Alentejo Vineyards

Day 1: Arrival in Lisbon, transfer to Estremoz
Day 2: Estremoz - Vila Viçosa, 14 or 41 mi. (23 or 67 km)
Day 3: Vila Viçosa round trip to Alandroal, 17 or 32 mi. (27 or 51 km)
Day 4: Vila Viçosa - Redondo, 18 or 25 mi. (29 or 41 km)
Day 5: Redondo - Évora, 32 mi. (51 km) 
Day 6: Évora round trip to Arraiolos, 29 or 43 mi. (47 or 70 km)
Day 7: Departure

Day 1: Arrival in Lisbon, transfer to EstremozAfter your arrival in Lisbon, you’ll be greeted and transferred to Estremoz (approximately 2 hours). During your welcome briefing, your guide will introduce the itinerary, assist with your bike fitting, and share an overview of the journey ahead. The rest of the day is yours to explore Estremoz, one of Alentejo’s famed “white cities.” Once home to King Dinis and Queen Isabel, Estremoz boasts centuries of royal heritage, marble architecture, and a charming old town framed by medieval walls. Take a leisurely walk and prepare for an unforgettable cycling adventure.

Accommodation: Pousada Castelo de Estremoz
Alternative hotel: Hotel Páteo dos Solares

Day 2: Estremoz – Vila Viçosa, 14 or 42 mi. (23 or 67 km)
Leave Estremoz and cycle through peaceful golden plains dotted with cork oaks and olive trees. Pass the small villages of São Bento do Cortiço and Orada, surrounded by rolling farmland and vineyards. Continue to Borba, a town celebrated for its marble buildings and fine wines, stop to explore and enjoy the relaxed rhythm of local life. Your destination, Vila Viçosa, is known as the “Princess of Alentejo,” home to the 16th-century Ducal Palace and graceful marble-lined streets steeped in history and charm.

Elevation gain: +200 m (short) / +500 m (long)
Accommodation: Pousada Convento de Vila Viçosa
Alternative hotel: Alentejo Marmòris Hotel & Spa

Day 3: Vila Viçosa round trip to Alandroal, 17 or 32 mi. (27 or 51 km)
Today’s ride is filled with heritage and natural beauty. Begin with Alandroal, a historic village crowned by a medieval castle overlooking the plains. Continue toward the Lucefécit Dam, a tranquil lake surrounded by olive groves and gentle hills. Pedal on to Terena, a picturesque village featuring a hilltop castle and the Shrine of Nossa Senhora da Boa Nova. On your return, visit the prehistoric Anta da Azenha dos Apóstolos dolmen before cycling back through open countryside and vineyards toward Vila Viçosa.

Elevation gain: +300 m (short) / +600 m (long)
Accommodation: Pousada Convento de Vila Viçosa
Alternative hotel: Alentejo Marmòris Hotel & Spa

Day 4: Vila Viçosa -  Redondo, 18 or 25 mi. (29 or 41 km)
Ride out of Vila Viçosa along quiet roads framed by olive groves and cork oaks. Stop in Alandroal to admire its well-preserved medieval castle and visit the charming Igreja da Nossa Senhora da Conceição. Continue through soft rolling hills toward Redondo, a town known for its pottery and traditional whitewashed homes. As you approach, the surrounding valleys open to beautiful views. End the day at a peaceful countryside retreat near Redondo, where you can relax and enjoy the calm of rural Alentejo.

Elevation gain: +400 m (short) / +500 m (long)
Accommodation: Convento de São Paulo
Alternative hotel: Monte do Pomar (dinner not included)

Day 5: Redondo - Évora, 32 mi. (51 km)  
Depart Redondo and cycle through open farmland, cork forests, and vineyards toward Évora. En route, stop in Santa Suzana and Nossa Senhora de Machede, two picturesque villages perfect for short breaks. Continue through the rolling countryside before reaching Évora, a UNESCO World Heritage city filled with historic treasures. Within its medieval walls, discover the Roman Temple, Gothic Cathedral, and Chapel of Bones. After a rewarding ride, enjoy exploring this ancient and vibrant city.

