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 dynamic 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 the blue and white painted villages that lie in between. Taste the succulent red wines of the area at a private wine tasting, enjoy local specialities and an 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 rich landscape.



17 Sep 2024 | 8 Oct 2024 | 22 Oct 2024 | 1 Apr 2025 | 15 Apr 2025 | 29 Apr 2025 | 13 May 2025 | 16 Sep 2025 | 7 Oct 2025 | 21 Oct 2025


Riding Level

Moderate with
Longer Hills

60KM Daily Average


  • Included night in Lisbon with her cosmopolitan charms
  • Stay in historic luxury Pousada hotels, monasteries & castles where royalty lived
  • Walking tour of Evora UNESCO heritage city with its Roman temple & mysterious Chapel of Bones
  • Private wine tasting and winery visit, savour local desserts
  • Relax & enjoy our dinner and stay at 5 star Convento do Espinheiro hotel
  • Achieve cycling right across Portugal from Sea to Spain!


11 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, we will show you where!

Bike Tour in Southern Portugal

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. Hawthorne

Calgary, Canada

Route Map


Guided Bike Tour in Portugal's AlentejoIntro 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 : 34 km | Ascent 252 m

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.

Cycle Tour in Portugal

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Guided Road Cycle Tour in Portugal's South, the Alentejo Ride: 57 km (option to ride up to 93 km) | Elevation Gain : 600 m 

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. Read about this historical hotel in our Blog.


Ride : 48 km+ | Elevation : 435 m 

Cycle 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 : 68 km | Elevation :  783 m 

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. Maybe take dinner in the great dining room in this most impressive building. You will feel like a king and queen staying in this once royal residence.

Bike Tours in the Alentejo, Portugal


Ride : 67 km | Elevation Gain :  613 m 


Bike this peaceful area with tiny villages and their traditional tile works, marble quarries 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 view over the two countries at the Templar Knight castle. Take a transfer back to Royal Vila Vicosa, a gentle town where you stay next to the Ducal palace in the peaceful former convent and enjoy a delicious meal for our celebration dinner. Well Done!


After a leisurely breakfast wander this pretty town and relish 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

Leisure Tour: Guided & Supported

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

Terrain: Rolling landscape, quieter roads

Group Size: 6 – 16 | Discounts for 4+ booking together

Riding Level

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


6 nights : (2 nights in a 5 star collection hotel, 3 nights in Luxury Pousada Hotels, 1 night in a 4 star city hotel in Lisbon)
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

Daily snacks (museli bars, fruit, etc and drinks)

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

Extras Included
  • Private walking city tour of Lisbon Baixa
  • Privately Guided tour of a winery & wine tasting
  • Private walking tour of fascinating Évora, Cathedral and not to be missed.. Chapel of Bones!
  • 24 speed Trek hybrid bike with front handlebar bag / map carrier.
  • Cycling Country Portugal cycling jersey, Bottle, Tee & Tags
  • Tour guide book of your route, its history & culture
  • Daily Route notes and maps
  • Experienced cycling guides and SAG van which follows route
  • 5% off your next Tour with us!

Included is a Trek hybrid bike with front handlebar bag / map carrier.
Or upgrade to a lightweight Trek Carbon road bike with compact crankset €210, EBike €275 or e-road bike €450

*Please note, sorry but we are unable to take people’s own bikes on this tour.


Transfers back to Lisbon designated centre Hotel on tour end date from Vila Vicosa 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.


