Amazing Alentejo

Ride Across Portugal

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Lisbon, Atlantic Coast, Evora, Estremoz, Monsaraz

7 DAYS, Fully Guided & Supported

Luxury Historical Monument Hotels




Cycling in Portugal is a virtual treasure trove of finds. Bike Portugal's many quiet routes in the Alentejo region as well as the cosmopolitan vibe of Lisbon. Pamper yourself in the most special collection of hotels, both luxurious and historic and with daily cycle routes designed to treat you too.

Experience the great seafaring heritage of the Portuguese capital, Lisbon before you start cycling into the tranquillity of the countryside of the Alentejo. Still mainly rural, bike through marble quarries, cork forests, olive groves and perhaps hear a unique type of polyphonic singing, so if you care to warble a few notes while pushing the pedals, you’ll fit right in.

Cycle to the UNESCO city of culture, Évora and see its atmosphere of medieval European and Roman ruins, the lovely towns of Estremoz and Monsaraz and their hilltop fortresses and the blue and white painted villages that lie in between. Taste the succulent red wines of the area and local specialities of the region, the fresh produce and seafood and the array of sweets to tempt any palate.

Stay in wonderful atmospheric historical monuments, now luxury Pousada hotels and including one of the Alentejo´s best hotels, the Convent do Espinheiro. This is surely a cycle trip for those who enjoy relaxing travel on two wheels, in a varied landscape and rich fabric of past civilizations, wonderfully preserved for the visitor.


Route Map


Intro drinks and walking tour

Lisbon, an ancient place, which as stories hint was founded by Ulysses and harboured many famous explorers is our start Its baking red tile roofs, windows hung with washing and a maze of streets, overlooked by the battlements of the medieval castle make it a wonderful place to begin our trip. We take a private guided tour of the city with Rita & Jose, residents of this illustrious place to fully enjoy it.


Ride Day - 34km (21m) / Ascent - 252m (827ft) 

We transfer out of the capital bustle to start our cycling journey near the coast. After a quick dip of the toe in the Atlantic, go through a natural reserve before heading inland to our impressive ancient castle hotel, high on a buff overlooking the pretty town of Alcacer do Sal, surrounded by… rice paddies! Yes, Portugal is one of Europe´s biggest consumers and growers of Rice. This place has been a castle for a thousand years and the crypt underneath is an excellent museum of Moorish and Roman remains. Dine in the elegant surroundings for our welcome dinner.

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Ride Day - 57km (35m) / Ascent - 600m (1968.5ft) (option to ride upto 92km/57m for those who want more miles)

 Roll through green lush scenery, passing farmers and town´s folk attending the local paddy fields. We head into the UNESCO heritage town of Évora with its magnificent medieval city walls before arriving at our very special place for the next 2 nights – the 15th century Convento do Espinhiero, now a 5 star luxury collection hotel and spa. Relax with a glass of wine by the pool with olive tree views.


Ride Day - 48km (30miles) / Ascent - 435m (1427 feet)

Winding country roads lead us to the beautifully located village of Arraiolos. Enjoy this place where for centuries they have perfected the skill of weaving, their woollen stitched, take an afternoon private guided walking tour of the city by our friend, Maria. Venture into the chapel of Bones (if you dare!). Let your imagination run wild as you spy the huge 17th century aqueduct and Roman temple of Diana – you’ll only wish you brought your toga! Head back and enjoy time at your rural retreat, maybe trying out the spa.


Ride Day - 68km / 42m / Ascent - 783m (2569m) 

We cycle across the taste-bud tingling Redondo wine region, try not to over indulge at our visit local vineyard´s produce! A beautiful forested pass brings us to the interesting market town of Estremoz. A most dramatic cityscape, its medieval castle (our hotel!) looms over the town’s gleaming marble cobbled streets. Take dinner in the great dining room in this most impressive building. You will feel like a king and queen staying is this once royal residence.

Bike Tours in the Alentejo, Portugal


Ride Day - 67km (42 miles) / Ascent - 613m (2011ft) 

Bike the Alentejo, Portugal

Bike this peaceful area with tiny villages and their traditional tile works and Moorish forts. An area of outstanding history and intrigue for centuries, we also can visit a Neolithic site! Arrive at Monsaraz, boasting an awesome hilltop castle and a panoramic vista of both Spain and Portugal. Admire the sunset over the two countries at the Templar Knight castle and enjoy a delicious meal for our celebration dinner.


