Portugal Alentejo Vineyards Cycling - 8 nights

Alentejo will surprise by its aromas, colors and heritage. Get ready for a gorgeous cycle over gentle hills and unspoiled golden landscapes. Discover ancient megalithic sites, medieval villages and historical cities. Visit several castles, palaces, monasteries, convents and feel like the queen or king of Portugal!

Find traditional handcraft arts like tiles, pottery or tapestries. Taste delicious gastronomy and the best wine of all times.

Price from : 1780 €
Region : Portugal
Duration : 9 Days / 8 Nights
Level : Active or Pro
Trip : Self-guided
Activity : Biking
Dates : Starts any day

Click below to see hotels versions.

Day 1 :   Arrival in Estremoz

Arrive at the Lisbon Airport or train station where we will meet you and transfer you Estremoz (about 2 hours). An old town where you might feel like a queen or king spending the night in a castle. This is an historical building converted into an hotel from where you can admire a superb view over Estremoz and the vast Alentejo plain. Orientation and bike set up upon arrival to the hotel.

Day 2 :   Loop to Estremoz

Option 1 : 27 Miles - 44 Km  Option 2 : 44 Miles - 71 Km 
Elevation gain 1 : 350 Meters  Elevation gain 2 : 700 Meters 

On the first day you will start cycling by pastoral fields, where the only sounds are the jangling bells of flocking sheep chirping. The landscape is rural passing some villages with the tipical Alentejo whitewashed homes outlined in blue and ochre trim. The wine culture will enter your path on this very first day, as you will visit a winery and start to taste red and white wine! But not much because you still have some kilometers to do, until your resting place.

Day 3 :   Estremoz to Vila Viçosa

Option 1 : 16 Miles - 26 Km  Option 2 : 41 Miles - 66 Km 
Elevation gain 1 : 300 Meters  Elevation gain 2 : 700 Meters 

After a delicious breakfast you will cycle through villages and historical landscapes. Stages of battles, conquers, old communities and great people. Towards Vila Viçosa, the capital of marble in Portugal, you can visit the Ducal Palace, built in the 16th and 17th centuries on the remains of Roman and Moorish buildings. You will have plenty of free time today, we suggest you to walk around and enjoy the charm of the streets at the center.

Day 4 :   Loop to Vila Viçosa

Option 1 : 29 Miles - 47 Km  Option 2 : 40 Miles - 65 Km 
Elevation gain 1 : 300 Meters  Elevation gain 2 : 700 Meters 

A gorgeous day is awaiting you! You will ride towards Spain by a landscape of cork trees, olive groves and flocks of sheep! Admire the beautiful Guadiana river that separates Portugal from Spain and make a stop to visit Juromenha, a picturesque village overlooking Spain. On this day you must face some uphills while return to Vila Viçosa, but your efforts will be reward with a delicious meal at night.

Day 5 :   Vila Viçosa to Monsaraz

Distance 1 : 34 Miles - 55 Km 
Elevation gain 1 : 600 Meters 

It is time to leave Vila Vicosa and ride towards south passing the village of Alandroal. On the way you will feel delight with oleander flowers, shrubs and trees, whose wood was used by local artisans. Arriving in Monsaraz notice that acient cultures and medieval architecture is close by. This village was occupied since the prehistoric era and megalithic monuments are a physical evidence of that. We suggest you to visit Menhir of Outeiro right before check in the new hotel.

Day 6 :   Monsaraz to Redondo

Option 1 : 29 Miles - 46 Km  Option 2 : 39 Miles - 62 Km 
Elevation gain 1 : 500 Meters  Elevation gain 2 : 700 Meters 

After a peaceful night rest, get up on your bike and prepare for a golden landscape until Redondo. Arriving at the hotel - museum you will find an impressive collection of tiles, remarkable ceramic work during centuries and Alentejo culture style. This building was a convent and might feel fascinated knowing that Kings were sleeping here since 1500. To finish the day challenge your taste and learn a bit more about Portuguese wine at the Museum in the center. Don't miss it!

Day 7 :   Redondo to Évora

Distance 1 : 30 Miles - 48 Km 
Elevation gain 1 : 450 Meters 

A beautiful day riding rolling hills of gold and green, through cork trees, pristine vineyards and pastoral countryside dotted by abandoned castles. After all this days rolling hills through past and present, old world heritage, modern local cultures, landscapes and wineries. Today you will arrive at the most beautiful historical city of the country and gather all this experiences in just one place. Can you imagine? Make your way there and don’t stop exploring!

Day 8 :   Loop to Evora

Option 1 : 29 Miles - 46 Km  Option 2 : 42 Miles - 68 Km 
Elevation gain 1 : 350 Meters  Elevation gain 2 : 600 Meters 

Évora is classified in UNESCO’s International Heritage and has 2000 years of history, but after a late breakfast it's time to explore the surroundings. Soon you will arrive in Arraiolos noted for its colorful, hand-stitched woolen tapestries. There must be one fitting of your living room back home! This is the last day riding so you have the opportunity to celebrate with portuguese wine. Saúde!

Day 9 :   Departure day

Time really goes fast when you are having fun! It is time to say goodbye, but we believe the moments and the memories you built have been all worth it. Our Guide will pick you up and drive you to airport.

Average / Day : Distance : 53.67 Km / 33.33 Miles - Elevation gain : 520.83 Meters

Click below to see hotels versions.

