Discover the Alentejo: A Wine & Culture Journey Through Portugal's Most Captivating Region

I am thrilled to co-host a trip to Portugal in May 2027 for our inaugural journey to Southern Portugal, proudly co-hosted by The District Pit. It promises to be a memorable week exploring one of Portugal's hidden gems — with exceptional wines, authentic cuisine, charming villages, and experiences that showcase the very best of the Alentejo region.

Travel + Leisure Magazine, The Wall Street Journal, and wine lovers around the world have been falling in love with Portugal for good reason. And nowhere captures that magic more completely than the Alentejo — a sun-drenched landscape of rolling cork forests, ancient villages, and wines that are rewriting the global conversation about what Portuguese wine can be.

This is not a typical wine tour. This is a full sensory immersion — into the landscape, the history, the food, and the people who make this region extraordinary. And I can't wait to experience it with you.

Why the Alentejo?

Tucked between Lisbon and the Spanish border, the Alentejo is Portugal's largest wine region and one of its most storied. It's a place where Roman temples stand beside medieval cathedrals, where prehistoric stone circles predate Stonehenge by more than 2,000 years, and where winemakers are crafting some of the most exciting bottles in Europe — many of which you'll taste firsthand on this journey.

Your Home Base: Évora

For six nights, you'll be based in Évora, a UNESCO World Heritage city that feels like stepping into another century. Cobblestone streets wind past Roman ruins, baroque churches, and whitewashed houses draped in bougainvillea — the perfect anchor for daily explorations in every direction.

Your accommodations: Mar de Ar Aqueduto, a stunning 5-star hotel set inside a beautifully restored 16th-century palace in Évora's historic center. Modern luxury wrapped in centuries of history — complete with a pool, spa, and sweeping views of the city's iconic aqueduct.

🔗 Learn more about Mar de Ar Aqueduto

The Day-by-Day Experience (May 17 - 23, 2027)

Day 1 — The UNESCO World Heritage City of Évora

Your journey begins at 10am with a private group bus pickup in central Lisbon for the scenic 1h20m ride to Évora.

Before lunch, you'll visit the hauntingly beautiful Bone Chapel (Capela dos Ossos) — one of Portugal's most extraordinary and thought-provoking landmarks. From there, wander the maze of narrow cobblestone streets before arriving at a beloved family restaurant that has been serving traditional Alentejo gastronomy for nearly 40 years.

After a long, leisurely lunch with wine, the afternoon brings visits to the 800-year-old Cathedral of Évora (Basílica Sé de Nossa Senhora da Assunção) and the 1,800-year-old Roman Temple — two of the most remarkable ancient sites in all of Portugal.

Each evening, you're free to enjoy the hotel's stunning common areas with their commanding views of the 16th-century aqueduct, or simply wander the enchanting streets of Évora at your own pace.

Day 2 — Cork, the Montado & Portugal's Stonehenge

Today is all about deep roots — both ancient and ecological.

Your morning begins in the Montado, Portugal's iconic cork oak forest, led by the always-engaging Andreia. You'll learn why cork is one of the world's most remarkable sustainable resources — and you'll never look at a wine cork the same way again.

Lunch follows at Senhor Daurindo's — a super traditional Alentejo feast accompanied by deeply local wines. This is the kind of meal you'll be talking about for years.

On the way back to Évora, you'll stop at Cromeleque dos Almendres, a prehistoric megalithic stone circle that predates Stonehenge by more than 2,000 years. Standing among these ancient stones in the quiet Alentejo landscape is a genuinely humbling experience.

Day 3 — Portuguese Royalty & Howard's Folly Winery

A day of regal history and serious wine — with a name that makes you smile.

The morning begins with a guided visit to the Royal Summer Palace of Vila Viçosa, the former seat of the House of Braganza and one of Portugal's most impressive royal residences.

Then it's on to Howard's Folly — funny name, serious wine. Lead winemaker David Baverstock is better known for running the wine operation at the legendary Esporão, but Howard's Folly is a newer, smaller venture created with his good friend Howard, who spent 30 years living in Hong Kong. The result is a winery with a fascinating story and wines that punch well above their weight.

Lunch is prepared by innovative Chef Bernardo, who crafts dishes designed to pair perfectly with Howard's wines.

Day 4 — Portugal's Best Hilltop Village

Today belongs to Monsaraz — one of the best-preserved medieval villages in all of Portugal, and arguably one of the most beautiful in all of Europe. Perched high on a hilltop overlooking Spain, its ancient ramparts and cobblestone lanes feel like a fairytale. If it were anywhere else, it would be overrun with tourists year-round.

On the way, you'll stop in São Pedro do Corval, Portugal's pottery capital, for some shopping and browsing among the artisan workshops.

Lunch is a lovely, unhurried affair on the covered patio of good friend João's family restaurant in Monsaraz — facing the shimmering lake and the Spanish frontier. A view and a meal you won't soon forget.

Day 5 — Roman Villa & Quetzal Winery

Today pairs ancient history with contemporary winemaking at its finest.

Your wine visit takes you to Quinta do Quetzal, a winery where art and wine share equal billing. Your visit will be led by winery head Reto Jorg, whose passion for both the land and the craft is immediately apparent.

Lunch is prepared by Chef João Mourato — a 29-year-old culinary talent who many believe is on a path to a Michelin star. The food will leave you speechless.

The afternoon brings a visit to the Roman Villa of São Cucufate, a remarkably preserved archaeological site that has been standing for over 1,800 years. Walking through it feels like a private window into the ancient world.

Day 6 — Estremoz Saturday Market & Monte Branco Winery

Your final full day is a celebration of markets, marble, and winemaking with strong opinions.

The morning begins at the Estremoz Saturday Market — one of the oldest outdoor markets in Europe, held in the stunning marble town of Estremoz. Browse local produce, ceramics, textiles, and artisan goods in a setting that has changed little over centuries.

Then it's on to Monte Branco, where owner and winemaker Luís Louro — practically born into the wine business — will share his deeply held convictions about winemaking. His tasting area overlooks a glorious sweep of Alentejo countryside, and lunch is served in the barrel room, surrounded by the wines you've just discovered.

Day 7 — Boa Viagem 🇵🇹

After an early breakfast and checkout, your private transfer departs Évora at approximately 8am for Lisbon airport — timed for most guests' noon departures.

If you're extending your stay in Portugal, breakfast is at your leisure, and the team can help arrange transfers at other times or to different destinations.

Boa viagem — safe travels, and thank you for sharing this journey with us.

What's Included

• 6 nights at Mar de Ar Aqueduto (5-star, Évora)
• Daily breakfast
• Daily long lunch or dinner — all wines and gratuities included
• All winery visits, tastings & cultural excursions
• Private transportation from Lisbon pickup through Sunday drop-off
• All wine tastings, generally including tapas

What's Not Included

• Airfare
• Trip insurance (recommended)

Pricing & How to Book

Per Person (double occupancy)	$4,300
Deposit to Reserve	$1,000
Single Supplement	+$800

Traveling solo? Single travelers are warmly welcome. To book as a solo traveler, please contact Leslie at Hello@thewineconcierge.co

👉 Reserve Your Spot — Book Now

Spaces are limited for this intimate group journey. A $1,000 deposit secures your place.

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