18PO_border_1600x670 19PO_climb_1600x670 19PO_flowers_1600x670 17PO-IMG_5497-1600x670 Trek Travel Portugal Cycling Vacation 16PO-evora_Photo-by-Jo-Paulo_1600x670 20POSG_tree_40_800x533 20POSG_fortress_40_800x533

Portugal Self-Guided Bike Tour

A journey through Alentejo region, where time stands still

Welcome to the Alentejo region of Portugal, which features gentle hills and unspoiled green and gold landscapes. During your Portugal self-guided bike tour, you will visit and stay in an historic castle and a former monastery, once inhabited by clergy, kings, and queens, and now converted into exquisite lodging. Trek Travel’s self-guided trip of Portugal offers you the opportunity to soak in the traditional small village vibe and enjoy your own pace of riding and sightseeing. Enjoy earthy wines and tasty regional delicacies like aged cheeses and ham produced from the black-footed pigs that devour the acorns falling from the region’s oak trees. Explore Roman heritage preserved in ancient towns like Évora, a UNESCO World Heritage site, where city walls and ruins of Roman baths still remain and live right in the middle of contemporary life. Pedal at your leisure through the breathtaking wilderness offered by the Serra de São Mamede Natural Park and feel the peace and relaxation in your soul as you are in a seamless bond with nature. And the best part, every moment will be on your own timeline with our curated itinerary in your back pocket.
$2599 Per Person
6 Days & 5 Nights
Rider Type: ?
3 - Active Non-riders Welcome
Hotel Style: ?
From $2599 per person View All Details
Trip Wows
Stay in two historical properties once inhabited by monks and queens and now converted into luxury hotels
Visit the UNESCO World Heritage site of Évora and learn about its unique history with a local guide
Explore the walled village of Marvão set on a great granite escarpment with sweeping views across the vast plains of the Alentejo
Discover the great biodiversity of São Mamede Natural Park as you ride through its amazing landscape
Indulge in the flavors of traditional Alentejo cuisine, together with the region’s fine red wines
A very well-conceived trip with fun routes, excellent food, and interesting side tours. We felt Trek was fully behind us whilst enjoying the freedom of self-guidance. And the Trek bikes inspired confidence!
-John, Trek Travel Guest

Dates & Prices

The Earlier You Book, The Greater The Rewards

We reward our guests with lower pricing and more dates to choose from the earlier you book. Rest assured, once you book, your price and date are guaranteed.
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Our trip on your schedule. Simply choose your own travel dates and we will handle the rest. Contact our Trip Consultants today at 866.464.8735 to get started.
Don't see your ideal travel date? 
Call us at (866) 464-8735 for custom date availability
Looking for a one of a kind, once in a lifetime experience?
Look no further. All you need to do is pick any open trip date, get your group together and we will do the rest. Private trip pricing is as follows:
  • 10+ Guests Price as advertised*
  • 8-9 Guests +$500 per person to trip price*
  • 6-7 Guests +$1,000 per person to trip price*
  • 4-5 Guests +$1,500 per person to trip price*
  • 2-3 Guests +$2,500 per person to trip price*
*Pricing, availability and guest minimums are all subject to change at any time. Certain dates have a minimum number of guests required, please contact us for details. Private pricing is not available on Ride Camp, Race, Special Edition or Cross Country style trips.
Looking for a date that you don’t see?
Look no further. Simply tell us your preferred travel dates and we’ll work together to deliver the same great trip on your custom schedule.
*Pricing, availability and guest minimums are all subject to change at any time. Certain dates have a minimum number of guests required, please contact us for details. Custom dates are not available on Ride Camp, Race, Special Edition or Cross Country style trips.
Want to customize this trip?
We've got you covered. We’ll work with you to build your perfect vacation from scratch, including your choice of riding, accommodations and dining options. With the help of our trip designers and travel experts, the world is available like never before.
*Pricing, availability and guest minimums are all subject to change at any time. Certain dates have a minimum number of guests required, please contact us for details. Custom trips are not available on Ride Camp, Race, Special Edition or Cross Country style trips.

