Portugal bike tour fully supported

Romantic Alentejo
Ride Across Portugal
Bike Tour - New Route For 2018!

8 daysLisbon, Atlantic Coast, Evora, Vila Vicosa and Monsaraz Bike Ride Across Portugal - from the Atlantic Ocean to the Spanish Border Fully Guided & SupportedLuxury Historical Monument Hotels
Easy Going to Moderate from 2,365 Euros (200 Euros off April Tour!)


The country of explorers, Portugal is a virtual treasure trove of finds. Here discover the many quiet routes that this country offers inland in the Alentejo region as well as the cosmopolitan vibe of Lisbon. Pamper yourself as we stay in the most special collection of hotels, both luxurious and historic, ranging from castles to convents.

Cycling in Andalucia in AprilExperience the great seafaring heritage of the Portuguese capital, its history well documented in its fine museums and monuments.

Amble through the Baixa shopping district, hear strains of Fado music and enjoy its funicular tram, which scales its many hills. Lisbon´s famous custard tarts and strong coffee make lovely memories before you head into the tranquility of the countryside.

Cycling in the AlentejoWatch this short video about the Romantic Alentejo tour. Fine eats, fine sleeps and of course fine Cycling Country!

Cycling in Andalucia in AprilSeparated by the Tagus River, the Alentejo is a south-central region of Portugal. Still mainly rural, you will also find marble quarries, cork forests, olive groves and a type of polyphonic singing, so if you care to warble a few notes while pushing the pedals, you’ll fit right in. Cycling in Andalucia in AprilExplore the UNESCO city of culture, Évora and its preserved 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, are relaxing cycle rides for all.

Cycling in Andalucia in AprilTaste the succulent red wines of the area and see how the fine stitching of the famous Arraiolos carpets is done. And when not on the bike, try the local specialities of the region, the fresh produce and seafood and the array of sweets to tempt any palate.

Staying 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 trip for those who enjoy relaxing travel on two wheels, taking in the sights of the pastoral but varied landscape and its most rich fabric of past civilizations so wonderfully preserved for the visitor.

Route Map

View Romantic Alentejo, Bike Tour Portugal in a larger map


  • Included night in Lisbon with her cosmopolitan charms, an unrivalled Capital
  • Stay in historic luxury Pousada hotels, 16th century 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 at a winery to savour this local delight
  • Relax and enjoy a spa treatment at our 5 star Convent Esphinero hotel
  • Visit Megalithic stone burial mounds and marble quarries
  • Achieve cycling right across the country from Sea to Spain!


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Day 1. Lisbon

Cycling in Andalucia in May Start off from Lisbon, one of Europe´s capital jewels and an ancient place, which as stories hint was founded by Ulysses and harboured many famous explorers. Baking red tile roofs, fish sold from doorways, windows hung with washing and bird cages and small narrow streets is what the old city, Alfama and Baixa, is made up of. Cycling in Andalucia in MayLisbon’s oldest districts have been inhabited since the 5th century, and today are a maze of streets, overlooked by battlements and full of wonderful pastry shops, galleries and a dynamic atmosphere. World War 2 Intrigue and Spy lore, mixed with medieval and Roman life, it is a wonderful place to begin our trip and we take a private guided tour of the city with Rita & Jose, residents of this illustrious place.

Day 2. Atlantic Coast

38km / 23m
Bike Tour of Andalucia with road bikes We transfer out of the bustle of Portugal's capital city to start our cycling journey near the coast. After a quick dip of the toe in the Atlantic, we start cycling through a natural reserve of herons and egrets before heading inland to our impressive ancient castle pousada accommodation for the evening, high on a buff overlooking the pretty town of Alcacer do Sal, surrounded by... rice paddies! Bike Tour of Andalucia with road bikesYes, 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. Dining in the elegant surroundings we enjoy a delicious repaste for our welcome dinner.

Day 3. Évora

55km / 34m (option to ride upto 92km/57m for those who want more miles)

Bike Tour in Andalucia in October We start the day rolling through green lush scenery, passing farmers and town´s folk attending the local paddy fields. Heading north, we make our way through pasture land to the town of Montemor. Bike Tour in Andalucia in OctoberWe 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 in the restored convent with its marvellous chapel tile work and take in the rural scenery with a glass of wine by the swimming with valley views of grazing cattle.



