You will be welcomed by a friendly member of our team at the hotel for an orientation, bike set up and briefing, to make sure you are all set for the adventure that awaits.

Then it's time to explore the city on foot and eat at one of the fantastic local restaurants within walking distance of the hotel.

Évora is one of Portugal’s most atmospheric historic cities, located in the heart of the Alentejo region and surrounded by rolling plains, olive groves, and vineyards. A UNESCO World Heritage Site, the city is best known for its exceptionally well-preserved Roman Temple, medieval city walls, and whitewashed streets lined with traditional houses and tiled façades.

The historic centre is compact and easy to explore on foot, with highlights including the Cathedral of Évora, Praça do Giraldo, and the Chapel of Bones, one of Portugal’s most iconic monuments. Évora also offers an excellent food and wine scene, showcasing classic Alentejo cuisine and local wines, making it an ideal stop to experience the region’s slower pace of life and rich cultural heritage.

Its calm atmosphere, historical depth, and beautiful surroundings make Évora a perfect contrast to Portugal’s coastal areas and the perfect place to start your tour.

With a contemporary, minimalist décor, the 4-star Évora Olive Hotel offers accommodation in the heart of Évora and features free WiFi throughout. The hotel boasts outdoor and indoor swimming pools and meeting facilities. Free private parking and secure bike storage is available on site.

Serving Portuguese cuisine, the Eborim restaurant also includes a grocery shop. Guests can have a drink at the hotel’s bar or relax in the lounge room. Wellness facilities include a fitness centre and massage rooms. There is a 24-hour desk for guests’ convenience.

Enjoy a beautiful first day of gravel cycling, starting along the brand new easy Eco-Pista from Evora all the way to Montoito on the old railway line, an excellent way to begin your tour. From Montoito you will join backroads and gravel tracks through ancient olive groves and traditional villages until the final climb to Monsaraz.

Monsaraz is a beautifully preserved medieval hilltop village overlooking the vast Alqueva Lake, in the heart of the Alentejo. Enclosed by ancient stone walls, the village is known for its narrow cobbled streets, whitewashed houses with traditional blue trim, and sweeping views across one of Europe’s largest artificial lakes and the surrounding countryside.

At its highest point sits Monsaraz Castle, offering panoramic views that are especially striking at sunset. The village has a peaceful, timeless atmosphere, with small artisan shops, local taverns, and a strong connection to Alentejo traditions, cuisine, and wine. Its remote setting and lack of modern development make it feel authentically untouched.

Monsaraz will be one of the most unforgettable places you will visit on this trip.

Nestled on the main street of the medieval village of Monsaraz, within its historic walls, Casa Dona Antónia is a charming and inviting retreat. The traditional façade—adorned with lush bougainvillea and crowned by three centuries-old chimneys—hints at the warm, authentic atmosphere found within.

Originally transformed into a guesthouse in the 1970s by Dona Antónia and Sr. Inácio, pioneers of local hospitality, the property holds a rich legacy of welcoming travelers to the region. In 2022, the guesthouse began a new chapter, following the end of a long-term lease, with thoughtful renovations that enhanced both its natural light and traditional character.

Today, Casa Dona Antónia offers five individually styled rooms, a spacious family suite, and a self-contained apartment—some featuring private terraces with sweeping views over the Alentejo plains. Each morning, guests are welcomed with a generous breakfast buffet showcasing homemade specialties and locally sourced ingredients.

Your second day of cycling starts off with a stunning descent from Monsaraz across the Alqueva reservoir and through small winding backroads and gravel tracks, finishing in the stunning Herdade do Sobroso, a luxury vineyard accommodation.

We have arranged something special for you on arrival...

Herdade do Sobroso offers an immersive wine tourism experience set within a 1,600-hectare Alentejo estate in the Vidigueira region of southern Portugal.

