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Explore Sintra’s fairytale castles, UNESCO sites, and a Portuguese winery in this private day tour from Lisbon. Ideal for lovers of history, charm, and wine.
When it comes to discovering the enchanting town of Sintra, this Private Tour with Wine Tastings offers a thoughtfully curated way to experience its stunning palaces, legendary castles, and exquisite wines. Designed for those who want to skip the crowd and enjoy a personalized journey, this tour combines cultural highlights with a relaxed wine tasting in the beautiful Colares region.
What we love most is the seamless private transfer service, which ensures you travel comfortably from Lisbon without the hassle of shuttle lines, plus the onboard Wi-Fi allowing you to share snapshots or plan your day on the go. A potential downside? The tour covers many sites in just one day, so it can feel rushed if you’re a slow-paced traveler or eager to explore every detail at each stop.
This experience is perfect for history buffs, romantic couples, or wine lovers looking for an authentic taste of Portugal’s cultural gems. If you value expert guidance, flexible transport, and a mix of sightseeing and wine tasting, this tour is a strong choice.


Sintra is one of Portugal’s most captivating destinations, famous for its whimsical palaces, mystical castles, and lush mountain scenery. This private tour aims to unlock its secrets while eliminating the stress of group travel or crowded shuttles. From the moment you’re picked up in Lisbon, the journey is tailored to your interests, with the added convenience of private modern transport that includes Wi-Fi — perfect for catching up with friends or checking your map.
The day kicks off with a visit to the Moorish Castle, perched about 3.5 km from Sintra’s historic center. This fortress dates back to the eighth century and offers sweeping views of the surrounding landscape. The walls have been restored in the romantic period, adding a charming touch to its ancient ruins. As one reviewer noted, “We loved the way the guide explained the history behind the Moorish walls, and the views from the tower are simply stunning.” Expect a fair bit of walking here, so comfortable shoes are a must.
Next, the tour takes you to the Park and National Palace of Pena. This is perhaps Sintra’s most iconic site, with its vibrant, eclectic architecture perched atop Monte da Pena. Built on the site of a former monastery, the palace symbolizes 19th-century Romanticism in Portugal. You’ll get a chance to stroll through its colorful halls and enjoy panoramic vistas over the Sintra mountains and coast. While the entrance fee isn’t included, the outside views alone make it worthwhile, and the guide will fill you in on the royal history that inspired this fairy-tale building.
A highlight of the trip is the Quinta da Regaleira, just a short walk from the historic center. This mysterious estate, built in the early 20th century, combines Gothic, Manueline, and Renaissance architectural elements with symbolic gardens filled with tunnels, wells, and secret passages. As one traveler put it, “The palace is like walking into a storybook, full of mythical and esoteric symbols.” Since the ticket isn’t included in the tour, you can choose whether to explore further on your own or simply admire the fabulous grounds.
Beyond the palaces, the tour also covers the Monserrate Palace — a fantastic example of Romantic architecture surrounded by lush gardens, created by William Beckford, who fell in love with Sintra’s landscape. Although not included in the standard itinerary, it’s a bonus for lovers of architecture and gardens alike.
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No trip to Sintra would be complete without tasting its unique wines, and this tour’s visit to Adega Regional de Colares is a true highlight. Colares wines are rare, produced from grapes grown in sandy soils, giving them a distinctive flavor profile. The winery tour explores how these wines are made and the history behind this small but cherished wine region.
The tasting itself is included in the tour, giving guests the chance to sample local wines amid the scenic vineyards. As one reviewer mentioned, “The wine tasting was an intimate experience, and the guide shared fascinating insights about Colares wines’ rarity and history.” Since the winery is a cooperative run by a few private producers, the experience offers a genuine taste of authentic Portuguese wine culture.

The private transfers are a significant advantage, providing a smooth experience from start to finish. The vehicle’s onboard Wi-Fi helps fill the time between sites, making it easier to plan your day or stay connected with loved ones. The tour typically lasts around 8 to 9 hours, giving ample time to see the main highlights without feeling hurried.
The tour is suitable for most travelers, with most needing only comfortable walking shoes. The group is exclusive — only your party — so you get personalized attention from the guide, and the pace can be adjusted to suit your interests.
Price-wise, at $191.17 per person, the value hinges on your interest in private transportation, guided commentary, and a curated itinerary. When you consider the cost of individual entries, private transport, and the wine tasting, this tour offers a good deal for those wanting a comprehensive, hassle-free Sintra experience.

One reviewer called it a “great day” and appreciated the long, leisurely lunch at a local restaurant, which added a genuine regional touch. Another pointed out that while the guide was engaging and knowledgeable, some felt the wine tasting was different from their expectations — emphasizing that Colares wines are quite exclusive and produced in small quantities. The key takeaway? The experience is authentic and intimate, but some sites may be less extensive than expected, especially if you’re eager to explore every detail.

If you’re looking for an all-inclusive, private day trip that combines history, architecture, and wine in a relaxed setting, this tour ticks all those boxes. It’s best suited for those who prefer a personalized experience over a large group, and who want the convenience of private transfers and insider knowledge from a guide. This tour appeals especially to history enthusiasts, wine aficionados, and travelers who want to avoid the logistical hassle of planning individual tickets and transportation.
It’s also a great choice for couples or small groups who value comfort and flexibility while exploring one of Portugal’s most enchanting regions.
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Is hotel pickup and drop-off included?
Yes, the tour includes hotel pickup and drop-off, making logistics straightforward and stress-free.
Are tickets included for the sites?
No, entry tickets for Pena Palace and Quinta da Regaleira are not included, so plan to purchase them separately if you wish to explore inside.
What is the duration of the tour?
The tour lasts approximately 8 to 9 hours, covering multiple sites and activities.
Can I customize the itinerary?
Since it’s a private tour, your guide can tailor the pace and focus to your interests, within the scheduled stops.
Is this tour suitable for children or elderly travelers?
Most travelers can participate, but comfortable walking shoes are recommended. Elderly travelers should consider mobility levels for sites with uneven terrain.
What should I wear?
Smart casual attire is suggested, along with comfortable shoes for walking and exploring.
What does the wine tasting involve?
You’ll visit a winery in Colares and sample local, rare wines, learning about their unique production process.
Is Wi-Fi available during the tour?
Yes, onboard Wi-Fi is provided, so you can stay connected or share your experiences instantly.
How far in advance should I book?
On average, this tour is booked about 22 days in advance, reflecting its popularity.

This Private Sintra Tour with Wine Tastings offers a well-rounded, intimate way to discover one of Portugal’s most magical towns. With personalized transport, expert guidance, and a chance to sample acclaimed local wines, it’s a compelling choice for travelers seeking depth and comfort. The combination of UNESCO-listed sites like Pena Palace and Quinta da Regaleira with a relaxed wine tasting makes it a balanced day out, perfect for those wanting to see the highlights without feeling rushed.
While the price might seem on the higher side, the inclusivity of private transport, guided insights, and a genuine wine experience provide good value, especially for travelers who appreciate curated, authentic adventures. If you’re eager to experience Sintra through a lens of comfort, culture, and local flavor, this tour is likely to satisfy all those desires.
In summary, this tour is ideal for those who prioritize convenience, personalized attention, and authentic cultural experiences. It’s particularly suited for small groups, couples, or anyone wanting to combine sightseeing with a taste of Portugal’s celebrated wines—all wrapped in a hassle-free, memorable day.