Cycling Alentejo, Portugal – discovering the famous wine country on a bike

Cycling Alentejo is an unforgettable way to explore this famous wine country. This region is renowned for it’s gastronomy, wines and both moorish and medieval heritage. It’s laidback rural appeal and flat backroads make it accessible to everyone who loves both road cycling or bicycle touring.

Want to know what it’s like to ride by the Alentejo region? Read below for a detailed, day by day description of our Alentejo bicycle tour.

Day 1 – Cycling Alentejo – Transfer from Lisbon to Marvão – Free day to explore Marvão

On the first day of your tour, we’ll welcome you in Lisbon and provide a comfortable transfer to the enchanting hilltop village of Marvão, located in the heart of Alto Alentejo-just a scenic 2.5-hour drive from the capital’s airport or your hotel. As you leave the bustling city behind, the landscape transforms into the serene beauty of inland Portugal, culminating at this hidden gem near the Spanish border.

Marvão is a unique and peaceful walled town perched atop the São Mamede mountain range, offering breathtaking panoramic views and a palpable sense of history. Once a strategic military outpost, this 9th-century fortress town is the ideal starting point for your journey through Portugal’s timeless landscapes.

After checking in at a charming boutique hotel nestled within the fortified walls-boasting stunning views of the surrounding countryside-you’ll have the opportunity to explore at your own pace. Wander through the cobbled streets, visit the impressively preserved castle, and soak in the atmosphere of a place where history comes alive. The castle’s origins are attributed to Ibn Marwan, a 9th-century Islamic knight, and it was later captured by Christian forces in the 12th century, adding to the town’s rich cultural tapestry.

Day 2 – Cycling Alentejo – Marvão – Crato – Alter do Chão

Your first cycling day begins in spectacular fashion with a long, invigorating descent from the hilltop fortress of Marvão. As you coast downhill toward Santo António das Areias and Beirã, take in the dramatic transformation of the landscape. This part of northern Alentejo is marked by imposing rock formations, expansive pastures, and the ever-present sight of grazing cattle, offering an authentic slice of rural Portuguese life.

As you glance back, you’ll spot Marvão once more, now a distant silhouette atop the Serra de São Mamede. It’s a humbling moment that reminds you how far you’ve already come.

Your next stop is the charming village of Castelo de Vide, home to one of Portugal’s most historically significant Jewish quarters (Judiaria), dating back to the 13th century. This beautifully preserved town invites you to step back in time as you cycle through its narrow medieval streets. Key highlights include the hilltop castle, the Synagogue and Jewish Museum, the Church of Santa Maria da Devesa, and the iconic village fountain. It’s also the perfect place to pause for a coffee break while soaking in the town’s peaceful atmosphere.

From Castelo de Vide, your route flows downhill once again before transitioning into the gently undulating rolling hills of Alentejo. As the landscape opens up, you’ll notice fewer rocky outcrops and a drier, more golden terrain that defines this region’s unique charm.

Your next landmark is Flor da Rosa, near the village of Crato. This peaceful hamlet is best known for the 14th-century Monastery of Flor da Rosa, originally built for the Order of Malta. Today, it has been elegantly restored and transformed into a stunning historic hotel. Guests on our premium package even have the opportunity to spend the night in this remarkable setting.

The final stretch of the day takes you along tranquil country roads to Alter do Chão, where your hotel awaits. This unique property is a beautifully preserved 16th-century convent, featuring original architecture, a historic chapel, and a serene swimming pool. It’s the perfect place to relax and refuel with some well-earned post-ride snacks.

Before dinner, we recommend a stroll through Alter do Chão to visit the nearby castle, located just a few steps from your hotel. Explore the town’s charming streets and discover some excellent local restaurants to complete your day of history, culture, and unforgettable cycling.

A cyclist in a bike tour approaches the Flor da Rosa Monastery, a 14th-century gem turned boutique hotel.

Day 3 – Cycling Alentejo – Alter do Chão – Estremoz – São Paulo Convent

On your second day of riding, you’ll explore the rolling hills of Alentejo, surrounded by the region’s iconic landscape. Your first stop is the village of Fronteira, one of the largest in the area. To get there, you’ll cross a narrow Roman bridge over the Vide River and begin a gentle ascent into the village center. It’s a great place to pause for a coffee or stock up on essentials, and you’ll likely spot friendly locals wearing their traditional Alentejano caps (bóinas), a charming cultural touch of the region.