After a leisurely breakfast wander the ramparts to view over the Portugal-Spain border. Look back at the route we´ve travelled together before going back to the hotel for a final coffee and a wave goodbye to this lovely area and each other before transferring back to Lisbon for onward afternoon connections. Boa Viagem!"

Trip details
Tour Style

Leisure Tour - Guided

Bikes - Road / Hybrid / Ebike

Route: Lisbon, Atlantic coast, Évora, Redondo wine region, Monsaraz

Group Size – 6 – 16

Riding Level

Easy Going to Moderate – Full van support enabling cyclists to cycle as little or as much as they want (Average of 50km per day). Quiet country roads and rolling countryside. Expect some climbs.


• 6 nights – (2 nights in a 5 star collection hotel, 2 nights in Luxury Pousada Hotels, 1 night in a 4 star city hotel in Lisbon, 1 night in a 4 star rural retreat)

• All bedrooms are private en-suite

• All hotels (except Lisbon) have swimming pools


13 meals – 3 Dinners, 3 picnic lunches, 1 local seafood lunch, 6 buffet breakfasts

3 dinners – 3 courses (inc wine/beer and water) in historical hotel restaurants and fine local inns full of local character

1 special lunch at a local seafood restaurant

Read about some of these treats in our Blog on Portugal Desserts!



Extras Included
  • Stay in Lisbon and enjoy a private walking city tour
  • Guided tour of a vineyard including wine tasting
  • Private walking tour of fascinating Evora and cathedral and not to be missed.. Chapel of Bones!
  • Hire of 24 speed Trek hybrid bike with front handlebar bag / map carrier (change to an Alu-carbon Road bike (110 Euros) or quality lightweight Trek Carbon road bike with compact crankset - 160 Euros, or Electric assist bike - 230 Euros)
  • Complimentary custom Cycling Country Portugal cycling jersey
  • Complimentary Cycling Country Tee Shirt
  • Complimentary Cycling Country water bottle
  • Tour guide book of your route
  • Daily Route notes and maps
  • Experienced guides
  • Daily snacks (museli bars, fruit, etc and drinks)
  • 5% off your next Tour with us!

Transfers back to Lisbon designated center Hotel on tour end date from Monsaraz included


2 leaders with full van support, provide refreshments, provide directional signs where required, transfer luggage and provide on-road assistance. 1 leader cycles with the group

Getting Here

The start point of the tour is Portugal´s capital city LISBON accessible by most airlines domestically and internationally and train / bus connections from destinations throughout Portugal.


The hotels on this tour are so truly historic and bound to make such an impression, that it is hard to just highlight two!

Enjoy the magnificent setting of Estremoz, with its incredible banquet hall, before relaxing poolside in its gardens overlooking the town. Alcacer do Sal, is our other beautiful Pousada stay and it is a treat as well. The finest accommodation awaits. If you aren't in the arms of Morpheus in the darkened hours with visions of opulence and majesty, you´ll need to work harder on the bike!

One of Portugal´s best hotels, a 5 Star luxury heaven, is our hotel in Évora, with views of the quiet countryside from the piety of this enchanting 17th century convent, its chapel testimony to Portuguese tile makers’ talents with a visit over to Évora where a Roman temple is only feet away. Relax in its outdoor pool or interior Spa.


Cycling in Andalucia, Spain"Cycling Country`s Amazing Alentejo is Amazing!

This was my first guided trip with Cycling Country, after having a wonderful self-guided trip using them in Andalusia. Wow! So impressed with the level of service, the knowledgeable guides and local insight. I cannot say enough good things about this small, family run company where the owners make sure every last detail is perfect. Top notch accommodations and great food. Challenging yet fun cycling routes."

D. Brandstetter - Calif, USA - April 2019


"What a delightful experience. I’ve traveled the world and this experience is right up there with the best. As a non biker I had a wonderful time and thank you again for arranging for my strange eating habits. There was not one thing I didn’t like about my experience. You guys are the best! I have already recommended this trip to my friends. Cycling Country gets an A+. I look forward to another trip with you and Geoff."

