Portugal, International

Portugal’s Alentejo Countryside Bike Tour

8 Days, 7 Nights |

$4,498 (2026 price) |

All Levels

INCLUDED ACTIVITIES

Cycling (bikes included). wine tastings (x2), historic sites and museum entry fees.

Discover and explore what we ultimately strive for in a cycling vacation–which is to simply “Pedal Happy”.

TOUR HIGHLIGHTS:

  • An 8-day, all-levels, bicycle tour of Portugal’s Alentejo countryside.
  • Cycle quiet roads and some bike paths through vineyards, cork farms, and ancient cities and towns.
  • Begin the tour in the ancient pre-Roman settlement of Évora, a UNESCO World Heritage site.
  • Taste regional wines and learn about prickly pear and cork farming, pottery, leather-working, and rug manufacture.
  • Spend a day exploring the fortified village and castle of Monsaraz and nearby prehistoric megaliths.
  • Relax in heart-warming hospitality and treat yourself to mouth-watering local cuisine.
  • Finish in Vila Viçosa where the streets are literally paved in marble!

Come cycle through the countryside of one of the oldest and sunniest countries in Europe with us! Often referred to as the breadbasket of Portugal, the Alentejo countryside has much more to offer than just vineyards, olive groves, farms and pastoral landscapes. Explore castles, convents, regional artists and craftspeople, marble quarries, cork farms, charming historical villages, and more as you cycle the scenic countryside. Stop to partake of the local gastronomy – from pastries to petiscos (Portuguese snacks) – and sample wines. Absorb the long history of the area which dates back to pre-Roman times. The great ancient city of Évora – now a UNESCO World Heritage Site – as well as small, fortified hamlets dating back to medieval times, tell the stories of wars with moors and Spain over the centuries.

PEDAL HAPPY: This tour cycles over mostly easy to moderate terrain with a challenging hill here or there. Most days involve some riding on cobblestones in the old cities and have some dirt or gravel sections. Two days have longer unpaved sections of bike path and road that are generally easy on the tires.

Itinerary

Day 01

Transfer from Lisbon and get settled in Évora, a UNESCO World Heritage site.

Meals

– Lunch is on your own today.
– Dinner (included)

Lodging

Convento do Espinheiro

Distance/Elevation

Short test ride. Cycling clothing not needed.

After pick-up at our meeting hotel in Lisbon we will shuttle (~1.5hrs) to the ancient pre-Roman settlement of Évora. There will be time to have lunch (if you haven’t already) on your own in the town center while we set up bikes for a short ride (4mi.) through the historic streets to our hotel for check-in. Casual (non-cycling) clothing is adequate for this brief test ride. In the early evening, we will meet for dinner and an overview of the tour. We will be spending the next three nights at the Convento do Espinheiro, a 15th-century recovered convent.

Day 02

Visit UNESCO monuments, pedal a rail trail, visit a castle, and sample award-winning Portuguese wine!

Meals

– Breakfast
– Lunch

Lodging

Convento do Espinheiro

Distance/Elevation

30.8 miles · +786 ft / -773 ft

UNESCO sites, small farms and a charming white and blue village are some of the highlights on our morning ride from the hotel to Arraiolos village – famous for its long history, local pastries, beautifully embroidered wool rugs, and the views from the castle. Much of the cycling is via a bike path built on an old railway. In the afternoon we visit the Fitapreta Winery for a tasting (included). Experience the 14th century palace setting as we get our first sample of some award-winning Portuguese wines! We return to Convento do Espinheiro after the ride. Dinner is on your own tonight.

Day 03

Explore prickly pears, cork farming and a whitewashed village on a ride from Évora.

Meals

– Breakfast
– Lunch
– Dinner

Lodging

Convento do Espinheiro

Distance/Elevation

41.8 miles · +1,120 ft / -1,119 ft

Cycle into the countryside this morning on your way to the visually stunning whitewashed village of Igrejinha, where the buildings are cheerfully trimmed in bright colors. Visit a family-run prickly pear farm to sample juice made from their fruits or tea from the flowers. Our last stop is at a cork factory to see the many uses for cork and how it is transformed from tree bark into various products. You can cycle from here back to Convento do Espinheiro, or shuttle in the van.

