18PO_border_1600x670 19PO_climb_1600x670 19PO_flowers_1600x670 17PO-IMG_5497-1600x670 POSG - Evora+Estremoz - Canva 3 Trek Travel Portugal Cycling Vacation 16PO-evora_Photo-by-Jo-Paulo_1600x670 POSG - Evora+Estremoz - Canva 1 POSG - Evora+Estremoz - Canva 4

Portugal Self-Guided Bike Tour

A journey through Alentejo region, where time stands still

Welcome to the Alentejo region of Portugal, featuring gentle hills and unspoiled green and gold landscapes under dazzling blue skies. Trek Travel’s self-guided trip of Portugal offers you the opportunity to soak in the traditional, small-village life and enjoy your own pace of riding and sightseeing. Enjoy earthy red wines that are gaining attention on the world stage and tasty regional delicacies like aged cheeses and ham produced from the black-footed pigs that feed on acorns from the region’s oak trees. Pedal at your leisure through rolling fields of wildflowers and olive trees, past medieval-walled villages that dot the hilltops with wheat fields and vineyards spread out below, and freckled with small flocks of sheep and goats grazing under majestic cork trees. During your Portugal self-guided bike tour, you will visit and stay in historic properties now converted into exquisite hotels. And the best part, every moment will be on your own timeline with our curated itinerary in your back pocket. Book your trip with confidence »
Learn if a self-guided trip is right for you »
$2199 Per Person
5 Days & 4 Nights
Rider Type: ?
3 - Active Non-riders Welcome
Hotel Style: ?
From $2199 per person View All Details
Trip Wows
Stay in historical properties now converted into luxury hotels
Ride through the vineyard-lined roads and quiet country lanes surrounded by olive, eucalyptus, and cork trees
Indulge in the flavors of the Alentejo cuisine, with centuries-old culinary traditions
Discover an area of outstanding wine production, offering extraordinary red wines
Explore the medieval walled village of Monsaraz with sweeping views across the vast plains of the Alentejo, the great Guadiana River, and to its neighbor, Spain
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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Single Occupancy
Available for 2021 and 2022. Our trip on your schedule. Simply choose your own travel dates and we will handle the rest. Price based upon double occupancy and may vary based on dates and hotel availability. Contact us 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. Choose your trip date, get your group together and we will do the rest. Private trip pricing is as follows:
2020 - June 1, 2021 Departures:
  • 6+ Guests    Price as advertised*
  • 4-5 Guests +$500 per person to trip price*
  • 2-3 Guests +$2,500 per person to trip price*
  • 1 Guest        Call us for pricing*

2021 Departures After June 1, 2021:
  • 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 +$3,000 per person to trip price*
  • 1 Guest        Call us for pricing*

Traveling with a small group? Consider semi-private trips.
For groups of up to six people, semi-private trips offer unique flexibility within a larger Trek Travel guided trip. Learn more »

*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.

Welcome to Évora, the capital city of the Alentejo and one of the finest tourist destinations of central Portugal. Don’t miss the opportunity of spending a couple of days in this delightful UNESCO World Heritage Site that boasts a vast array of fascinating attractions. Your Trek Travel guide will meet you at the Albergaria do Calvário hotel at 11:00 AM on the first day of your Portugal Self-Guided Bike Tour. After a 30-minute shuttle, you'll arrive to the hilltop village of Évoramonte where you’ll enjoy lunch at a local cafe with amazing views and discuss the details of the week ahead. Following lunch, your guide will spend some time familiarizing you with your Trek bicycle to ensure a comfortable fit. Then you'll set off on your first ride, riding on quiet, rural roads. Your ride today sets the tone for the week; there is a peacefulness of the Alentejo landscape which reflects the unhurried pace of life of this region! A final climb will lead you to the beautiful fortified town of Estremoz, situated 500 meters above the surrounding landscape. Cycling through the labyrinth of cobbled streets of the 'cidade velha' (old city) you’ll reach your luxurious historic hotel, within the walls of a 13th-century castle. After taking some time to refresh, set aside a moment for a drink poolside, watching the sun set behind the hills before deciding your plan for dinner tonight. You might enjoy the fantastic cuisine in the hotel’s elegant dining room or perhaps try the neighbouring restaurant that was once the town jail!

