Portugal’s Alentejo region is a place where time stands still. It’s a region bursting with vibrant hues, proud of its bold reds and crispy white wines, and it’s just the perfect place to explore on two wheels. This self-guided bike tour promises a unique exploration of this area over a week—you’ll discover ancient megalithic sites, typical whitewashed villages, endless vineyards, Roman remnants, and medieval fortified cities. You’ll stay in historical castles and convents, now renovated into the most charming accommodations imaginable, and you’ll discover Alentejo’s cuisine. Pictures really don’t do it justice. You’ll just have to come here, to one of our favorite places in the world, and see it to believe it.
Portugal’s Alentejo region is a place where time stands still. It’s a region bursting with vibrant hues, proud of its bold reds and crispy white wines, and it’s just the perfect place to explore on two wheels. This self-guided bike tour promises a unique exploration of this area over a week—you’ll discover ancient megalithic sites, typical whitewashed villages, endless vineyards, Roman remnants, and medieval fortified cities. You’ll stay in historical castles and convents, now renovated into the most charming accommodation imaginable, and you’ll discover Alentejo’s cuisine. Pictures really don’t do it justice. You’ll just have to come here, to one of our favorite places in the world, and see it to believe it.
Depending on your fitness level and how easy you want this tour to be, the itinerary can be adjusted. You will get all the necessary maps and route information for both the shorter and the longer route. In the itinerary below, you will find both options—their distances and elevation gains.
Once you land at Lisbon Airport, your guides will drive you to Estremoz, a gorgeous “white city” where royalty once lived. This old town will make you feel like a queen or king, especially as you’ll be spending the night in a castle! A historical building has been converted into a hotel, from which you can admire a superb view over Estremoz and the vast Alentejo plain. Take a stroll around the city and get some rest for tomorrow, as that’s when the cycling begins!
Accommodation: Pousada Castelo Estremoz
Discover battle stages, villages of conquerors, and old communities that have rippled their influence through time and are now great hospitable people. Towards Vila Viçosa, the capital of marble in Portugal, you can visit the Ducal Palace, built in the 16th and 17th century on the remains of Roman and Moorish buildings. You will have plenty of free time today, so we suggest you walk around and enjoy the charm of the streets close to the town center.
Meals: Breakfast
Longer route: 67 km (41.6 miles), +500 m (+1,640 ft)
Shorter route: 23 km (14.3 miles), +200 m (+660 ft)
Accommodation: Pousada Convento Vila Viçosa
What a gorgeous day before you! Today, you will ride toward Spain through landscapes overflown with cork trees, olive groves, and flocks of sheep. Admire the beautiful Guadiana River that separates Portugal from Spain, and make a stop to visit Juromenha, a picturesque village overlooking Spain. Today, you will have to face some uphills while returning to Vila Viçosa, but your efforts will be rewarded with a delicious meal in the evening.
Meals: Breakfast
Longer route: 51 km (31.7 miles), +600 m (+1,970 ft)
Shorter route: 27 km (16.8 miles), +300 m (+985 ft)
Accommodation: Pousada Convento Vila Viçosa
After a good night’s rest, leave Vila Viçosa in the morning. Ride through the cork forest while the warm wind and a peaceful atmosphere accompany you. When you arrive at the hotel museum in Redondo, you will find an impressive collection of tiles. A remarkable ceramic work that is centuries old and, essentially, a reflection of Alentejo’s cultural style. This building used to be a convent. You’ll be fascinated by how the Kings were sleeping here since the 1500s! To finish the day, challenge your taste and pallet by learning more about Portuguese wine at the Wine museum in the center. Don’t miss it!
Meals: Breakfast and dinner
Longer route: 41 km (25.5 miles), +500 m (+1,640 ft)
Shorter route: 29 km (18 miles), +400 m (+1,310 ft)
Accommodation: Convento de São Paulo
Today is another beautiful day, riding hills of gold and green. Discover cork trees, pristine vineyards, and a pastoral countryside dotted by abandoned castles. After all these days of rolling hills and traversing through past, present, and old-world heritage, the time has come to finally arrive at the most beautiful historical city in the country. Évora is a once-in-a-lifetime experience. Make your way there and discover this gorgeous town!
Meals: Breakfast
Single route: 51 km (31.7 miles), +400 m (+1,310 ft)
Accommodation: Pousada Convento de Évora
Évora is classified as a UNESCO World Heritage Site and has a 2,000-year-old history. After a late breakfast, it’s time to finally explore the surroundings and get to know this unique town. Soon, you will arrive in Arraiolos, noted for its colorful, hand-stitched woolen tapestries. There must be space back home to fit one in your living room! This will be the last day of riding, and you will have the unique opportunity to celebrate with some Portuguese wine right at its birthplace! Saúde!
Meals: Breakfast
Longer route: 70 km (43.5 miles), +600 m (+1,970 ft)
Shorter route: 46 km (28.6 miles), +400 m (+1,310 ft)
Accommodation: Pousada Convento de Évora
All good things come to an end, and so does this adventure. It’s highly recommended that you stay longer in the area because Portugal has a lot to offer! If you’re heading home, you will be picked up and transferred to Lisbon Airport (1.5-hour ride).