Description: Accompanied by a guide, you will set off to discover the vineyard and the winery, where you will taste four wines (Cellar Selection range, Arché White, and Grande Reserva Red), accompanied by a tasting of regional cheeses and cured meats.

Approximate duration: 1 hour 30 minutes

Herdade do Sobroso is a picturesque wine estate nestled in the heart of the Alentejo, near the Guadiana River and surrounded by the serene landscape of the Serra do Mendro. Blending the charm of rural Portugal with refined comfort, it offers a unique retreat where vineyards, olive groves, and cork forests stretch as far as the eye can see. The estate produces award-winning wines and provides immersive enotourism experiences, including tastings, cellar tours, and regional cuisine served in a beautifully restored farmhouse.

For cyclists, Herdade do Sobroso is a true gem. Quiet country roads, rolling hills, and scenic riverbanks create ideal riding conditions, with routes that pass through historic villages, open plains, and shaded forest trails.

After a rewarding day in the saddle, guests can relax by the pool, enjoy a massage, or sample local wines while taking in panoramic views of the surrounding countryside. Secure bike storage and a peaceful atmosphere make this an excellent base for those exploring Alentejo on two wheels.

This day you cycling into the heartlands of the Alentejo, skirting Beja, the region's historic capital. You will finish the day at the incredible Vila Galé Alentejo Vineyards Hotel - a superb hotel right in the middle of the rolling fields of vines.

Vila Galé Alentejo Vineyards is a welcoming 4-star countryside hotel set in the peaceful rolling plains of Albernoa, between Beja and Aljustrel—an ideal base for cyclists exploring the heart of the Alentejo. Surrounded by quiet country roads and vast open landscapes, the hotel offers easy access to scenic rides through olive groves, vineyards, and sleepy villages. After a day of riding, guests can unwind in bright, air-conditioned rooms with private balconies overlooking the countryside, and store their bikes securely on-site.

The hotel blends rural charm with comfort and offers a variety of relaxing experiences, from wine tastings at its own Casa de Santa Vitória winery to horse-drawn carriage rides and even a mini-zoo. The on-site Hunting Pavilion Restaurant serves hearty Portuguese cuisine and international favourites—perfect for refuelling after long rides. Cyclists can also recover at the health club, complete with an indoor pool, hot tub, and Turkish bath, making this a perfect stopover for active travellers seeking both adventure and relaxation.

Today you will experience more of the typical Alentejo countryside - through miles of olive groves and vineyards. Most of the route is on small, paved backroads which are a joy to ride. Look out for storks roosting up high!

Alvito is a small and peaceful historic town in the Alentejo region of southern Portugal, known for its traditional architecture and relaxed rural atmosphere. At its heart is the medieval Castle of Alvito, now a historic pousada, along with charming churches and quiet streets that reflect the town’s long history. Surrounded by typical Alentejo countryside, Alvito is an ideal stop for those looking to enjoy local culture, open landscapes, and a slower pace of life.

Nestled within the ancient walls of a beautifully restored 15th-century castle in the heart of the Alentejo, Pousada Castelo Alvito blends medieval with modern. As a designated National Monument since 1910, this intimate 20-room castle retains its original Islamic, Gothic, and Manueline architectural details. Guests can wander through sheltered courtyards, relax in gardens and take refreshing dips in the pool set alongside the castle walls.

Pousada Castelo Alvito offers secure and convenient bike storage, ideal for riders exploring the region’s scenic, low-traffic roads. After a day of pedaling through olive groves and rolling wheat fields, cyclists can recharge with regional Alentejo cuisine made with produce from the castle’s own vegetable gardens, enjoy a cool post-ride swim, and enjoy time in the atmospheric vaulted restaurant or reading lounges. Staff also happily assist with laundry and gear logistics, ensuring seamless support for your stay.

This is your final day of cycling through quiet traditional villages and along long winding gravel tracks back into Evora, where you will stay in the same hotel as you started in.