After arriving at the Lisbon airport, a private shuttle will transfer you approximately two hours to Estremoz, a strategically built town that was once key to Portugal’s struggle to stay independent from its Spanish neighbors. A Trek Travel guide will welcome you at your luxury hotel and then fit and familiarize you with your bike and the itinerary for your Portugal self-guided bike tour. Then, it's off on your first adventure through pastoral fields, where the only sounds are the jangling bells of flocking sheep. The ride will take you to Vila Viçosa, the capital of marble in Portugal, a laid-back, friendly, and beautifully maintained town whose most interesting attraction is the Ducal Palace. Next, continue your ride to Borba, a small town of beautiful white houses, renowned for its excellent wines and olive oil, where you can visit the local winery Adega de Borba for an included private tour and tasting. The ride will finish at the hotel, a former castle converted into a historical hotel that offers a superb view over the city of Estremoz and the vast Alentejo plain. Take a bit of time for a drink poolside, watching the sunset before enjoying a meal cooked in traditional Alentejo style at the hotel’s restaurant.

Today's Ride:

Estremoz to Vila Viçosa Loop
Approximately 29 miles with 1,390 feet of climbing


Pousada Castelo de Estremoz

Included Meals:

Social Hour | Dinner

This morning you'll take your bike and ride through gently rolling countryside noted for producing high-quality wines toward Évora, a UNESCO World Heritage site. You'll pass by its impressive 16th-century aqueduct, then take an expert-led walking tour with a local guide to the Temple of Diana, an ancient Roman temple dating back to the first century and the town’s most famous landmark. You will finish your tour at the Bone Chapel, perhaps one of the most memorable monuments of Évora, where the walls are lined with bones of the long-deceased, exhumed from the city's graves as the city expanded to allow further burials. Enjoy lunch on your own and take your time to explore a maze of perfectly maintained cobbled streets with traditionally painted houses. A variety of delightful shops provide a great opportunity to buy presents and souvenirs. A private shuttle will await you to take you back to Estremoz where dinner is at your leisure at the restaurant of your choice in town or at the hotel.

Today's Ride:

Estremoz to Évora (with shuttle back)
Approximately 43 miles with 2,100 feet of climbing

Avid Option:

Estremoz to Évora via Montoito (with shuttle back)
Approximately 51 miles with 2,600 feet of climbing


Pousada Castelo de Estremoz

Included Meals:


This morning you will say goodbye to Estremoz, and you will make your way north through more vineyards, alongside olive groves, and past convents and castles dating to Medieval times. Be prepared to ride over cobblestone streets as you pass through villages with the typical Alentejo white-washed homes outlined in blue and ochre trim. Stop in the peaceful Alter do Chão to admire its medieval castle, an authentic architectural masterpiece! You will finish the ride at Pousada do Crato, a former palace, convent, and castle that has been converted into a luxury hotel and will be your home for the next three nights. Tonight take advantage of your included dinner at the hotel's fine restaurant.

Today's Ride:

Estremoz to Crato
Approximately 41 miles with 2,400 feet of climbing

Avid Option:

Estremoz to Crato with Aldeia de Mata Loop
Approximately 64 miles with 3,000 feet of climbing


Pousada Mosteiro do Crato

Included Meals:


Northern Alentejo boasts Portugal’s most bio-diverse environments and offers breathtaking wilderness, lake, and forest walks, all set in 55,000 hectares of protected area named Serra de São Mamede Natural Park. Today the rolling plains give way to steeper climbs through this fascinating territory. At your own pace, take your bike and immerse yourself in all the beauty that nature has to offer. Ride past chestnut and cherry trees, oaks, vineyards, and olive groves as you observe rare birds of prey such as the vulture, kite, or Bonelli eagle - the symbol of the park. If you feel like climbing a bit more, take the opportunity to extend your loop to Alegrete, where you can admire fantastic views! Our recommendation for lunch today is Sever Rio in Portagem, a peaceful and quiet restaurant located on the banks of the river Sever, where you can refuel with exquisite food before heading back to the hotel. After some relaxation time by the pool, prepare for another taste of Alentejo cuisine for dinner at the hotel's delicious restaurant.

