Relaxed wine cycling tour through the beautiful central Alentejo

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Recommended times of year:

Autumn, for beautiful vineyard colours

Bike Type: Gravel, MTB or hybrid

Number of riding days: 5

Tour Type: Self-Guided

Closest Airport Lisbon

Km / day: Short: 25-40km Long:50-70km

Elevation gain / day: 300-600m

Overall Difficulty: Easy - Medium

Accommodation: Rural Hotels

Experience the stunning landscapes and vineyards of interior Portugal on our wine cycling holiday!


Are you passionate about wine AND cycling? Then you will adore this wine cycling tour in the Alentejo. It’s designed to be a relaxed, cultural and easy cycling tour, suitable for all levels. The focus is on the landscapes, the beautiful vineyards and of course, the wine! Each day you will be given a fantastic wine tasting tour, so that by the end of the trip you will have experienced a wide range of the best Alentejo wines.
More information coming soon…


What’s Included?

5 spectacular days of cycling
4 wine tasting experiences at the end of the day in our handpicked vineyards
5 Nights Hotel accommodation
Airport transfers to and from Lisbon Airport to your first and from your last hotel
Buffet breakfast
GPX files of all stages
Personal assistance throughout the booking process
Detailed tour information pack prior to departure
Detailed daily itinerary (km, elevation, points of interest)
Liability and Personal Accident Insurance
5* service – our promise!

Not Included

Dinner (although we can make recommendations and make bookings should you wish!)
Extras, e.g. Bike Hire, Cycling Jersey, Single Room Supplement

Alentejo Wine Cycling Tour Itinerary

Please note this is only an indication as external factors such as available hotels might impact which exact routes are followed. You will receive a detailed itinerary once you have booked.


We will meet you in Lisbon Airport and take you straight out of the city to the nearby historic town of Evora, just over a 1hr drive away.

This will mean that every pedal stroke of your cycling trip is truly fantastic; no large busy roads to navigate and no traffic.

We recommend you spend the evening exploring the beautiful streets of Evora, the Roman Temple and the chapel of the bones

Evora to Redondo

On leaving Evora you will head straight out onto gentle gravel tracks into the Alentejo countryside. You will go through the charming small village of Redondo, where we recommend having a coffee in the centre and watch the world go by. We have chosen the accommodation tonight for you to enjoy some real peace and tranquility in a truly beautiful and ancient setting – probably a world away from ‘real life’.

Redondo – Monsaraz

This day will take you to one of my personal favourite hilltop towns in all of Portugal  – Monsaraz. It’s stunning cobbled streets will make you feel you have stepped back in time 100 years, and there is a peace and tranquility about the place that is simply magical.

Monsaraz to Vila Viçosa

Today you will head down from Monsaraz, which overlooks one of the largest reservoirs in Europe towards the beautiful ‘Princess of the Alentejo’ – Vila Viçosa, famous for marble.

You will experience typical Alentejo landscapes – rolling farmland, cows and cork oak trees interspersed with beautiful small blue and white villages.

Vila Viçosa – Monforte

Today is a special one! You will leave Vila Viçosa and head through Borba, also famous for marble production.

You will experience typical Alentejo landscapes – rolling farmland, cows and cork oak trees interspersed with beautiful small blue and white villages.

You will finish the day at Torre da Palma, a world renowned luxury wine hotel. Relax, enjoy the vineyards, taste the wine (wine tour and tasting included) and indulge in the peace and beauty of the landscape.

Monforte – Estremoz

Today’s route is relatively easy, with rolling small roads and easy gravel tracks winding through olive groves and peaceful Alentejo countryside.

This evening you will enjoy another wine tasting evening at Tiago Cabaco Winery within walking distance from the hotel.

Depart – Transfer to Lisbon

We will organise a transfer for you to Lisbon from Estremoz in the morning, leaving time in the afternoon to enjoy one of the most beautiful cities in all of Europe before your onward travel.

We hope you will have enjoyed a truly rich cultural and historic experience with us over the last few days!



Send us a reservation request below for the Alentejo Gravel Wine Tour and one of our friendly team will get back to you within 1 working day to help finalise and plan your trip.

Don’t forget! We create bespoke trips too – anything you would like to add, please don’t hesitate to ask us and we will do our best to make your ideas a reality.



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Do you like the sound of our Alentejo Wine Tour? You might also be interested in our other cycling holidays…

Authentic Algarve Gravel Cycling Holiday

For the gravel riders. Enjoy an off road / gravel cycling holiday in the Algarve! Let us introduce you to the best tracks and trails in the beautiful Algarve, both along the coast and inland.


Alentejo Self-Guided Gravel Bikepacking Tour

For the bikepackers. An adventure is on the horizon! Escape your normal routine and join us for a truly new and exciting gravel bikepacking experience into the Alentejo.

Faro to Lisbon Self-Guided Gravel Tour

Road Cycling Holiday Portugal

For the gravel tourers. This is a fantastic gravel trip for anyone wanting to experience a wide range of landscapes – west coast, rolling Alentejo plains and the beautiful Algarve backroads.


Authentic Algarve Road Cycling Holiday

Road Cycling Holiday Portugal

For the roadies. An unforgettable week of road riding in the Algarve. Not just bikes – this cycling holiday is also about enjoying the Portuguese culture, gastronomy and incredible landscapes too!


738km North to South N2 Cycling Tour

Road Cycling Holiday Portugal

For the challenge-seekers. A stunning road cycling holiday with a goal to achieve! Put your cycling legs to the test during this 6-day Challenge. A total of 738km, along Europes longest road.



What is your cancellation policy?
You can book in confidence with a very flexible cancellation policy which can be read in detail here.

We strongly recommend that you travel with adequate travel insurance to cover the cost of flight cancellation and holiday cancellation.


Am I too slow?

Definitely not! We pride ourselves on providing holidays for all abilities, and our Alentejo Wine Tour is no exception.

Having said that, there are two trips that do require a reasonable level of fitness – the Alentejo Bikepacking Adventure and the N2 Challenge. Both of these trips have a minimum number of kilometres to complete each day.

Can I hire a bike?

Of course. Just get in touch to let us know exactly what you would like and we will give you a quotation.

I would like to create my own bespoke holiday - can you help?

Of course! We would love to help you put together the perfect cycling holiday for you and your group.

We can assist with:

  • Booking hotels, villas or BnB’s
  • Hiring bikes
  • Plotting cycling routes (road or off-road)
  • Hiring guides
  • Car Hire
  • Booking restaurants
  • Recommending cafes
  • Airport transfers

We charge really reasonable prices for all of the above, making your life as the organiser really easy. Let us know what you have planned and we will help you plan an unforgettable week of cycling in Portugal for you!

Get in touch!

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