Multi Day Bike Tour Best Seller Winter Cheaper Sustainable

Castles and Wine

Sleep in castles and palaces and taste the best wines

Duration

8 days

Distance

263 km

Level

Medium

Location

Alentejo

Portugal cycling castle and wine bike tour
  • Stay in historic castles, convents and palaces
  • Heritage cycling through Évora and medieval villages
  • Award-winning wines
  • Marble landscapes
  • Traditional crafts

Cycle through the heart of the Alentejo, a landscape shaped by medieval castles, marble villages and sweeping vineyards.

This journey reveals fortified hilltop towns, the UNESCO city of Évora, and the serene expanse of the Alqueva Lake.

Along the way, meet artisans who keep ancient crafts alive and taste the region’s celebrated wines, olive oils and traditional flavours. From convents and palaces to rural estates, each place you visit reflects the history, character and warmth of the Alentejo.


See No Rush tour option if you want upgraded hotels.


For an easier start, the tour can be done in reverse, with more downhill stretches and extra time to explore Évora or enjoy a leisurely afternoon at the hotel.

Program of Castles and Wine

The perfect bike tour itinerary for you

Pedal Through History and Wine

Arrival and Briefing



Transfer from airport (included in PLUS tours)

Arrive early at the airport and head to the charming medieval village of Arraiolos, famous for its castle and embroidered rugs. After checking in, relax by the pool, wander the picturesque streets, or soak in the tranquil atmosphere.


At 5 PM, join a welcome drink and briefing by our local guides to meet fellow travelers and get an overview of the upcoming routes a relaxed way to kick off your Portuguese adventure.

Food & Tasting
  • Welcome drink
  • Dinner at local restaurant (included in PLUS tours)

Accommodation

Pousada de Arraiolos, built in a wonderful 16th century convent, with swimming pool, 2 km from Arraiolos

Casa do Plátano, a very charming guest house in the village centre


Cycling from Arraiolos to Évora


Cycle through the historic village of Arraiolos, passing whitewashed houses. Learn about the typical weaving, a centuries-old craft and taste the local sweet.

Climb to Arraiolos Castle, one of the few round castles on the Iberian Peninsula, and enjoy wide views over the Alentejo plains. Ride through rolling countryside, olive groves and vineyards.

Stop at Fita Preta Winery, set in a restored 14th-century palace, for a tasting of award-winning wines. Alternatively, visit an aromatic herbs farm to sample teas, honey, and olive oil.


Visits
  • Arraiolos historic village
  • Arraiolos Carpet Museum
  • Arraiolos Castle

Food & Tasting
  • Pastéis de Toucinho, local sweet
  • Wine tasting at Fitapreta or aromatic herbal infusions at Be Aromatic
  • Picnic lunch (Included in PLUS only)

Accommodation

Monte do Serrado de Baixo, Our charming countryside guesthouse with swimming pool

Hotel Mar de Ar Muralhas - 4*, Located inside Évora’s historic walls, with swimming pool


Premium upgrade

Hotel Mar de Ar Aqueduto, A beautifully restored 16th-century convent next to Évora’s iconic aqueduct

Cicioso Boutique hotel, located in the historical center in a restaured 20th century manor house.

Cycling Details

Distance: 30 km (overnight in Évora) or 43 km (overnight at Monte do Serrado de Baixo)

Difficulty: Easy+ to medium

Terrain: Rolling terrain, with some dirt roads

Total ascent: 360 m


Cycling to Évora and megalithic area


Start exploring Évora, a UNESCO World Heritage Site, and discover its rich history and striking architecture. Enjoy a wine tasting at the Évora Wine Tour Shop, a perfect introduction to the region’s flavors.

Ride into the countryside, passing through holm oak forests and open meadows dotted with grazing cattle and birdsong. The route leads to some of Europe’s most impressive megalithic sites. A day which blends history, nature, and cultural discovery.


Visits
  • Évora city center (UNESCO World Heritage Site)
  • Bones Chapel
  • Évora Cathedral (13th century)
  • Zambujeiros’ Dolmen
  • Almendres’ Cromelech
  • Almendres Menhir
  • Mitras’ Church

Food & Tasting
  • Wine tasting at Ervideira Wine shop (included in supported tours)
  • Picnic lunch (included in supported tours)

Accommodation 

Return to your guesthouse for a relaxing evening after a full day of exploration.


