Private Wine Tour in Alentejo
This five-day private wine tour takes you from Lisbon into the Alentejo, combining winery visits and lunches with stays near Évora and Monsaraz. Designed for wine lovers also seeking luxury, it brings together superb wines, ultra-charming hotels, and excellent dining.
Alentejo is a supremely romantic wine region in southern Portugal (just north of the Algarve), where you will find soft rolling hills covered in vineyards, cork forests, whitewashed villages, and medieval castles. The Alentejo is wonderfully unspoiled, with medieval hamlets perched on hilltops and peaceful landscapes reminiscent of the African Savannah.
Some of Portugal’s most famous wines come from the Alentejo, including Cortes de Cima, Herdade dos Coelheiros, Mouchão, and the pioneering Esporão. Over the next few days, you will enjoy private winery visits, vineyard walks, and special tastings with the winemakers and owners themselves. Taste a range of Portuguese and international grape varieties, including Aragonez (the local name for Spain’s Tempranillo grape), Touriga Nacional, Trincadeira, Castelão, Tinta Caiada, Syrah, Cabernet Sauvignon, Arinto, Antão Vaz, and Roupeiro.
You will visit medieval Estremoz, with its castle and darling wine and pottery shops, and charming little villages like Monsaraz. Tour Évora with a private guide and take in its quaint little old town, including the Roman temple and the spooky Chapel of Bones.
Enjoy private lunches with winemakers at the winery and stay at two of Portugal’s loveliest luxury hotels (one a converted convent, the other a magnificently restored farm estate).
If you are looking for an original destination off the beaten path, with luxury hotels and top-notch wines, contact us for more information on this extraordinary wine tour of the Alentejo.
As featured in
Signature journey
Highlights include luxury transportation, private winery visits, lunches with estate hosts, cork forests, Évora and Monsaraz, and four nights in luxury hotels.
Day 1Lisbon- Igrejinha- Arraiolos -Évora
Five star hotel in Evora
This morning, your chauffeur will pick you up at Lisbon Airport or your hotel in Lisbon, and you will travel to the Alentejo wine country! Your first stop today is the tiny village of Igrejinha, where you’ll visit the wild Herdade dos Coelheiros estate, taken over by Alberto Weisser and Gabriela Mascioli in 2015. This couple fell in love with the gorgeous estate, made it their home, and invested considerably in the new era of Coelheiros.
This extensive estate not only produces wines but also farms walnuts and cork trees. Tour the property by Land Rover, taking in the beautiful landscapes, and finish with a tasting of their white and red wines.
Carry on to the nearby village of Arraiolos, famous for its “Tapetes de Arraiolos” (embroidered rugs); you will have noticed that their designs inspire the Coelheiros bottle labels. Enjoy some free time for lunch, visit the tapestry museum, and take a stroll around.
Then carry on to your luxurious hotel near the town of Évora. Check in, relax, walk on the beautiful grounds, or enjoy the spa. Tonight, enjoy a welcome dinner at the hotel’s gourmet Divinus restaurant. Taste refined dishes paired with elegant wines. Welcome to the Alentejo!
Day 2Évora – Redondo - Évora
Roman temple in Évora
Your first stop this morning is only a 10-minute drive away, so you’ll have time for a leisurely breakfast before your chauffeur takes you to Cartuxa Winery, just outside Évora. The Eugénio de Almeida Foundation owns the winery; it’s a charity focused on the cultural, educational, social, and spiritual development of the local region.
When you taste the wines, you will not doubt how Cartuxa has grown to its level of success; even the mid-level table wines EA are notable. But what many will know Cartuxa for is Pêra-Manca. Both the red and white are exquisite wines – pure finesse and harmony in a bottle.
It’s then about a 20-minute drive to Herdade de São Miguel. The estate combines vineyards, cork forest and grazing pastures for sheep and the very adorable donkeys. Your lovely host, Joana, will lead you through the winery, estate and tasting before taking you to Alexandre Relvas’s home for a family wine lunch. In the mid-afternoon, you will head back to Évora, where your private guide will be waiting to take you on a guided walking tour of the main sights. You will visit the Templo Romano (1st-century Roman temple), the Igreja de São Francisco and its macabre Capela dos Ossos, and stroll through the Jardim Público.
This evening is free to dine on your own; you may like to check out Fialho in Évora’s old town, casual yet utterly charming. This restaurant serves authentic Alentejo dishes, all washed down with cracking wines from their impressive cellar.
