The windswept cliffs and dramatic views over the endless ocean are a true highlight and a powerful reminder of nature’s scale. Finally, glide along the coast through pine forests and dunes to Praia do Guincho, a breathtaking beach framed by mountains and sea spray, before rolling into the vibrant seaside town of Cascais. Here, charming marinas, historic mansions, and waterfront promenades mark the perfect end to a truly spectacular ride. We toast to our adventure, then transfer some 30 minutes into the historic centre of Lisbon. Gather once more for a final night dinner to share memories and celebrate this truly grand Iberian voyage!

This morning, you may choose to depart Lisbon, or stay a few days longer in this elegant and intriguing city.