Douro Valley and Lisbon 5 Day PRIVATE Tour – Port Wine Region, Porto and Lisbon

Imagine spending five days in Portugal, exploring the country’s most iconic sights, picturesque towns, and renowned wine regions—all in a private, comfortable setting. This comprehensive Douro Valley and Lisbon 5-Day Private Tour offers a tailored experience that takes you from medieval castles and charming coastal villages to vibrant cities and lush vineyards, all with the convenience of private transportation and expert guides like David. Priced at around $2,188 per person, this tour is perfect for travelers looking for a balanced mix of culture, scenic beauty, and delicious food and drink.

What we really love about this experience is the attention to detail—from the insider visits to local specialties like Ginjinha sour cherry liqueur in Óbidos, to the stunning river cruise in the Douro Valley. Plus, the flexibility built into the itinerary means you can choose options like wine estate tours or skip certain attractions if you prefer a more relaxed pace. A potential consideration is that some activities, such as entry to the Pena Palace, may involve long lines during peak seasons, though the option to skip the interior helps mitigate this. This tour suits those who want a well-rounded, authentic taste of Portugal without the stress of planning or navigating on their own.

Key Points

• Private, Comfortable Transportation: Enjoy the journey with air-conditioned vehicles, WiFi, and no crowded buses.
• Authentic Experiences: Visit local towns, taste regional wines, and explore iconic landmarks guided by knowledgeable local experts.
• Flexible Options: Choose to add or skip activities like wine tastings or palace visits, tailoring the tour to your interests.
• Scenic Highlights: Expect breathtaking views from viewpoints and river cruises, perfect for photos and relaxing.
• Cultural Immersion: Walk through historic neighborhoods, sample local pastries, and learn about Portugal’s rich past.
• Ideal for Curious Travelers: Perfect for those who appreciate a personal touch, authentic cultural encounters, and stunning scenery.

A Deep Dive into the 5-Day Itinerary

Day 1: From Medieval Walls to Ocean Waves

Your journey begins at Óbidos, a well-preserved medieval town surrounded by ancient walls. This spot is a favorite among travelers for its fairy-tale vibe and charming cobbled streets. Your guide will showcase key sights like the castle and introduce you to Ginjinha, a sour cherry liqueur that many describe as a must-try and a delightful way to kick off the trip. As one reviewer put it, “David is an amazing tour guide. We toured through Lisbon and Sintra and saw amazing architecture, learned history and of course, ate great food and pastries.”

Next, you’ll head to Nazaré, famed for its enormous wave breaks and surfing legends. While the big waves are primarily winter phenomena, Nazaré remains a lively town with fantastic seafood, where you’ll stop for a traditional lunch with ocean views. Expect to see a place full of local stories and a genuine, laid-back coastal feel.

Your last stop on this day is Aveiro, often called the “Portuguese Venice” for its charming canals. Here, you might want to hop on a boat ride, crossing the canals while sampling Ovos Moles, a sweet egg-based pastry. This stop is a great introduction to the country’s sweet tooth and its art nouveau architecture.

Day 2: Vineyards, River Views, and Panoramas

The day starts with a scenic drive into the Douro Valley, one of Portugal’s crown jewels. The highlight is visiting a top-rated wine estate like Quinta do Pópula (though not compulsory), perched above the Douro River. Here, you’ll learn about Port wine production and enjoy tastings paired with regional cheeses and smoked meats. The views from the estate are spectacular—a perfect backdrop for memorable photos.

Afterward, you’ll visit Pinhão for a Douro River cruise—a peaceful hour on the water that shows off the lush landscape from a different vantage point. As one guest shared, “The Douro River cruise is included, and it’s a peaceful way to see the vineyards and landscape.” If time allows or if you prefer, you can have lunch before the cruise.

In the late afternoon, you’ll visit Casal de Loivos, a viewpoint offering sweeping views of the valley, ideal for capturing the essence of the region’s natural beauty.

