Vila Viçosa, Alentejo, Portugal. Photo via Flickr:Rosino

Overlooking Estremoz, Alentejo, Portugal. Photo via Flickr:Francois Philipp
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Alentejo Vineyards

Portugal Bike Tours

A cycling adventure in Portugal’s wine country

This is a gorgeous bike tour in the Alentejo region of Portugal, over gentle hills through unspoiled green and gold landscapes. You will visit and stay in several historical castles, palaces, monasteries and convents, once inhabited by clergy, kings, and queens, and now converted into exquisite lodging.

During your cycling adventure, you will discover ancient megalithic sites and traditional handcrafted arts like hand-stitched tapestries and Portuguese tiles tucked away in artisan shops. Vineyards, gnarled cork trees, and hilltop medieval villages dot the landscape.

The foodie will delight in the many culinary delights to be enjoyed featuring exquisite local meats, fish, cheese and the best Portuguese wines. In fact, you will have the opportunity to visit a few local wineries, learn about wine production and sample the best wine in the world!

Your cycling adventure will feature Vila Viçosa, Portugal capital of marble, considered a jewel in the treasure chest of Alentejo, and Evora, a wonderful walled town with many Roman vestiges found in its medieval architect that has earned it World Heritage status by UNESCO.

Come and discover why Portugal has been voted one of the top ten travel destinations by Traveller's Choice on this historical Alentejo Bike Tour!


  • Experiencing the charm and character of historical hotels and convents
  • Fields of cork trees, olive trees and vineyards
  • Wineries and wine tasting
  • Arraiolos - famous for its rugs
  • Amazing white marble quarries
  • Évora - a World Heritage town classified by UNESCO

Re-live history itself in each stone, each glance, and each object!

Want to see more bicycle tours in Portugal? We have something for everyone.

Where You’ll Stay

You will stay in charming historical hotels and inns. Please ask us for a sample hotel list!

What’s Included

  • Self-guided:
  • 6 or 8 nights accommodation
  • Breakfasts
  • Maps and GPS device for navigation
  • Hybrid bicycle rental including helmet, tool kit, pump, lock, handle, handlebar bag, and flat/spd pedals
  • Route descriptions and pre-departure information pack
  • Emergency service
  • Liability and personal accident insurance
  • Lisbon Airport transfer to first hotel and briefing about tour
  • Transfer from last hotel to Lisbon
  • Luggage transfer

What’s Not Included

  • Remaining meals
  • Bicycle protection
Length7–9 days
From1119 Rates
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Tour Dates

Possible any day from late September to May 2017. Departures in summertime possible but please note temperatures can reach up to 104 degrees F in the afternoon.

Skill Level

This is an easy to moderate tour on mostly flat terrain with some rolling hills (max 500 meter gradient) on 100% paved roads. This tour will suit those who have some experience and average fitness through regular exercise. Be prepared to cycle at least 4 hours.

Day-To-Day Itinerary

7 Day Tour

Day 1: Arrival
Day 2: Estremoz - Vila Viçosa, 16 or 41 mi. (26 or 66 km)
Day 3: Roundtrip around Vila Viçosa, 29 or 41 mi. (47 km or 65 km)
Day 4: Vila Viçosa -  Redondo, 25 mi. (40 km)
Day 5: Redondo - Évora, 30 mi. (48 km) 
Day 6: Roundtrip around Évora, 29 or 43 mi. (46 km or 68 km)
Day 7: Transfer to Lisbon

Day 1: Arrival
You will be welcomed at  Lisbon airport and transferred  to Estremoz (2h). Lodging this evening is in a castle converted into a historical hotel, Pousada Rainha Santa Isabel, from where you can admire a superb view over the city of Estremoz and the vast Alentejo plain.

Day 2: Bike from Estremoz to Vila Viçosa, 16 or 41 mi. (26 or 66 km)
Today you can choose a leisurely ride or a slightly more difficult one; its up to you! Upon departing historical Estremoz, the ride leads to another historical place, Vila Viçosa, the capital of marble in Portugal. Here you can visit the Ducal Palace, built in the 16th and 17th centuries on the remains of Moorish, possibly even Roman buildings. For centuries it hosted a brilliant court and was a hub of intellectual life. In 1640, Joao IV was the first of the Dukes of Bragança to ascend the Portuguese throne. Although Lisbon then became the seat of the monarchy, Joao IV and his successors continued making frequent visits to Vila Viçosa. (330 m or 700 m elevation change)

