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Large cork oak trees in a vibrant meadow of yellow and purple wildflowers under a light blue sky with wispy clouds.

Luxury Alentejo Tours made for you

Enjoy the best of Alentejo with a private journey designed just for you

Vineyards, beaches and ancient ruins

Covering almost a third of the country, Alentejo is a vast region of cork plantation, wheat fields, vineyards and clusters of historic hilltop towns. Its name means beyond the Tajo, and it stretches south from the River Tajo to the northern mountain ranges of the Algarve.

Explore the rolling hillsides, rugged peaks, endless plains and its sweeping Atlantic beaches. Vast swathes of sand lay sheltered between rocky cliffs and over 100km of the coastline is part of the South West Alentejo and Costa Vicentina National Park, an area rich in animal and plant life.

Heading inland, Alentejo is littered with Roman ruins, crumbling Moorish castles, marble towns and whitewashed villages. The UNESCO towns of Évora and Elvas are home to baroque bell towers, temples and mighty fortresses and there are plenty of smaller atmospheric towns with winding cobbled streets to explore.

Much of the population make a living from the huge agricultural estates, and Alentejo feels a world away from Portugal’s bustling cities. Take time to enjoy the relaxed way of life, experience its rustic cuisine and world-class wine, and the chance to explore this tranquil and beautiful region.

  • Vines in a vineyard in Alentejo region, Portugal, at sunset.
  • Portugal , the District of Evora . Immersed in the green village of Monsaraz outside walls. Bright , sunny spring day , beautiful clouds .
  • catedral Evora, Portugal
  • Sines, Portugal - September 14, 2019: Sunset over the Praia da Ilha do Pesseguiro and the fort and islands of Santo Alberto, Portugal

From our experts

Experiences picked by our Alentejo specialists

Walk the Costa Vicentina clifftops

Discover the dramatic coastline and rolling countryside of the South West Alentejo and Costa Vicentina National Park

Trace Roman ruins across open plains

Encounter Roman ruins across Alentejo’s sprawling landscapes

Wander Évora and Elvas

Be charmed by the authentic towns of Évora and Elvas

Taste the region's wines

Sample some of the region’s world-class wines

A word from one of our experts

Alentejo is a delightful part of Portugal, with beaches that stretch as far as the eye can see. Enjoy the tang of sea salt in the air on a hike along its rugged coastline, or marvel at the remains of roman ruins within the UNESCO World Heritage town of Évora. The possibilities are endless.

Murray Mitchell Senior Travel Designer

Luxury accommodation in Alentejo

There are many incredible places to stay in Alentejo. Here are some of our favourites, hand picked by our travel designers:

Why book with Jacada?

  • Personalised design

    We’ll plan your trip around your specific interests, tastes and preferences, providing helpful tips and honest advice based on first-hand knowledge of the destination.

  • Authentic experiences

    Our expert guides and brilliant travel concierges are hand-picked to provide a genuine experience, bringing your destination to life with care and passion.

  • Responsible travel

    Our luxury trips are designed with responsible travel principles that prioritise travel experiences that are both good for you and good for the planet.

Trip inspiration

Get inspired with our Portugal example trips and then get in touch to plan your own adventure

9 days From $11,824

The Highlights of Portugal

From the historic beauty of Alentejo and the highlights of Lisbon, to the pretty coastal town of Cascais and Porto’s ancient port cellars, Portugal can easily…

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12 days From $16,253

An Insider's Trip to Portugal

See a different side to Portugal. On this two-week trip, explore lesser-known villages and towns that invite you to journey deeper. Head to the far north where…

Explore trip

Ready to plan your adventure?

Whatever you want from your Alentejo tour, our team of expert travel designers are ready to help.

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Where else to visit

Meet your Europe team

When to visit

For hiking, birdwatching and general exploring in the South West Alentejo and Costa Vicentina National Park, it’s best to avoid the warmest month of August, when conditions may be too hot. May, June and September are particularly rewarding for exploring Alentejo, as warm temperatures but fewer crowds make for a pleasant experience.

Outdoor Activities

March - May / September - October

Beach Break

June - September

When Is the Best Time to Visit Portugal?

Portugal travel guides

Plan your trip to Alentejo

Whatever you want from your adventure in Alentejo, our team of expert travel designers are ready to help.

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Don't take our word for it

“We enjoyed our first trip with Jacada…”

We enjoyed our first trip with Jacada and it surely won't be our last! Every detail and moment of our trip was perfectly planned. We were met every step of the way with courteous and knowledgeable drivers and guides. We really appreciated the local guides and the commitment they had to make every day special. Thank you Jacada for the…

Amy Schulz Trustpilot ★★★★★

“heavenly honeymoon”

My wife and I used Jacada to plan our honeymoon to French Polynesia. Working with the Jacada team was fantastic and effortless. Every question was quickly answered. Every hiccup was quickly addressed. We felt like we were in the hands of experts who are equally passionate about travel, and who were committed to helping us have the trip of a…

MJ Trustpilot ★★★★★

“Jacada Travel has been outstanding”

We enjoy traveling and we have used Jacada Travel for some wonderful trips over several years. We have never been disappointed. In 2024 we took a Safari in Botswana Africa and walked with the gorillas in Rwanda planned by Jacada and the itinerary was amazing. In 2025 we had planned a trip to Antartica ( with another company ) but…

Lisa Schrage Trustpilot ★★★★★

“Communication and organization were…”

Communication and organization were excellent. The Jacada team was helpful and genuinely interested in our experience. The guides were personable, knowledgeable, and clearly enjoy their work. Vehicles were spotless, timely, and coordinators managed our every need brilliantly. I will recommend Jacada to friends and family. The only way to travel!

Andrew Woodcock Trustpilot ★★★★★

“Iceland 8 Days”

We had a wonderful trip planned through Jacada. We enjoyed the venues and the excursions. This is a beautiful place we'd recommend to anyone who wants to go on a new adventure.

The Reynolds Trustpilot ★★★★★

Behind the scenes in Portugal

Through the Positive Impact Collection, we celebrate the truly remarkable properties that make a meaningful difference in the world. Herdade da Malhadinha Nova offers an immersion in both nature and tradition. Join us as we journey behind the scenes and explore how this stay encapsulates the essence of Alentejo through its gastronomy and viticulture.

Your trip, your story

We craft trips deeply personal, delightfully surprising and entirely one of a kind. Every Jacada journey begins in conversation with a travel designer, a specialist in their destination of expertise. Behind each journey is a wealth of insight, gathered over years of on-the-ground exploration.

Once you’re booked, you’ll meet your concierge. Based in the region you’re visiting, they’ll take care of all the details so your mind is at rest. They make the trip truly special – and truly yours.

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