What you get on this adventure: 7-day self-guided bike tour in Alentejo Accommodation for 6 nights in historical convents and castles that were renovated into the most charming hotels imaginable (ensuite double/twin room) 6 breakfasts Dinner on Day 4 (set menu, drinks excluded) Airport transfers (Lisbon Airport to the first hotel on Day 1 & last hotel to Lisbon Airport on Day 7) Transfers during the tour as listed in the itinerary Luggage transfers Pre-departure information pack (checklist, general travel information, tour information) Digital information book before the tour (daily information, daily maps, restaurant recommendations…) Personalized bike fitting & helmet Liability and personal accident insurance Local support number Navigation app & GPS tracks What’s not included: Flights to Portugal Bike rental — available upon checkout (you 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) Lunches and dinners Drinks GPS device (Garmin Oregon) — available at an additional cost upon checkout (but you’re welcome to bring your own GPS advice and the guides will send you the tracks) Single supplement — available at an additional cost upon checkout City taxes (some locations impose tourist tax, up to 3 euros per person per night, payable in cash in person only) Anything else not mentioned in the included section

How fit do I need to be?

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.

What do I need to bring?

Here’s a list of the equipment you need to bring: Day pack large enough for everything you might need throughout the day Water bottle or hydration bladder (2L capacity) Comfortable shoes Comfortable cycling clothes (cycling pants/shorts, t-shirts, long sleeves) Gloves Spare clothes for layering Waterproof rain jacket Comfortable jacket to wear at the end of the day Slippers Towel Swimsuit Sunhat Energy bars & snacks for the day Toiletries (sunscreen, hand sanitizer, bug spray, toilet paper etc.) Personal medications Sunglasses Camera — optional (but recommended) 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: Hybrid bike ($150) — GHOST square bike Hybrid e-bike ($270) — GHOST E-Teru BOSCH Carbon road bike ($235) — brand or model depends on availability 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.

What is a self-guided tour?

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 age requirements

Group sizes and pricing For this self-guided bike tour in Alentejo, it takes at least 2 people for it to run. Self-guided bike tours in Alentejo can also be arranged for larger groups. Contact us to make arrangements. Min. age requirements If you are older than 18, you’re good to go. Minors younger than 18 can join the bike tour in Alentejo on a case-by-case basis, but must be in the presence of a parent or legal guardian. If your group has cyclists under the age of 18, contact us prior to booking to make arrangements.

Getting there and meeting location

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.

Safety measures and insurance

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!

ALENTEJO | PORTUGAL

Self-Guided Bike Tour Through Alentejo & Its Vineyards

5.00 ()

Season

Year-round

Duration

7 days (5 days of cycling)

Accommodation

Incredible renovated castles & convents

Difficulty

Self-guided tour

Accommodation, route notes, maps, luggage transfers, breakfast, airport transfers, local support, and more included

Guide

Portugal Nature Trails

Questions, additional dates, private groups

Book a call

From $1,490 () / 7 days

Book now

Intro
Itinerary
Brochure
Guides
Accommodation
Reviews
Things to know

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.

Adventure highlights

Feel like royalty

Nights will be spent in historical castles, palaces, monasteries, and convents, which were renovated into lovely accommodation
Fall in love with the colors & the patterns

Portuguese traditional handcrafted tiles, pottery, tapestry, and embroidery make for a perfect souvenir & reminder of your stay
Move at your own pace

There are two route options, choose the one you love more and pedal through Alentejo, stopping for pics or breaks whenever you want to

Itinerary

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: Pousada Convento Vila Viçosa
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

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Meet your guide

5.00

Portugal Nature Trails

Portugal Nature Trails is a local adventure company offering the most outstanding hiking and cycling tours throughout Portugal. Since 2004, they’ve been organizing adventures with a strong emphasis on respecting the local culture, nature, and communities. Exploring the country’s wildest and most well-preserved regions while tasting the best local food and wine, spending nights in charming accommodations, and reshaping the travel experience—this is what Portugal Nature Trails is all about.

Accommodation

Pousada Castelo Estremoz

The Pousada Castelo Estremoz is a 13th-century castle built by Dom Dinis for Queen Santa Isabel. Perched within the city’s historic center, it offers the perfect starting point to explore on foot, with stunning views from the Torre de Menagem (Tower). This luxury hotel features panoramic vistas of Estremoz and the surrounding Alentejana lowlands from its lush gardens and outdoor pool. Guests can enjoy the game room, restaurant, bar, and spacious, elegantly decorated rooms, many of which retain their classic 18th-century charm.

There is also a restaurant within the hotel, where you might have dinner—dining here brings a blend of traditional Portuguese cuisine with modern Alentejo influences. Visitors can explore nearby landmarks, manors, and wineries, and every Saturday, the lively Weekly Market at Praça Dom José I adds to the charm of this historic destination. Please note that if this or any other accommodation isn’t available, an alternative will be offered.

Pousada Convento Vila Viçosa

The Pousada Convento Vila Viçosa is located in a village rich in history and charm. It is housed in the former Convent of the Chagas de Cristo, a 16th-century convent commissioned by Jaime IV, Duke of Bragança. Surrounded by picturesque gardens, it offers a serene escape—guests can unwind by the outdoor pool, enjoy a game in the games room, or relax in the drawing room, which features a piano. The rooms, decorated in warm tones, are equipped with modern amenities, including television and free Wi-Fi. There are also 11 unique themed rooms, each with its own special character.

The restaurant, located in the former convent refectory, offers a delightful taste of Alentejana cuisine, paired with traditional convent sweets. In summer, dining in the Cloisters, surrounded by 16th-century frescos, provides a truly enchanting experience. The pousada’s rich history is intertwined with the legacy of the powerful Bragança family, with the convent, church, and nearby Ducal Palace standing as witnesses to a grand historical era.

