Private Sintra & Colares Wine Half-Day Tour: Historic Centre, Azenhas do Mar & Wine Tasting
Escape the crowds and discover a different side of Sintra. Explore the charming UNESCO-listed historic centre, admire the spectacular cliffs of Azenhas do Mar, enjoy a guided wine tasting in Portugal's historic Colares wine region, stand at Cabo da Roca—the westernmost point of continental Europe—and return to Lisbon along the beautiful Guincho coastline.
Itinerary
This itinerary can be customized to meet your needs and preferences. Send me a message with your requests!
Meeting Point
Hotel Pick-up
- Meet me at your hotel in Lisbon before heading to Sintra.
Historic Centre of Sintra
Wander through Sintra's charming UNESCO World Heritage centre, known for its royal history, colourful streets and traditional pastry shops.
Azenhas do Mar
Visit one of Portugal's most picturesque seaside villages, dramatically perched on the cliffs overlooking the Atlantic Ocean.
Colares Wine Tasting
Discover one of Portugal's oldest wine regions during a guided tasting of local wines while learning about the unique sandy-soil vineyards and centuries-old winemaking traditions.
Cabo da Roca
Stand at the westernmost point of continental Europe and enjoy breathtaking Atlantic views.
Guincho Coastal Drive
Relax on one of Portugal's most scenic coastal roads, passing wild beaches, sand dunes and dramatic Atlantic landscapes.
Hotel Drop-off
Return comfortably to your hotel in Lisbon.
Ending Point
Lisbon
Want to personalize this tour?
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This tour can be customized to meet your needs and preferences. Click below to send me a message with your requests.
Inclusions & Exclusions
Private transportation in a comfortable Station Wagon/Estate Mercedes E Classe, air-conditioned vehicle
Hotel pick-up and drop-off in Lisbon
Professional local guide and driver
Guided wine tasting in Colares
Fuel, tolls and parking fees
Bottled water
Food and additional beverages
Personal expenses
Tour Important Information
Comfortable walking shoes are recommended.
Please bring a light jacket, as weather conditions along the coast can change throughout the day.
The wine tasting is exclusively for guests aged 18 and over.
This tour includes moderate walking on cobblestone streets and uneven surfaces.
The itinerary may be adjusted due to weather, traffic or local conditions to ensure the best possible experience.
If you have any dietary restrictions or allergies, please let me know in advance so I can inform the winery.
Hotel pick-up and drop-off are available within Lisbon city centre. Other locations may be available upon request.
Cancellation Policy
- Free cancellation - 8 days prior to meeting time
- 50% Refund - 3 to 7 days prior to meeting time
- No Refund - Within 2 day(s) prior to meeting time
About Tour Guide Diogo C.
Hello, I’m Diogo — a private Lisbon tour guide, sommelier, and host, with a background in hospitality and Portuguese culture.
I’ve worked for many years in the hospitality world in Portugal and London, including as a sommelier, and I studied the WSET Level 3 in Wines in London. I’m also the co-founder of a Portuguese wine brand in Alcácer do Sal, which gives me a strong connection to local producers and the countryside beyond the cities.
While wine is an important part of my background, my tours are not limited to food and wine. I design private, tailor-made tours from Lisbon that can focus on culture, history, landscapes, architecture, and everyday local life, or combine these elements naturally with wine and gastronomy when it makes sense.
I work exclusively with private guests and small groups, creating experiences at a relaxed pace and shaped around each guest’s interests. Whether you’re visiting Portugal for the first time or returning to explore more deeply, my goal is to offer an authentic, personal perspective rather than a standard sightseeing tour.
I look forward to welcoming you and helping you experience Portugal in a genuine, unhurried way.
Reviews
Ross M.