Historic Hotels on Portuguese Bike Tour 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 and its castle Pousada with amazing 360 views over the town from its pink marble tower and its incredible banquet hall. Relax poolside in lovely gardens overlooking the town. Estremoz Castle Estremoz Pousada is a treat for the senses, with its own outdoor swimming pool, grand salon, fountains and ancient towers.
Road Bike Tours in Portugal’s Alentejo Convent HotelIf 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 but Vila Vicosa’s tranquil former 16th century Convent will lull you to sleep no problem.
Historic hotel On Bike Tour in Portugal - ConventOne of Portugal´s best hotels, a 5 Star luxury heaven, is our hotel in Évora, Convent do Espinheiro with views of the quiet countryside from the piety of this enchanting 17th century convent, its enchanting chapel testimony to Portuguese tile makers’ talents and the organ is a marvel.
Convent hotel on Bike Tour in Portugal A hotel full of history, legends and charm, you will love exploring this building for it is full of lovely nooks to settle in.
Historic hotel on your Portuguese Road Bike Tour Boasting an ideal location near UNESCO heritage city of Évora, the doors open out onto gardens, olive trees and small pastures.
Cycle Tour Luxury Hotel in Portugal A well regarded restaurant and relaxing spa, it is a lovely hotel to enjoy your days and nights in.
Beautiful Hotels on an Portuguese Bike TourAnother nice stay is in Lisbon, where you are central to all sights! Set a in a great location, Hotel Marques de Pombal Hotel offers comfort with a flare of Portuguese charm right in the heart of the city steps away from the boutiques and bars of tapas with bountiful Portuguese and International cuisine you have the choice to explore.
Road Bike Tours in Andalucia - Hacienda Hotel Another highlight hotel to enjoy the historical route, is the stunning Alcacer Castle Hotel, a beautiful stay a mix of modern & ancient. A fine meal surely awaits and you will slumber well here.

“Amazing cycling in Portugal
We had a fabulous time with a great group of people riding the ‘Amazing Alentejo’. Our guides Geoff and Jose where fantastic, nothing was ever a hassle or bother, even when they had to pivote due to the terrible weather conditions. At each location it we were staying the night, also included a tour of either the village or a wine tasting. Each night we stayed in either Castle’s or Convents that had been converted into 5 star accommodation. This is our third ride with Cycling Country and would highly recommend them. We will be back in the near future for another amazing riding experience.
Cheers from Australia!”
R.&D. Guy – Vic,Australia – Oct 2023

“Biking across Portugal from the Atlantic in the southern Alentejo area to the border of Spain was the ideal adventure.
We had a choice of touring, E-bike, or hybrid style bicycle. The accomodations were lovely and we were served delicious picnic lunches or fine dinners, all reasonably priced for our custom group of 16. We’ll be back in 2024 for the Bordeaux tour.
G. Colley – Georgia, USA – May 2023

“I had the pleasure of going on my second Cycling Country bike tour last month, and it was even better than my first experience. Maggi, Geoff, and their team went above and beyond to create a truly unforgettable trip with their level of personal attention and professionalism.
From the moment I arrived, I was impressed with the level of detail and organization that had gone into planning the tour. The itinerary was well-designed, with plenty of time to explore each destination and enjoy the local culture. The accommodations were excellent, and the food was delicious and picnic lunches exceptional.
But what really made my trip special was the people. The Cycling Country team is made up of incredibly kind, knowledgeable, and helpful people who are truly passionate about cycling. They were always there to offer support and encouragement, and they went out of their way to make sure everyone had a great experience.
I would highly recommend Cycling Country to anyone looking for a memorable and enjoyable bike tour. I know I’ll be back!”
M. Zadeh – Georgia, USA – May 2023

“The hotels alone are worth the trip…
The Portugal tour ALENTEJO was amazing, weather was perfect in March/April timeframe, very nice scenery, spectacular hotel/castle, amazing food. Tour offer a good variety of landscape, some challenging at times but all well worth it. I can’t get over the magnificent Castle and former Monastery we stayed in, just the hotel alone are worth the trip!!!. It was a guided tour and Geoff was fantastic and very helpful and knowledgeable about the places visited and all around way of life there. A must do…”
C. Nadine – Texas, USA – April 2023