Cycling Details

Distance: 46 km, with transfer back; 72 km, cycling from the farm and back

Difficulty: Medium + without transfer, Medium with transfer

Terrain: Mostly gentle rolling dirt roads

Total ascent: 400 m



Cycling from Évora to Reguengos de Monsaraz


Peaceful ride on a cycling lane through the quiet Alentejo countryside. You can stop in small villages or enjoy a picnic in nature.

Visit Nossa Srª de Machede to see a local leather artisan, then continue to Valongo Castle, rich with Roman history. From there, choose the local ecotrail, asphalt road, or a dirt track. Wine lovers can also visit a nearby winery with clay-pot-aged wines.


Visits
  • Nossa Srª de Machede (local leather artisan)
  • Castle of Valongo

Food & Tasting
  • Local café
  • Adega José de Sousa (traditional clay pot wine aging)
  • Lunch and Dinner at local restaurant (included in PLUS tours)

Accommodation

Solar de Alqueva, Comfortable country hotel with swimming pool


Premium Option

Herdade de S. Lourenço do Barrocal, A charming country estate with award-winning architecture, where you can enjoy local wine and olive oil. For this option, we recommend staying 2 nights, with the cycling route adapted accordingly.


Cycling details

Distance: 50 km (if you slept in Évora) or 59 km (if you slept at our guesthouse)

Difficulty: Medium

Terrain: Undulating roads

Total ascent: 210 m



Cycling from Reguengos de Monsaraz to Monsaraz


Today’s destination is the fortified village of Monsaraz, a historic stronghold on Portugal’s border with Spain. Along the way, you’ll pass through the pottery village of S. Pedro do Corval, where local artisans craft and paint clay pots with remarkable skill.

Cycle toward the Alqueva dam reservoir, the largest artificial lake in Europe, and pause for a scenic lunch. Finish the day with the climb to Monsaraz castle and enjoy stunning views over the surrounding countryside and the medieval village below.


Visits
  • Patalim family pottery shop
  • Alqueva dam reservoir
  • Monsaraz castle and medieval village

Food & Tasting
  • Lunch at the dam with reservoir view (included in guided and van-assisted tours)
  • Dinner at local restaurant (included in guided and van-assisted tours)
  • Wine tasting at Ervideira Wine Shop Monsaraz

Accommodation

Estalagem de Monsaraz, Lovely hotel just by the castle, with swimming pool

Casa Dona Antónia, Charming bed & breakfast inside the medieval castle


Cycling details

Distance: 31 km

Difficulty: Easy+ with the main challenge being the last climb to Monsaraz

Terrain: Mostly flat roads with one ascent to the castle

Total ascent: 330 m



Cycling from Monsaraz to Vila Viçosa


Bike from Monsaraz to Vila Viçosa, the marble capital of Portugal and one of Europe’s largest marble-producing regions. The so-called “white gold” shapes the landscape, from the wide streets to the grand buildings, and remains a key part of the local economy.

Enjoy a picnic lunch and visit an impressive fortified sanctuary with a fascinating story. Continue to witness a rare sight of distinctively colored lagoons before finishing your day at your accommodation, set in an elegant, aristocratic setting.


Visits
  • Fortified sanctuary with historical tale
  • Colored lagoons viewpoint
  • Local artisan

Food & Tasting
  • Picnic lunch
  • Dinner at a local restaurant (included in guided and van-assisted tours)

Accommodation

Pousada D. João IV, Built in a historic convent, with swimming pool

Solar dos Mascarenhas, Charming boutique hotel in a manor house, with swimming pool


Premium Upgrade

Marmoris Hotel (5 stars), Elegant property featuring extensive marble applications in architecture and décor


Cycling details

Distance: 60 km

Difficulty: Medium

Terrain: Undulating roads with some climbing

Total ascent: 560 m



Cycling from Vila Viçosa to Estremoz

Today’s ride from Vila Viçosa to Estremoz is gentle, giving you the perfect opportunity to savor the local flavors along the way. Stop at taverns to enjoy Petiscos (local snacks), letting your senses delight in the region’s culinary offerings.

As you approach Estremoz, take time to admire the surrounding landscapes and the elegant marble architecture that marks this final stage of your journey. The day concludes with dinner and closing celebrations in a historic 15th-century jailhouse reserved for nobles only! Finish with a climb to the marble Donjon tower of Estremoz castle, where you’ll spend the night.


