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Portugal: Alentejo

 April 26 - May 5, 2023 
$5,200 (double occupancy)
$750 single supplement 
Arrive and Depart from the Lisbon airport  

Want to see horses and carriages, gypsies with mules, Moorish-inspired houses with big chimney pots and whitewashed villages that stretch over hills? This trip takes you through the rural inland area of the Alentejo, which is close to the Spanish border, through landscapes rife with cork oaks, wheat fields and olive trees. It marries the region's mystic past with its tranquil present. 

You'll indulge with luxurious accommodations and superb cuisine between visits to medieval castles and Roman ruins. History is plentiful; there are prehistoric remains and Roman ruins abound.


We'll cycle through Medieval towns clustered with churches and castles, which were part of the fortifications against the Spanish. Medieval hilltop towns like Monsaraz are simply magnificent. Local crafts and arts are flourishing, especially pottery and paintings. 

The meals and wine are a particular highlight, and there will be a large variety of local specialties. You will fall in love with the flavours of Portuguese cuisine. 


The bicycling is moderate, averaging between 30 to 40 miles daily. 



The trip price includes 6 dinners and all breakfasts, with luxury accommodations 4-star hotels (4 two-night stays and 1 one-night stay).  

The accommodations are among the best Portugal has to offer. In Crato, Arraiolos, and Vila Vicosa, the hotels (belonging to the Pousada chain) are converted historical buildings. Near Monsaraz, we will stay in a luxury countryside hotel at the foot of the Medieval fortified town. All hotels have outdoor swimming pools. 

Arrival and Departure

Pick up and drop off at the Lisbon airport. 


Day by Day

  • Crato (2 nights):  Enjoy the stay in the 14th-century castle. Bicycle through the lovely countryside to Castelo de Vide and learn about its history.

  • Avis (1 night): Visit the oldest Portuguese horsefarm. Climb the hill into historical Avis, enjoy a gourmet dinner with great views over olive trees and vineyards.

  • Arraiolos (2 nights): Bike the quiet countryside of gently rolling terrain. Stay at a luxury Pousada, formerly the convent of Nossa Senhora Da Assunção. Visit the local museum and workshops where embroidered wool rugs and carpets have been made since the Middle Ages. Cycle to Evora, and admire the Roman temple.

  • Vila Vicosa (2 nights): Cycle through lush countryside, admire the marble towns, enjoy Vila Vicosa, once the center of the hunting grounds for the Portuguese royalty.

  • Telheiro (2 nights):  Cycle to the historic village of Monsaraz. Bike to Reguengos de Monsaraz, famous for its local wine and wool rug factory. Check out the pottery at Sao Pedro do Corval.  Visit the cute 13th century hilltop town of Monsaraz.

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