Today's Ride:

Crato to Portagem Loop
Approximately 47 miles with 3,700 feet of climbing

Avid Option:

Crato to Portagem via Alegrete Loop
Approximately 59 miles with 4,700 feet of climbing


Pousada Mosteiro do Crato

Included Meals:


Your journey continues in the Alto Alentejo through flowering landscapes, past castles, and through picturesque white villages. Serra de São Mamede will reveal in all of its great splendor today as you pedal past two of its hidden gems! Castelo de Vide dominates the surrounding landscape and awaits your visit through the flower-lined cobbled lanes which wind up to the castle. Explore the whitewashed cottages of the Jewish Quarter with their distinctive granite, gothic doorways and stop at the Fonte de Vila (town fountain) which dispenses Castelo de Vide’s mineral water, well known for its healing properties. Only a few kilometers further and considered by the New York Times one of the "Top 1000 Places to See Before You Die" you will find the walled town of Marvão. Perched on a granite crag of the São Mamede Mountain, the town stands out for its imposing castle and its neolithic and Roman remains. Enter through the large stone archway and walk the castle walls with spectacular views into Spain and into the Alentejo breadbasket. Tonight, celebrate a wonderful self-guided biking adventure in this magical region with one last dinner at the hotel or other restaurant of your choice!

Today's Ride:

Crato to Marvão Loop
Approximately 50 miles with 4,000 feet of climbing

Avid Option:

Crato to Marvão Loop
Approximately 57 miles with 5,000 feet of climbing


Pousada Mosteiro do Crato

Included Meals:

Breakfast | Dinner

You're Portugal self-guided bike tour is coming to a close. Take this morning to sleep in and relax, savoring a long breakfast or perhaps go on a final early-morning ride around Crato to soak up the flavors of this beautiful region. A Trek Travel guide will meet you at the hotel at 10:00 AM to take your bike and say farewell before you board on a private shuttle to Lisbon.

Today's Ride:

Crato to Alter do Chão Loop
Approximately 23 miles with 1,500 feet of climbing

Included Meals:



hotel image

Pousada Castelo de Estremoz

Estremoz, Portugal

Located in a castle originally built for Queen Santa Isabel in the 13th century, this luxury hotel offers panoramic views of Estremoz and the vast Alentejo plain from the palace gardens and outdoor pool. The rooms at Pousada Castelo de Estremoz feature classic décor, several still maintaining characteristics of the 18th century. The restaurant serves gourmet cuisine that combines traditional Portuguese cooking with contemporary elements. Guests can enjoy a glass of regional wine in the castle’s grand dining hall.
hotel image

Pousada Mosteiro do Crato

Crato, Portugal

Originally a 14th-century convent, then a palace, and subsequently a castle, Pousada Mosteiro do Crato has been converted into a luxury hotel by carefully blending the traditional with modern conveniences. Located on the northern edge of the Alentejo region, the hotel is an architectural masterpiece that consists of different buildings reflecting the architectural changes throughout the ages including Gothic, Moorish, and Renaissance styles. All rooms are decorated with warm colors and dark wooden furniture. Guests can enjoy local Portuguese dishes as well as international cuisine in the restaurant. The hotel’s elegant swimming pool is surrounded by beautiful, lush gardens and is the perfect place to relax and unwind under the hot Alentejan sun.

What's Included

For us, the details matter most

Every moment of a Trek Travel bike trip has more than you could have ever dreamed. More romance. More scenery. More choice. It's the little additions to every Trek Travel cycling vacation that make it truly special. And that's how we help you create more memories.


