Portugal Self Guided Bike Tour in the Alentejo
Charming Heritage meets the best wine producers: A journey through Alentejo
Welcome to Alentejo, a captivating region of Portugal bursting with aromas, colors and rich cultural heritage. This is more than a cycling adventure—it’s an immersion into a world where history, nature and gastronomy combine to create unforgettable memories. Picture yourself gliding over gentle hills, surrounded by the region’s iconic golden landscapes. The roads wind through unspoiled countryside, where ancient megalithic sites whisper stories of the past, and medieval villages invite you to wander their charming streets. Each turn unveils another treasure, from historical cities steeped in tradition to timeless landmarks that have witnessed centuries of Portuguese history. Your journey doesn’t just let you explore these sites—it allows you to live them. Rest your head in majestic castles, opulent palaces and serene monasteries, experiencing the grandeur of royalty with every stay. Walk in the footsteps of knights and nobles, surrounded by the elegance and beauty of these architectural marvels. This is your chance to venture on a unique journey that engages all your senses. From the stunning landscapes to the rich history and unbeatable gastronomy, Alentejo offers everything you need for a cycling tour of a lifetime.
This tour is available as a 9 day tour or a 7 day tour.
2026 Price: 7 Day Tour - From €1700 per person double occupancy 9 Day Tour - From €2200 per person double occupancy
Single Supplement for 7 day tour: €750 Euros
Single Supplement for 9 day tour: €975 Euros
Bike Rentals: Hybrid bike/ €250 Euros, Carbon road bike rental: €380 Euros, Electric Hybrid bike / €420 Euros, Electric Road bike / €685 Euros
Price Includes:
- Transfers from and to Lisbon at the beginning and end of the tour
- 6 – 8 nights lodging
- 6 – 8 breakfasts
- 1 dinner
- luggage transfers
- Ride with GPS routes
- cell phone support
Price Does Not Include:
International flights, bike rentals, lunches and dinners.
Tour Difficulty
Portugal is hilly country and each day you can expect 30 to 70 km of riding. On several days, you will have a short and long option.
- Difficulty: Moderately Hilly
- Road Conditions: Smooth & Paved
Tour Highlights
- Breathtaking landscapes
- Charming and historical hotels
- Uncrowded paved roads
- Vineyards and cork forests
- Excellent Gastronomy and wines
Sample Itinerary
For a 7 Day Tour, eliminate Day 2 and 5. The 7 day tour goes from Vila Viçosa to Redondo and does not go to Monseraz.
Day 1 ARRIVAL IN LISBON – We can pick you up at the airport or at a hotel in the city.
After your arrival, we will drive you to the friendly Estremoz.
Our guide will pick you up and drive you to your accommodation in Estremoz. Estremoz is one of the “white cities” in Alentejo. You can recognise it from far away for its white houses, spread across a hill. They are embraced by old walls and protected by the impressive donjon. The people of Estremoz are friendly and hospitable, like everybody in Alentejo, south of Portugal. House of many kings and queens of Portugal, especially King Dinis and Holy Queen Isabel, Estremoz has a substantial heritage. Both in terms of culture and archeology, which we can see in the many monuments spread across the city. It is one of the most important municipalities in the whole Alentejo from the historical standpoint. Take a deep breath and prepare yourself for an unforgettable tour.
Day 2 – ESTREMOZ Loop BIKE | Short 44 km, climb 400 m | Long 71 km, climb 700 m
A journey through history and scenic beauty.
This cycling loop around Estremoz is a perfect blend of history, natural landscapes, and charming countryside. Along the route, you’ll visit fascinating landmarks such as the Roman Villa of Santa Vitória do Ameixial and the quaint village of Fronteira, before returning to Estremoz’s majestic charm. As you pedal away from the historic center of Estremoz, you’ll pass rolling hills and fields adorned with olive trees, vineyards, and cork oaks, the hallmark of the Alentejo region. The first highlight of your ride is the Roman Villa Santa Vitória do Ameixial, an archaeological treasure that offers a glimpse into life in Roman Lusitania. Marvel at the mosaics and ruins that hint at the grandeur of this ancient villa, set amidst the tranquil Alentejan countryside. Take a moment to appreciate the contrast between the villa’s historic elegance and the timeless beauty of the surrounding landscape. The route weaves through a patchwork of golden plains and green pastures, dotted with rustic farmhouses and grazing sheep. You’ll soon arrive in the village of Fronteira, a quaint and welcoming stop steeped in history. Known for its role in the famous Battle of Montes Claros in 1665, Fronteira’s charm lies in its whitewashed houses with colorful trims and its peaceful atmosphere. The return journey takes you through open countryside, offering expansive views of Alentejo’s unspoiled beauty.
