Experience the Charm of Alentejo: Évora, Monsaraz & Wine Tasting

This tour offers a perfect escape from Lisbon’s bustling streets into the tranquil, rolling hills of Alentejo. For approximately 8 hours, you’ll visit the UNESCO-listed Évora with its Roman ruins, the medieval fortified village of Monsaraz, and indulge in a local wine tasting that captures the region’s rich viticultural tradition. The price sits at around $109 per person, making it a fairly accessible way to see some of Portugal’s most authentic sights outside the capital.
What makes this experience particularly appealing? First, the small group size (up to 8 travelers) ensures you get more personalized attention and a relaxed atmosphere. Second, the knowledgeable guides, such as Rodrigo or Adrian, who share stories, curiosities, and local insights, make history come alive. We appreciate how they blend storytelling with practical tips, making the day both educational and fun.
One thing to consider is the long drive—the journey out to Alentejo does take some time, but the scenery en route makes it worthwhile. Also, the tour does not include lunch, so you might want to plan for a meal either in Monsaraz or bring your own snacks.
This tour suits travelers who love history, scenic landscapes, and good wine, especially those eager to experience Portugal’s lesser-trodden regions with an intimate group. If you’re after a mix of culture and tasting local flavors, this is a solid choice.
Key Points

- Authentic Experience: Visit two historic towns, Évora and Monsaraz, both filled with character.
- Expert Guides: Guides like Rodrigo or Adrian make the history and stories engaging.
- Scenic Landscapes: Enjoy views of vineyards, cork trees, and olive groves typical of Alentejo.
- Wine Tasting: Sample regional wines in a relaxed setting, often praised as a delightful highlight.
- Flexible Options: Upgrade to a private tour for a more personalized experience.
- Limited Group Size: A maximum of 8 travelers ensures attentive service and a relaxed atmosphere.
If wine interests you, we've examined these other wine experiences in Lisbon
Detailed Review of the Tour

The Journey Begins: Leaving Lisbon
Your day starts at Alameda Cardeal Cerejeira in Lisbon, where a comfortable, air-conditioned minivan awaits. The small group size promises an intimate experience, ideal for chatting with guides and fellow travelers. The drive into Alentejo offers a scenic preview of Portugal’s countryside—vast plains, cork oak forests, and vineyards stretch in all directions.
Travel time from Lisbon is substantial but part of the appeal; it’s a chance to relax, chat, or enjoy the landscape. The long-drive is made more pleasant by the passionate guides who share insights about local agriculture, history, and regional quirks.
Stop 1: Exploring Évora’s UNESCO Heritage Site
The first major stop is Évora’s historic center, a city often called a “living museum.” During the roughly four-hour visit, you’ll see landmarks like the Roman Temple, Gothic Cathedral, and the famous Chapel of Bones.
The Roman Temple, dating back to the 1st century AD, is a striking remnant of Portugal’s ancient past. The Gothic cathedral, Portugal’s largest, features impressive stained glass and intricate stonework. The Chapel of Bones, which many find both eerie and fascinating, is decorated with skulls and bones, a reminder of mortality that dates back to the 16th century.
Our guide’s enthusiasm makes these sights come alive. As one reviewer noted, “Susan was a great guide. Very informative and interesting. The Chapel of Bones was a highlight.” You’ll walk through narrow medieval streets, soaking up the authentic atmosphere of this city museum.
The Charm of Monsaraz
After Évora, the tour takes you to Monsaraz, a fortified hilltop village that feels like stepping back in time. The winding cobbled streets, medieval walls, and panoramic views of the Alentejo plains make this a photographer’s dream. Here, there’s a chance to explore the castle, walk along the ancient walls, and soak in the spectacular vistas of vineyards and distant hills.
One reviewer called Monsaraz the “unexpected highlight”, noting how the views from the walls are “like nothing I’ve ever seen—extraordinary.” The village retains its charm with local cafes and artisan shops, perfect for a relaxed exploration.
Keen to taste more of Lisbon? We've looked into these other food and drink experiences
- Lisbon Small-Group Food Tour with 18 Tastings in Alfama District
- Wine and Cheese Tasting Lunch in Portuguese Wine Bar
- Lisbon Private Walking Food Tour With Secret Food Tours
- Heart of Lisbon Food Tour: Baixa, Chiado & Bairro Alto
- Lisbon Walking Food Tour: Tapas and Wine with Secret Food Tours
- Portuguese Cuisine: Small-Group Lisbon Food Tour with 17 Tastings
Wine Tasting: Savoring Local Flavors
The tour includes a visit to a local winery, where you’ll taste various wines distinctive to the region. The reviews repeatedly praise the quality and variety of the tastings, with many saying it was a highlight of the day.
In one review, a traveler described the wine tasting as “really unique,” with different grape types and aromas that you wouldn’t find elsewhere. The relaxed setting allows plenty of time for questions and enjoying the flavors. It’s a great way to understand Alentejo’s wine culture and appreciate how geography and climate influence the taste.
Practical Details: Transportation and Timing
The air-conditioned minivan keeps everyone comfortable during the long day. The tour’s total duration is approximately 8 hours, with a carefully balanced itinerary—enough time to enjoy the sights without feeling rushed.
Because the tour is kept small, you’ll find it easier to ask questions, get personalized attention, and enjoy a more authentic experience. The group size and attentive guides contribute to a friendly, relaxed vibe, as many reviews highlight.
What’s Not Included
Note that lunch is not provided, giving you flexibility to choose where to eat—whether in Monsaraz or elsewhere. Travelers often bring snacks or plan to dine in Monsaraz, where local cafes serve hearty regional dishes with views.
Pricing and Value
At around $109, this tour offers good value considering the transport, guided tours, and wine tasting included. Reviews consistently mention the excellent guides and the variety of experiences—from ancient ruins to medieval streets and wine sampling.
Many travelers find the trip worth the long drive because of the authenticity and scenic beauty of the stops—less touristy, more genuine. The private upgrade option also appeals if you prefer a more customized experience.
Who Will Enjoy This Tour?
This experience is perfect for travelers interested in history, architecture, and local culture, especially those who appreciate small-group outings. It suits those who want to see less touristy spots with a more relaxed pace. If you love wine, the tasting is a definite bonus, especially as reviews highlight the quality and uniqueness of the regional wines.
It’s also great for photographers or anyone wanting to capture stunning landscapes and authentic Portuguese villages. The tour’s pace and content are ideal for adults looking for a well-rounded, enriching day out.
The Sum Up

