
- 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
Gallery of Castles and Wine bike tour
Tour costs & what’s included
This is a multi day bike tour
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 dateThe 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
Castle & Wine Tour Reviews
Reviews from our 5-star clients
Our Google Rating
5.0
From 30 reviews
Our Tripadvisor Rating
4.9
Tripadvisor Rating from 147 reviews
2025 Travelers' Choice
#1 of 29 Outdoor Activities in Evora
You may also like
View All ToursCycling in Paradise
Stay at our countryside farmhouse and enjoy a completely flexible cycling holiday in Portugal. Choose your own days and routes with no packing and no transfers, just relax and ride. Explore Alentejo’s rich heritage, visit local producers, and enjoy authentic tastings along the way.

Castles and Beaches
Cycle through the Alentejo's castles, wineries and whitewashed villages before reaching the unspoilt Atlantic Vicentina coastline.

Along the Coast
Bike along Portugal’s wild Atlantic coast: dramatic cliffs, hidden coves, pristine reserves and the freshest seafood.





