Hotel Convento de São Paulo

Hotel Convento de São Paulo, nestled in the Serra D’Ossa hills, offers a peaceful retreat in a former 12th-century convent. The property is surrounded by extensive gardens, historic fountains, and over 50,000 intricately painted tiles that add to its charm and grandeur! Guests can unwind in beautifully restored rooms, some of which were once the monks’ cells, blending modern comforts with a historic ambiance.

The hotel features a restaurant, as well as a bar, games room, and multiple banquet spaces. Whether lounging by the outdoor pool, exploring the fresco-filled Cloisters, or taking in the serene gardens, guests will find plenty of ways to relax.

Pousada Convento de Évora

Pousada Convento de Évora, sitting in the historic heart of Évora, offers a unique blend of history and luxury. Housed in a former 15th-century convent, the hotel’s rooms retain much of their historical character, combining old-world charm with modern comforts.

Guests can enjoy the Pousada’s renowned Loios restaurant, known for its delicious regional cuisine with a contemporary twist. The dining experience is enhanced by the restaurant’s setting within the convent’s cloisters. During the summer months, the poolside bar serves refreshing snacks to complement the Alentejo heat, while the hotel’s indoor spaces, including the bar and common areas, offer cozy retreats in winter.

5.00 (5 reviews)

Christina e (source: Trip Advisor)

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.

DaveBritishColumbia (source: Trip Advisor)

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.

Tom P (source: Trip Advisor)

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 ‼️

Maurice M (source: Trip Advisor)

Really well organised. Great booklet to guide us. Tailored to what we wanted to do. We opted for the self guided tour. So we got 2 GPSs between four of us with the route clearly marked in purple. Only time we got into trouble was when we assumed that we knew better than the GPS and took a “short cut” and got lost!! …. Hats off to Diane and the team at Portugal Nature Trails. …. friendly and efficient

Stephen W (source: Trip Advisor)

Very professional organisation . Brand new hybrid bikes , great detailed information , maps , garmins and emergency phones all supplied . Hotels good for tired cyclists at the end of each day and good advice supplied on where to eat. Would definetely use them again for trips in Portugal .

Things to know

What you get on this adventure:
- - 7-day self-guided bike tour in Alentejo
  - Accommodation for 6 nights in historical convents and castles that were renovated into the most charming hotels imaginable (ensuite double/twin room)
  - 6 breakfasts
  - Dinner on Day 4 (set menu, drinks excluded)
  - Airport transfers (Lisbon Airport to the first hotel on Day 1 & last hotel to Lisbon Airport on Day 7)
  - Transfers during the tour as listed in the itinerary
  - Luggage transfers
  - Pre-departure information pack (checklist, general travel information, tour information)
  - Digital information book before the tour (daily information, daily maps, restaurant recommendations…)
  - Personalized bike fitting & helmet
  - Liability and personal accident insurance
  - Local support number
  - Navigation app & GPS tracks
What’s not included:
- - Flights to Portugal
  - Bike rental — available upon checkout (you 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)
  - Lunches and dinners
  - Drinks
  - GPS device (Garmin Oregon) — available at an additional cost upon checkout (but you’re welcome to bring your own GPS advice and the guides will send you the tracks)
  - Single supplement — available at an additional cost upon checkout
  - City taxes (some locations impose tourist tax, up to 3 euros per person per night, payable in cash in person only)
  - Anything else not mentioned in the included section
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:
- - Day pack large enough for everything you might need throughout the day
  - Water bottle or hydration bladder (2L capacity)
  - Comfortable shoes
  - Comfortable cycling clothes (cycling pants/shorts, t-shirts, long sleeves)
  - Gloves
  - Spare clothes for layering
  - Waterproof rain jacket
  - Comfortable jacket to wear at the end of the day
  - Slippers
  - Towel
  - Swimsuit
  - Sunhat
  - Energy bars & snacks for the day
  - Toiletries (sunscreen, hand sanitizer, bug spray, toilet paper etc.)
  - Personal medications
  - Sunglasses
  - Camera — optional (but recommended)
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:
- - Hybrid bike ($150) — GHOST square bike
  - Hybrid e-bike ($270) — GHOST E-Teru BOSCH
  - Carbon road bike ($235) — brand or model depends on availability
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
- - For this self-guided bike tour in Alentejo, it takes at least 2 people for it to run.
  - Self-guided bike tours in Alentejo can also be arranged for larger groups. Contact us to make arrangements.
Min. age requirements
- - If you are older than 18, you’re good to go.
  - Minors younger than 18 can join the bike tour in Alentejo on a case-by-case basis, but must be in the presence of a parent or legal guardian.
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
- - In case of cancellation within 48 hours after booking, the amount paid is fully refundable.
  - For cancellations 90 or more days before the trip, you are eligible for a 70% refund of the trip price.
  - For cancellations 0-89 days before the trip, there is no refund.
Flexible
- - In case of cancellation within 48 hours after booking, the amount paid is fully refundable.
  - For cancellations 90 or more days before the trip, you are eligible for a full refund of the trip price.
  - For cancellations 60-89 days before the trip, you are eligible for a 50% refund of the trip price.
  - For cancellations 0-59 days before the trip, there is no refund.
Super Flexible
- - In case of cancellation within 48 hours after booking, the amount paid is fully refundable.
  - For cancellations 60 or more days before the trip, you are eligible for a full refund of the trip price.
  - For cancellations 0-59 days before the trip, you are eligible for a 50% refund of the trip price.