Cycle through history, over Roman bridges and by medieval monasteries along roads winding through the picturesque rolling Alentejo plains region of Portugal and into the neighboring sunbaked Extremadura, Spain.
Our 6 day cycling trip will give you a rich introduction to one of the most beautiful regions of Portugal and its close ties to life across the border in neighboring Spain. Cycling in the Alentejo is ideal because it combines a complex history with quiet country roads winding through olive orchards, vineyards and fields of grain. Every day is filled with picturesque rides, visits to historical points of interest and good food and wine. Explore Evora, the former capital of Portugal and taste wine and have lunch at a local winery estate. In the town of Vila Viçosa, once home to the royal family, you’ll learn about the significance of the local marble industry. And venture across the border to Olivenza, Spain and learn about its fascinating history and how it was once a Portuguese town. Head down to a Lusitano horse breeding farm and wander the cobbled streets of a border village where the Jews took refuge during the Inquisition. Finally climb up to the impressive castle town of Marvão high above the plains with panoramic views of the entire region. This is a once in a lifetime trip that must not be missed!
Trip Highlights
- Spin along the quiet country roads of Portugal’s Alentejo and Spain’s Extremadura regions (including a former smuggler’s route) through golden plains dotted with statuesque cork and olive trees, fields of wildflowers and impressive castle towns
- Discover the fascinating, intertwined histories of Portugal and Spain
- Visit the fortified town of Elvas, with its towering aqueduct and Olivenza, a former Portuguese village in Spain
- Cycle to a traditional Portuguese wine estate for delectable lunch and wine-tasting
- Stay in the beautifully preserved UNESCO World Heritage City of Évora and visit the Gothic Cathedral and famous Temple of Bones
Activities – Cycling, Walking
Activity Level 2, 3 or 4 – Moderate Plus. You need to be in good physical shape to best enjoy the trip activities and to avoid sore muscles. We recommend you prepare your body by exercising regularly for 2 months prior to departure. Walking/hiking, running and regular cycling as well as cardio and weight training will all be beneficial. The better shape you are in, the more you’ll enjoy everything your tour has to offer. In this case, the tour is Level 3 (Moderate), with extra optional sections that raise the activity level to Level 3-4 (Moderate Plus).
Bike rides: 6 + 4 optional rides | Total 246 mi. / 397 km (41 mi. / 66 km avg/day) | + 15,977 ft / 4.870 mt ELE GAIN (2,664 ft / 812 mt avg/day):
| DEPARTURE/RETURN LOCATION: | Hotel Lisboa Plaza, Lisbon | |||||
| DEPARTURE TIME: | Please arrive by 9:00 am for a welcome brief and departure at 9:45 am. | |||||
| RETURN TIME: | Approximately 6 pm. | |||||
| WHAT TO WEAR: | Comfortable cycling gear such as shorts and jersey, shoes with clips if desired. | |||||
| INCLUDED: |
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| NOT INCLUDED: |
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| SINGLE SUPPLEMENT: | €100/night (2026) | |||||
| SMALL GROUP SUPPLEMENT (2-3 guests): | €600/guest |
Alentejo cycling and winery dinner, walking tour to the Temple of Diana and other Évora attractions.
Highlights:
- Welcome dinner at a local winery restaurant
- Walking tour of the UNESCO World Heritage Site City of Évora
Our guides will meet you in Lisbon, Portugal at 9am for a short brief and to get acquainted with the group. Then we’ll head east towards the Spanish border to the Alentejo region and the former Portuguese capital of Évora. The Alentejo is a world away from busy, hilly streets of Lisbon, with rolling hills of golden plains and wildflowers, cork tree estates, generations-old olive groves, and sheep and cattle dotting the meadows. After arriving at the sleepy village called Arraiolos, known for its handmade carpets , we complete a bike fitting and cycle leisurely to Evora for a delicious lunch before heading out for a walking tour of the local sites. Tonight we’ll enjoy Alentejo specialties in a delightful winery restaurant.
Biking: 16 mi | 1hr30 | + 557 ft elevation gain.
Walking tour: 1hr30
Driving: 1hr45
Meals: Lunch / Dinner
Hotel: Hotel M’ar de Ar Aqueduto | Évora
Border crossing: explore Vila Viçosa the marble capital and cycle to Elvas and across to Olivenza, Spain.