Day 3Évora – Reguengos de Monsaraz – Monsaraz
Esporão winery, Alentejo
This morning, check out of your Évora hotel and travel with your luggage, driving southeast for about 45 minutes to the splendid Esporão estate near Reguengos de Monsaraz. This is one of Portugal’s leading wineries, producing excellent wines and olive oils. You will enjoy a private guided wine tour, followed by a tasting of a selection of their wines.
Next, sit down to lunch in their bright, airy restaurant, relax, and enjoy a seasonal menu paired with wine. The kitchen draws on produce from the estate’s organic gardens and local and national producers.
Visit the marvelous little whitewashed fortified village of Monsaraz, where you can enjoy some free time for a digestive walk and explore the hamlet on your own.
In the late afternoon, you will move on to your next abode: the delightful São Lourenço do Barrocal Hotel, your home for the next two nights. Take time to just “be” here; it’s so peaceful and relaxing. Spend the evening gazing at the night sky while sipping on a glass of wine.
Day 4Estremoz – Redondo – Monsaraz
Hilltop town of Estremoz
This morning, you will head to Estremoz, with time for coffee and a stroll through the medieval center before continuing to Dona Maria Wines by Julio Bastos. The palace and estate are also known as Quinta do Carmo.
Your host, Isabel, leads you through a tasting of her husband’s superb wines before taking you to lunch in her family’s 18th-century dining room, with many original features still immaculately preserved. Lunch is a typical Alentejo affair, which might include rich tomato soup with a poached egg, cod over home-grown spinach, and a selection of local sweeties to finish.
After lunch, a scenic 30-minute drive will lead you to Redondo, where the majestic Herdade da Maroteira awaits. This estate combines cork forest and vineyards. Although they produce only 95,000-100,000 bottles annually, their emphasis on quality over quantity means new releases are quickly snapped up. Fortunately, they reserve a special stock exclusively for their visitors.
Your enthusiastic host, José, promises an adventurous 4×4 ride through the picturesque cork forest. Along the way, you’ll stop at a vantage point to take in the surroundings. From there, your journey continues to the vineyards, culminating in a tasting session at the house. Here, you’ll be introduced to the Dez Tostões White, a pure Antão Vaz, followed by a harmonious red blend of Aragonês, Alicante Bouschet, Touriga Nacional, and Syrah. Lastly, savor the Cem Reis White, an unadulterated Viognier. Cheers to an unforgettable experience!
After your visit, your chauffeur will take you back to your hotel near Monsaraz. Enjoy your final evening in the Alentejo; you may like to dine at the hotel.
Day 5Monsaraz - Lisbon
Cheers, and hope to see you again soon!
This morning your driver will take you to Lisbon’s airport, with departure timed to allow for the journey and your flight check-in. This concludes your wonderful wine-tasting adventure in Portugal’s romantic Alentejo region. We hope you had a great time!
Genevieve has spent more than 20 years creating private food and wine journeys across Spain, Portugal and France. She regularly visits the regions featured in these collections, meeting winery, hotel, local guides, and restaurant partners, exploring new experiences, and reviewing feedback from Cellar Tours guests. Her role is to help travelers choose the wine region, itinerary style, and pace that best match their interests—not simply the destination with the most famous name.
Our custom itineraries include chauffeur-led transportation, carefully selected hotels, private winery appointments & tastings, restaurant planning, and support before and during your travel.
International flights, travel insurance, personal expenses, optional spa treatments, gratuities and meals or tastings not listed in your itinerary are usually not included unless specifically stated.
All wine visits and tastings are private and pre-arranged for your party.
Yes, 100%. Share mobility considerations, allergies, dietary preferences, and pacing needs early so we can adapt hotels, transport, restaurants, and visits wherever possible.
Cheryl and Chris Davin, Massachusetts
The quality of the hotels was excellent, particularly Lapa Palace and the Convent hotel in Evora
Vintage House was also lovely. Pacheca was fantastic – good tour, great descriptions of their work, great tasting. The enthusiasm and detail of the owner was one of the highlights of our trip. The real joys of Esporão were the location, the wines and the restaurant. Sintra was gorgeous, Obidos was gorgeous, Evora was gorgeous, the boat ride down the Douro was great. Victor, our driver/guide, did all towns on the tour and he was remarkably good. He gave us great details of the places we were visiting, he knew the answers to 95% of the questions we asked and had reference to find out the other answers while we explored the towns. He did a good job of guiding us, giving us insight and advice, but leaving us alone time to explore the different towns.