Trek Domane SL 7 Disc

It isn’t the cycling vacation of a lifetime unless you have the industry’s best bike to match. In 2019, we upgraded our fleet to feature the award-winning Domane SL 7 with Shimano Ultegra Disc brakes. Because when you combine the lightweight stability and comfort of the Domane with the superior safety and stopping power of disc brakes, you get a match made in cycling heaven. And the best part? It’s included in the trip price. Ride confidently, comfortably and longer in the most beautiful destinations around the world with the new Domane SL 7. Learn More


Trek Electric-Assist Verve+

With its Low-Step frame design, hopping on and off the Trek Verve+ is super easy. The front suspension will take the edge off any bumps in the road and the Bosch system will keep you smiling from ear to ear. The integrated battery keeps this bike looking sleek as you pedal through amazing terrain. Learn More


  • Five nights of accommodation at handpicked hotels
  • Expertly designed daily routes
  • Daily breakfast
  • Two dinners
  • One social hour of drinks and hors d'oeuvres
  • Ride a Trek Domane SL 7 disc or Trek Electric-Assist Verve+
  • Up to three daily route options on riding days
  • Trek Travel Bontrager cycling jersey to keep
  • A Trek Travel water bottle to keep
  • Each bike is equipped with a Garmin Edge 1030 GPS computer, flat pack, front and rear Bontrager Flare R lights, a Bontrager saddle and pedals (Shimano clipless road pedals, Shimano clipless mountain pedals, caged or flat pedals)
  • All gratuities for drivers, local experts, and hospitality staff
  • Bontrager WaveCel helmets
  • All luggage transfers and transportation during your trip
  • A few extra activities


  • Trek Domane SL 7 disc carbon road bike with Shimano Di2 electronic shifting
  • Trek Electric-Assist Verve+ also available in a limited quantity
  • Trek Travel Bontrager cycling jersey to keep
  • A Trek Travel water bottle to keep
  • Shimano clipless road pedals, Shimano clipless mountain pedals, caged or flat pedals
  • Bontrager WaveCel helmet
  • Bontrager men's and women's specific saddles
  • Bontrager front and rear Flare R lights and a flat pack
  • Garmin Edge 1030 GPS computer
  • Upgrade your bike to include carbon wheels (+$200)
  • Coupon valued up to $500 off a new Trek Bicycle. Your coupon will be delivered via email.
  • For the most comfortable ride, you may choose to bring your own pedals, saddle, and helmet on the trip. Your guides will install your gear on the first day during your bike fit.


Gratuities for your Trek Travel guides are not included in your trip price. We recommend tipping 7.5-10% of your trip price for the guide team. Local currency is preferred and unless you want to tip separately, guides will divide tips amongst themselves. Please tip your guides at your discretion, based on their level of professionalism, guest care and service.
  • Airfare and transportation to and from the trip pick-up/drop-off locations
  • Lodging before and after the trip
  • Personal items purchased during the trip
  • Optional activities not scheduled by Trek Travel
  • Meals are not included, except for daily breakfast and two dinners. On self-guided trips, Trek Travel invites you to explore the local cuisine at your leisure

More Information

Rider Level: 3 - Active?

39 miles
233 miles
2,563 feet
15,379 feet
The terrain of the Alentejo region is a vast area of gently rolling plains in the south and steeper hills in the north (São Mamede Natural Park). This trip is best suited for our Type 3 Riders. Those who wish to ride every mile but are concerned about their physical ability may want to try our electric bike option—you still get a workout but can climb alongside even the strongest rider. Type 4 Riders will enjoy the extra mileage the avid route options offer.
Our Trek Travel Portugal self-guided bike tour offers non-riding options for travel companions who don’t want to spend any time in the saddle. Some of these options may need to be scheduled before your trip–please contact one of our Trip Consultants for more information. Expenses and/or related transportation to these activities may not be included in the trip price. Some non-riding options on this trip are:
  • Hotel spa and pool
  • winery tour and tasting
  • Historical and cultural walking tour of Évora
  • hiking in Serra de São Mamede Natural Park
  • Visit of walled village of Marvão

See itinerary for specific daily ride distances and elevation options. On all of our cycling vacations, Trek Travel strives to find quiet, paved secondary roads or bike paths to experience a region; busy roads are avoided as much as possible. Our itineraries are an approximation of our trips. Trek Travel strives to offer every guest a vacation of a lifetime on every trip. At times routes, hotels, activities, etc. listed here may change at the discretion of the trip designer or guides to improve the trip experience.