“An Unforgettable Day in Évora and Alentejo with an Exceptional Guide”
This was one of the best day trips I have ever taken, and Diogo made all the difference. We started with a drive to Évora, where I visited the ancient Roman Temple of Diana and the medieval cathedral. Along the way, Diogo shared the history of the regions we would be visiting, as well as an introduction to Portugal’s wine culture and winemaking traditions. After a relaxing visit to Évora, I enjoyed my first wine tasting of the day. Diogo is a sommelier, and his knowledge added tremendously to the experience. He explained the origins of the grapes, the characteristics of the region, and the different wines I would be tasting, which made me appreciate them even more. We then had a fantastic lunch featuring local cuisine at a charming restaurant recommended by Diogo. It was exactly the kind of authentic, relaxed dining experience I was hoping for. From there, we visited a cork factory, where I learned a remarkable amount about how cork is harvested and processed and the many products it is used to create—from wine stoppers to textiles and furniture. We finished the afternoon at a beautiful vineyard estate, where I took a jeep tour of the property followed by another excellent tasting of Portuguese wines. This was my third tour with Diogo, and once again he created an amazing experience. From selecting memorable places to visit, to sharing his knowledge of Portugal’s wine culture, history, and traditions, Diogo added tremendous depth to the entire day. He designed the perfect day trip, with an ideal balance of history, culture, wine, and food—all at a relaxed and enjoyable pace. Diogo’s charming personality, background as a sommelier, extensive knowledge, and genuine passion for what he does make him an exceptional guide. I would not hesitate to book more tours with Diogo the next time I am in Lisbon. He is not only an outstanding guide, but a wonderful person, and I cannot recommend him highly enough.
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Diogo C.
Ross, this is such a wonderful review — thank you. It was a pleasure putting this day together for you and, even more importantly, sharing a part of Portugal that I love so much. I’m especially happy that the balance between history, wine, food and the more authentic side of the Alentejo worked so well. For me, the best days are the ones that don’t feel rushed, where there is time to understand a place, enjoy a great meal, discover something unexpected and, of course, drink some good Portuguese wine along the way. Having you join me for three different tours during your stay made the experience particularly special. Thank you for your trust, your curiosity and your great company throughout the trip. I genuinely hope our paths cross again in Portugal — there are still plenty of places and wines left to discover!
Ross M.
“Amazing perspective on old Lisbon”
Diogo took me back in time during this tour of Alfama, Graça, and Mouraria - the areas of Lisbon that were not lost to the devastating earthquake or tsunami. His family goes back generations in Lisbon, so he has deep local knowledge, experience, and first-hand accounts to be able to teach me so many things I would have missed if I tried to visit on my own. Buildings, such as Alfama Grill, are still crooked from the earthquake; however, the areas of Lisbon we saw today largely survived while other parts of the city were destroyed and had to be rebuilt. These areas are not as touristy as others in Lisbon and Diogo knows them so well. We explored areas that I never would have discovered on my own. Simply put, Diogo makes the difference between a good trip and a great memorable experience, where you return much more connected with the local history, culture, and tradition. He impressed me so much that I did a total of three tours with him on my 5-day Lisbon visit! I cannot recommend him enough.
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Diogo C.
Ross, thank you so much for taking the time to write such a thoughtful review. It was a real pleasure showing you a side of Lisbon that goes beyond the usual landmarks and tourist routes. Knowing that you came away feeling more connected to the city, its history and traditions means a great deal to me. And the fact that you chose to experience Lisbon with me three times during the same trip is honestly the greatest compliment I could receive. I really enjoyed our conversations, your curiosity, and the way you approached each experience. Thank you for trusting me with your time in Lisbon — I hope there will be a fourth tour next time you’re back! All the best, Diogo
Ross M.
“Amazing local knowledge and insights!”
Having been born and raised in Lisbon, Diogo knows the city like the back of his hand! This allowed him to add amazing insights into the history and culture of Belém, Riverside, Estrela, and Príncipe Real from a local’s experience and viewpoint – creating depth and a heightened level of understanding. He knows the hidden gems and best viewpoints. On top of this, he has a very kind and engaging personality. I came away from this tour with a stronger appreciation of the city. I liked it so much that I booked two other tours with Diogo and all three were truly amazing. I highly recommend him!
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Diogo C.
Ross, thank you — this means a lot to me. Lisbon is my home, so being able to share the city from a local perspective is one of my favourite parts of what I do. But what made these tours particularly enjoyable was your curiosity and willingness to look beyond the obvious. I’m incredibly grateful that you enjoyed the first experience enough to book two more. Three tours together in five days is quite a compliment, and I honestly had a fantastic time showing you different sides of Lisbon and Portugal. Thank you for your trust, your great company and for taking the time to write such a generous review. I hope this is not the last time I get to show you around Portugal! Until next time, Diogo
$220/ per group
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