Portugal bike tour fully supported

Romantic Alentejo
Ride Across Portugal
Bike Tour

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 2,565 Euros


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!

Separated by the Tagus River, Alentejo is a south-central region of Portugal. Still mainly rural you will also find marble quarries, cork forests and a type of polyphonic singing, so if you care to warble a few notes while pushing the pedals, you’ll fit right in. Explore 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 artisan 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
  • 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
  • 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, 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, is made up of. Lisbon’s oldest district has been inhabited since the 5th century, and today is a maze of streets, overlooked by the battlements of the medieval castle. 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! 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. 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. 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 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 Continuing on, we cycle across the taste-bud tingling Redondo wine region, try not to stop enroute to over indulge at a local vineyard´s produce! An afternoon cycle over a beautiful forested pass brings us to the interesting market town of Estremoz. A most dramatic cityscape, its medieval castle looms over the town’s gleaming marble cobbled streets and we make our way up to stay the night at this pousada. As the light in the countryside dims, we take our 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. The 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. Arrive 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 picnic lunches & 7 buffet Breakfasts
  • Extras Included
    • Stay in Lisbon and enjoy a private walking city tour with the group. What an easy and relaxing way to start!
    • Guided tour of a vineyard including wine tasting
    • Private walking tour of fascinating Evora and entrance to her 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  
01 May to 08 May, 2017* Guaranteed 2 Go! Eur 2,565 8 days
30 September to 07 October 2017* Eur 2,565 8 days
May 2018 tbc - please ask Eur 2,565 8 days
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 10 May 2017 and 09 October 2017 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 8 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


"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

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