Averages and totals are calculated from our "Today’s Ride" options.

Travel Details

How to Get There

Lisbon Portola Airport (LIS)
10:00 AM
A Padaria Portuguesa, Rua Mouzinho da Silveira 2, 1250-042 Lisbon, Lisbon, Portugal

Say Farewell

Lisbon Portola Airport (LIS)
11:00 AM
Lisbon Portola Airport, Lisbon, Portugal


We suggest that you arrive at least one day prior to the trip start, which will enable you to adjust to the time zone (GMT-6) and minimize the risk of missing the trip start due to flight-related delays. We recommend that you fly into Lisbon Portola Airport (LIS). Public transportation is inexpensive and easy to use from the airport. You can take the Metro with a one-way ticket for about two euro or get the daily pass, which allows you to use the metro, bus, trams and trains for six euro. More info can be found here: http://metro.transporteslisboa.pt/eng/ Alternatively, taxis are plentiful and cost approximately 15 to 25 euros to Lisbon center.

A private shuttle will pick you up at the A Padaria Portuguesa (Rua Mouzinho da Silveira 2, 1250-042 Lisbon) at 10:00 AM on the first day of the trip. You'll then shuttle approximately two hours to your first trip hotel where you will be welcomed by a Trek Travel guide. Your guide will fit and familiarize you with your bike for the week and speak to the specifics of cycling in the area before you venture on the roads of Alentejo at your leisure.

If you will be late for the pick-up or are going to miss it altogether, please inform your guides. You will receive an email a week before the trip start with their names and contact details. If you cannot reach them, please call our first hotel, Pousada Castelo de Estremoz (+351 268 332 075), and leave a message with your expected arrival time and contact details.

View our pre hotel recommendations


A Trek Travel guide will meet you at 11:00 AM at the hotel Pousada do Crato to take your bike and equipment. You’ll depart by private shuttle to Lisbon Portola Airport, the trip will take approximately two hours. Please do not schedule a flight out before 2:30 PM on the last day of the trip to allow plenty of time for any unforeseen delays. If you are staying in Lisbon, the shuttle will also stop in the center of town at A Padaria Portuguesa (Rua Mouzinho da Silveira 2, 1250-042 Lisbon).

View our post hotel recommendations

Planning For Your Trip

Packing and Weather

The south central region of Alentejo sees favorable temperatures year round, but spring is the best time to visit with average temperatures from from 55F-75F. Even with only an average of six to eight days of rain, there is always a chance for a spring shower, so rain gear is recommended. Packing List

Before and After Your Trip


Before & After: Lisbon, Portugal

Lisbon, known as the city of seven hills, is the capital city of Portugal and is overflowing with great café culture, music, art, and history. You'll be enchanted by the narrow, cobbled streets, white washed walls, ochre roofs, and colorful splashes of ceramic tiles. Be sure to walk the streets of some of the many storied neighborhoods and certainly don't pass up a pastéis de nata, Portugal's mouthwatering custard tart. We recommend the following accommodations for your pre and post-trip hotel:

Why Trek Travel

Our Bikes

Our unrivaled selection of Trek Bikes sets the bar for quality and comfort. From the all-new, ultra smooth Trek Domane SL 7, to the new Trek Electric-Assist XM700+ and the comfortable Trek 7.6 FX Hybrid, to our numerous upgrade options, you deserve the best ride on your vacation.

Our Guides

Our guides are trained to make your trip magical. They aren't just experts in riding; they're trained in delivering uncompromising service in ways you won't believe. We know that it's the unexpected surprises that make a trip magical. That's why our guides pride themselves on anticipating your needs before you ask.

Your Day. You Decide.

Our vacations are built to deliver the ultimate in flexibility, from extreme relaxers to hard-core roadies. You pick your mileage, itinerary and experiences. We take care of the rest.

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