Romantic Alentejo Bike Tour

9 daysLisbon, Atlantic Coast, Evora, Vila Vicosa and Monsaraz Bike Ride Across Portugal - from the Atlantic Ocean to the Spanish Border Fully Guided & SupportedLuxury Pousadas & 4 Star Hotels
Easy Going to Moderate


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 luxurious and historic hotels ranging from castles to convents.

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

Amble through the Alfama shopping district, hear Fado music and enjoy its funicular tram, which scales its many hills.

Lisbon’s cathedral with its extravaganza of pipes, the museum of the queen's carriages and the most delicious cheesecake tarts and strong coffee make lovely memories before you head into the tranquillity of the countryside.

Watch 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, it is known as the "bread basket" and here 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. Here the rolling fields and dappled shadows of the rock outcrops that Alentejo's towers and fortresses guard are delightful to navigate around. Being agriculturally based with towns that still cultivate a variety of skilled crafts, it is a pleasure to explore and find a few souvenirs to take home in your handle-bar bag.

Taste 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 fine historical monuments, now luxury Pousada hotels, 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


  • Lisbon's cosmopolitan charm and exciting Alfama area
  • Stay in historic luxury Pousada hotels, converted monasteries and castles where kings and queens once lived.
  • Fascinating Evora UNESCO heritage city with its Roman temple, aqueduct and mysterious Chapel of Bones
  • Medieval towns of Estremoz and eagles nest Monsarez
  • Cork wood forests and wine vineyard experiences
  • Megalithic stone burial mounds and marble quarries
  • Achieve cycling right across the country from Sea to Spain!



Day 1. Lisbon

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
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. Dining in the elegant surroundings we enjoy a delicious repaste for our welcome dinner.

Day 3. Arraiolos

55km / 34m (option to ride upto 92km/57m for those who want more miles)
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 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. Then relax in the restored 16th century pousada convent with its marvellous chapel tile work and take in the scenery with a glass of wine on the large terrace with valley views of grazing cattle and Arraiolos´ walled fortress high above.

Day 4. Évora

46km / 24m
A lovely morning start to some cycling as our winding country roads lead us into the Unesco Heritage city of Évora by way of small hidden villages and a rail to trails path. Arrive in Evora, with its twisting cobblestone streets giving hint of its Moorish heritage. 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. Staying in one of Portugal´s most famous pousadas, the enchanting Loios Convent, you are in Évora´s heart. Let your imagination run wild as you spy the huge 17th century aqueduct and Roman temple of Diana outside the hotel's front door, you'll only wish you brought your toga!

Day 5. Estremoz

69km / 42m
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.

Day 6. Vila Viçosa

50km / 32m
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. Vila Viçosa

Take a well earned rest day to explore this town with it pink marble sidewalks and cobblestones, or just relax poolside in the gardens of this fascinating and historic hotel. This town is full of interesting museums, shops and small cafes, aside from its palace and castle! Enjoy a free night to try a local speciality such as Alentejo Gaspacho.

Day 8. Monsaraz

56km / 35m
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 Templer Knight castle and enjoy a homecooked meal for our celebration dinner.

Day 9. Lisbon

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

    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 - there will be a support van all the way 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
    • 8 nights - (6 nights - Luxury Pousada Hotels / 1 night in a 4 star rural retreat / 1 night in a 4 star city hotel in Lisbon)
    • All bedrooms are private en-suite
    • All hotels (except Lisbon) have swimming pools
  • Food
    • 8 buffet breakfasts
    • 4 dinners of 3 courses including wine/beer and water (2 elegant dinners in Pousadas)
    • 4 picnic lunches
  • Extras Included
    • Guided private walking city tours of Lisbon and Evora
    • Entrance to Evora's Chapel of bones
    • Guided tour of a vineyard including wine tasting
    • Transfer to the pottery area of the Alentejo
    • Hire of 24 speed Trek hybrid bike with front handlebar bag / map carrier (Orbea Road bike - 120 Eur / Trek Madone Carbon - 150 Eur / Ebike - 150 Eur)
    • 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 to Lisbon designated city centre Hotel on tour end date back from Monsaraz.

  • 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 (a designated hotel) 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 our hotel in Arraiolos, with views of the village above from the piety of this enchanting convent, its chapel testimony to Portuguese tile makers' talents and then 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  
08 April to 16 April, 2015 Eur 2,365
9 days
28 September to 06 October, 2015 (SOLD OUT!) Eur 2,365 9 days
(continue on into Spain with the Enchanted Andalusia tour starting on 17 April 2015 or 07 Oct 2015 to make a Trans Iberian adventure - transfers and accommodation for 1 night in Seville included - 10% 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

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.

Privacy Policy | EU Cookie Policy | © Cycling Country 2003 - 2015