Traverse Alentejo by bicycle on this week-long trip through the villages and vineyards of the lesser-known Portuguese region. Discover ancient megalithic sites, castles, monasteries, and rich historical tradition as you cycle over the rolling hills of this unspoiled golden landscape. Along the way, you'll go wine tasting, sample the local cuisine, and clock over 120 miles on your bike.


  • Sample several local wines as you travel through the region
  • Explore historic castles, convents, palaces, and more
  • Discover the romantic countryside as you cycle through meadows and forests
  • Learn about centuries-old crafting traditions still alive in Alentejo's villages

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Portugal Estremoz
Day 2 Estremoz to Vila Viçosa Vila Viçosa
Day 3 Vila Viçosa Loop Vila Viçosa
Day 4 Vila Viçosa to Redondo Redondo
Day 5 Redondo to Évora Évora
Day 6 Évora Loop Évora
Day 7 Departure  

Detailed Itinerary

Day 1: Arrive in Portugal

A peek through the entrance of the 13th-century Estremoz Castle

Welcome to Portugal! Make your way from the airport in Lisbon to the town of Estremoz in Alentejo, about two hours away. This medieval walled city is famous for its white marble houses and buildings, and its many surrounding wine estates. Tonight you'll stay in a castle that's been converted into a hotel with an excellent vantage point over the town and vast Alentejo plains.

Day 2: Estremoz to Vila Viçosa

Vila Vicosa
The grand Ducal Palace in Vila Viçosa

Fill up on a delicious breakfast before mounting your bike for the first excursion of the trip. Cycle through historic villages and sites to reach Vila Viçosa. This sparkling marble town will be your base for the next two nights. Visit the impressive 16th-century Ducal Palace and the town's long plaza lined with orange trees. You'll have plenty of time today to wander around the charming town center.

Distance: 16 miles (26 km) for the short option; 41 miles (66 km) for the long option 
Elevation: 985 feet (300 m) on short ride; 2,300 feet (700 m) on long ride

Day 3: Vila Viçosa Loop

The ruins of the Juromenha fortress overlooking the border with Spain

Today, you'll ride towards Spain surrounded by a pastoral landscape of olive groves, cork trees, and wandering sheep. Admire the beauty of the Guadiana River that defines the border of Portugal and Spain, and stop to explore the sleepy medieval village of Juromenha on the banks of the river. On the way back to Vila Viçosa you'll tackle some hills, but will be rewarded with a delicious meal when you arrive in the evening.

Distance: 29 miles (47 km) for the short option; 40 miles (65 km) for the long option
Elevation: 2,300 feet (700 m) for either ride

Plan your trip to Portugal
Customize your trip with help from a local travel specialist.

Day 4: Vila Viçosa to Redondo

The landscape along the road from Vila Viçosa to Redondo

After a relaxing night in Vila Viçosa, mount your bike and ride through the quiet meadows and cork tree forests until you reach Redondo. This sleepy town with whitewashed houses is famous for its long tradition of producing colorful pottery. Here, you'll find that your lodgings for tonight are also a former convent and current museum.

Explore its impressive tile collections and centuries-old ceramic work that represents Alentejo's signature style. Roam the halls and rooms of the 12th-century convent, where Portuguese kings and queens used to sleep. In the evening, head to the Redondo Wine Museum for a delicious tasting and some insight into Portuguese wine culture and history.

Distance: 18 miles (29km) for the short option; 25 miles (40 km) for the longer option
Elevation: 1,300 feet (400 m) on the short ride; 1,640 feet (500 m) on the long ride

Day 5: Redondo to Évora

Overlooking the city from atop the Evora Cathedral

Today you'll enjoy a picturesque ride along the golden green rolling hills of the countryside to get to the city of Évora. Pedal through cork tree forests and past sun-baked vineyards, and see if you can spot some historic castles along the way. Once you arrive in Évora, there is plenty to see and do.

This charming, old-world city is simply oozing with beauty, culture, and flavor, from its medieval cathedral to its Roman temple to its distinctive cuisine. Stumble upon stunning streetscapes as you wander its narrow roads, visit an ancient megalithic site, and visit some of its many museums. Although its main square, Praça do Giraldo, was once a major site of public executions and rebellion during the Spanish Inquisition, it now lends itself to excellent people watching as you sip on a coffee or enjoy some fine dining in the evening.

Distance: 30 miles (48 km)
Elevation: 1,475 feet (450 m)

Day 6: Évora Loop

The medieval hilltop castle of Arraiolos

Now that you've explored Évora, today you'll ride in a loop of its surroundings. Start with a late breakfast, then head back into the Alentejo countryside. You'll come to the town of Arraiolos, noted for its medieval castle and vibrant, hand-embroidered woolen tapestry rugs (which make for excellent souvenirs!). End your last cycling day by celebrating with a glass of locally-produced wine. Saúde!

Distance: 28.5 miles (46 km) for the short option; 42 miles (68 km) for the longer option
Elevation: 1,150 feet (350 m) on the short ride; 1,970 feet (600 m) on the long ride

Day 7: Departure

A vineyard near Evora

As your week in pastoral Alentejo comes to a close, finish up any shopping or exploring, and take in the last views of its gorgeous landscapes. Your guide will pick you up in Évora and drive you back to Lisbon for your flight home, or on to your next destination. 


Map of Alentejo Cycling Adventure - 7 Days
Map of Alentejo Cycling Adventure - 7 Days