B. Peterson - USA - Oct 2018

"Amazing Trans Iberian Cycling Tour! My wife and I just completed the Trans Iberian ride from Lisbon to Granada with a few days in Sevilla. It was a great trip, interesting and well organised. Amazing landscapes and villages. We are glad we chose to go with Cycling Country, who are based in southern Spain after being set up by Geoff and Maggi 13 years ago. Great local guides ( thanks Geoff, Maggi, Javier, Dani and Balbino) with a professionally run operation. Accommodation was also great and in many cases the same ( or more interesting) than more expensive tour options. If you are interested in cycling in Spain or Portugal I'd thoroughly recommend Cycling Country. Visited May 2017"
A & L. Hood - Australia - May 2017

"Maggi & Geoff,
What a delight to meet you and be included in this memorable bike tour. Flexible was certainly the key word and you two epitomized that word. Loved getting to know you and we wish you and your daughter the best."
D & D. Crawford - CA, USA - April 2016

"Thanks so much for a super time! Despite the soggy conditions you made the trip fun and full of lovely surprises. You are very accommodating and kind and it was a pleasure to travel with you. Would love to do France in the future! Meanwhile, Happy Riding and be Well!"
J. Logan - NY, USA - May 2016

"Dear Maggi, Dean and David,
Thanks so much for sending these Portugal photos along! I'm sorry I didn't meet you, Maggi, but I really enjoyed meeting Dean and David and want to let you know what a fine job they did during our trip. Always cheerful, always helpful and always going the extra mile or kilometer to keep everyone happy."
J. Bremner - WA, USA

"My spouse and I are experienced cyclists and have been on a number of very good bike tours (self guided and group) over the years. The Cycling Country - Alentejo Tour was the best we've ever done. Highly recommended."
J & L - Calgary, Canada

"We really enjoyed this wonderful tour. The accommodation was just incredible, the route and well thought out stops made for great cycling days, but meeting you all and riding with Cycling Country will be my lasting memories. Thanks again for such a fantastic trip through Portugal."
Susan Trutor - Adelaide - Australia

"This was my 3rd. trip with this small company (Cycling Country) and all 3 have been exceptional.
The company provides top quality rental bikes and the trip is fully supported; meaning 2 vans and a third guide on a bike to take care of all needs on the road.
The route is on quiet country roads and the accommodations were all 4 & 5 star in renovated convents and monasteries. Guided tours of Lisbon and Evora were provided as well as visits to a winery, marble quarry and pottery exhibits.
This is a great trip for any level of cyclist who wants to experience some of the diverse culture and history of Portugal. Great value for a first rate bike tour.
I can't say enough about this excellent tour with Cycling Country"
Ian Taylor - October 2014

Testimonials from previous cyclists are always available and we enjoy receiving the feedback after tours. It helps us improve our services and offer you an even better experience. Please feel free to contact us if you would like a reference to talk to. Others have also posted reviews on the independent travel website .


Select Date to Ask for Information and Availablity!



from €2,529


  • Included night in Lisbon with her cosmopolitan charms
  • Stay in historic luxury Pousada hotels, converted monasteries and castles where kings and queens once lived
  • Guided tour of Evora UNESCO heritage city with its Roman temple, aqueduct and mysterious Chapel of Bones
  • Medieval towns of Estremoz and eagles nest Monsarez
  • Local wine tasting and savour local desserts
  • Relax and enjoy the afternoon with a spa and massage treatment at our 5 star Convent Esphinero hotel
  • See Megalithic stone burial mounds and marble quarries
  • Achieve cycling right across the country from Sea to Spain!


10 years of running this wonderful tour and still love doing it. Every time is different!

Unbelievable Value for a tour packed with experiences and unmissable unique luxury hotels

For a small country, Portugal has phenomenal food to try

My spouse and I are experienced cyclists and have been on a number of very good bike tours (self guided and group) over the years. The Cycling Country - Alentejo Tour was the best we've ever done. Highly recommended.

J & L

Calgary, Canada



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