Cycling and Pousadas Adventure in Alentejo, Portugal

An adventure across a beautiful land


Portugal has been producing some terrific wines lately, so I decided to head there for some bicycling and wine tasting. Even though the Duoro is home to Portugal's most popular wines, I headed to the Alentejo region to stay in some lovely pousadas I've had my eye on.

Pousadas are a network of luxury hotels located in some of the most historically important buildings in Portugal, including castles, palaces and convents. It's like staying in a luxury museum with a pool and a fantastic restaurant.

Alentejo is at the forefront of Portugal's wine revolution and the region is home to some fantastic reds. The land is flat and the sun was shining in early April and I was on my way.

Photo courtesy of Portuguese_eyes via Flickr/cc

The Week Begins

I started my week-long journey in Alvito, where I stayed in the Pousada de Alvito, a 15th century castle in the middle of town. I took a stroll through the castle gardens before settling into a nice bottle of local Alentejo red and dinner at the pousada.

On my first day of cycling, I headed off into the Alentejo plain towards Ėvora. The riding was flat and I had a steady tailwind that made it feel like I was being pushed forward. I pedaled through tiny towns, passing people moving in that slow, rural pace you find in the country. I checked out some pottery in Viana do Alentejo in a shop near the town's castle before visiting the Church of Senhora de Aires. I had a nice lunch at a local tasca (a typical cafe in the region) before pedaling on to Evora.
There, I stayed in the Pousada de Evora, next to the Roman ruins in town. I tasted some delicious local Cartuxa red wine by the pool before dinner and a good night's sleep.


Photo courtesy of


Olives, Wine and a Dam

The next day I cycled through olive groves, stopped for a break in Nossa Sra. de Machede at another tasca, and rode to the Castle of Valongo where I took another rest. I ended the day's ride with a wine tasting at the Reguengos de Monsaraz winery before dinner.

From Reguengos, I cycled to Monsaraz where I struggled up the final climb into town after a flat day's stage. The reward is an amazing view from the castle of the Alqueva dam, the largest artificial lake in Europe.


Photo courtesy of King Coyote via Flickr/cc

Convents and Castles

Continuing on in the morning, I headed to Vila Vicosa and the Pousada de D. João IV, set in the former Convent of Chagas de Cristo. The Pousada has kept all of the convent cells, retreats and oratories built by the nuns intact. The restaurant was fantastic, as was the Pera Manca I drank with dinner.

The last stop of my Portugal journey was Estremoz, a city amid the Alentejo plain with wonderful architecture and an imposing tower of the castle in town. I stayed in the castle, now the Pousada Rainha Sta. Isabel. I celebrated my last night with a tasting of wines by João Portugal Ramos, the well known local wine maker. It was bliss.


Photo courtesy of

How To Learn More

If you'd like to see the bike tour I developed from my trip, take a look at BikeSherpa's Luxury Bike Tour Portugal - Castles, Wine and Sunshine. You can stay at many of the same pousadas I did and sample the delicious wines, too.

Robert Reimann is founder and CEO of BikeSherpa, a boutique bike tour company with trips in 16 countries in Europe. He's a native New Yorker that lives in Dresden, Germany.

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  • Alentejo (Portugal) Is a great place to taste good food with fantastic wine.
    Great red wines.

    Jun 04, 2012 at 5:59 PM

  • Hi Snooth
    Come to the Vini Portugal Grand tasting this wednesday and look for Enoforum.
    Taste some great Alentejo reds - white as well.
    Look for Herdade Da Comporta - it is from the coastal region of Alentejo - DOC Setubal Penninsula.
    Let me know if you need an invite -

    Jun 04, 2012 at 8:01 PM

  • Snooth User: NeuWiner
    1065872 1

    Esporao offers outstanding reds- TN, Quatro castas and the Private Reserve. 2008 is an outstanding year for all three wines. However, it is Setubal's Quinta da Bacalhoa Cabernet Sauvignon that impressed me the most. Cheers Alentejo!

    Jun 04, 2012 at 9:23 PM

  • Snooth User: badeye
    160608 6

    Filipe has that right. Alentejo wines are consistently good, and are on par with anything from Douro and Dao (and most everywhere else, for that matter). And the food! Pork and clams(!) Alentejano is one of the world's great dishes. Try it at Luar de Janeiro in Evora, assuming you can find it on those back streets.

    Jun 04, 2012 at 10:43 PM

  • I have been in Portugal last year in august: I found great food, great wine, beautiful places, no traffic at all on the routes, low rate for hotel, restaurant...It's a place to be! Taste EA wines.

    Jun 05, 2012 at 2:36 AM

  • Taking the cue I shall try on cycle at Bordeaux next year.This year I have just done Tuscany,Chianti,Veneto and Ferenze areas of Italy.Wonderful experience.
    Notes on Portugal too collected.

    Jun 05, 2012 at 11:57 PM

  • Excellent article. The Alentejo is also great for hiking. Particularly its Rota Vicentina:

    Jun 16, 2013 at 2:29 PM

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