This full-day tour from Lisbon to Évora and Monsaraz offers a genuine taste of Portugal’s Alentejo region—its landscapes, history, and flavors. The combination of UNESCO monuments, a medieval hilltop village, and regional wine tasting makes it a well-rounded experience for those wanting to escape the city and explore Portugal’s quieter, authentic side.
The guides’ local knowledge and the small group setting create a friendly, personalized atmosphere that enhances the overall experience. The value is solid, considering the transportation, guided visits, and tastings included. While the long drive is a consideration, most travelers find the scenery and highlights well worth the time.
If you’re eager to explore historic towns, enjoy scenic views, and sample regional wines in a relaxed setting, this tour fits the bill. It’s particularly suited for history buffs, wine lovers, and travelers seeking an authentic, less touristy experience in Portugal.
Frequently Asked Questions

How long is the total tour?
The entire experience lasts about 8 hours, including travel time, sightseeing, and wine tasting.
Is lunch included?
No, lunch is not included, giving you flexibility to eat in Monsaraz or bring snacks.
What is the group size?
The tour is limited to a maximum of 8 travelers, ensuring a more intimate and personalized experience.
Are the monuments tickets included?
Yes, all monument tickets are included, so you won’t need to worry about extra costs at the sites.
Can I upgrade to a private tour?
Yes, there is an option to upgrade for a more personalized, private experience.
What is the price?
The tour costs around $108.91 per person, which covers transportation, guides, and wine tasting.
How is the transportation arranged?
Transport is provided via air-conditioned minivan, which is both comfortable and convenient for the long day.
Is the tour suitable for all travelers?
Most travelers can participate, and the small group size makes it accessible for a variety of ages and mobility levels.
This tour strikes a fine balance between guided exploration and free time, making it ideal for those wanting a taste of Portugal’s historic and scenic treasures without the hassle of planning. Whether you’re a history enthusiast, a wine connoisseur, or simply seeking a peaceful escape into Portugal’s countryside, it promises a memorable day.
More Wine Tours in Lisbon
- Sintra Wine Tour, Pena Palace, Cascais, Cabo da Roca from Lisbon
- Serra Arrábida-Azulejos Natural Park private tour and wine tour departure Lisbon
- Lisbon: Private Full-Day Wine Tasting Tour in a premium car
- Sintra: Full-Day Tour from Lisbon with Wine Tasting
- Lisbon Private Wine Tasting Experience
- Lisbon: Sailing with history and wine
More Food & Drink Experiences in Lisbon
More Tour Reviews in Lisbon
More Lisbon experiences we've covered
- 15 Best Wine Tours In Lisbon
- The 3 Top Vegan & Vegetarian Tours In Lisbon: Which Is Best?
- We Rank The 15 Best Lunch Experiences In Lisbon
- 15 Must-Try Food Tours In Lisbon
- The 15 Most Popular Dinner Experiences In Lisbon
- The 15 Top Dining Experiences In Lisbon: Which Is Best?
- 4 Must-Try Craft Beer Tours In Lisbon
- Lisbon’s 5 Top Coffee Tours
- The 4 Best BBQ Experiences In Lisbon
- We Rank The 15 Best Workshops & Classes In Lisbon
- 15 Top-Rated Lisbon Walking Tours
- 6 Top-Rated Lisbon Snorkeling Experiences