It's a great chance to explore a little more of Evora that you might not have seen the first day, as well as enjoy a meal out in one of the numerous fantastic restuarants within walking distance of the hotel.

Pousada Convento de Évora, officially known as the Pousada dos Lóios, is a unique historic hotel set within a beautifully restored 15th-century convent in the heart of Évora’s UNESCO-listed old town. The building combines Gothic and Manueline architectural details with calm cloisters, vaulted corridors, and elegant courtyards, offering a strong sense of history throughout the stay. Guests can enjoy traditional Alentejo cuisine in the former monks’ refectory, relax in peaceful communal spaces, and step directly outside to explore Évora’s main monuments, making it an atmospheric and highly central base for discovering the city.

We will be sorry to see you leave!

We will arrange a transfer for you from the hotel to Lisbon in the morning to suit your schedule.

If you'd prefer another night in Evora we can add that to your trip itinerary too, just let us know!

Temperatures in the Alentejo during the summer can be very hot. We recommend doing this tour in Spring or Autumn where temperatures are between 25-30 degrees celcius, but Winter can also be fabulous and very quiet too. Southern Portugal is exposed to the Atlantic weather, so expect some wind too, especially on day 5 as we make our way down the west coast!

This trip suits riders who are used to riding back to back days and being in the saddle for up to 5hrs at a time. Each day will consist of between 30-50% gravel track sections (imagine a 4x4 gravel track suitable for vehicles as well) and the rest small quiet tarmac roads.

There might be the odd very short more technical section or river crossing at certain times of year, but we have done our very best to ensure there is no hike-a-bike in this tour!

Evening meals are not included in this trip, but we will recommend restaurants for you to enjoy.

We support small, local cafes and restaurants, and we recommend eating where you can ‘how the locals do’. The food in interior Portugal is often more simple than on the Algarve coast, with menus regularly changing with the region and season.

All dietary requirements will be happily catered for – just let us know what you require, or what your likes or dislikes are.

If you book a self-guided tour, we are always on the end of the phone. This means that if you need mechanical support, want to change a booking, or anything else which may crop up on the road, our friendly (bilingual!) team are here to help.

Please note that due to availability, accommodation may vary from the hotels listed above.

Depending on your group size, we may be able to offer you a choice of hotels. This is one of our premium tours, where we do our best to choose some of the most special, historic and unique hotels for you to enjoy during your adventure.

• Transfers from Lisbon to Evora and return.

• 6 nights premium accommodation in high quality 4-5* bike-friendly accommodation

• Buffet breakfast each day

• Premium Wine Tour + Tasting experience, with cured meats and cheeses at Herdade de Soboroso.

• Restaurant reservations each evening

• Detailed route planning (adapted personally to you), GPX files given in advance plus itinerary

• Large luggage storage (bike boxes for example) throughout

• Civil Liability Insurance

• Telephone support whenever you should need it.

• 5 star Service – our promise

• Dinner - although restaurants can be reserved for you.

• Lunch and coffees bought at cafes en route.

• Flights

• Other costs not listed above

• Luggage transfers + mechanical support vehicle (€360/group per riding day) = €1,800

• Luggage transfers (€150/group per riding day for groups up to 5) = €750

• Luggage transfers (€200/group per riding day for groups 6+) = €1,000

• Guide (€260 per guide per riding day) = €1,300

We have a range of rental bikes to suit different styles and budgets, including e-bikes. Below are a few examples. For full details and prices, see our website.

• Megamo. SRAM APEX AXS. 12 speed.

• Megamo. SRAM Apex Eagle. 12 speed.

• Megamo Lande Premium e-Gravel. Bosch Performance Line.

• Megamo e-Gravel. Bosch 600wh.

Our bike rental partners are scaled to support large group, of 40+ riders.

Paradise Cycling Tours Unipessoal LDA

Bairro da Boavista 6
8100-016 Alte
Portugal
NIPC 517913704
RNVAT 11760

Contact:
Fiona Hunter Johnston +351 931325694

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