Highlights:
- Stunning facade of Vila Viçosa palace, located in the heart of the marble country
- Elvas and its towering 16th c. aqueduct
- Ponte de Ajuda bridge, a relic of the war
- Olivenza, a Portuguese village in Spain
Today we’ll hop in the van for a short transfer to Vila Viçosa, the heart of the Portuguese marble industry and the impressive royal palace founded by the House of Braganza. After a walkabout we’ll get on our trusty bikes and head east to Elvas, an imposing fortified town with a magnificent aqueduct and break for coffee. We continue to Embarcadero de Olivenza where we’ll have a refreshing picnic along the banks of the Guadiana reservoir. A short van transfer takes us to the village of Olivenza, a historically disputed section of the Portuguese-Spanish border where we’ll see a Templar castle and other interesting local sites on foot. After a fun-filled day we return to our hotel, a converted convent in Alter do Chão, a quiet village known for its royal horse breeding estate nearby. Tonight we’ll dine on local specialties in a charming local restaurant.
Biking: 32 mi | 3hrs30 | 1148 ft elevation gain
Walking tour: 1hr
Driving: 2hr30
Meals: Breakfast / Picnic Lunch / Dinner
Hotel: Convento D’Alter | Alter do Chão
How to be an Alentejano: cycle through olive orchards to the whitewashed villages of Monforte and Fronteira
Highlights:
- Roman Bridge of Monforte
- Typical Alentejo village life: Monforte and Fronteira
- Coudelaria De Alter – a Lusitano horse breeding and riding center
- Alter do Chao Castle and Renaissance Fountain
Today we’ll get to live like locals and take a loop ride from our hotel to the nearby village of Monforte with its Roman bridge (and incidentally, famous for its award winning sheep’s cheese) through olive orchards to Fronteira, where we’ll enjoy a picnic lunch by the river. On our return to Alter do Chão we’ll spin through Cabeço de Vide, a spa town with thermal waters, used for over 4000 years and with the ruins of a Roman bathhouse. This afternoon, we visit the Coudelaria d’Alter, where Lusitano horses are bred, and learn about Portugal’s rich equestrian traditions. Before dinner, you may relax by the pool or stroll through the village to admire the local Renaissance fountain. Tonight we dine at our convent hotel.
Biking: 45 mi (32 mi + 12 mi optional) | 4hrs30 | + 1,804 ft / 550 mt
Walking: on your own in Alter do Chão
Driving: none
Meals: Breakfast / Picnic Lunch / Dinner
Hotel: Convento D’Alter | Alter do Chão
Lusitano horses, the Templars and Vestiges of Secret Jewish Traditions
Highlights:
- Mosteiro Flor da Rosa – a fortified 14th monastery converted into a Pousada
- Castelo de Vide with Jewish quarter and museum
- The dramatic fortified hilltown of Marvao
We’ll hop on our bikes from the door of our hotel and spin to the impressive 14th c. Flor da Rosa monastery which has been beautifully converted into a hotel and take a break at a local café for a special hearty soup. After a well-deserved rest we head to the more challenging portion of our ride that takes us to another fortified spa town of Castelo de Vide. We’ll park our bikes and explore the steep winding cobblestone streets of the Jewish quarter and visit the hidden synagogue, now a tiny museum. For most of our guests, this is when we hop in the van to Marvão. However, there is an optional rewarding ride up to this dramatic fortified village straight to the doors of our hotel. Tonight we dine at our hotel.
Biking: 41 mi (32 mi + 9 optional) | 4hrs40 | + 3,313 ft elevation gain
Walking: 1 hr
Driving: none
Meals: Breakfast / Lunch / Dinner
Hotel: Hotel El Rei Dom Manuel | Marvão
A prehistoric Menhir, Border Smugglers, Pueblos of Spain, and a Roman Bridge
Highlights:
- Menir of Meada (the tallest prehistoric stone monument in Iberia)
- Smugglers route and “Salto do Cavalo” (small border between Portugal and Spain)
- Valencia de Alcántara (Castle and typical Spanish pueblo)
- Marvão border (official border between Portugal and Spain)
- Alameda dos Freixos Fraxinus excelsior (European ash)
We’ll cycle directly from our hotel to visit the Menir de Meada, an imponent prehistoric stone monument, likely to be over 4000 years old and one of a network of such monuments found in the Alentejo and throughout Europe. Following a coffee break at a former train station beautifully decorated with tiles, we cross the border to Spain via the “Salto do Cavalo” or “horse jump” crossing and head to Valencia de Alcántara, for a walkabout the castle town and a free lunch on your own. That’s it for today’s cycling unless you’re ready for more and take the optional ride back to our hotel. Your afternoon is free to explore Marvão and its breathtaking views. Tonight we dine together within the castle walls.