Visits
  • Palace Ducal of Vila Viçosa
  • Marble museum
  • Local taverns for tasting Petiscos/snacks
  • Estremoz castle and marble Donjon tower
  • Irmãs flores local artisans

Food & Tasting
  • Lunch of several Petiscos/snacks (included in guided and van-assisted tours)
  • Closing celebrations dinner in the historic jailhouse (included in guided and van-assisted tours)

Accommodation

Pousada Rainha Stª Isabel, Built in a palace, with swimming pool.

OR

Pateo dos Solares, Charming boutique hotel in a palace, with swimming pool.


Cycling details

Distance: 33 km

Difficulty: Easy+

Terrain: Undulating roads, with some climbs

Total ascent: 275 m




Departure



Transfer to airport (included in PLUS tours)



Self-Guided

On a self-guided tour, you are free to explore at your own pace, following detailed route instructions and maps. You will travel independently, managing your own time and handling small bike repairs and maintenance on your own.

Before you set off, you’ll receive a personal tour and bike briefing by a local guide, giving you all the essential tips for a smooth and enjoyable ride. You’ll also have access to a personalized navigation app, making it easy to follow your route and explore the region confidently.

With 24-hour phone support, historical notes, and local dining suggestions, you can discover the landscapes, history, and hidden gems on your own rhythm, stopping wherever and whenever the adventure calls.



Van Support

Van-supported tours give you guidance and reassurance while still allowing you to cycle independently. A guide drives the support vehicle, staying nearby so you can follow along at your own pace. They will stop at interesting points to share stories, history, and local insights.

Your journey begins with a personal tour and bike briefing by a local guide, and a personalized navigation app helps you stay on track. For all guided tours, there is also a daily briefing before each ride, so you know exactly what to expect each day. Water, fruit, and occasional local wine tastings along the route keep you refreshed as you cycle through the region.



Van Support Plus

Van Support Plus includes all the benefits of Van Support, with added comfort and thoughtful touches. You’ll start with a personal tour and bike briefing by a local guide and a personalized navigation app, ensuring you feel confident and ready. Daily briefings guide all rides, while airport transfers and carefully prepared meals allow you to relax and enjoy every moment.

This option combines the freedom of independent cycling with extra comfort, support, and full meals featuring local gastronomy, creating a more indulgent and seamless experience.



Guided

Guided tours immerse you in the region with the expertise and company of our cycling guides. One or two guides accompany you on the bike, while a support vehicle follows to carry luggage and provide assistance.

Before the adventure begins, you’ll have a personal tour and bike briefing by a local guide, plus a personalized navigation app. Each day, a daily briefing ensures you know the route, highlights, and tips for the day’s ride. Along the way, your guides share hidden gems, fascinating stories, and provide water, fruit, and occasional wine tastings, creating a memorable journey full of camaraderie and local insight.



Guided Plus

Guided Plus combines expert guidance with maximum comfort and culinary delights. Your experience begins with a personal tour and bike briefing by a local guide and access to a personalized navigation app. Every day starts with a daily briefing, setting the tone for smooth, exciting rides.

With airport transfers and thoughtfully prepared meals, plus the full support of our guides, you can focus entirely on the adventure. You’ll cycle through the region fully immersed in its landscapes, history, and flavors, accompanied by passionate guides and fellow travelers who share your love of exploration.




Map with routes

Tour costs & what’s included

This is a multi day bike tour

Compare Prices

Self-Guided
Van Support
Van Support Plus
Guided
Guided Plus
Price per person (minimum 4 adults)
1 150 €*
2 305 €*
2 750€*
2 800 €*
3 300 €*
Price per person (minimum 2 adults)
1 330 €*
3 350 €*
3 960 €*
4 455 €*
4 950 €*
Price per person (group tour dates)
-
-
-
-
4400 €
*plus season supplement if applied
Season supplement
Apr 1 to Oct 31 and
190 €
190 €
190 €
190 €
190 €

Easter, Christmas, New Year's Eve and national holidays under request

Single Supplement
Single**
530 €
530 €
530 €
530 €
530 €
Single*** - April, May, June and Oct
890 €
-
-
-
-

