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Cycling and Wine Tours in Portugal

From Lisbon, venture into the royal history of Portugal with visits and stays in castles, palaces, monasteries, and convents. Book this holiday to enjoy the gorgeous scenery and stop to learn about the wine production locally, as you discover vineyards, rows of gnarled cork trees and medieval villages perched on hilltops, with ancient megalithic sites, traditional hand craft workshops, and much more. In addition to the great wine, this region will present you with a unique gastronomical experience, with cheese specialties to pair with your wine and many culinary delights, all specifically Portuguese!


  • Visit to a winery and wine tasting
  • See Alqueva, the biggest lake of Europe
  • Discover fields of cork trees, olive trees, and vineyards
  • Explore the wine country and find numerous local producers
  • See amazing white marble quarries
  • 5 nights accommodation


5 days with instruction in English
Spoken languages: English
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Convent of Sao Paulo

Keen to appreciate its uniqueness, the Convento de Sao Paulo invest in a new form of status in relation to this location. Secluded in the quietness and isolation of the western slopes of the Serra d'Ossa mountain, the Monastery of Sao Paulo was built in 1182 by hermit monks seeking the ideal place to live and pray in peace and quiet. In the heart of the Alentejo province, halfway between the town of Estremoz and the village of Redondo, it is now a comfortable and refined hotel. Several historical accounts confirm that the convent has lodged, over the centuries, some prominent figures of Portugal's history like King D. Sebastiao, King D. Joao IV and D. Catarina de Braganca who, in 1661, married the English King Charles II. The library of the Convent still holds a canvas depicting King D. Sebastiao's stay at the convent, in 1577, on his way to Northern Africa where he died in the battle of Alcacer Quibir. These and other tales and stories are just some of several different reasons that make the Hotel Convento de S. Paulo a marvellous and exciting place to stay.

The Pousada of Estremoz

The Pousada of Estremoz is situated in a privileged place, as is the Castle Estremoz. It is an authentic museum which has a range of antic furniture, wall tapestries, iron decorative pieces and porcelain from other times. D. Dinis ordered the construction of this building for his wife, the queen Santa Isabel, which has given its name to the pousada. Placed in the old city, this was the stage of battles, love and treason. This luxury hotel in Estremoz offers from its gardens and pool, a magnificent panoramic view of Estremoz and the Alentejo plain. The pousada's 29 rooms are spacious and worthy of royalty with beautiful canopy beds which invite you to stay for a relaxing night.

The Pousada de Vila Viçosa

The Pousada de Vila Viçosa, opened in 1996, is installed in the historical center of this Alentejo city. The Pousada is found in the old Convento Real das Chagas de Cristo (The Royal Convent of Stigmas of Christ) ordered built by D. Jaime, the fourth Duke of Bragança in the sixteenth century. D. Jaime ordered the building of this religious house to serve as Pantheon for the ladies of the house and to welcome his daughters from his second marriage who could not decently marry.

Hotel Horta da Moura

Horta da Moura emerges over the banks of the river Alqueva, with the imposing walls of the medieval village of Monsaraz lurking in a spectacular landscape and environmental framework. A rural hotel of excellence; it is a place full of history.

Pousada dos Lóios

Staying the night at the Pousada de Évora, the Loios Convent, means visiting a long distant past, and having the privilege of reliving the history of every stone, every object, including the simple and rudimentary cubicles of the old Canon Regulars’ dormitories, which today have been converted into bedrooms with affable decoration. The walls of the city of Évora, which have been classified as a Heritage of Humanity by UNESCO, hide in their interiors one of most beautiful Pousadas of Portugal. This luxurious hotel in Évora is found in the historical center of the city, between the Gothic Cathedral of Évora and the Temple of Diana. Here you will find that the history, the finesse and the luxury are the vectors that gave rise to this majestic hotel.


Day 1

Transfer from Lisbon airport (LIS) to Convent S.Paulo, close to the village of Redondo, in the countryside not far from Spain. Your lodging is in a beautiful convent on the hills. Dinner will be included tonight. Upon arrival, you will participate in an orientation, as you get outfitted on bikes and cover the days ahead.

