DAY 1. LISBON WALKING TOUR, ALCÁCER

Begin your unforgettable cycling tour in Lisbon, a city steeped in history, famously founded by Ulysses and home to many renowned explorers. With its iconic red-tiled roofs, charming streets, and the medieval castle overlooking the city, Lisbon offers a perfect starting point for your adventure. Enjoy a private guided walking tour with our local expert José, who will share the stories and secrets of this ancient city.

After exploring Lisbon, we’ll transfer south to the picturesque town of Alcácer do Sal, arriving at our own historic Castle hotel, a stunning blend of luxury and heritage. A bike set-up is followed by time to explore this gateway town to the Atlantic coast. Indulge in a welcome group dinner as we discuss the forthcoming cycle through the scenic Alentejo region.

DAY 2. ALCÁCER TO ÉVORA

Ride: 57 km | Gain: 595 m

From our impressive castle hotel, high on a buff, admire the expansive view of rice paddies! Yes, Portugal is one of Europe’s biggest consumers and growers of rice. Cycle into the quiet countryside, full of flowers and grazing cows, heading past the classic blue and white trimmed village houses. Take a coffee stop in a tiny village café, full of local charm. 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, today 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. Hopefully, no ghosts appear tonight as we dine in the impressive dining room.

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.

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 but Vila Vicosa’s tranquil former 16th century Convent will lull you to sleep no problem.

One of Portugal’s great hotels 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.  Our October 13th tour, chooses to stay next to the enchanting city walls in Évora, giving cyclists the opportunity to enjoy this fascinating town after dark!

A hotel full of history, legends and charm, you will love exploring this building for it is full of lovely nooks to settle in.

Boasting an ideal location near UNESCO heritage city of Évora, the doors open out onto gardens, olive trees and small pastures.

A well regarded restaurant and relaxing spa, it is a lovely hotel to enjoy your days and nights in.

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.

Alcacer Castle Hotel, built on centuries of History, lets you dream big!

“Bike Tour in Portugal’s Alentejo
We came back from another amazing cycling trip with Cycling Country. This time we did the Awesome Alentejo in Portugal. We have now done two trips with Cycling Country and are already booking our third for 2026. We were a group of 10 and that is not an easy task to keep all of us happy, entertained and safe. And you did it effortlessly! Thank you Geoff, Jody and Jose for the amazing experience that you gave us. You guys made the trip an unforgettable adventure! We biked and biked and biked and loved every day with new routes, incredible accommodations and delicious food. So looking forward to next October and our next cycling tour with you.
Written November 13, 2025.
D. Williams, Edmonton, Canada – mid Oct 2025

“Cycling Country is top notch!
Cycling Country is an amazing local bike company that gives excellent services, top rate accommodations and high quality bikes. Would HIGHLY recommend them over the large, well known bike trip companies for a more personalized experience. Maggie was very accommodating and the guides were great. Would love to do all their trips in the future! The only downside to our June trip in Portugal was the heat, would recommend you plan for a spring trip if you want to do the Alentejo region of Portugal. Wonderful experience otherwise.
K. Hoyle, Hawaii, USA – mid June 2025

“Cycling Country what a adventure
Not sure where to start as outstanding from day, one with the tour of Lisbon. The organization of hotels, tours, food, etc. was better than ever expected. The bike ride tour was great but a lot of the gratitude goes to our two tour guide riders. Jose and Miguel two great individuals to spend six days with riding bikes, going on tours, etc. They were great to be with always putting our safety and pleasure making sure we are taking care of number one. Due to cancellation, there was only four of us, but it was great to spend that time with a couple from Canada you couldn’t ask for a better couple to be paired up with. While your riding 5-6 hours a day stopping to view along the way. Then at night your staying in castles, monasteries and nice old hotels you feel like a king and queen..
M. Fitterer, Washington, USA – May 2025

“Two-wheeling Castle to Castle! Bike trip rich in history, great guides, beautiful terrain, outstanding accommodations in luxurious pousadas, delicious foods, quaint villages and towns…the Amazing Alentejo tour is definitely AMAZING!😁
We sooooo appreciated the pools each afternoon as we were biking in pretty hot temperatures for us Canadians just coming off winter months!
P. Brodie, USA – May 2025

Tremendous cycling – Some cycling tour companies provide so much support you feel you are cycling in a bubble, while others leave you to solve lots of itty bitty issues. Cycling Country gets the balance just right, which makes their Trans Iberian tour a tremendous experience. Highly recommended!
A. Bailey, Sydney, Australia – May 2025

“Wonderful Portugal and Spain cycling.
We chose the double Trans-Iberian tour from Lisbon in Portugal to Granada in Spain. Both the Portuguese and Spanish tours were fabulous. We were in Portugal in the last week of April and the wildflowers were stunning, fields and fields of colour and movement. The riding was mostly rolling hills on intimate country roads with the occasional modest climb, easy on an ebike, a bit of a workout for our roadbikers. The riding in Spain felt quite different. Vast open vistas over endless olive groves and longer, steeper climbs giving way to endless views. Geoff and the guides (Jose, Miguel and Guille) were wonderful; always available to help out, answer questions, unjam chains, prepare delicious picnic lunches, always with a smile. I feel like the tour strikes just the right balance between guiding and letting be. The app with all the daily routes and directions allows people who want to, to ride ahead, or stop to take photos without fear of getting lost. The routes are so well planned, mostly on quiet country roads with pretty scenery. The pre-planned visits to special landmarks and historic buildings were also great. The accommodations were special, mostly quite luxe and unique. If you have the time, the budget and the legs for it, I definitely recommend this tour!”
Y.Leonard, Sydney, Australia – May 2025

“Cycling Country Bike Tours Amazing Alentejo – excellent trip!!
Our bike tour through Portugal’s Alentejo region with Cycling Country Bike Tours was amazing! Our guides Geoff and Jose took great care of us, they were kind and funny and worked very hard to make sure our group was having fun, eating well, and just enjoying the “ride”. We saw some absolutely beautiful countryside with wildflowers, cork orchards, cows, sheep, nesting storks, castles and more. The roads had very little traffic and took us through some quaint little towns. Our accommodations were top notch, we were spoiled with coffee breaks, picnic lunches and lovely dinners. Mixed in with the bike riding, we had some City tours, wine tasting and a bit of touristy shopping. Most of all we enjoyed the company or our tour guides and fellow bikers – we hope to meet again. Thank you to Geoff, Jose and Maggi for taking us on this great adventure!”
M. Arellano, Oregon, USA – April 2025

“Portuguese Bike Tour
My wife and I just completed the Amazing Alentjo tour with Cycling Country. We have done quite a few bicycle trips over the years and must say this was one of the most enjoyable we have done. The route was beautiful, the accommodations were stunning and the guides were outstanding. If you are contemplating a bike tour to Portugal, you should put this tour at the top of your list.
E.&MJ – Sequm, Washington – May 2024

“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

“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 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

“EXCEPTIONAL!
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 .