9 days
All year

This is a charming heritage cycling trip passing by the best wine producers. Alentejo will surprise you for its excellence, aromas, colors, and heritage. Get ready for the gorgeous cycle over gentle hills and unspoiled golden landscapes. Discover ancient megalithic sites, medieval villages, and historical cities. Visit and stay in Castles, Palaces, Monasteries, Convent and feel like the Queen or King of Portugal! Look for traditional handcraft arts like tiles, pottery or tapestries. Taste the delicious gastronomy and best wines of all times. Not enough? Well, we can also suggest some more challenging cycling trips, be it by road or mountain-bike!


9 days

8-nights double room with breakfast Transfer on day of arrival from Lisbon Airport to the first Hotel
Transfer from last Hotel to Lisbon Airport Transfers during the program
Luggage transfer during program  D4 dinner
Trip information / Road-Book One GPS /2 persons
Live Tracker device with SOS
Meals, except otherwise referred Please request more information in case of extras
– Supplements for individual room and solo trips – Alternative Trips Road or Mountain Bike
– Guided Trip – Additional activities & Experiences

Recommended: April – June; September-November

Minimum Travelers:  2

Day 1

Arrival at Lisbon Airport 

Leave the airport for a two-hour drive to EstremozFree evening spending the night at the Castle. 

Day 2

Estremoz Loop (Short 44km +350m | Long 71km +700m) 

You’ll start cycling crossing shepherd fields, where the only sounds are the jingling bells of flocking sheep. 

The typical Alentejo whitewashed homes outlined in blue and ochre and the local wine culture will keep you company on this very first day, during your visit to a winery estate. 

Day 3

Estremoz to Vila Viçosa  (Short 26km +300m | Long 66km +700m) 

Cycle through villages and historical landscapes towards Vila Viçosa – stage of battles, conquers, old communities and great people. Known as the capital of marble you can’t miss visiting the Ducal Palace. You will have plenty of free time today. Check-in at the local “Pousada” and walk around the charming village. 


Day 4

Vila Viçosa Loop (Short 47km +300m | Long 65km +700m) 

A gorgeous day is awaiting you! You will cycle towards Spain by a landscape of cork trees, olive groves and flocks of sheep! Admire the beauty of the Guadiana river  the border between Portugal and Spain and make a stop to visit Juromenha, a picturesque village overlooking Spain. 

On this day you must face some uphills while returning to Vila Viçosa. 

Day 5

Vila Viçosa to Monsaraz (55km +600m) 

Leave Vila Viçosa and cycle south passing the village of Alandroal and the territory of ancient tribes faithful to the mysterious god EndovelicusCycle the steep hill to the fortress village of Monsaraz and enjoy the view over the Alqueva Dam. Check-in at the Hotel. 

Day 6

Monsaraz to Redondo (Short 46km +500m | Long 62km +700m) 

Enjoy a golden landscape until Redondo. Arriving at the 16th century convent-hotel you will find an impressive collection of century-old tiles and remarkable ceramic works of the Alentejo culture. To finish the day’s challenge learn and taste a bit more about Portuguese wines at the Wine Museum. 

Day 7

Redondo to Évora (48km +450m) 

A beautiful day cycling rolling hills of gold and green, crossing cork trees, groves pristine vineyards and graze the landscape countryside dotted by abandoned castles. Today you will sleep at an impressive historical city and UNESCO World Heritage. Make your way there and don’t stop exploring! 

Day 8

Évora Loop (Short 46km +350m | Long 68km +600m) 

Leave Évora’s 2000 years of history behind you and go explore the surroundings. The day leads you to Arraiolos – noted for its colorful, hand-stitched wool tapestries. This is your last cycling day so you have the opportunity to shop and celebrate your trip with good wine.

Day 9

 Departure day 

End of program.  The transfer will take you back to Lisbon.

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