Alentejo - Heritage and Wine Country

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  Tour Operator  Live Love Ride


 7 days (Bike: 5 days)

  315 km  (~63km per day)


 Some hills, Quiet roads, Paved / sealed

Guided, Self-Guided



Road bike tour in Alentejo, cycling by USA Today's 2014 best wine country of the world, visiting it's castles and heritage.

Bike tour in Alentejo, perfect for road cycling, where you’ll get to discover the millennial history, culture and traditions of one of the world’s best wine countries, from north to south of the region. Start riding by the castles and monasteries of Marvão, Crato, Estremoz, discovering the medieval heritage of Portugal, explore the marble region of the Alentejo and its renaissance palaces, the fortified villages atop of the Alqueva and enjoy a week long ride in these peaceful rolling hills while exploring local wine cellars, sleeping in convents and discovering the UNESCO world heritage sites of cities like Évora, Vila Viçosa and Monsaraz.

Discover the amazing history, culture and traditions this wine region has to offer. Voted Best Wine Region of the world in 2014, Alentejo is a picturesque and charming place, where you’ll fall in love with the whitewashed villages, medieval castles, sunbathed plains and the secular traditions and lifestyle. Visit the UNESCO world heritage sites in √âvora, the fortified village of Marv√£o, the former Palace of the Portuguese Kings and the rural lifestyle of the local homesteads;

Ride the never-ending rolling hills and the hidden trails between the fields. The car-free roads and trails of the Alentejo provide a great atmosphere for bike tours and its topography makes it a great region for beginner and intermediate riders. You’ll have plenty of time to stop and check out the “Sobreiros” and visit the “Antas” along the way.

With its trademark gastronomy, wine and amazing accommodations, the Alentejo is a great destination to experience the best of Portugal, where luxury meets tradition. You’ll get to sleep in Convents and dine in some of the country's best restaurants, harmonizing every meal with amazing wines;

Admire the Alqueva Dark Sky Reserve, visit the Esporão Wine and Olive Oil “Herdade”, experience a boat ride in Europe’s biggest artificial lake and try an amazing array of experiences the Alentejo has to offer!

Tour Information





Cost From

Guided    1990

Self-Guided    1390


March 28, May 23, June 13, October 24 2021 or On demand

Guided 22 Sep 2019

Single Supplement


Group Info

Please ask


Transfer in from arrival airport to start of the tour and transfer out from end of the tour to departure airport
6 nights in charm 4 star hotels, in double/twin bedroom with breakfast included
Rental of a Road, Touring or MTB bike (Scott Addict 20 or Scott Aspect 930), helmet and spares;
Detailed briefing, bike fit and routebook provided before the tour by a local guide
Personal guide accompanying your group, providing restaurant reservations, booking of local experiences and all passenger transfers throughout the tour;
Support vehicle (SAG Wagon) throughout all the rides
Luggage transfer between hotels
Nutrition, hydration and snacks during our rides;
Garmin GPS with preloaded daily tracks
Access to the Live Love Ride app, that you can use to navigate and explore the best this tour has to offer
Personal accidents insurance during our tour
Portuguese mobile cellphone for contact with your local guide
Live Love Ride Jersey


Lunches and dinners
Personal expenses
Gratuities (optional);


Self-guided tour from €1390
Premium upgrade to charm 5 star hotels ( or superior rooms) €300
Child and non-cyclist discounts
Ride along guide 2100€ (per group)
E-bike upgrade €150
Halboard €270 | Full-board €540


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While great care has been taken to show full and correct tour details, unfortunately transcription errors do occur and, although we continually seek to eliminate these, we apologise for any mistakes. Plans or bookings should not be made exclusively based on information shown on this website but must be confirmed with the tour operator.