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18 Oct 2026
24 Oct 2026

DISCOVER: Alentejo Wines

Experience Portugal Like Never Before

18 Oct 2026
24 Oct 2026

Alentejo Wines

$7,950
Lead Guide:

Sérgio Paulinho

ABOUT THIS TRIP

Much of the inGamba team of soigneurs and mechanics call Portugal home. This special trip 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 odyssey through the Alentejo, you’ll get to know it intimately from the vantage point of your saddle. We’ll be based in Estremoz at Casa do Gadanha, an elegant boutique hotel in the heart of town, so each morning begins with a quiet roll past marble squares and castle walls. Nestled among miles of cork oak, olive groves, and vineyards, this ancient region is regarded as one of the most beautiful in Portugal and is steeped in the history and culinary culture that make the Alentejo so irresistible—think long lunches, local talha wines, and whitewashed villages linked by serene, undulating roads.

Arrival Details

Airport City: Lisbon, Portugal
Pick-Up Location: InterContinental Hotel Lisbon
Pick-Up Time: 8:30-8:45am

Departure Details

Airport City: Lisbon, Portugal
Drop-Off Location: InterContinental Hotel Lisbon
Drop-Off Time: Lisbon Airport (11am), InterContinental Hotel Lisbon (11:15am)

What's Included?

*Pre/post-trip lodging is not included. Our transfers operate on a time slot basis, starting from a designated meeting point. †Flights are not included
**Beverages ordered by guests beyond normal amounts and away from group activities will incur additional charges

MEET THE GUIDES

Sergio

Sérgio Paulinho

The World Tour veteran

After an impressive pro career that started back in 2003, Sérgio Paulinho joined the inGamba team at the start of 2022 after his retirement. But we’ve known him for a long time, as not only did he race against our founder João Correia, but he was also a teammate of our star guide Manuel Cardoso back in the day. A two-time national champion in Portugal, Sérgio has also won stages at the Tour de France and Vuelta a España, and in 2004, he won a silver medal in the road race at the Athens Olympics. So it’s fair to say the man has pedigree! It isn’t the racing victories that impress us most about Sérgio though, it’s his personality, his friendly nature on and off the bike, and the fact that he’s always ready with a smile. That said, if you find yourself running out of gas on a big climb, it certainly helps to have someone like him beside you!

THE TRIP AT A GLANCE

START LOCATION:

Lisbon

FINISH LOCATION:

Lisbon

TOTAL ELEVATION:
4,417m
TOTAL DISTANCE:
406km
DAYS RIDING:

6

GROUP SIZE:

8-14

LONGEST DAY:

Day 6
Sousel Loop. 85km

BIGGEST CLIMBING DAY:

Day 3
Redondo Loop 894m

View Bike Options

DAY BY DAY BREAKDOWN

1

Estremoz Test Ride

Sunday | 33km & 344m

We begin with a gentle loop around Estremoz, a historic hilltown famed for its marble quarries – the “white gold of Alentejo”. Flat roads and easy miles let you spin the legs and take in the scenery of vineyards and olive groves. Overlooking our route is Estremoz’s medieval castle, where Queen Isabel of Portugal spent her final days. It’s a relaxed warm-up ride that blends natural beauty with the town’s rich cultural heritage, setting the stage for the adventures to come.

2

Vila Viçosa Loop

Monday | 79km & 748m

Today’s ride leads to Vila Viçosa, known as the “Princess of Alentejo” and set in the heart of marble country. The approach is mostly rolling terrain, surrounded by olive orchards and marble outcrops. In town, we’re greeted by the imposing Ducal Palace with its 110-meter marble façade, a legacy of the Braganza dynasty that called this royal town home for 500 years. With over 150 marble quarries in the area, nearly every building here gleams with local stone. Cycling through ornate plazas and tree-lined boulevards, you can sense the opulence of a bygone era while enjoying the village’s laid-back charm.