Elevation gain: +400 m
Accommodation: Pousada Convento Évora
Alternative hotel: M'AR De AR Aqueduto

Day 6: Évora round trip to Arraiolos, 29 or 43 mi. (47 or 70 km)
Start your final cycling day in Évora and head out through the open plains of Alentejo. Visit the Dolmen of Valéria, an ancient megalithic burial site surrounded by farmland, before continuing to Arraiolos, renowned for its colorful hand-stitched wool tapestries and hilltop castle. Pass through the quiet village of Igrejinha before returning to Évora. The route offers a perfect mix of culture, history, and scenery, a fitting conclusion to your Alentejo cycling experience.

Elevation gain: +400 m (short) / +600 m (long)
Accommodation: Pousada Convento Évora
Alternative hotel: M'AR De AR Aqueduto

Day 7: Departure
Enjoy breakfast before your transfer back to Lisbon (approximately 1.5 hours). Depending on your schedule, you may wish to extend your stay in Évora or explore more of Portugal’s beautiful Alentejo region.

Day 1: Arrival in Lisbon, transfer to Estremoz
Day 2: Estremoz round trip, 27 or 44 mi. (44 or 71 km)
Day 3: Estremoz – Vila Viçosa, 14 or 42 mi. (23 or 67 km)
Day 4: Vila Viçosa round trip to Alandroal, 17 or 32 mi. (27 or 51 km)
Day 5: Vila Viçosa - Monsaraz, 35 mi. (56 km)
Day 6: Monsaraz - Redondo, 30 or 40 mi. (49 or 65 km)
Day 7: Redondo - Évora, 32 mi. (51 km) 
Day 8: Évora round trip to Arraiolos, 29 or 43 mi. (47 or 70 km)
Day 9: Departure

Day 1: Arrival in Lisbon, transfer to Estremoz
After arriving at Lisbon Airport, you’ll be greeted and transferred to Estremoz (approximately 2 hours). Estremoz is one of Alentejo’s famed “white cities,” easily recognized by its whitewashed houses clustered on a hill surrounded by medieval walls and a tall castle keep. Known for its royal history and marble craftsmanship, the town was once home to King Dinis and Queen Isabel. Take the rest of the day to explore the old quarter, enjoy the warm hospitality of the locals, and prepare for your cycling adventure.

Accommodation: Pousada Castelo de Estremoz
Alternative hotel: Hotel Páteo dos Solares

Day 2: Estremoz round trip, 27 or 44 mi. (44 or 71 km)
Today’s cycling loop around Estremoz blends history, nature, and rural charm. Ride through gently rolling hills and landscapes dotted with vineyards, olive trees, and cork oaks. Visit the Roman Villa of Santa Vitória do Ameixial, a fascinating archaeological site that offers a glimpse into ancient Roman life, and continue to Fronteira, a peaceful village known for its colorful houses and historical connection to the 1665 Battle of Montes Claros. Return to Estremoz surrounded by Alentejo’s golden fields and tranquil countryside.

Elevation gain: +400 m (short) / +700 m (long)
Accommodation: Pousada Castelo de Estremoz
Alternative hotel: Hotel Páteo dos Solares

Day 3: Estremoz – Vila Viçosa, 14 or 42 mi. (23 or 67 km)

Cycle south from Estremoz through undulating farmland filled with cork oaks and olive groves. Pass through São Bento do Cortiço and Orada, quiet rural villages that showcase Alentejo’s serene lifestyle. Continue toward Borba, a town famed for its marble architecture and fine wines. Your day ends in Vila Viçosa, the “Princess of Alentejo,” where the 16th-century Ducal Palace dominates the town square. Its elegant streets and marble façades reflect centuries of noble heritage.

