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: Roundtrip around Vila Viçosa, 30 or 41 mi. (48 or 66 km)
Day 4: Vila Viçosa - Redondo, 18 or 25 mi. (29 or 41 km)
Day 5: Redondo - Évora, 32 mi. (51 km) 
Day 6: Roundtrip around Évora, 28 or 43 mi. (46 or 70 km)
Day 7: Transfer to Lisbon

Day 1: Arrival in Lisbon, transfer to Estremoz
You will be welcomed at Lisbon Airport and transferred to Estremoz (approx. 2-hours). Lodging this evening is in a historic castle converted into a luxury hotel, Pousada Castelo Estremoz, from where you can admire a superb view over the city of Estremoz and the vast Alentejo plain.

Accommodation: Pousada Castelo de Estremoz (Superior Room)

Day 2: Estremoz -  Vila Viçosa, 14 or 41 mi. (23 or 67 km)
Today you can choose a leisurely ride or a slightly more difficult one, it is up to you! Upon departing historical Estremoz, the ride leads to another historical place, Vila Viçosa, the capital of marble in Portugal. Here you can visit the Ducal Palace, built in the 16th and 17th centuries on the remains of Moorish, possibly even Roman buildings. For centuries it hosted a brilliant court and was a hub of intellectual life. In 1640, Joao IV was the first of the Dukes of Bragança to ascend the Portuguese throne. Although Lisbon then became the seat of the monarchy, Joao IV and his successors continued making frequent visits to Vila Viçosa. 

Elevation gain: +200 or 500 m
Accommodation: Pousada Vila Viçosa (Classic Room)

Day 3: Roundtrip around Vila Viçosa, 30 or 41 mi. (48 or 66 km)
You are in for a gorgeous day! You will ride towards Spain through a landscape of cork trees, olive groves, and flocks of sheep. Following the loop of the Guadiana River, you make a stop in Juromenha, a picturesque village overlooking Spain. Returning to Vila Viçosa, you do have some climbing to do but can opt for an easier route. 

Elevation gain: +600 or 900 m
Accommodation: Pousada Vila Viçosa (Classic family room)

Day 4: Vila Viçosa -  Redondo, 18 or 25 mi. (29 or 41 km)
Upon departing from Vila Viçosa, you will cycle on an old country road leading through a cork forest. In Alandroal village, the town’s medieval castle will entice you to take a break, or perhaps the opportunity to enjoy a delicious coffee and pastry in the main square will be enough. Back on the saddle, your ride continues on quiet and tranquil roads, through small villages and leading to a hillier region, the “Serra da Ossa”. In the village of Redondo, you can visit a pottery workshop or the wine museum “Enoteca”, and try some of the best Alentejo Wine. Your accommodations this evening is a beautiful convent on the hill, São Paulo, situated in the quiet isolation of the western slopes of the Serra d’Ossa mountain. The Monastery of São Paulo was built in 1182 by monks seeking the ideal place to live and pray in peace and quiet. 

Elevation gain: +400 or 500 m
Accommodation: Convento de São Paulo (Sāo Paulo room)

Day 5: Redondo - Évora, 32 mi. (51 km) 
The riding today is simply beautiful, on rolling hills of gold and green dotted with cork trees, olive groves, and flocks of sheep, through typical Alentejo villages of white-washed homes outlined in blue and yellow trim. As you pedal through cork groves, vineyards, and pastoral countryside dotted by abandoned castles, you will appreciate the Portugal of the old and the new. You will end your day in Évora which is classified in UNESCO’s International Heritage list, with its legacy of 2000 years of history. Évora is considered one of the most beautiful cities in Portugal since ancient times. 

Elevation gain: +400 m
Accommodation: Pousada Convento de Évora (Classic room)

Day 6: Roundtrip around Évora, 28 or 43 mi. (46 or 70 km)
What better place to have either a rest day or an opportunity for you to decide to have a short ride or a longer ride! If you decide to ride, and you probably will, the route leads to Arraiolos, noted for its colorful hand-stitched woolen tapestries. In the afternoon, cycling through small typical villages, you will have the opportunity to stop at a local winery for a tasting.

Elevation gain: +400 or 600 m 
Accommodation: Pousada Convento de Évora (Classic room)

Day 7: Transfer to Lisbon
You have earned the chance to sleep in and then linger over breakfast. The included 1h30 transfer to Lisbon can be arranged at the time that you prefer.

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, 30 or 41 mi. (48 or 66 km)
Day 5: Vila Viçosa - Monsaraz, 35 mi. (56 km)
Day 6: Monsaraz - Redondo, 30 or 40 mi. (48 or 64 km)
Day 7: Redondo - Évora, 32 mi. (51 km) 
Day 8: Évora, 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 welcomed and transferred to Estremoz (approx. 2-hour drive). Tonight's lodging is in a historic castle converted into a boutique accommodation that offers a superb view over the city of Estremoz and the vast Alentejo plain.