Day 3: Roundtrip around Vila Viçosa, 29 or 41 mi. (47 km or 65 km)
You are in for a gorgeous day! You will ride towards Spain through a landscape of cork trees, olive groves, and flocks of sheep! Following the loop of the Guadiana river, you make a stop in Juromenha, a picturesque village overlooking Spain. Returning to Vila Viçosa, you do have some climbing to do but can opt for an easier route. (700 m or 1100 m elevation change)

Day 4: Vila Viçosa -  Redondo, 25 mi. (40 km)
Upon departing from Vila Viçosa, you will cycle on an old country road leading through a cork forest. In Alandroal village, the town’s medieval castle will entice you to take a break, or perhaps the opportunity to enjoy a delicious coffee and pastry in the main square will be enough. Back on the saddle, your ride continues on quiet and tranquil roads, through small villages and leading to a hillier region, the “Serra da Ossa”.  In the village of Redondo, you can visit a pottery workshop or the wine museum “Enoteca”, and try some of the best Alentejo Wine. Your accommodations this evening is a beautiful convent on the hill, São Paulo, situated in the quiet  isolation of the western slopes of the Serra d’Ossa mountain. The Monastery of São Paulo was built in 1182 by monks seeking the ideal place to live and pray in peace and quiet. (500 m elevation change)

Day 5: Redondo - Évora, 30 mi. (48 km) 
The  riding today is simply beautiful, on rolling hills of gold and green dotted with cork trees, olive groves, and flocks of sheep, through typical Alentejo villages of white-washed homes outlined in blue and yellow trim. As you pedal through cork groves, vineyards, and pastoral countryside dotted by abandoned castles, you will appreciate the Portugal of the old and the new. You will end your day in Évora which is classified in UNESCO’s International Heritage list, with its legacy of 2000 years of history. Évora is considered one of the most beautiful cities in Portugal since the ancient times. (450 m elevation change)

Day 6: Roundtrip around Évora, 29 or 43 mi. (46 km or 68 km)
What better place to have either a rest day or opportunity for you to decide to have a short ride or longer ride! If you decide to ride, and you probably will, the route leads to Arraiolos, noted for its colorful hand-stitched woolen tapestries. In the afternoon, cycling through small typical villages, you will have the opportunity to stop at a local winery for a tasting. (350 m or 600 m elevation change)

Day 7: Transfer to Lisbon
You have earned a the chance to sleep in and then linger over breakfast.  The included 1.15-hour transfer to Lisbon can be arranged at the time that you prefer.

9 Day Tour

Day 1: Arrival
Day 2: Roundtrip around Estremoz, 28 or 44 mi. (44 km or 71 km)
Day 3: Estremoz - Vila Viçosa, 16 or 41 mi. (26 or 66 km)
Day 4: Roundtrip around Vila Viçosa, 29 or 41 mi. (47 km or 65 km)
Day 5: Vila Viçosa -  Redondo, 25 mi. (40 km)
Day 6: Redondo - Évora, 30 mi. (48 km) 
Day 7: Roundtrip around Évora, 29 or 43 mi. (46 km or 68 km)
Day 8: Évora to Montemor, 27 mi. (44 km)
Day 9: Transfer to Lisbon

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Email or Call 800-951-4384 +1 570-965-2064

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Customer Feedback

  • J. Sheldrick 7 months ago

    The accommodation was excellent! (although we weren't very please with the location of our room in Evora at the Pousada Convento dos Loios as we were right next to the eating area which was occupied by diners from 7 am for breakfast and up to 10 pm for dinner)

    However, there are two things something that could easily have made the trip more enjoyable: putting kick stands on the bikes and improving the maps and written directions.
    It was incredibly annoying not to be able to stand the bikes up as we stopped frequently for pictures and most of the time, there wasn't anything to lean the bikes against. Having to lay them down on the ground sometimes resulted in the rear pannier getting knocked off centre which then meant readjusting it.

    Even though a gps was provided and was invaluable, we found the maps to be very poor most of the time, one time even the local tourist office couldn't help us! It would be very helpful if simple written directions were included on how to best leave the hotel and / or town to start the day's journey.

    We were impressed with the care and attention given to the safety aspect with the tools and equipment provided including a phone. We very much appreciated being picked up by Francisco at the train station in Pinhal Novo and also by Sofia who drove us from Evora to our hotel in Sintra. Thanks again!

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