Elevation gain: +200 m (short) / +500 m (long)
Accommodation: Pousada Convento de Vila Viçosa
Alternative hotel: Alentejo Marmòris Hotel & Spa

Day 4: Vila Viçosa round trip to Alandroal, 17 or 32 mi. (27 or 51 km)
Today’s ride takes you through peaceful scenery and historic villages. Begin with Alandroal, where the medieval castle overlooks the plains below. Continue to the Barragem de Lucefécit reservoir before cycling to Terena, home to a hilltop castle and the Shrine of Nossa Senhora da Boa Nova. On your return, visit the Anta da Azenha dos Apóstolos, a prehistoric dolmen that highlights the region’s ancient roots. The final stretch passes through open countryside back to Vila Viçosa.

Elevation gain: +300 m (short) / +600 m (long)
Accommodation: Pousada Convento de Vila Viçosa
Alternative hotel: Alentejo Marmòris Hotel & Spa

Day 5: Vila Viçosa - Monsaraz, 35 mi. (56 km)
Leave Vila Viçosa and cycle through tranquil farmland and cork forests toward Alandroal, where you can pause to enjoy a coffee near the castle walls. Continue south through quiet villages until you reach the Alqueva region, home to Europe’s largest artificial lake. Along the way, visit the Menhir da Bulhoa and the Cromeleque do Xerez, ancient megalithic monuments surrounded by Alentejo’s rolling landscape. Arrive in Monsaraz, a magical walled village perched high above the plains, where medieval charm and breathtaking views abound.

Elevation gain: +500 m
Accommodation: Convento da Orada (upgrade available)
Alternative hotel: Estalagem de Monsaraz (dinner not included)

Day 6: Monsaraz - Redondo, 30 or 40 mi. (49 or 65 km)
Start your day with panoramic views of Alqueva Lake before cycling downhill from Monsaraz through quiet valleys and timeless villages. Visit Terena and admire its medieval castle, then continue to Redondo, a picturesque town famous for its pottery and traditional whitewashed houses. Your accommodation, a converted convent filled with beautiful tilework, offers the perfect place to relax and appreciate the serenity of the Alentejo countryside.

Elevation gain: +600 m (short) / +800 m (long)
Accommodation: Convento São Paulo
Alternative hotel: Monte do Pomar (dinner not included)

Day 7: Redondo - Évora, 32 mi. (51 km) 
Depart Redondo and ride through a mosaic of vineyards, olive groves, and golden plains. Pass through Santa Suzana and Nossa Senhora de Machede, two tranquil villages that embody Alentejo’s pastoral beauty. Continue to Évora, one of Portugal’s most remarkable cities and a UNESCO World Heritage Site. Inside its ancient walls, explore the Roman Temple, Gothic Cathedral, and Chapel of Bones, all testaments to Évora’s 2,000 years of history.

Elevation gain: +400 m
Accommodation: Pousada Convento Évora
Alternative hotel: M'AR De AR Aqueduto

Day 8: Évora round trip to Arraiolos, 29 or 43 mi. (47 or 70 km)
Today’s loop ride begins in Évora and ventures into the surrounding countryside of olive groves and vineyards. Visit the Dolmen of Valéria, an ancient megalithic site, then continue to Arraiolos, a charming town known for its colorful hand-stitched wool tapestries and hilltop castle. Pass through the peaceful village of Igrejinha before returning to Évora, where you can enjoy one last evening celebrating your adventure through Alentejo.

Elevation gain: +400 m (short) / +600 m (long)
Accommodation: Pousada Convento Évora
Alternative hotel: M'AR De AR Aqueduto

Day 9: Departure
Enjoy a leisurely breakfast before your transfer back to Lisbon (approximately 1.5 hours). You may choose to extend your stay in Évora or explore another part of Portugal’s Alentejo region before heading home.

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