** For solo traveller contact us


** For solo traveler contact us.


Single** - Apr 1 to 30 Jun and 1 Set to Oct 31 and Holidays
-
890 €
890 €
890 €
890 €
Transfers
Airport transfer to first hotel - price per person minimum 2 pax
120 €
120 €
-
120 €
-
Airport transfer from last hotel - price per person minimum 2 pax
155 €
155 €
-
155 €
-
Airport transfer to 1st hotel - min 2 pax
-
-
-
-
-
Airport transfer from last hotel - min 2 pax
-
-
-
-
-
Rentals
Bicycle rental with helmet, rear rack and pannier
110 €
-
-
-
-
Gravel bike rental
170 €
60 €
60 €
60 €
60 €
E-bike rental
220 €
110 €
110 €
110 €
110 €
Extras
Cycling shorts
65 €
65 €
65 €
65 €
65 €
Extra cycling jersey
20 €
20 €
20 €
20 €
20 €
Portugal Best Cycling cooking apron
20 €
20 €
20 €
20 €
20 €
Departure different than Monday
150 €
150 €
150 €
150 €
150 €
Food restrictions
-
-
90 €
-
90 €

We are happy to supply vegan and gluten free meals. If you require this options, please let us know at the time of booking. Produce for these meals are quite expensive, so we are obliged to charge an extra fee.

Upgrade
Day 2 and 3 - Mar de Ar Aqueduto 5 stars, Convento do Espinheiro ou Pousada dos Loios
From 30 €
From 30 €
From 30 €
From 30 €
From 30 €
Day 4 - Herdade do Barrocal
From 250 €
From 250 €
From 250 €
From 250 €
From 250 €

Book your trip

Subject to availability, you can do this tour at any date as a private guided tour or as a self guided tour.

Book your own date

The fact that a group date is full does not mean you cannot do a private tour on that date. So contact us anyway!

Guided group tour dates

September
Type of tour Self-Guided
Start Date 14-09-2026
End date 21-09-2026
October
Type of tour Guided Plus
Start Date 19-10-2026
End date 26-10-2026
November
Type of tour Guided Plus
Start Date 09-11-2026
End date 16-11-2026
Map

Castle & Wine Tour Reviews

Reviews from our 5-star clients

My husband (73) and I (68) had a wonderful time cycling the Alentejo Castle & Wine Tour the first week of November. Chris brought his recumbent and I rented an e-bike (Cube) with its incredible “turbo” assist. Made hills a piece-of-cake. The weather cooperated for the most part with temperatures in the mid-60s and rain on only one day of our trip. Our guides – Sadeq, Mario, Philipa, and Juan (?) – were very accommodating. While we attempted to ride the 30 to 60 km planned routes, we could shorten them to meet our needs. I needed to bail for one day after coming down with stomach flu, but was back in the saddle the next day. Thereafter, I had to cut back on the cheese and rich Portuguese food, eating mostly French fries until our last fabulous meal at the Acadeia in Estremoz. The tour was a nice mix of riding and sightseeing. I especially enjoyed the wine tasting at Fitapreta. Portugal Best Cycling and its parent company Turaventur are local outfits. So, the guides really know their stuff. We worked with biketours.com in the US to book our tour. We highly recommend Portugal Best Cycling!

By Wasima R, USA, November 2025

The Castles and Wine trip was amazing.Everything was very well organized and well communicated.The routes were scenic and on safe side roads or bike paths. Our guide, Paul, was very fabulous. He was very knowledgeable regarding local history and landmarks and made to most delicious picnic lunches.
We have done many cycling trips. This one is probably one of our favourites.

By Doreen H, September 2024

Our week spent biking on the ‘Castles and Wines’ of Portugal’ tour was a dream come true. The trails were gorgeous, the bikes were top-notch, the hotel accommodations were great, as were the wines and food, and our guide Manuel was the best that we’ve ever had. His enthusiasm, positive personality, passion for and knowledge of Portugal made this trip fantastic. We looked forward to each day and were sad when the week was over. We look forward to future trips with Manuel and this wonderful company. Two thumbs way, way, up!!

By Sue, May 2024

We did the 7 day Castles and wine tour with Paulo as our trusty bike guide. We could not have asked for a better trip. The entire team go out of their way to ensure your tour runs smoothly and will tailor the trip based on your preferences. Our expectations were exceeded with the quality of restaurants and attention to detail. You will feel genuinely welcomed to Portugal by the staff who provide an authentic experience visiting off-the-beaten-path sites and chatting with the locals. We did the fully guided trip and Manuel welcomed us each day with lunch in interesting spots, by a lake, in an Olive grove or sourced out the best little cafes for lunch. We arrived at our hotels with our bags already in the room and all we had to do was jump in the pool to cool off. We felt spoiled and would go again in a heart beat.

