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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 one of the world’s most charming and unique destinations. On this week-long, point-to-point odyssey you’ll get to know Portugal, all from the vantage point of your saddle.

Starting in Lisbon, the oldest city in Western Europe, we’ll head south through the countryside toward Alentejo, the sparsely populated, agrarian southern region known as Portugal’s breadbasket.

The landscape is a tapestry of oak trees, olive orchards and vineyards. They produce almost half of all the wine made in Portugal here, and in some neat synergy, it’s also the largest producer of cork in the world. This is a destination with a deep culinary tradition, famous for first-class local ingredients and rich, uncomplicated cooking.

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 F12 Disk with SRAM RED eTap AXS
  • Daily Bike Wash
  • One 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 2. Alqueva loop. 111km

Biggest Climbing Day:

Day 2. Alqueva loop. 1,156m


Day by Day Breakdown


Évora Test Ride

Bem-vindo a Portugal! Our trip begins in Evora, 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.


This point-to-point takes us north, from the Convento do Espinheiro to the wonderful wine hotel Torre de Palma, which was built in 1338. While there are no major climbs to speak of, the terrain will be undulating throughout the day so be sure to conserve some energy for the home straight.


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.

TORRE DE PALMA – São Lourenço do Barrocal

This point-to-point takes us from Torre de Palma south to our new home in São Lourenço do Barrocal, in the heart of Alentejo. There is a sustained climb to the midway point at Vila Viçosa, but in general 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.


Riding around São Lourenço do Barrocal 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.


Tonight you are in for a treat as we will be staying at the wine hotel, Torre de Palma, which was built in 1338. We’ll pass some picturesque towns like Borba and Vila Viçosa, the historic center of Monforte in the final kilometers, but other than that it will be mostly quiet, rural roads through the rolling countryside. The day’s longest climb only gains a couple of hundred meters, but don’t let that fool you into thinking that this ride will be flat because we’ll be going up and down all day, and by the finish you should have developed a healthy appetite for some fine Portuguese food and wine.


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 Guides

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.

Bruno Pires

The Mountain Goat

Bruno is inGamba’s pocket rocket for the mountains, having lost none of his snap since retiring from the World Tour. A former Portuguese national champ, he has raced Grand Tours and monuments alongside the likes of Alberto Contador, so there is no better wheel to have when the pace heats up or the road gets steep.




Pinarello Dogma F12 Disk


ZIPP Service Course SL




Speedplay (or your own)


Selle Italia


Zipp 302 Carbon Clinchers


Vittoria Corsa CX


Elite Custom Race


Elite Corsa Team


Garmin Edge 820