3

Redondo Loop

Tuesday | 81km & 894m
We pedal through golden plains and cork oak forests towards Redondo, a quaint Alentejo town celebrated for its artisanal pottery and robust wines. Nestled at the foot of the Serra d’Ossa hills, Redondo charms us with whitewashed houses, a tiny medieval castle, and family-run pottery studios where centuries-old ceramic traditions live on. This region’s winemakers still honor ancient methods – some ferment their rich reds in huge clay talha (amphora) jars, just as the Romans did. After cruising past vineyards, we might pause to savor a sip of local talha wine or admire earthenware handiwork, experiencing Redondo’s rustic blend of history and homegrown hospitality.
4

Vieiros Loop

Wednesday | 57km & 542m
A scenic loop carries us north on quiet backroads to the sleepy village of Veiros. We spin by pastoral fields – where the only sounds are distant sheep bells – before reaching this whitewashed hamlet with its modest 14th-century castle. Though Veiros is tranquil today, it holds a noble secret: it once belonged to the House of Bragança and was the birthplace of the family’s first duke, who would found Portugal’s last royal dynasty. Standing by the old castle walls and pillory, you can imagine medieval knights guarding these lands. This ride feels like a journey back in time, as we cycle through living history and return enriched by the village’s stories.
5

Évora Monte Loop

Thursday | 71km & 630m

We cruise across open plains until the road ramps upward toward Évora Monte, a fortified village perched on a solitary hill. The climb is steady, leading to the ancient gates of Évora Monte and its striking Renaissance castle, distinguished by thick knot-like bands encircling its round bastions. From the hilltop, breathtaking views sweep across the Alentejo, an ocean of rolling wheat fields, cork forests, and distant villages. After absorbing the panorama, we enjoy a thrilling descent from the castle walls back to the tranquil countryside.

6

Sousel Loop

Friday | 85km & 853m

Our final loop explores the rural charms around Sousel, a land of ancient olive groves and gentle hills. We ride through quiet lanes flanked by gnarled olive trees, passing manor houses and farmland that reflect Alentejo’s slow pace of life. The normally flat plains are briefly interrupted by the limestone heights of Serra de São Miguel. A short detour up there rewards us with a 360º vista over the endless plains: to one side, patches of cork oak forest; to the other, mosaic fields and the village of Sousel itself, known for its fine olive oil and hunting heritage. It’s a fitting end to our journey, blending panoramic natural beauty with a touch of local tradition.

7

DEPARTURE

Saturday
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.

STAYING LONGER?

Adventure Continues…
Do you plan to come a few days early, or stay on after your inGamba adventure has ended? Our concierge can help you plan with a carefully curated selection of hotels, restaurants, bars, and guides. All of our recommendations have been hand-picked by a team of local experts, so you can spend more time enjoying all that this destination has to offer.

The latest version of the DOGMA features an advanced fiber with remarkable tensile strength, which enables Pinarello to improve the bike’s lateral stiffness performance. With this enhancement, the New DOGMA F is engineered to tackle any road challenges, establishing itself as a reliable option for all kinds of rides.

In addition, it comes equipped with the new SRAM RED AXS, the lightest electronic groupset to date. The controls have been redesigned to offer smooth, comfortable ergonomics for a wide range of hand sizes. What makes this groupset stand out is the effortless braking, allowing for one-finger braking with minimal effort. The RED brakes now require 80% less effort when braking from the hoods and 33% less effort from the drops, delivering more power and reducing hand fatigue.

WHEELSET:

Zipp 303 S Carbon Tubeless

FRAMESET:

Pinarello New Dogma F

COCKPIT:

MOST Talon Ultra Fast

TIRES:

Vittoria Corsa N.Ext

GRUPPO:

New SRAM RED AXS (Powermeter Included)

BOTTLE CAGES:

Elite Custom Race

PEDALS:

Speedplay

BIDON:

Elite Jet

SADDLE:

Prologo

COMPUTER:

Garmin Edge 1040

COLOUR:

inGamba Red

The NYTRO GRAVEL has a pure road racer DNA which upon launch marked an era in the E-BIKE/GRAVEL world. Featuring an iconic design, the Nytro Gravel is perfect for anyone looking for a road bike with powerful support for the toughest climbs.

WHEELSET:

Zipp 303 S Carbon Tubeless

FRAMESET:

Nytro Gravel E-Bike
(available for an additional fee)

COCKPIT:

ZIPP Service Course SL

TIRES:

Vittoria Corsa N.Ext

GRUPPO:

SRAM RED eTap AXS

BOTTLE CAGES:

Elite Custom Race

PEDALS:

Speedplay

BIDON:

Elite Corsa Team

SADDLE:

Prologo

COMPUTER:

Garmin Edge 1030

COLOUR:

Saturn Silver

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