Day 2

Start the trip by coming down from the hills of “Serra da Ossa”. Pass by the village of Redondo where you can visit a pottery workshop or the wine museum “Enoteca”, and try some of the best Alentejo wine. Continue rolling through the natural landscape and pass some villages with the typical Alentejo white-washed homes outlined in blue and ochre trim. At arrival to Estremoz, it is recommended that you visit their famous winery, with excellent wines and a rich gastronomy; info will be included in your documentation. Lodging will be in a castle converted into a historical hotel, from where you can admire a superb view of the city of Estremoz and the vast Alentejo plain. Dinner will be on your own tonight.

Day 3

After breakfast at your leisure, you will have time to make it a relaxing day of riding and visiting. Leave the historical Estremoz and ride to another historical place, the Vila Viçosa, the capital of marble in Portugal, where you can visit the Ducal Palace. Dinner will be on your own.

Day 4

Leave Vila Viçosa riding on an old road and passing through a cork forest. At the village of Alandroal, you can contemplate the town’s medieval castle while enjoying a delicious coffee and pastry in the main square. Continue riding through quiet and tranquil roads, crossing small villages and passing close to “Alqueva” lake. In the region, you will find Iron Age dolmens and menhirs - ancient stone constructions - which were the sites of fertility rites. You can visit The Menhir of Outeiro, 3 kilometers north of Monsaraz, and one of the tallest ever discovered. Dinner will be included tonight.

Day 5

A beautiful day riding rolling hills of gold and green, dotted with cork trees, olive groves, and flocks of sheep. Pass by typical Alentejo villages of white-washed homes outlined in blue and yellow trim. Ride nice roads viewing cork trees and pristine vineyards, through pastoral countryside dotted by abandoned castles, to the village of Nossa Senhora de Machede. Your day will end in Évora, which is classified in UNESCO’s International Heritage list. This town is considered one of the most beautiful cities in Portugal since ancient times, and is also rich in top quality restaurants and gastronomical delights.

Day 6

Relax this morning over a well-deserved and long breakfast. Transfer to Lisbon will take place at your preferred time. If time allows, you will pass by a local artisan well known for their authentic Portuguese crafts, on your way.

Included excursions

  • Travel to Estremoz
  • Travel to Evora
  • Travel to the village of Nossa Senhora de Machede
  • Visit the Alqueva lake
  • Visit the Menhir of Outeiro
  • Visit the village of Alandroal
  • Visit the village of Redondo
  • Visit Vila Viçosa


From Lisbon, you will venture into the royal history of Portugal with visits and stays in castles, palaces, monasteries, and convents; these magnificent places were once inhabited by the clergy or the Queens and Kings of Portugal and now are converted into exquisite historical lodgings known as Pousadas. Your journey will begin in Lisbon, and will take you through Redondo, Estremoz, Vila Vicosa, Monsaraz, and Evora.


In addition to the rich wine, the region is a unique gastronomical experience, with cheese specialties to pair with your wine and many other culinary delights, all specifically Portuguese, and all waiting for you to discover them! Included in the price are a few grand meals, but there will be plenty of occasions for you to go out and sample exquisite local meats and cheeses, delicious local cuisine and authentic regional dishes, along with the best Portuguese wines.

Things to do (optional)

  • Admire the scenery
  • Attend local events
  • Go shopping
  • Learn about the region's history
  • Sample local cuisine
  • Visit local artisans
  • Visit local wineries
  • Visit museums

What's included

  • 5 nights accommodation
  • All trip planning and onward travel services
  • Cell phone (for local calls only)
  • Customer incentives and post trip offers
  • Daily breakfast
  • Dinner on day 1 and 4 (without drinks)
  • GPS Garmin for navigation (1 per 2 travelers)
  • Local Lisbon based emergency support by phone
  • Luggage transfers from hotel to hotel
  • Orientation on day 1 at wine museum with gift bottle of wine, or cafe with pastry
  • Personalized departure transfer from Evora to Lisbon
  • Personalized Lisbon transfer by vehicle to first hotel
  • Pre-trip documents including GPX files for personal device if requested
  • Riding routes with maps and cue sheets
  • Suggestions for visitation and dining
  • Wine tasting on day 2 at Joao Portugal Ramos Winery (3 wines 1 cheese)

What's not included

  • Additional meals
  • Drinks
  • Hotel gratuities
  • Optional activities
  • Personal expenses
  • Travel insurance

How to get there

Arrival by airplane

Arrive at Lisbon Portela Airport (LIS) for pick-up and transfer to your hotel. The transfer is included in the price.

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