Day 4. Évora Loop Ride to Arraiolos

46km / 24m

Cycling in Andalucia in May A lovely morning start to some cycling as our 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 cross stitched tapestries and carpets vibrant and intricate pieces of art. Arrive back in Evora, and take an afternoon private guided walking tour of the city by our friend, Maria. Venture into the chapel of Bones (if you dare!) and see the last remains of the city´s former residents. 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.

Day 5. Estremoz

69km / 42m
Bike Tour of Portugal with road bikes We cycle across the taste-bud tingling Redondo wine region, try not to stop enroute to over indulge at a local vineyard´s produce as we will be doing that this afternoon! A good cycle over a beautiful forested pass of eucalyptus trees brings us to the interesting market town of Estremoz. Bike Tour of Portugal with road bikesA most dramatic cityscape, its medieval castle looms over the town’s gleaming pink marble cobbled streets and doorways, we make our way up to stay the night at this pousada. As the light in the countryside dims, take in the fantastic 360 degree view from the orginal 13th century tower and then go down to take your 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.

Day 6. Vila Viçosa

50km / 32m
Bike Tour in the Alentejo We continue our exploration by journeying onto Vila Viçosa, famous for its elaborate Ducal Palace, home to the last royal family of Portugal. Bike Tour in the AlentejoThe route takes us into this town’s orchard area, its glowing marble quarries and ending in the town´s tranquil tree-lined avenues and quiet plazas. So pretty is it that it was even given by King Afonso IV as a wedding gift to his bride, Doña Brites. Stay in the elegant monastery pousada beside the palace with its verdant garden and hidden niche chapels. Enjoy a group dinner where old and new portuguese recipes are fused perfectly.

Day 7. Monsaraz

56km / 35m
Bike Tour of Andalucia with road bikes A relaxing day through the peaceful area and its tiny villages with their traditional tileworks and Moorish forts. It is an area known for its brilliant coloured ceramics and it will be hard to not want to take some home when you pass the outside stalls with their brilliant shades of pottery glazes. Bike Tour of Andalucia with road bikesArrive at Monsaraz, boasting an awesome hilltop castle and a panoramic vista of the Guadiana River and dam which separates Spain from Portugal. Relax here, admiring the sunset over the two countries at the Templar Knight castle and enjoy a homecooked meal for our celebration dinner.

Day 8. Lisbon

Bike Tour of Andalucia with road bikes 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

  • Trip Style
  • Discovery - Guided

    Bikes - Hybrid / Road / Ebike

    Small Group Size: 6 - 16

    Route: Lisbon, Atlantic coast, Évora, Redondo wine region, Villa Vicosa, Monsaraz See Map for route

  • Activity 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.

  • Accommodation
    • 7 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, 1 night in a 4 star rural retreat)
    • All bedrooms are private en-suite
    • All hotels (except Lisbon) have swimming pools
  • Food
    • 15 meals - 4 Dinners, 4 picnic lunches, 7 buffet breakfasts
    • 4 dinners - 3 courses (including wine/beer and water) in the historical hotel restaurants and fine local inns full of local character
    • 4 delicious picnic lunches & 7 buffet Breakfasts
  • Extras Included
    • Stay in Lisbon and enjoy a private walking city tour with the group.
    • Guided tour of a vineyard including wine tasting
    • Private walking tour of fascinating Evora and cathedral and not to be missed.. Chapel of Bones!
    • Visit to the pottery area of the Alentejo and pick up some great souvenirs
    • Hire of 24 speed Trek hybrid bike with front handlebar bag / map carrier (change to a lightweight Trek Madone Carbon road bike with compact crankset - 160 Euros, or Electric assist bike - 175 Euros)
    • Complimentary custom Cycling Country Portugal cycling jersey
    • Complimentary Cycling Country water bottle
    • Tour guide book of your route and all sightseeing stops
    • Route notes and maps
    • Experienced guides
    • Daily snacks and refreshments (muesli bars, fruit etc and drinks)
  • Transfer
  • Transfers back to Lisbon designated city centre Hotel on tour end date from Monsaraz included

  • Staff
  • 2 leaders with full van support to pick up souvenirs, provide refreshments, act as guides, offer tips and insights throughout the day, 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 which is accessible by most airlines domestically and internationally as well as by train or bus connections from destinations throughout Portugal. Please see our Getting Here page for more details.


"And from this slumber you shall wake, when true love's kiss, the spell shall break." Brother's Grimm, Sleeping Beauty

Well, there will be no question that the former inhabitants in our accommodation during this tour built the walls great and broad, as you will drift in blissful sleep in silence as the ancient castles and monasteries keep your secrets. Castles with crenulations and stretching views, dining halls, witness to scenes of Hamlet style proportions, alabaster pillars carved with cherubs and frescos still clinging with medieval paint tints; 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!