By Lise F, October 2023

We did the self-guided Castles and Wine tour in Portugal and could not have had a better experience. We are very experienced bikers, and have done simillar tours in France, Italy, Germany, Austria, Slovakia and Hungary, and no tour company to date has matched thier level of professionalism, and attention to detail. The routes and day to day instructions were also the best and most accurate we have encountered. Mario's presentation the day before we started was funny, and professional.

It says a lot when the tour company asks you to check in at the end of the day, to ensure you arrived safely. No other company has done this, and it showed an unepected level of caring and concern. In fact I fell and fractured my arm while riding and Teresa helped me every step of the way, from securing a taxi for me to get emergency care to helping me naviagate the Portugese healthcare system. she was fantastic! If you plan to bike in Portugal, Portugal Best Cycling truly is the best!

By Lori, October 2019

My husband (73) and I (68) had a wonderful time cycling the Alentejo Castle & Wine Tour the first week of November. Chris brought his recumbent and I rented an e-bike (Cube) with its incredible “turbo” assist. Made hills a piece-of-cake. The weather cooperated for the most part with temperatures in the mid-60s and rain on only one day of our trip. Our guides – Sadeq, Mario, Philipa, and Juan (?) – were very accommodating. While we attempted to ride the 30 to 60 km planned routes, we could shorten them to meet our needs. I needed to bail for one day after coming down with stomach flu, but was back in the saddle the next day. Thereafter, I had to cut back on the cheese and rich Portuguese food, eating mostly French fries until our last fabulous meal at the Acadeia in Estremoz. The tour was a nice mix of riding and sightseeing. I especially enjoyed the wine tasting at Fitapreta. Portugal Best Cycling and its parent company Turaventur are local outfits. So, the guides really know their stuff. We worked with biketours.com in the US to book our tour. We highly recommend Portugal Best Cycling!

By Wasima R, USA, November 2025

The Castles and Wine trip was amazing.Everything was very well organized and well communicated.The routes were scenic and on safe side roads or bike paths. Our guide, Paul, was very fabulous. He was very knowledgeable regarding local history and landmarks and made to most delicious picnic lunches.
We have done many cycling trips. This one is probably one of our favourites.

By Doreen H, September 2024

Our week spent biking on the ‘Castles and Wines’ of Portugal’ tour was a dream come true. The trails were gorgeous, the bikes were top-notch, the hotel accommodations were great, as were the wines and food, and our guide Manuel was the best that we’ve ever had. His enthusiasm, positive personality, passion for and knowledge of Portugal made this trip fantastic. We looked forward to each day and were sad when the week was over. We look forward to future trips with Manuel and this wonderful company. Two thumbs way, way, up!!

By Sue, May 2024

We did the 7 day Castles and wine tour with Paulo as our trusty bike guide. We could not have asked for a better trip. The entire team go out of their way to ensure your tour runs smoothly and will tailor the trip based on your preferences. Our expectations were exceeded with the quality of restaurants and attention to detail. You will feel genuinely welcomed to Portugal by the staff who provide an authentic experience visiting off-the-beaten-path sites and chatting with the locals. We did the fully guided trip and Manuel welcomed us each day with lunch in interesting spots, by a lake, in an Olive grove or sourced out the best little cafes for lunch. We arrived at our hotels with our bags already in the room and all we had to do was jump in the pool to cool off. We felt spoiled and would go again in a heart beat.

By Lise F, October 2023

We did the self-guided Castles and Wine tour in Portugal and could not have had a better experience. We are very experienced bikers, and have done simillar tours in France, Italy, Germany, Austria, Slovakia and Hungary, and no tour company to date has matched thier level of professionalism, and attention to detail. The routes and day to day instructions were also the best and most accurate we have encountered. Mario's presentation the day before we started was funny, and professional.

It says a lot when the tour company asks you to check in at the end of the day, to ensure you arrived safely. No other company has done this, and it showed an unepected level of caring and concern. In fact I fell and fractured my arm while riding and Teresa helped me every step of the way, from securing a taxi for me to get emergency care to helping me naviagate the Portugese healthcare system. she was fantastic! If you plan to bike in Portugal, Portugal Best Cycling truly is the best!

By Lori, October 2019

Our Google Rating

5.0

From 30 reviews

Our Tripadvisor Rating

4.9

Tripadvisor Rating from 147 reviews
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