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Discover Portugal’s UNESCO sites, medieval charm, and wine culture on this private full-day tour from Lisbon to Évora, Monsaraz, and a renowned winery.


This tour departs from Lisbon with hotel pickup and drop-off included, making it a seamless experience. The journey begins with a comfortable private vehicle winding through the lush Alentejo countryside, known for its vineyards, olive groves, and gentle rolling hills. This part of the trip sets a relaxed tone, offering views that highlight Portugal’s agricultural beauty.
The drive to Reguengos de Monsaraz takes about 2.5 hours, giving ample time to enjoy the landscape and ask questions. The guides often provide insights into local traditions and the area’s history, making the ride informative as well as scenic.
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Upon arriving at the winery in Reguengos de Monsaraz, visitors are greeted by stunning vineyard landscapes. This region was named the European Capital of Wine in 2015, and the winery combines traditional and modern winemaking techniques.
The guided tour explores the vineyards and facilities, where staff explain the grape varieties and climate conditions that influence the wines’ flavors. Participants get to taste a selection of wines during the visit, making this a true highlight for wine lovers. The experience emphasizes the passion and craftsmanship behind Portuguese wines.

Next, the tour visits Monsaraz, a medieval village perched on a hilltop with breathtaking views of the surrounding Alentejo plains and Alqueva Lake. The village’s narrow cobbled streets and ancient stone walls create a charming atmosphere, ideal for strolling and photography.
The guided walk through Monsaraz offers insights into its history and architecture. Visitors enjoy free time for exploration or shopping, with opportunities to purchase local crafts or sample regional delicacies. The village’s breathtaking backdrop makes it a perfect spot for scenic photos.

The next stop is Évora, a city classified as a UNESCO World Heritage site for its well-preserved architecture and archaeological sites. The Roman Temple, also known as the Temple of Diana, stands prominently in the historic center and showcases ancient Roman engineering.
The Évora Cathedral offers panoramic views from its rooftop, providing a sweeping look over the city and surrounding countryside. The tour includes walking through narrow streets, where visitors can admire various architectural styles from different periods.
More Great Tours NearbyOne of the most distinctive attractions in Évora is the Chapel of Bones. This intriguing site is decorated with human skulls and bones, arranged artistically to serve as a reminder of life’s transience. The guided entrance is included in the tour, though visitors should be aware that the eerie atmosphere may not appeal to everyone.
The Chapel of Bones offers a reflective experience about mortality, contrasting with the city’s other more traditional religious sites. The guides provide context to help visitors understand the symbolism and history behind this unusual chapel.
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Throughout the day, the guides share stories about Évora’s Roman roots, the medieval history of Monsaraz, and the wine culture of the region. These narratives enrich the experience, making the visits more meaningful. The blend of ancient ruins, medieval streets, and modern viticulture demonstrates the region’s layered history.
The overall pacing of the tour balances guided visits with free time, allowing for both educational insights and personal exploration. The private group setting ensures a more personalized experience, avoiding crowds and offering flexible interaction with the guide.
The tour offers hotel pickup and drop-off, private transportation, and a professional guide who speaks multiple languages including English, Spanish, Portuguese, and French. Included are entrance fees to the Chapel of Bones and a wine tasting in Reguengos de Monsaraz, along with bottled water to stay refreshed.
Lunch is not included, so travelers may want to bring snacks or plan to eat during free time in Monsaraz or Évora. The tour is suitable for those comfortable with moderate walking—comfortable shoes are recommended.
This full-day experience lasts about 8 hours and is available with check availability for different starting times. Travelers benefit from the option to reserve now and pay later, providing flexibility in planning. Cancellation is free up to 24 hours in advance, offering peace of mind.
The private group nature ensures an intimate experience, and the small group size enhances personalized attention from the guide. The tour is ideal for those interested in combining history, culture, and wine in one seamless day trip from Lisbon.
This Private Full Day Évora, Monsaraz, and Winery Day Trip offers an excellent balance of cultural exploration, scenic beauty, and wine tasting. The inclusion of UNESCO sites and unique attractions like the Chapel of Bones makes it stand out.
The professional guides and private transportation create a comfortable, personalized environment. Visitors who appreciate historic sites, medieval villages, and wine experiences will find this tour well worth the price of $180 per person.
While the tour provides a rundown, lunch is not included, so planning ahead is advisable. The moderate walking required at sites like Évora and Monsaraz may be challenging for those with mobility issues. Visitors should also be prepared for the eerie nature of the Chapel of Bones if sensitive to such atmospheres.
This tour from Lisbon delivers a balanced day filled with history, culture, and scenic views. Its private group setting and expert guides make for an engaging and tailored experience. Suitable for history enthusiasts, wine lovers, and those wanting to explore lesser-known Portuguese gems without the hassle of planning.
The combination of UNESCO sites, medieval charm, and wine tasting ensures a memorable day, especially for travelers eager to see the essence of Alentejo in one trip.
Is the tour suitable for children?
The tour is designed for adults, and some sites like the Chapel of Bones may be disturbing for children. Comfortable shoes and moderate walking are required.
What languages are available for the guide?
The guides speak English, Spanish, Portuguese, and French.
Can I customize the tour?
Since it is a private group, the itinerary can be flexible within the scheduled stops, but major changes should be discussed in advance.
Is lunch included?
No, lunch is not included, so travelers should plan to bring snacks or eat during free time.
How long is the drive from Lisbon?
The drive to Reguengos de Monsaraz takes approximately 2.5 hours, with scenic views en route.
What is the price per person?
The tour costs $180 per person, including all listed activities and transportation.
Are there any age restrictions?
Participants must be over 18 years old to participate in the wine tasting.
What should I bring?
Comfortable shoes are recommended, and bringing water and a camera is encouraged for photos of the stunning landscapes.
How do I book this tour?
Reservations can be made with Delighted Tours Portugal, with options to reserve now and pay later.