Alentejo

Alentejo - vineyard cycling

This wonderful cycling holiday takes you through a green, gently undulating landscape dotted with medieval towns, vineyards, cork oaks and olive trees. You’ll stay in authentic castles, monasteries and palaces that once belonged to Portugal’s royal family and clergy, now offering magnificent accommodation for our guests. You will also have the opportunity to explore Evora, a historic city with many Roman remains and a UNESCO World Heritage Site.

As well as visiting vineyards, you’ll also learn the art of wine production and sample some of the best wines in the world. Authentic Portuguese handicrafts, such as tiles and ceramics can be found along the way, and the Alentejo is also known for its delicious and flavourful cuisine. Enjoy long, delicious meals dominated by bread, beans, olives, locally produced meats and cheeses. This is the perfect cycling holiday for food and wine lovers with an interest in culture and history!

Difficulty level

The daily stages vary between about 26 and 70 km and every day there is a shorter or longer tour to choose from. The journey is entirely on tarmac and is slightly hilly. We rate the trip as easy: 2 on a 5-point scale.

Weather conditions

The climate in the area is very mild, as it is close to the Atlantic Ocean. Temperatures average around 15°C throughout the year and extreme temperature fluctuations are rare. The summer months tend to be dry and warm, while spring and autumn are mild and ideal for cycling, although there is some risk of rain.

Highlights

  • Charming and historic hotels with lots of character.
  • Stunning green landscape, lined with cork oaks and olive trees.
  • Alentejo's flavoursome cuisine, vineyards and wine tasting.
  • Evora, a historic city and a UNESCO World Heritage Site.

Quick facts

Travel duration: 7 days/ 6 nights
Travel period: 4/1 - 15/12
Grade:
Easy. Average 25-50 km/ 150-400 m per day. Day by day trip grading, see "program" on each trip.
2
Accommodations:
Trip type: Self guided cycling holidays
Price example: From 1,360
Meals: Breakfast

Prices per person in EUR

This trip is available from 4/1 – 15/12, with any arrival day.

7 days/ 6 nights From 1,360 Book your trip

Period 4 people, 2 double rooms Double Room - shared bed Twin Room - separate beds TRP - Triple Room SGL - Single Room
2025-10-27 2025-12-15 1,360 1,430 1,430 1,430 2,060
2026-01-04 2026-03-26 1,360 1,430 1,430 1,430 2,060
2026-03-27 2026-04-05 1,590 1,660 1,660 1,660 2,210
2026-04-06 2026-04-26 1,650 1,720 1,720 1,720 2,270
2026-04-27 2026-06-26 1,590 1,660 1,660 1,660 2,210
2026-06-27 2026-10-15 1,650 1,720 1,720 1,720 2,270
2026-10-16 2026-10-26 1,590 1,660 1,660 1,660 2,210
2026-10-27 2026-12-15 1,360 1,430 1,430 1,430 2,060
Book your trip

Prices quoted are per person and include:

  • Private transfer to/from the airport
  • Briefing meeting with our local guide on arrival day
  • Accommodation 6 nights incl. breakfast
  • 1 dinner
  • Mobile app with GPX files for digital maps and navigation
  • Digital roadbook with all travel information (in English)
  • Information sheet with practical information for the trip
  • Luggage transport
  • 24-hour emergency phone for urgent matters

Not included:

  • Bike hire
  • Transport to and from destination
  • Lunches and dinners
  • Other not mentioned under what is included

Optional extras:

  • Bike hire
    • 21-27 speed hybrid bike incl. helmet, repair kit: 194 Euro
    • Electric bike incl. helmet, repair kit: 347 Euro
  • Extra hotel nights at the start or end of the trip: Contact us for prices.

Itinerary

Day 1 Arrival in Estremoz

Your journey starts in Estremoz, a historic town where you will stay in the royal town castle, a historic building and now a hotel. From here, you will enjoy stunning views of Estremoz and the vast Alentejo plain.