Day 3 –
Cycle from Estremoz to Vila Viçosa | Short 23 km, climb 200 m, Long 67 km, climb 500 m
A mosaic of historic landmarks, charming villages and the serene beauty of the Alentejo countryside.
As you leave Estremoz, you’ll cycle through rolling golden plains dotted with cork oaks and olive trees, a quintessential Alentejan landscape that sets the tone for your journey. Start heading north to São Bento do Cortiço, a small and peaceful village surrounded by picturesque countryside. The quiet roads and rural scenery make this section of the route a relaxing introduction to the day. Take a moment to soak in the views and the timeless charm of this agricultural heartland. Continue through gently undulating terrain to Orada, a quiet and charming village. This part of the route showcases Alentejo’s tranquil beauty, with vineyards, olive groves, and fields stretching to the horizon. Orada’s peaceful ambiance is the perfect backdrop for a short rest before continuing your ride. Head toward Borba, a town famed for its wine and marble. As you approach, you’ll notice vineyards lining the roads, inviting you to pause and sample the region’s celebrated wines. The town itself is a delight to explore, with its marble-clad buildings, charming squares, and a laid-back atmosphere that embodies the spirit of Alentejo. Your journey culminates in the regal town of Vila Viçosa, a place of historical grandeur and natural beauty. Known as the “Princess of Alentejo,” Vila Viçosa is home to the stunning Ducal Palace, built with the region’s signature marble. Explore the town’s elegant streets, and take in the serene atmosphere that perfectly complements the rich cultural heritage you’ve discovered along the way.
Day 4 – CYCLE VILA VIÇOSA LOOP BIKE | Short 27 km, climb 300 m | Long 51 km, climb 500 m
Explore the region’s rich heritage, tranquil countryside and breathtaking landscapes.
Todays’ route is a blend of peaceful roads and lush scenery, setting the stage for a memorable day. Your first stop is Alandroal, a picturesque village steeped in history. The town is dominated by its well-preserved medieval castle, which offers panoramic views of the surrounding plains. Wander through its charming streets, lined with whitewashed houses trimmed in vibrant colors, and soak in the tranquil atmosphere. Head toward the Barragem de Lucefécit, a serene reservoir nestled amid rolling hills and olive groves. Continue your journey to the village of Terena, a hidden gem that exudes medieval charm. The highlight here is the Castle of Terena, perched atop a hill overlooking the village and its surrounding landscapes. Don’t miss the Shrine of Nossa Senhora da Boa Nova, a unique religious site that adds to Terena’s allure. As you cycle back toward Vila Viçosa, visit the Anta da Azenha dos Apóstolos, a prehistoric dolmen that showcases the region’s ancient past. This megalithic structure stands as a testament to the area’s rich archaeological heritage and offers a fascinating glimpse into Alentejo’s distant history. The final stretch of your ride takes you through open fields and vineyards, with the silhouette of Vila Viçosa’s Ducal Palace guiding you back to town.
Day 5 – CYCLE VILA VIÇOSA to MONSARAZ BIKE | 55 km, climb 500 m
A journey through history, nature and timeless beauty.
This remarkable cycle tour to Monsaraz leads you through the Alentejo’s most iconic landscapes and historical landmarks. Heading south, you’ll pedal through the rolling Alentejo countryside, where golden fields and olive groves stretch as far as the eye can see. The first stop is the charming village of Alandroal, home to a striking medieval castle. Pause here to admire the castle’s imposing walls and enjoy a stroll through the quaint streets lined with whitewashed houses. The village exudes a quiet charm, offering a perfect spot to recharge before continuing your journey. As you cycle further south, you’ll approach the tranquil shores of Alqueva Lake, the largest artificial lake in Europe. The shimmering blue waters contrast beautifully with the surrounding green hills and cork oak trees. Heading closer to Monsaraz, you’ll encounter the Menir da Bulhoa, a standing stone that dates back to the Neolithic period. This ancient monument, surrounded by the quiet Alentejo landscape, offers a fascinating glimpse into the region’s prehistoric past. Just a short ride before your amazing accommodations, you’ll visit the Cromeleque do Xerez, a unique stone circle with an intriguing history. These megalithic stones are a mystical sight, evoking a sense of wonder about the people who created them thousands of years ago.
