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Portugal: Alentejo


Much of the inGamba team of soigneurs and mechanics call Portugal home. This special randonnée is an opportunity to share their intimate knowledge and discover Alentejo, the sparsely populated, agrarian region known as Portugal’s breadbasket, that is also one of the world’s most charming and unique destinations. Alentejo is famous for rich, uncomplicated cooking and for its salt cod, sheep’s cheese, black pork, olive oils, mushrooms – and its wine. The region makes almost half of Portugal’s total, and in some neat synergy, it’s also the largest producer of cork in the world.

On this week-long, point-to-point odyssey you’ll get to know it intimately, all from the vantage point of your saddle. Starting in the ancient city of Évora, we’ll wind our way through the unspoiled countryside toward Monsaraz, not far from the border with Spain. Nestled amongst the vast miles of oak trees, olive orchards and vineyards, this ancient village is regarded as one of the most beautiful in Portugal and is steeped in the history and culinary culture that makes Alentejo so irresistible.

You can read more about what this trip is like on our blog, or check out this article from Travel + Leisure, who traveled to Alentejo with inGamba. 

Included With Trip:

  • All lodging*
  • All food and beverages**
  • Pinarello Dogma F with SRAM RED eTap AXS
  • Daily Bike Wash
  • Custom Castelli × inGamba cycling kit
  • Daily post-ride massage from a professional soigneur
  • Laundry service for cycling clothing

*Pre/post-trip lodging is not included

**Beverages ordered by guests beyond normal amounts and away from group activities will incur additional charges

Trip at a Glance

Start Location:


Finish Location:


Days Riding:


Group Size:

8 – 12

Total Distance:


Total Elevation:


Longest Day:

Day 3. Alqueva loop. 111km

Biggest Climbing Day:

Day 3. Alqueva loop. 1,156m


Day by Day Breakdown


Évora Test Ride

Bem-vindo a Portugal! Our trip begins in Évora, a small city that’s considered to be one of the most beautiful in Portugal and is protected as a UNESCO World Heritage site. Evidence can still be seen of its Megalithic and Roman past, and in particular the Roman Temple of Évora is a popular landmark. This is an easy ride to shake off the cobwebs and make sure everything on your Pinarello is to your liking. If something isn’t quite right, now is the time to speak to the mechanic.

ÉVORA – Monsaraz

This route begins in Évora and sets out eastwards to our new home in Monsaraz in the heart of Alentejo. The roads will be rolling all day and usually they’re completely empty as we ride through the plains and the olive groves typical of this area.


A stunning loop that tours the wonderful wetlands and reservoir created by the Alqueva dam on the River Guadiana. There are no big climbs, but expect plenty of what we call “Portuguese rollers,” the leg-sapping hills that look small on paper but take their toll over the course of a long day in the saddle. Your aperitivo will definitely be earned after this ride.


Riding around Monsaraz is like stepping back in time, into a land of little villages and farms stretching out in every direction, criss-crossed by empty, undulating roads. This route begins by heading north as far as Venda, before turning toward Montoito and and then south to home, passing through Reguengos de Monsaraz, a historic town of a few thousand people that is actually the second-largest in the region. Aside from the occasional tractor, we can expect to have the road to ourselves all day.

Monsaraz – Torre de Palma

This point-to-point route brings us to our new base at Torre de Palma. Just shy of 90 kilometers, it should test your stamina, but also reward your efforts with some stunning countryside and plenty of quiet roads. The first half of the ride is undulating with a period of sustained climbing beginning around kilometer 24 and going as far as Vila Viçosa, which was once home to the Portuguese royal family. From there, it’s all downhill (in a good way) to our next hotel, which was originally built in 1338.


This route begins with a short climb followed by a long descent, all in the gorgeous surroundings of the Serra de São Mamede Natural Park. We pass the medieval fortress of Castelo de Vide at the edge of the reserve and then, after 32km, we change direction and head south through the plains of Alentejo, passing through quiet villages and past crumbling ruins of Portugal’s rich past. The Castelo de Alter do Chão is particularly impressive.


This is our final morning together and after a leisurely breakfast, it will be time to say goodbye, or at least arrivederci, until we meet again. Transfers to the airport will be arranged by our hard-working crew but if you’re planning on staying a few extra days, let us know if we can help with reservations or a few recommendations. 

YOUR Guide

Manuel Cardoso

The Quiet Crusher

Manuel Cardoso is no longer sitting on the front of the pack, pulling everyone along at what some would describe as a “brisk” pace and what others are unable to describe at all, because they're too busy gasping for breath and holding onto the wheel in front of them for dear life. Manuel is now sitting just slightly off the back of the pack. As I look back, I realize he has that look on his face. The look which struck fear in the hearts of the Pro Peleton for many years. The look which is part grin, part mischievous child and all business. He is about to start some shenanigans. Sure enough, just a few kilometers later and Manuel has picked one lucky contestant out of the pack and they are sitting-in, waiting, like predators, for the perfect moment. For Manuel, just like when he raced pro, this is when the road turns slightly up, a spot in the road where it gets tough for everyone. And he accelerates with his breakaway “partner” in tow. It is something to see. He ramps it up to a speed with which no one can latch onto the back and with such precision you have to question whether or not you actually want to try and close the gap he has created. And you can’t see it, but you just know, he is grinning from ear-to-ear.




Pinarello Dogma F


ZIPP Service Course SL




Speedplay (or your own)


Selle Italia


Zipp 303 S Carbon Tubeless


Vittoria Corsa


Elite Custom Race


Elite Corsa Team


Garmin Edge 1030