Meals: Breakfast
Please note that accommodations are subject to availability and it may not be possible to book the exact accommodations listed day-by-day in the itinerary (in case there is a detailed list).
Also note that your chosen dates for the tour are not guaranteed until confirmed by the guide. If the guide is unable to secure your preferred dates/accommodation, you’ll get a full refund!
We booked two self guided bicycle trips with Portugal Nature Trails (PNT) in May 2023, Alentejo Vineyards and Easy Wild Coast. PNT exceeded our expectations in all regards. We rented e-bikes. Without them we would have had trouble with the distance and elevation (although we are fit and active we are in our late 60s). My spouse is 4ft 10 in (147 cm). PNT fitted her with a new adult ladies XS. Worked perfectly for her. The PNT representative tuned the bikes for us and made sure we were comfortable before he left us to start the self guided trips. The navigation app, Ride With GPS, worked well but on a couple of occasions we had to practice our orientation skills. All part of the adventure. The routes were off road or on back roads with little traffic. Accommodations, which always included breakfast, were above average. Recommendations in the information package for lunch and dinner were excellent. Transportation from Lisbon to the start of the first trip, between trips and back to Lisbon was on time. During the booking process PNT were patient and flexible with our requests for modifications to the itinerary. In summary we would recommend Portugal Nature Trails to anyone wanting a self guided, adventurous bike tour.
We have loved every self guided hiking trip we have taken with PNT. Four in total . We highly recommend them . The trails ,support, track, accommodations, staff , food and GPS were all exceptional. We have been fortunate to have great weather each time . Already planning our next one ‼️
What you get on this adventure:
What’s not included:
*Please note that accommodations are subject to availability and it may not be possible to book the exact accommodations listed day-by-day in the itinerary (in case there is a detailed list).
If you’d like to join this bike tour in Alentejo, a good fitness level is required. A great thing about this tour is that you’re the one who chooses how easy you want to make it! You will get all the necessary maps and route information for both the shorter and the longer route.
In the itinerary, you will find both options—their distances and elevation gains, but you can expect between 41-70 km (25.5-43.5 miles) per day if you’re taking the longer route, and 23-51 km (14.3-31.7 miles) pre day for the shorter route. You will be cycling mostly along rolling hills and on paved roads only (cobblestone roads here and there while crossing some villages). Keep in mind that you will be cycling for 6 days in a row, getting from one hotel to the other.
You can make this tour easier by renting a hybrid e-bike, as this will give you a good push and some additional power! Read more about bike rentals below.
Here’s a list of the equipment you need to bring:
Dress comfortably and for the weather in clothes you can move in. We suggest bringing clothing appropriate for the season. Layers are best and don’t wear jeans.
Yes, you can! Skip the hassle of dragging your bike to this bike tour in Alentejo, and simply rent it. These are the following rentals available, prices are per person, for the whole week:
You can rent these upon checkout. Note that the model may vary depending on availability. By renting one of these bikes, you also get a helmet, water bottle, handlebar bag, and a rear rack & bag. You will also get a tool kit to change chains, repair flats, and keys to adjust the bike, as well as a small air pump and a lock.
Feel free to bring your own pedals and your own seat—the guiding company will help you change these upon your arrival. Alternatively, you can let us know what type of pedals you use and your guides will do their best to accommodate you.
A self-guided tour is an independent exploration without a formal guide leading the way. Instead of being part of a group with a tour leader, you will navigate the tour yourself, using resources provided by the operator.
By going on this self-guided bike tour in Alentejo, everything will be arranged and waiting for you! This includes accommodation, breakfasts, airport transfers, luggage transfers, digital information pack, personalized bike fitting, optional bike rental, local support, and more. It’s a fully carefree experience, maximizing your enjoyment of the region.
Group sizes and pricing
Min. age requirements
If your group has cyclists under the age of 18, contact us prior to booking to make arrangements.
To get to your self-guided bike tour in Alentejo, it’s best to fly into Lisbon Airport (LIS), which is where you’ll get picked up. The transfer is included in the price and it takes around 2 hours to reach your first hotel of the trip.
There’s no set time of arrival, but make sure to fly in at a reasonable time, giving you enough time for a transfer, settling into the hotel, and taking a stroll through the city.
We highly recommend that you cover all your bases with both emergency medical and travel insurance. To make your booking and traveling experience as carefree as possible, we partnered up with Redpoint—the official 57hours insurance partner!
Redpoint tailors their insurance packages for adventure travel, offering a comprehensive travel program, even in remote locations. Trip cancellation, natural disasters, pandemic coverage, medical evacuation, primary medical expenses—regardless of the travel interruption that may happen, Redpoint will have you covered.
Once your booking is confirmed and your trip is paid in full, you will be offered to purchase Redpoint’s insurance. If you need any help or require more information, let us know and we will be happy to help!
Deposits
You can secure one of the set dates with a 30% deposit upon booking. The remaining 70% of the trip price is to be paid 90 days prior to departure, at the latest.
Cancellations
Booking fees are non-refundable in all cases. During checkout, however, you can choose one of 57hours’ flexibility options:
Basic
Flexible
Super Flexible
Amazing self-guided cycling trip down the coast!lovely accommodations along the way. The staff at Portugal Nature Trails were so friendly and helpful. Can’t wait to come back.