Back on the road, you’ll ride along peaceful secondary roads with minimal traffic. The clean air, open countryside, and patchworks of vineyards and olive groves create a serene and truly authentic cycling experience. The route then leads you through Sousel and onwards to the historically rich town of Estremoz.

Once you arrive in Estremoz, its historical importance becomes instantly clear. Dominated by a 12th-century castle and former jail, this town once played a key role in Portugal’s primary line of defense. Today, wine production is its most prominent industry, with numerous acclaimed wineries operating in and around the area. You’ll also notice the abundant use of marble throughout the city—from sidewalks and public art to the façades of buildings like the castle and old jail—thanks to the region’s natural marble deposits.

Take time to explore the city center, where you’ll find excellent options for lunch or a snack. Estremoz has a thriving food scene, with restaurants like Mercearia Gadanha and Cadeia Quinhentista among the most highly rated.

If you’ve selected our premium hotel package, your accommodation tonight will be the elegant Pousada de Estremoz, a former royal palace. From there, take a stroll to the famed Ivory Tower and enjoy panoramic views over this magical city.

Quiet backroads and golden landscapes make Alentejo a dream destination for cycling enthusiasts.

Day 4 – Cycling Alentejo – São Paulo Convent – Monsaraz

Leaving behind the beautiful São Paulo Convent (or Estremoz, depending on your overnight stay), your day begins with a peaceful, extended descent toward the nearby village of Redondo. From there, the route joins a quiet national road that gently rolls through the scenic countryside, leading you to Alandroal—a beautifully preserved village where the castle stands proudly as the central landmark.

Alandroal is a perfect spot for a short break. Grab a coffee and try some of the delicious local pastries, a simple pleasure that’s hard to beat after a good morning ride.

From Alandroal, the road becomes even quieter, with virtually no traffic. You’ll ride under the sun through a tranquil landscape of olive trees, vineyards, and cork oaks, all around you. The atmosphere is peaceful and immersive—ideal for connecting with the land at your own rhythm.

Along this stretch, you’ll cross a serene lake hidden in the countryside, which is actually part of the Alqueva Reservoir. This is the largest artificial lake in the Iberian Peninsula. As you continue riding, you’ll soon realize just how vast it is when you reach your destination for the day.

After passing the lake, the road winds through large olive plantations and gently returns to rolling terrain for the final kilometers of the ride.

As you approach the final stretch, you’ll begin to notice a dramatic ridge rising on the horizon. At its summit is Monsaraz, one of Portugal’s official Seven Wonders and your overnight destination. To reach it, you’ll tackle the steepest climb of the day. It’s a short but rewarding ascent, a test for your legs and a treat for the soul. The views become increasingly spectacular as you climb, especially as the Alqueva Lake comes into full view.

Just before reaching the walled village, you’ll come to a roundabout where a viewpoint awaits on the left. Be sure to stop here and take in the breathtaking panorama of the lake and surrounding plains. Although artificial, the lake was created in 2002 following the construction of a dam for water supply and irrigation, and it has since blended seamlessly into the natural landscape. From this vantage point, it’s easy to forget it was ever man-made.

Your hotel is just a few meters ahead, located conveniently at the entrance to Monsaraz. This small and comfortable property offers a swimming pool and peaceful atmosphere, perfect for a well-deserved rest after your ride.

Exploring Monsaraz is a must. This one-of-a-kind village was reclaimed from the Moors in the 12th century and played a crucial role in defending the region against Spanish invasions. Mostly built from lime and shale, Monsaraz is home to a remarkable church, cobbled streets that feel frozen in time, and a quiet charm that makes it a perfect spot for sunset. Grab a glass of local wine and watch the sky change over the vast Alentejo plains.

Be sure to visit the castle, partly in ruins but still the highest point in the village, where you’ll enjoy unforgettable views of the Alqueva Lake.

For dinner, we highly recommend Sabores de Monsaraz, located right in front of your hotel. It’s a truly sui generis place with some of the best food you’ll find in Alentejo. There’s no need to worry about choosing from a menu—just let Dona Isabel, the owner, take care of you. Her warm hospitality and incredible cooking will be a highlight of your stay.

Monsaraz, one of Portugal’s most charming hilltop villages, blends history, wine, and warm hospitality.