Today's Ride:

Évoramonte to Sousel to Estremoz
Approximately 33 miles with 2,014 feet of climbing


Pousada Castelo de Estremoz

Included Meals:


Today you'll ride from the magnificent town of Estremoz towards the Alentejo plains characterized by never-ending planted fields, vineyards, and symmetrical olive groves. Pedal past Borba, a bustling town of white houses and cobbled roads, and reach the royal town of Vila Viçosa, the capital of marble in Portugal. This laid-back and beautifully maintained town was once home to the Dukes of Bragança, who had chosen this town as their place of residence at the impressive 'Paço Ducal’. Continue your ride to the fortified castle town of Alandroal which, along with nearby Terena and Juromenha, was an important stronghold during the days of the conquest. Here is a great place to enjoy lunch at your leisure and explore the medieval castle. You may choose to tackle the climb over the cork-tree forested Serra d'Ossa, or take a more relaxed route on quiet, meandering roads. Before finishing your ride, just a short distance from the hotel, the route takes you to one of our favorite wineries in Estremoz, a local treasure that stands out amidst the plethora of surrounding wine producers. Alentejo is the largest wine-producing region in Portugal and it has the perfect conditions to create full-bodied wines that are gaining international recognition. If you feel like it, pop into the winery to experience the region's flavors first-hand, and enjoy not only their wines but their beautiful property and views of Estremoz. Tonight, an array of Alentejo specialties are at your fingertips. Your guide will provide you with names of their favorites in town.

Today's Ride:

Estremoz to Alandroal via Vila Viçosa loop
Approximately 50 miles with 2,619 feet of climbing

Short Option:

Estremoz to Arcos to Borba loop
Approximately 27 miles with 1,610 feet of climbing

Avid Option:

Estremoz to Alandroal to Redondo loop
Approximately 58 miles with 3,956 feet of climbing


Pousada Castelo de Estremoz

Included Meals:


While we take care of transferring your luggage to your next hotel, you'll head south today following the Spanish border and enjoying what might be considered the most beautiful ride of the week! Passing by Alandroal, enjoy the quiet roads virtually void of traffic which allows you to focus on the surrounding and ever-changing landscapes of olive groves, eucalyptus forest, pig farms, and village life. You will pass by the Alqueva reservoir, the biggest of its kind in western Europe. You will then catch sight of the castle town of Monsaraz, set high atop the surrounding area. One short but solid climb will challenge your legs but treat your soul to astonishing views overlooking the Guadiana river, which defines the border with Spain. The beautiful village of Monsaraz, one of the villages winning the title of “Seven Wonders of Portugal”, is also one of the oldest settlements in Portugal and has been a strategic place of defence over the ages. Now it is populated with artisanal shops and restaurants; it is the perfect spot to enjoy a special glass of wine and perhaps a delicious regional dessert before you finish the last stretch of the ride. Only a few kilometers below the town, you’ll find your hotel, a 19th century farming village converted into an exquisite 5-star property of understated luxury, surrounded by ancient holm oaks, olive groves, and vineyards. We suggest you pamper yourself with a spa session before indulging in the delights of their Alentejo cuisine. The hotel’s restaurant serves seasonal, organic produce dishes prepared with the freshest ingredients from their vegetable garden and farm estate.

Today's Ride:

Estremoz to Monsaraz via Alandroal
Approximately 53 miles with 2,559 feet of climbing

Avid Option:

Estremoz to to Élvas to Monsaraz
Approximately 73 miles with 3,387 feet of climbing


São Lourenço do Barrocal

Included Meals:


This morning savour your first exquisite breakfast at your luxury retreat before deciding your plans for the day. If you want to make a more leisurely departure and opt for a softer ride, we suggest you follow our short route that will take you to a renowned local winery, noted for producing high-quality wines and excellent olive oils. Here you can enjoy lunch paired with earthy wines, where you can really taste the mineral-rich terroir. The other two riding options will have you ride at your own pace alongside pastoral fields, where the only sounds are that of the jangling bells on flocks of sheep. Stop along the way for a cafe with the locals in the small village of Terena, as you admire the medieval castle. You may choose to extend your loop through Alandroal or take a more relaxed route on quiet, meandering roads. The golden fields, under blue skies, extend as far as the eyes can see and hill profiles are marked here and there by the ubiquitous cork oaks. This ride truly embodies the peace and tranquillity of the Alentejo region, where time stands still. Tonight dinner is at your leisure at the restaurant that best suits your mood, perhaps opting for a short taxi ride to the locals’ favourite Taverna “Os Templarios”. Don’t miss the opportunity of celebrating a fantastic week in this magical region over a superb dinner on the restaurant terrace with spectacular views across the Alentejo!