Accommodation: Pousada Castelo de Estremoz (Superior room)

Day 2: Estremoz, round trip, 28 or 44 mi. (44 or 71 km)
Cycling through pastoral fields, this is a peaceful ride where the only sounds are the jangling bells of grazing sheep and birdsong. As you continue biking the rolling natural landscape, the route leads through villages with the typical Alentejo white-washed homes outlined in blue and ochre trim. A visit to a local winery with possible wine tasting is possible.

Elevation gain: +400 or 700 m
Accommodation: Pousada Castelo de Estremoz (Superior room)

Day 3: Estremoz - Vila Viçosa, 14 or 42 mi. (23 or 67 km)
Choose a leisurely ride or a slightly more difficult one, it is up to you! Upon departing historical Estremoz, the ride leads to another historical place, Vila Viçosa, the capital of marble in Portugal. Here you can visit the Ducal Palace, built in the 16th and 17th centuries on the remains of Moorish, possibly even Roman buildings. For centuries it hosted a brilliant court and was a hub of intellectual life. In 1640, Joao IV was the first of the Dukes of Bragança to ascend the Portuguese throne. Although Lisbon then became the seat of the monarchy, Joao IV and his successors continued making frequent visits to Vila Viçosa. 

Elevation gain: +150 or 500 m
Accommodation: Pousada Convento de Vila Viçosa (Classic family room)

Day 4: Vila Viçosa, 30 or 41 mi. (48 or 66 km)
You will cycle towards Spain through a landscape of cork trees, olive groves, and flocks of sheep! Admire the Guadiana river, which separates Portugal from Spain, and make a stop to visit Juromenha, a picturesque village overlooking Spain. You have to cycle uphill towards the end to return to Vila Viçosa but it is well worth the effort.

Elevation gain: +600 or 900 m
Accommodation: Pousada Convento de Vila Viçosa (Classic family room)

Day 5: Vila Viçosa - Monsaraz, 35 mi. (56 km)
Leaving Vila Viçosa behind, you ride on an old road through a cork forest. At Alandroal village, contemplate the town’s medieval castle while enjoying a delicious coffee and pastry in the main square. Continue riding on quiet roads through a tranquil landscape you will pass through small villages and close to “Alqueva” big lake. In the region are Iron Age dolmens and menhirs, which were the sites of fertility rites. You can visit The Menhir of Outeiro, 3km north of Monsaraz, and one of the tallest ever discovered (5.6 m/18 ft).

Monsaraz is a tiny fairytale-walled village that maintains a delightful medieval atmosphere. It was originally fortified by the Knights Templar, and today it's 150 or so permanent residents live in ancient white houses with outdoor staircases and wrought-iron balconies.

Elevation gain: 600 m

Accommodation: Convento da Orada

Day 6: Monsaraz - Redondo, 30 or 40 mi. (48 or 64 km)
When you arrive at the hotel museum in Redondo, you will find an impressive collection of ancient tiles, essentially a reflection of Alentejo's cultural "style". This building used to be a convent and for some, it might be fascinating to know that kings have slept here since the 1500s. To finish the day, challenge your taste and pallet by learning a bit more about Portuguese wine at the wine museum in the center. 

Elevation gain: +500 or 700 m
Accommodation: Convento São Paulo (Sao Paulo room)

Day 7: Redondo - Évora, 32 mi. (51 km) 
A beautiful day riding hills of gold and green, through cork forests, pristine vineyards, and a pastoral countryside that is dotted by abandoned castles. After all these days of rolling hills, traversing through past and present and old-world heritage, the time has come to finally arrive at the most beautiful historic city of the country. Here, all your experiences will be gathered into one. Évora is considered one of the most beautiful cities in Portugal.

Elevation gain: +400 m
Accommodation: Pousada Convento Évora (Classic room)

Day 8: Évora, 29 or 43 mi. (47 or 70 km)
Évora is classified as a UNESCO World Heritage Site and has 2000 years of history. After a late breakfast, it's time to finally explore the surroundings and get to know this unique place. Soon, you will arrive in Arraiolos, noted for its colorful, hand-stitched woolen tapestries. This will be the last day of riding and you will have the unique opportunity of celebrating with some Portuguese wine right at its birthplace! Saúde!

Elevation gain: +400 or 600 m
Accommodation: Pousada Convento Évora (Classic room)

Day 9: Lisbon
Relax this morning over a well-deserved and long breakfast. Transfer to Lisbon Airport at your preferred time. (approximately 1h30 hour drive)

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