Day 04

Cycle a recently constructed bike path to see leather artisans, pottery masters, another castle and a winery.

Meals

– Breakfast
– Lunch
– Dinner

Lodging

Horta da Moura

Distance

44.2 miles · +1,077 ft / -1,303 ft

Most of the route today is on a brand-new, peaceful, traffic-free, cycling path, hopping off the path here and there to enjoy some quaint little villages en route. Highlights along the way include leather artisans in the traditional village of Nossa Sra. de Machede, pottery masters São Pedro do Corval, and the mysterious Castle of Valongo. Visit a winery (included) where their best wines are still aged in massive clay pots. Spend the next two nights at Horta da Moura near Monsaraz.

Day 05

Explore Monsaraz – one of the “7 wonders of Portugal!”

Meals

– Breakfast
– Dinner

Lodging

Horta da Moura

Distance/Elevation

12.7 miles · +919 ft / -916 ft

Today, we take a short ride to explore the fortified village and castle of Monsaraz. On our way we will stop to marvel at some prehistoric megaliths over 6,000 years old and pedal to the shores of nearby Alqueva Lake – Europe’s largest reservoir – on the border with Spain. Monsaraz is a centuries-old stronghold that has been occupied by every major civilization going back to pagan times. We highly recommend the hike up to Monsaraz Castle to enjoy the breathtaking views. Lunch is on your own here and the rest of the day is yours to explore this well preserved piece of history. Spend another night at Horta da Moura.

Day 06

From Monsaraz we ride through the marble capital of Portugal to Vila Viçosa – the “princess of the Alentejo region.”

Meals

– Breakfast
– Lunch
– Dinner

Lodging

Pousada de Vila Viçosa

Distance/Elevation

34.7 miles · +2,176 ft / -1,526 ft

Today’s ride takes you to the marble capital of Portugal, one of the largest marble producing areas in Europe. Known locally as “white gold,” marble not only shapes the actual landscape of the region, but it has also provided (literally) the building blocks for the streets – yes, marble streets! – as well the area’s most towering buildings. After lunch and a visit to an impressive, fortified sanctuary with a captivating history, you’ll enjoy a rare view over vibrant, colored lagoons formed by marble extraction. Continue cycling to Vila Viçosa, a small village often described as an open-air museum. We spend the last two nights of our tour here in a perfect blend of history and comfort at Pousada de Vila Viçosa, established in the 16th century as an “aristocratic convent” primarily housing women from noble or wealthy families.

Day 07

Cycle to Estremoz – nicknamed the “white city” for its white marble buildings.

Meals

– Breakfast
– Lunch
– Dinner

Lodging

Pousada de Vila Viçosa

Distance/Elevation

28.8 miles · +1,170 ft / -1,178 ft

Today’s ride is fairly easy, providing us with the perfect opportunity to take our time. Pedal from tavern to tavern stopping to savor local delicacies – petiscos (Portuguese snacks) – along the way. Try not to overeat! Marvel at all the white marble when we reach Estremoz. Don’t forget your sunglasses! Climb the 13th century castle’s “donjon” tower for more unforgettable views before cycling back to Estremoz alongside vineyards and more marble quarries. Explore more artisan shops and enjoy a celebration dinner on our last night in Vila Viçosa.

Day 08

Departure Day. Breakfast included.

Meals

– Breakfast

Sadly, it is time to say goodbye to your new friends and the wonders of Alentejo countryside. After breakfast (included), we transfer you back to Lisbon at 10am. Drop-offs will be at our meeting hotel in Lisbon between noon and 1pm. If you are flying out today, we ask you to arrange your departure flight for 5pm or later.

Dates

Dates
Guaranteed
This means that the tour will definitely depart as scheduled and not be canceled.
Price
Availability
Dates
Single Supplement
Price
$1,215
Single supplement required for solo travelers. Limited availability.
Dates
Oct 10, 2026
Guaranteed
This means that the tour will definitely depart as scheduled and not be canceled.
Price
$4,498
Availability
Private Departure
Dates
Oct 24, 2026
Guaranteed
This means that the tour will definitely depart as scheduled and not be canceled.
Price
$4,498
Availability
Closed, call for waitlist

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