“Portuguese Cycling Tour – A Charming Trip”
Each day during the ride, the scenery got better and better. We had perfect weather, the accommodations were topnotch, the food incredible and our guides, the Javiers, were the best. They made our transitions seamless, and they worked together efficiently and professionally while maintaining a sense of comradery with the group.”
J. Mills – Texas, USA – Oct 2022

Bike Tour with Pousada hotels“Autumn Alentejo BikeTrip”

“Great cycling trip. Friendly and informative guides (Balbino and Dani) and a great group of cyclist of approx equal riding abilities. The Company also organised fantastic hotels, from converted monasteries to castles. The side tours were fantastic and pitched at the right level of intensity after a day of riding.
Of special note was the olive oil tasting .. fantastic.
I recommend Cycling Country to anyone, and I am watching with interest for their plans to run a tour in Morocco.”

J. Woolford – Vic, Australia – Oct 2019


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

“Romantic Alentejo cycling Tour at its best!
This is our 2nd cycling country tour and Maggi And Geoff we’re exceptional hosts, guides, friends and cyclists.
The incredible attention to detail from picnics to accommodation, routes, dinners, coffee stops and support van was second to none.
We had a small group and this made our experience even more resonant.
We would recommend Spring as the most beautiful time to cycle through Portugal. Weather was mild and the wildflowers were in full bloom.
We will be back again and again!!!!!
Thank you again for this memorable trip.”
S. Wall – Brisbane, Australia – May 2018

“Fantastic bike trip!!
We had a group of ten (all family) and this was our second ride with Cycling Country. We had a variety of bicycling experience but Cycling Country not only made it work but made everyone have a fun experience. Alentejo area of Portugal is beautiful and the roads are quiet for biking. Maggi and Geof were very knowledgeable and took great care of us. They really wanted us to be happy. The bikes that they had were top notch. I used an electric assist bike to help me up the big hills and that made the trip stress free for me. Cycling Country picked great restaurants and inns for us to stay at. They also set up a few walking tours that were great. If you are looking for a biking company, pick this one. They will take exceptional care of you!”

G. & M. Barkley – Illinois, USA – September 2017

“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 – May

“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 – Vancouver, Canada, October 2014

From our first contact to the gorgeous photos that were taken and sent to us when we got home, this company is EXCEPTIONAL! My husband and I are novice cyclists but wanted to do a tour while in Europe. We chose the Romantic Alentejo in Portugal with Country Cycling. Our guides, the owners and one associate, are not only passionate about cycling but about ensuring that everyone has the best experience possible. The equipment is excellent, the routes are well thought out and the accommodations are amazing, not to mention the wonderful picnics and dinners along the way. We felt pampered, challenged and completely safe!”
B. Price – April 2013

“Amazing accommodations, great cycling route and personalized service
Cycling Country delivered an outstanding 9 day cycling trip from Lisboa to the Spanish border through the Alentejo region of Portugal. Everything from the two walking tours (in Lisboa and Evora) to the accommodations (most were luxurious pousadas (renovated monasteries, convents or castles with swimming pools)) to the hearty breakfasts and group suppers to the well planned cycling routes was top notch. Geoff, Maggi and Dean were personable, accommodating, fun, informative and obviously love cycling. The weather was unseasonably hot but the support van was available to provide water to keep all hydrated or provide a lift if someone so desired. The route is through primarily rolling agricultural area and small towns and had only a few short climbs. A highlight for us was the stay in Monsaraz — a beautiful character hotel in a quaint town that is perched on top of a large hill and has amazing 360 degree view of the land below! What a sunset! What an early morning ride to the Spanish border while the sun was rising!”
S. Riley – Toronto, Canada, Oct 2011

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. Others have also posted reviews on the independent travel website .







Continue on into Spain with the Enchanted Andalucía tour to make a Trans Iberian adventure – transfers and accommodation for 2 nights in Seville at the 4 star tour hotel included and a 5% combined trip discount!



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