Today's Ride:

Monsaraz to Terena loop
Approximately 41 miles with 2,095 feet of climbing

Short Option:

Monsaraz to winery
Approximately 29 miles with 1,110 feet of climbing

Avid Option:

Monsaraz to Terena loop
Approximately 52 miles with 2,876 feet of climbing


São Lourenço do Barrocal

Included Meals:


Your 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 loop ride up and round Monsaraz, and to the nearby recreational beach area, to soak up the flavors of this beautiful region. A Trek Travel guide will meet you at the hotel at 11:00 AM to take your bike and say farewell before you depart.

Today's Ride:

Monsaraz and Beach Loop
Approximately 14 miles with 966 feet of climbing

Included Meals:



hotel image

Pousada Castelo de Estremoz Hotel

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

São Lourenço do Barrocal

Monsaraz, Portugal

This long-standing Portuguese estate located in the foothills of the medieval village of Monsaraz has been in the same family for 200 years. The 780-hectare estate has meadows, vineyards, centuries-old olive groves, an orchard and walled gardens. The hotel offers guest rooms and houses with countryside views. Every room is filled with amenities including air-conditioning, a Nespresso coffee machine, free bottled water, a digital safe and Susanne Kaufmann bath products. This spectacular 5-star hotel has free WiFi throughout, a Susanne Kaufmann spa, a fitness studio, an outdoor pool and laundry services. At the hotel's restaurant the food is focused around time-honoured dishes that let the flavours of Alentejo shine.

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


  • Four nights of accommodation at handpicked hotels
  • Daily breakfast
  • Day 1 lunch with the guide
  • Daily lunch and dinner recommendations
  • Ride a Trek Domane SL 7 disc or Trek Electric-Assist Verve+
  • Up to three daily route options on riding days
  • Trek Travel water bottles to keep
  • Each bike is equipped with a flat pack, frame pump, phone mount, and front and rear lights
  • Bontrager helmet (optional if you do not bring your own)
  • Bontrager saddle (we suggest you bring your own for the most comfortable fit)
  • Shimano clipless pedals or flat pedals (optional if you do not bring your own)
  • All luggage transfers during your trip
  • A bike lock, all necessary chargers, and a floor pump
  • Bike fit on the first day to help you find your optimal position for comfort, with recreational or avid set-up along with saddle preference
  • Ride With GPS app on your phone to navigate and get all the information you need on your self-guided adventure
  • Optional daily phone or video call with the guide to prep you for the next day’s adventure
  • Support on the ground in case of emergency


  • Trek Domane SL 7 disc carbon road bike with Shimano Di2 electronic shifting or Trek Electric-Assist Verve+, available in a limited quantity
  • Trek Travel water bottles to keep
  • Shimano clipless road pedals, Shimano clipless mountain pedals, or flat pedals (optional if you do not bring your own)
  • Bontrager helmet (optional if you do not bring your own)
  • Bontrager men's and women's specific saddles
  • Bontrager front and rear Flare R lights
  • Each bike is equipped with a flat pack, frame pump and phone mount
  • A bike lock, all necessary chargers, and a floor pump
  • Coupon valued up to $500 off a new Trek Bicycle. Your coupon will be delivered via email prior to your trip.
  • 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 guide are not included in your trip price. We recommend tipping 7.5-10% of your trip price, preferably in the local currency. Please tip your guide at your discretion, based on their level of professionalism, guest care, and service.
  • Airfare and transportation to and from the trip meeting/departing locations
  • Lodging before and after the trip
  • Personal items purchased during the trip
  • Optional activities not scheduled by Trek Travel
  • While we provide daily breakfast and one lunch, the other meals are not included. On self-guided trips, Trek Travel provides restaurant recommendations and invites you to explore the local cuisine at your leisure.

More Information

Rider Level: 3 - Active?