We go from the dynamic 4 star Hotel in Lisbon, on the city´s main avenue of spies and war intrigue to Alcacer´s ancient castle pousada, where you can take a dip in the pool under the shadow of its defensive ring. On to one of the Alentejo´s best hotels, a 5 Star luxury heaven, our hotel in Evora, with views of the quiet countryside from the piety of this enchanting convent, its chapel testimony to Portuguese tile makers' talents with a visit over to Evora where a Roman temple is only feet away.


The hotels on this tour are so truly historic and bound to make such an impression, you will want to stay up and wander the halls in your bathrobe. Enjoy the magnificent setting of Estremoz, with its incredible banquet hall, before relaxing poolside in the gardens of the royal convent at Vila Vicosa beside the Durcal Palace. The finest accommodation awaits.


Dates & Prices

Dates Price  
28 April to 05 May 2018 Eur 2,365 8 days - Special Offer - reduced by 200 Euros!
29 September to 06 October 2018 Eur 2,565 8 days
More dates to follow - Please enquire!
(*continue on into Spain with the Enchanted Andalusia tour starting on 07 May 2018 and 08 October 2018 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!)
OR Custom Dates if booking with a group of 6 or more (check for availability)
Single Supplement Eur 495
*Price includes all local taxes. Single supplements apply (see individual trip details).
Please note we transact in Euros.
convert price to currency of your choice

Enquire About This Tour


Fantastic Bike Trip! - October 2017"
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! "

M. Barclay - U.S.A

Amazing Trans Iberian Cycling Tour! - May 2017"
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. "


Alentejo Road Bike Tour - 2016"
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."

I. Taylor - Van, Canada

EXCEPTIONAL Alentejo Tour - 2016!"
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."

Barbara P - Calgary, CAN

"Romantic Portugal",
Our cycling tour from Lisbon to Spain was remarkable. Short daily "meetings" with individual maps were very helpful. Routes were excellently chosen, visiting villages, vineyards, olive groves, cork trees and an amazing marble quarry. Also to know at the end of the day we would be staying, mostly, in castles, fit for a "King and Queen" with meals to satisfy the hungry appetites.
Our tour guides and hosts, Maggi and Geof kept us extremely happy.
Thankyou for an excellent cycling holiday."

Laura S. - Espanola, Canada

"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

"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, accomodating, 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! Highly recommended."

Sonja T - Edmonton, Canada

"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

"Wonderful Trip, great personal service, fabulous accomodations!! My wife and I and another couple did cycling country's Portugal trip called their Romantic Alentejo tour. Last Year, we did Cycling County's Spain Andalusia trip and it was great. So, looking to do another trip with Geoff and Maggie the owners, and Dean the fanatical ex-competitive racer , we joined them again this year in Portugal. One of the 3 always rotates and gets stuck driving the support van and the lucky other 2 get to cycle as they are all crazy for cycling. Their trip leaves from Lisbon, but stops at the Atlantic Ocean on the way out of town so you can take a dip and say that you biked from the Atlantic Ocean to Portugal's border with Spain. Its a small "company" - owned by Geoff and Maggie who make sure everything goes perfectly. The Portugal trip mostly stay in Pousada's - a high end chain of hotels renovated from 400 year old Monasteries. Every one of these was different and special and fancy in their own way. Inevitably, they were at the top of a cobblestone road hill often in a walled town. (At least it's easy getting moving in the morning though - a nice run downhill.) I would say that compared to their Andalusia Spain Trip, the cycling is a little easier, the food in Portugal is better and the accommodations were over the top fancy. But I would also say that the scenery in Spain was "bigger", especially where we went though days of yellow sunflower fields as far as the eye could see to the horizon. Both their Spain and Portugal were great trips and I would recommend either. I did the trip with my wife of 31 years (so you can guess at our ages), and she did great. You don't have to worry if different people go different speeds. With two of them on the road and the support van, eventually everyone makes it to the hotel in plenty of time for dinner or a swim and dinner. Oh, the bikes were good Trek bikes, and if anything needs adjusting they are all pretty good bike mechanics too! "

Mark & Myra - Toronto, Canada

Cycling Country S.L. is registered as a limited liability company (No. B18907741) and licenced as a fully bonded travel agency in Andalucia, Spain (No. 184031-2) in compliance with Spanish and European Law. Cycling Country and the cyclist logo are a Registered Trade Mark.

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