Biking: 54 mi (37 mi + 17 mi optional) | 5hrs45 | + 3,937 ft. elevation gain
Walking: 1 hr
Driving: none
Meals: Breakfast / Dinner
Hotel: Hotel El Rei Dom Manuel | Marvão
The Vineyard Landscapes of Sao Mamede Natural Park and a Touch of Spain
Highlights:
- Vineyard landscape of São Mamede Natural Park
- Panoramic mountain views
- The smugglers route between Portugal and Spain
- “Roman” bridge of Portagem (medieval border)
Today we admire the quiet beauty and tiny villages found in São Mamede Natural Park following country roads lined with hedges and plane trees and tiny vineyards. Incredible panoramic views will reward our climbing before we take a jaunt across the border into Spain and back again soon after. We’ll walk along the riverside in Portagem with its historically intriguing bridge, a key crossing point for thousands of Jews expelled from Spain entering Portugal in the 15th c. Following lunch in an excellent restaurant in Portagem, its farewell, with a van transfer to Lisbon, where you’ll arrive before dinner time. Farewell! Adeus! Adios!
Biking: 55 mi (34 mi + 21 mi optional) | 6hrs20 | + 5,216 ft elevation gain
Driving: 2hr30 transfer to Lisbon
Meals: Breakfast / Lunch
Although we do our very best to adhere to the schedule above, the itinerary is subject to change for numerous reasons beyond our control, including weather and terrain conditions.
What’s Included
- Full use of high-quality, Trek 7.4 FX bicycles with GPS unit and front pouch
- Bike maintenance as needed
- Guilt-free van support with snacks and water
- Highly experienced and enthusiastic bilingual guides / mechanics
- Entries for specific monuments, events or points of interest
- Gratuities for all accommodations and group meals
- Baggage transfers and handling.
- Wine with group lunches and dinners
- Lodging and meals as indicated below
- A group digital photo album of your trip
- A complimentary Terracotta Journeys t-shirt
Accommodations
Hotels, 5 nights in 3 hotels:
- Évora: 1 night
- Alter do Chão: 2 nights
- Marvão: 2 nights
Meals
4 dinners, 3 lunches and 2 picnics:
Day 1: Lunch and wine tasting / Dinner
Day 2: Breakfast / Picnic / Dinner
Day 3: Breakfast / Picnic / Dinner
Day 4: Breakfast / Lunch / Dinner
Day 5: Breakfast / Dinner
Day 6: Breakfast / Lunch
*Reserve your 2027 trip by May 31, 2026 and lock in 2026 pricing—saving €200 per person.
Please contact us for dates.
Tour Reviews
I am an avid traveler and have hired many travel companies and I can say that Pedro and Eva provided the best experience for me, ever! The ease and response time during planning was exceptional. They always got back to me within 24 hours and always with positive results. When we arrived in Lisbon, Portugal, our hotel was spectacular with a European breakfast that we out of this world. I even took a video to share with my friends! The staff of Hotel Lisboa Plaza were attentive and engaged. We were off to a great start! When we met Pedro and his team, Nuno and Jose, they were enthusiastic and provided all of the information that we needed to have a safe and enjoyable journey. The accommodations, the Trek bikes and gear, the incredible meals and wine, the historical tours and landmarks were beyond my expectations. We all felt like family by the end of the trip. I highly recommend and I will be taking more Terracotta Journey’s!
Connie B
Our individual group of 11 cyclists chose Terracotta Journeys to see Portugal. The owner, Eva, responded to our questions with patience before our trip began and other owner, Pedro, stayed with our group the whole time- I guess I didn’t expect the owner to actually be our guide and driver. He took care of anything and everything with professionalism and care. Our other guides José and Nuno were total experts. They also were very caring, experienced, and hard workers. They helped in areas outside their job scope ie after-tour- travel and accident care, and we are very grateful. Because of them, we enjoyed our trip as much as we did. It is a beautiful region, food I will always miss and the memories of what I call- the trip of a lifetime. Thank you to your whole team. I hope to journey with you again.
Erika T
What a great trip!! Pedro and Eva know how to make this work for our group of 11 cyclist. Pedro, Nuno, and Jose were very accommodating of all of our needs!! Vegetarians, don’t feel like riding today, pick me up at the bottom of the hill, can you grab some ice for our bottles for the next stop, all of that kind of personal stuff made this a top notch trip and they did great with taking care of all of our needs. Highly recommend this trip it was so much fun and will book again.
Tee Dee
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