38 miles
193 miles
2,050 feet
10,253 feet
The terrain of the Alentejo region is a vast area of gently rolling plains with a few short, steeper climbs. 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.
There are a variety of non-riding options on this trip for riders who want to take the afternoon off or travel companions who want to spend little or no 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. Except as specified in the itinerary, expenses and transportation to these activities are not included in the trip price. Some non-riding options on this trip are:
  • Enjoy the hotel pool in Estremoz and the hotel spa in Monsaraz
  • Enjoy a winery tour and tasting
  • Take a guided walking tour of Évora
  • Visit Elvas, a UNESCO world heritage site
  • Guided cork forest hike
  • Explore the artisanal shops in the perched medieval village of Monsaraz

See itinerary for specific daily ride distances and elevation options. On all of our cycling vacations, Trek Travel seeks 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)
11:00 AM
Albergaria Do Calvário, Évora

Say Farewell

Lisbon Portola Airport (LIS)
11:00 AM
São Lourenço do Barrocal, Monsaraz


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 euros. More info can be found here: http://metro.transporteslisboa.pt/eng/ Alternatively, taxis are plentiful and cost approximately €15 to €25 to Lisbon center.

We suggest that you spend a couple of days before the trip in Évora, the capital city of the Alentejo, where you will meet your guide on the first day of your self-guided bike tour. The most comfortable way to get to there from Lisbon is by private shuttle. We suggest you contact our local driver ahead of time to arrange the transfer. Our Trip Consultants can provide you with our recommended local contact information. The trip takes approximately 80 minutes and costs about €100. Payment by credit card is accepted, except American Express.

There are four daily trains that run from central Lisbon to Evora, leaving from the Gare do Oriente station (on the red metro line). The trip is about one hour and a half and costs about €16 for first class. The Évora train station is a 20-minute walk (or quick taxi ride) from Praça do Giraldo in the historic centre. Find schedule and ticket purchase information here:www.cp.pt/passageiros/en

Alternatively there are regular buses throughout the day between Lisbon and Évora. The trip will take about one hour and 45 minutes and a one-way ticket costs about €12. The service is carried out by Rede Expressos / Renex. In Lisbon, catch the bus at Sete Rios Bus Terminal (metro‘s blue line). Évora Bus Terminal is a 10-minute walk from Praça do Giraldo in the historic centre. Please, book your ticket as early as possible here: www.rede-expressos.pt

Your Trek Travel guide will meet you at the hotel Albergaria Do Calvário in Évora (Travessa dos Lagares, 3, 7000-565 Évora, Portugal) at 11:00 AM on the first day of the trip. Together you will shuttle 30 minutes to the ride start start in Évoramonte, where you will enjoy lunch together at a local cafe and your guide will give you a brief orientation of the week ahead. Following lunch you may change into your cycling gear and here your guide will fit you to your Trek bike and make sure you are well prepared for the week ahead. After a safety talk, and a few tips about cycling in the area, you will venture at your own pace on the roads of Alentejo at your leisure.

If you will be late for the meeting or are going to miss it altogether, please inform your guide. You will receive an email a week before the trip start with their name 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 São Lourenço do Barrocal to take your bike and equipment and say farewell before your departure.

We recommend to contact our local driver to arrange any transfer to Lisbon or other destinations. Our Trip Consultants can provide you with our recommended local contact information. A transfer to Lisbon takes approximately two hours and costs about €200. Please allow adequate connection time for any ongoing travel to accommodate possible traffic delays.

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, with its display of wildflowers, and autumn with its clear, crisp days are the best times 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 of a shower, so rain gear is recommended at any time of year. Packing List

Before and After Your Trip


Before: Évora, Portugal

Évora, capital of the Alentejo province, is well worth a visit. This delightful UNESCO World Heritage Site boasts a vast array of fascinating attractions, conveniently located within the walls of the historic city. Take a stroll through its narrow, winding lanes to discover some striking architectural works, from an elaborate gothic cathedral to the cinematic columns of a Roman Temple, to the picturesque town square. Aside from its historic and aesthetic virtues, Évora is also a lively university town, and its many restaurants serve up hearty Alentejan cuisine. We recommend the following accommodations for your pre-trip hotel:


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 having a pastel de nata, Portugal's mouthwatering custard tart. We recommend the following accommodations for your post-trip hotel:

Customer Reviews

Why Trek Travel

Our Bikes

Our unrivaled selection of Trek Bikes sets the bar for quality and comfort. From the ultra-smooth Trek Domane SL 7 to the Trek Electric-Assist Verve+, you deserve the best ride on your vacation. Plus, we offer a range upgrade options to take you the extra mile.

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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