Day 2 Cycle from Estremoz to Vila Viçosa - 67 or 23 km

After a hearty breakfast, you’ll cycle through villages and historic landscapes with traces of historical battles and conquests. Today’s ride will take you to Vila Viçosa, the marble capital of Portugal, where you can visit the Ducal Palace, built in the 15th and 17th centuries. You’ll have plenty of free time today, so we suggest you get out and enjoy the centre and the charm of the streets.
67 km (23 km), +500 m (+200 m)

Day 3 Cycle the Vila Viçosa loop - 27 or 51 km

A wonderful day in sight! The tour is a loop that starts and ends in Villa Viçosa. You start the day by heading towards Spain, through a landscape of cork trees and olive groves. Enjoy the experience of the beautiful Guadiana River, which separates Portugal from Spain. We reccomend a stop in Juromenha, a picturesque village overlooking Spain.
27 km (51 km), +600 m (+300 m)

Day 4 Cycle from Vila Viçosa to Redondo – 41 km or 29 km

After a quiet evening, you will leave Vila Viçosa. Through cork forests, warm winds and a cosy atmosphere you will arrive in Redondo. The town’s combined hotel and museum houses an impressive collection of tiles and ceramics, dating back centuries and typical of the Alentejo. This building was once a monastery and tonight it is your turn to sleep where kings slept in the 15th century! The day ends with a wine tasting at the wine museum, located in the city centre.
41 km (29 km), +470 m (+400 m)

Day 5 Cycle from Redondo to Evora – 51 km

Today you will cycle on rolling green hills, past pristine vineyards and abandoned castles. Here, the past meets the present and ancient world heritage meets modern local cultures. Today’s destination is Evora, the most beautiful historic city in the country and a UNESCO World Heritage Site. Get out and enjoy this gem when you arrive!
51 km, +400 m

Day 6 Cycle the Evora loop - 46 km or 70 km

Évora has more than 2000 years of history to tell, but after a late breakfast it’s still time to explore the surroundings. Today’s loop will take you to Arraiolos, a town well known for its colourful, hand-knitted woollen tapestries – a must-have in your living room at home! This is the last day so once back in Evora, we recommend a worthy ending with a good, local meal and Portuguese wine. Saúde!
46 km (70 km), +400 m (+600 m)

Day 7 Departure day

We at EverTrek hope you have had a great trip!
We hope to see you again.

Accommodations

During this trip you will stay in 4 & 5-star hotels.

7 days/ 6 nights

NightPlaceAccommodation
Night 1EstremozHotel *****
Night 2Vila ViçosaHotel *****
Night 3Vila ViçosaHotel *****
Night 4RedondoHotel ****
Night 5EvoraHotel ****
Night 6EvoraHotel ****

Route map

Getting to the destination

Plane

The nearest airport to fly to is Lisbon Airport (LIS).

Transfer

Private transfer to/from Lisbon Airport is included in the tour price.

Our travelers’ reviews

Scroll down to read reviews from our guests.

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Reviews

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1 - 5
Review for alentejo
5/5
Enjoyable cycling in Alentejo
Our cycling was a warm and magical experience. The cycling on the first day was quite short, and despite stopping for a coffee in Borba, we arrived early at our Pousada in Vila Vicosa. The hotel was an old monastery and the tranquility was total. The cycling during the following days was easy, but a bit hilly most of the time. We cycled through endless plains with cork oaks and eucalyptus. All the hotels were great, but the highlight was Convento de Sao Paolo with its pools, terraces, and fantastic food.
Review for alentejo
4/5
Alentejo and Vineyards
We are very satisfied with our trip. The accommodations were very nice, especially the hermitage. The bikes were very good. The GPS worked very well most of the time. On the first day, Lennart was wearing sunglasses, and we went the wrong way because the colors appear differently then. A warning might be in order. On a couple of days, we had trouble getting the GPS started, but that was resolved. At times, there were many vehicles driving very fast.
Review for alentejo
4/5
Alentejo and vineyards
Premiere cycling with you after previously using a competitor. The GPS navigation was a very positive surprise 👏👏 worked perfectly (power bank a must though). The transfer was also no problem. Very satisfied with the accommodation (Interesting/exciting monasteries). Very good bikes. What was less good was that some sections had heavy and dense traffic, where a slightly smaller and calmer road would have been preferred. The Portuguese cuisine was nothing to write home about, but of course that is not your fault. We will most likely return next year. /Christer
Review for alentejo
4/5
Alentejo-cycling
++: The accommodation was really good, especially the former monastery Convento de São Paulo in Redondo — definitely worth adding an extra night! +: Good bikes +: All transfers and luggage transport worked flawlessly • Some sections were a bit too busy with cars and trucks, with virtually no shoulder. • We had a bike GPS and it worked well, BUT it was unnecessarily complicated to export the routes in the correct format from the RideWithGPS mobile app. Using the app on the phone does not work in practice — it drains the battery far too quickly. Evertrek should really address this. We are definitely satisfied!