Day : 1, 2

Located in a castle originally built for Queen Santa Isabel in the 13th century, this luxury hotel offers panoramic views of Estremoz and the vast Alentejo plain from the palace gardens and outdoor pool. The rooms at Pousada Castelo de Estremoz feature a classic décor, several still maintaining characteristics of the 18th century.

Day : 3, 4

Formerly a convent, this hotel near the historical village of Vila Viçosa is set in lush, landscaped gardens. It has an outdoor swimming pool, a spacious terrace and a restaurant. The elegant rooms at the Pousada Convento de Vila Viçosa are decorated in warm colours. They have wooden furniture, cable TV and a marble bathroom with a bath tub.

Day : 5

Just 2 km from Monsaraz Castle, Monte Alerta is surrounded by a meditation garden, organic orchard and next to the largest artificial lake in Europe, the Alqueva. It features an outdoor pool, hot tub and free Wi-Fi. Decorated in bright colours, Monte Alerta’s rooms have traditional furnishing and tiled floors. All the air-conditioned rooms have an LCD TV and a private bathroom. Guests can start their day with a breakfast buffet of local produce. They can also enjoy their coffee in Monte Alerta's gardens or around the pool.

Day : 6

Surrounded by vast, tree-lined gardens, the charming Convento São Paulo offers 2 outdoor pools and a tennis court. Housed in a former Alentejo convent, it dates back to the 12th century. Rooms are individually decorated with antique furniture. Each is equipped with air conditioning and a flat-screen TV with satellite channels. The marble bathrooms come with bathtubs or showers. The welcoming ambience of A Cascata Bar is a good option for relaxation. Guests can also socialise around the big fireplace or play snooker.

Day : 7, 8

Located in between Évora’s Gothic cathedral and the Templo de Diana, this renovated convent features a courtyard swimming pool together with characteristic arched corridors and vaulted ceilings. The spacious, air conditioned rooms at Pousada de Évora – Lóios are individually styled and decorated with wooden furniture. They include a minibar, work desk and private bathroom with bathtub and shower. Guests can enjoy Portuguese dishes in Pousada’s restaurant, which has a chic indoor dining hall and a covered terrace by the pool. There is also a bar and a large lobby with plenty of seating.

Bikes available for your tour

The characteristics of this bike are presented as an example and are not guaranteed
Please note that any bike changes during the trip may incur an extra fee.

Hybrid bike - Standard
FOCUS KRATER LAKE - ( or equivalent)

You can go for a sporty ride on almost any bike, but few are as versatile as FOCUS cross bikes. They glide effortlessly along roads and ensure ample comfort and puncture-resistance on forest tracks. The seat position is balanced to suit both Sunday outings and a quick spin after work. The robust aluminum frame FOCUS 1.0 Trekking is made according to the latest state of the art. The tube set therefore was butted to bring only material to the necessary places of the power flow. A clean look were offered because the brake caliper sits on the chainstays.



GPS are included on most of our tours since 2008. We change the units every 2 years and always invest in the best models. Simple to use, easy to read, yet sophisticated devices they are available on all of our tours. The routes described in your roadbook are stored as tracks in the GPS unit. You simply have to follow the line shown on the GPS, and enjoy. 1 GPS for every 1-3 people


Our roadbooks are complete packages of information that will help you to guide yourself through the itinerary that we have planned and laid out. We have invested significant time and incorporated the feedback of our customers over many years (since 1997!) to make our roadbooks even better. Our roadbooks include: color maps, highlighted routes, touristic information, orientation points to reach hotels, and easy to follow step by step directions (cue-sheets). Please note that for custom itineraries you will not have cue sheets. Only maps and GPS routes.


Our Travelbooks are complete packages of information that will help you to guide yourself through the itinerary that we have planned and laid out. You will find information about the hotels, itinerary, regional informations...


  • 8 night’s Bed and Breakfast with private bath.
  • Daily breakfast
  • Hybrid bike rental included
  • Personalized welcome orientation
  • Detailed ROAD BOOK, including details maps, touristic information
  • 1 GPS per couple
  • Daily luggage transfers
  • Arrival transfer from Lisbon to your first hotel
  • Departure transfer from last hotel to Lisbon
  • Comprehensive trip literature
  • All technical and emergency support any day

What's not included

  • Airfare to and from the trip
  • Lodging before and after the trip
  • Step by step itinerary and cue sheets
  • Drinks
  • Hotel city taxes
  • Some meals are not included in each destination, which gives you the opportunity to explore regional cuisine on your own. You will find all information needed with our team support in your roadbook.


  • International airport in Lisbon

We recommend booking wine tastings in advance if you want to stop at wineries along your route, if you are interested please contact your tour consultant. 

Tour rates

Contact our tour consultants for more information and an exact rate based upon your travel dates.

Price from* & per person Double occupancy Single supplement
(traveling with a group)
Solo traveler
(traveling alone)
Standard 1780 € 630 € 2690 €
*Rates vary according to hotel availability and specific start date. Please contact us for triple room rates


GPS Included
Biking Roadbook Included
Travelbook Included

Bikes available

Bikes available Options per person
Road Bike Rental
    Standard 90 €
Electric Assisted Bike
    Standard 175 €

Please note that any bike changes during the trip may incur an extra fee.
Bot scann is mandatory