Day 6 – CYCLE MONSARAZ to REDONDO BIKE | Short 50 km, climb 600 m | Long 65 km, climb 800 m
Historical landmarks, serene landscapes and traditional architecture.
Start your day in Monsaraz, one of the most picturesque villages in Alentejo. Perched on a hilltop, Monsaraz offers breathtaking panoramic views of the surrounding plains and Alqueva Lake. Take a moment to explore the narrow cobbled streets, visit the Monsaraz Castle, and enjoy the peaceful atmosphere of this medieval village before setting off on your journey. Your first stop is Terena, a small but historic village known for its Castle of Terena and charming narrow streets. The castle, which dates back to the 12th century, offers a glimpse into the region’s medieval past. After leaving Terena, follow the winding roads toward Redondo, a picturesque village known for its beautiful whitewashed houses and traditional Alentejan charm. As you approach the village, the surrounding hills and valleys offer spectacular views, and the welcoming atmosphere of the village invites you to slow down and take in the surroundings. Redondo is also famous for its pottery, so be sure to admire the local craftsmanship as you explore the village. Your ride concludes at a peaceful accommodation just north of Redondo, where you can unwind and reflect on the day’s journey. Surrounded by the tranquility of the Alentejo countryside, this serene location is the perfect place to relax after a day of cycling through the stunning landscapes of southern Portugal.
Day 7 – CYCLE REDONDO to ÉVORA BIKE | 51 km, climb 400 m
A delightful blend of natural beauty, historic villages and captivating landscapes.
Begin your adventure in Redondo, a village known for its picturesque streets and traditional pottery. As you leave the village, you’ll cycle through vast fields and olive groves, typical of the Alentejo landscape, with golden plains stretching toward the horizon. Your first stop is Santa Suzana, a quaint village nestled in the heart of Alentejo. This charming village is surrounded by farmland, and its calm streets are ideal for a brief stop. Next, continue your ride towards Nossa Senhora de Machede, a small village with a rich history. The village is home to the Church of Nossa Senhora de Machede, a beautiful structure with a peaceful atmosphere. This village offers a perfect spot to pause and enjoy the surrounding landscapes, as it sits amidst rolling hills dotted with cork oaks and vineyards. Your final destination is Évora, one of Portugal’s most fascinating historic cities and a UNESCO World Heritage Site. As you approach the city, the landscape gradually transforms into the urban setting of this ancient city, known for its well-preserved Roman ruins, medieval walls, and stunning churches. Don’t miss the Roman Temple of Évora, the Cathedral of Évora, and the Chapel of Bones – all must-see landmarks. After a day of cycling through the beautiful Alentejo countryside, you’ll have the opportunity to explore the rich history and vibrant culture of Évora.
Day 8 – CYCLE ÉVORA LOOP BIKE | Short 46 km, climb 400 m | Long 70 km, climb 600 m
A unique opportunity to experience the essence of Alentejo.
Start your adventure in Évora, a UNESCO World Heritage city famous for its well-preserved Roman ruins and medieval architecture. After exploring the city’s rich history, you’ll head out into the serene countryside. As you cycle along quiet roads, the flat, open terrain of Alentejo begins to unfold, with olive groves, vineyards, and golden fields stretching as far as the eye can see. Your first stop is the Dolmen of Valéria, an impressive prehistoric megalithic structure dating back thousands of years. This ancient burial site, surrounded by peaceful farmland, offers a glimpse into the region’s early history. The dolmen stands as a testament to the ancient peoples who inhabited this land, and it provides a tranquil spot to pause and take in the rural beauty of Alentejo. Cycle towards the charming town of Arraiolos, famous for its traditional tapestries. This picturesque town is known for its historic Arraiolos Castle and winding streets lined with whitewashed houses. As you explore, take the time to admire the local craftsmanship, particularly the exquisite handwoven rugs that have become a symbol of the town. The scenic views of the surrounding hills and countryside add to the charm of this historical gem. Cycle towards the small village of Igrejinha. The village’s simple charm is the perfect place to slow down and appreciate the slower pace of life in this region. Begin your return journey to Évora, riding through rolling hills and expansive farmland. The landscape will continue to unfold with beautiful views of the Alentejo countryside, offering a serene and rewarding ride. As you approach Évora, take in the sight of the city’s skyline, with its historic landmarks coming back into view.
Day 9 – Departure
Our splendid program comes to an end, we hope you take home wonderful memories. Our Guide will pick you up according to your schedule time. The drive time to the Lisbon Airport takes around 2 hours. Do not schedule flights out of Lisbon before mid-afternoon.