Day 5 – Cycling Alentejo – Monsaraz – Évora

Start today’s ride with a gentle descent from Monsaraz, taking in the sweeping views over the beautiful Alqueva Lake. After this scenic start, you’ll enter a flat stretch that continues for about 15 kilometers toward Reguengo de Monsaraz.

Halfway through this section, you’ll pass through the small village of São Pedro do Corval, known across Portugal for its traditional pottery. We recommend stopping to visit some of the local artisan workshops, where potters are often working live in their studios, continuing centuries-old techniques.

Back on your bike, the route takes you into Reguengos de Monsaraz, home to Herdade do Esporão, Portugal’s largest winery. With over 700 acres of vineyards and olive groves, as well as a wine museum and historic aging cellars housed in a castle, it’s an impressive destination that showcases the rich winemaking tradition of the region.

Leaving Reguengos, the ride continues along quiet roads that wind through village after village. The scenery remains deeply authentic, with untouched landscapes and friendly locals that embody the spirit of Alentejo.

In Montoito, you have the option for a quick coffee break or to continue on until you spot an unexpected sight rising from the countryside: Valongo Castle, surrounded by vineyards. Built around 1280, this structure once served both military and noble purposes, and today it stands as one of the best-preserved examples of medieval architecture in Portugal.

From there, you’ll pass through Nossa Senhora do Machede, another opportunity for a relaxed stop, before beginning the final leg of the ride toward Évora.

You’ll finish the day in Évora, a UNESCO World Heritage city and the cultural heart of the Alentejo region. Your hotel for the next two nights is ideally located within the ancient city walls, making it the perfect base for exploring the historic center on foot.

Évora is packed with remarkable landmarks. Visit the grand Gothic Cathedral, dating back to the 12th century, and the haunting Church of São Francisco, which houses the famous Chapel of Bones, its walls lined with human bones and skulls. Just a short walk away is the Temple of Diana, a well-preserved Roman structure from the 1st century, and the Giraldo Square, the city’s main gathering place since the 16th century.

The presence of Évora University adds youthful energy to this deeply historic city, blending heritage with a vibrant atmosphere full of life, culture, and great gastronomy. You’ll need time to explore it all, but don’t worry—tomorrow offers another opportunity to dive deeper into this unforgettable city.

Day 6 – Cycling Alentejo – Évora – Arraiolos loop

For your last day in the saddle, you’ll enjoy a short and gentle loop ride from Évora to Arraiolos, designed to give you plenty of time to relax and explore Évora in the afternoon.

Departing from your hotel inside the walled city, you’ll begin the ride heading north along a quiet national road. Soon, you’ll leave the main road behind and transition to peaceful rural backroads, where the characteristic Alentejo landscape surrounds you with its wide-open skies and tranquil atmosphere.

Along the way, you’ll pass by some of the region’s most renowned wineries, including Cartuxa and Fita Preta. These are excellent options for a post-ride wine tasting if you’re looking to savor one last flavor of Alentejo.

When you reach Arraiolos, you’ll be halfway through today’s ride. Here, the only climb of the day awaits—a gentle ascent through cobbled streets lined with the traditional whitewashed houses painted in blue and yellow. At the top sits the 13th-century Arraiolos Castle, partly in ruins but full of character. Take your time to walk the perimeter of the castle walls and enjoy stunning 360-degree views across the region. From here, you’ll be able to spot Évora to the south and the Serra D’Ossa to the east—where you conquered the longest climb of the tour just a few days ago.

At the summit, don’t miss the Nossa Senhora do Castelo Church, a beautifully preserved and still-active chapel, painted in the signature white and blue colors of the region.

After descending from the castle, ride into the heart of Arraiolos, where we recommend a coffee stop and a visit to one of the local tapestry shops. Arraiolos is famous for its handmade wool and jute tapestries, known as Tapetes de Arraiolos. This traditional craft has been practiced here since the 17th century, though the Ponto de Arraiolos stitching style dates back even further.

Leaving Arraiolos, you’ll follow a flat section through quiet backroads toward Igrejinha, passing the small but scenic Divor Dam. The final stretch of the ride brings you over gentle rolling hills, dotted with cork oak trees and vineyards, offering a peaceful and fitting end to your cycling journey through Alentejo.

Back at your hotel in Évora, the afternoon is yours to enjoy. Whether you choose to explore more of the city or unwind with a wine tasting at one of the nearby wineries, this final day offers the perfect balance of riding, culture, and relaxation.