Day 3: Porto’s Charm and Port Wine Cellars

The vibrant city of Porto awaits, starting with a guided walk through its historic center. Expect visits to S. Bento Station, famous for its azulejo tile work, and Lello Bookshop, rumored to have inspired Harry Potter’s library. You’ll also see Clérigos Tower, the Ribeira district, and the imposing Porto Cathedral. The city’s compact center makes walking the best way to soak up its lively atmosphere, but transport can be arranged for those who tire.

In the afternoon, crossing the Dom Luís I Bridge transports you into Vila Nova de Gaia, home to the port wine cellars. You’ll get the chance to sample various port and Douro wines, gaining insight into Portugal’s most famous export. This blend of historic sights and wine tasting makes Porto a perfect mix of culture and flavor. One reviewer described it as a “great exploration of Porto’s history and wine culture,” emphasizing their appreciation for the guide’s knowledge.

Day 4: Palaces, Mysteries, and Coastal Views

This day takes you to Sintra, often described as a storybook town full of palaces and mysterious estates. The Palace of Pena is a highlight, with breathtaking architecture perched atop the hills—though note that during peak season, entry might involve long lines, which is why the option to enjoy only the gardens is a good tip.

Next, explore the National Palace of Sintra, with its ornate rooms and local pastries like Queijadas and Travesseiros. Our favorite is the Quinta da Regaleira, a mystical estate full of tunnels, symbols, and the famous Initiation Well—a must-see for those interested in stories and symbolism.

On the way to the coast, you’ll pass by Palace of Seteais and Monserrate Palace—beautiful buildings with lush gardens. Then, stand at Cabo da Roca, the westernmost point of mainland Europe, and take photos of the Atlantic crashing against the cliffs. Boca do Inferno provides another dramatic coastal scene for picture-taking.

Day 5: Lisbon’s Historic Heart and Stunning Views

The final day is dedicated to Lisbon, starting with the Cathedral of Lisbon and then moving through scenic viewpoints like Miradouro da Senhora do Monte, offering nearly 360-degree panoramic views of the city. The Igreja de São Vicente de Fora and the Pantheon are next, offering insight into Lisbon’s religious heritage.

The historic Alfama district, with its narrow, winding streets, is an ideal place to feel like a local, smelling grilled sardines and snapping photos of tiny houses. You’ll also visit the Mosteiro dos Jerónimos, Vasco da Gama’s tomb, and the Belém Tower, iconic symbols of Portugal’s age of discoveries.

For a sweet treat, no visit to Lisbon is complete without Pastéis de Belém custard tarts—some say they’re the best—and a walk through the Time Out Market, where food stalls showcase Portugal’s culinary diversity. The tour ends with a visit to the Padrão dos Descobrimentos, a monument celebrating Portuguese explorers.

Why This Tour Offers Great Value

This tour balances luxury and authenticity—private transportation ensures comfort, while expert guides like David bring local insights that you simply can’t get from a guidebook. The inclusion of a Douro River cruise and wine tastings adds memorable touches, elevating the experience beyond just sightseeing.

The flexibility—such as choosing whether to visit certain palaces or wine estates—means you can tailor this trip to your interests. On top of that, the small group size or private setting guarantees a more personal and relaxed atmosphere, ideal for those who want to absorb Portugal at their own pace.

Pricing at just over $2,180 per person might seem steep, but considering the private transportation, guided expertise, multiple days of varied experiences, and inclusions like the Douro cruise, it’s a strong value for travelers craving comfort and authenticity. Plus, the reviews consistently praise guides like David for their knowledge and enthusiasm, making the experience both educational and fun.

Who Is This Tour Best For?

This trip suits travelers who want a rundown of Portugal without the hassle of planning each detail. If you’re keen on wine tasting, local food, and historical sites, you’ll appreciate the curated stops and insider tips. It’s ideal for those who value private transportation—particularly if you prefer a stress-free experience—and want to explore off-the-beaten-path towns like Óbidos and Aveiro.

It’s also perfect for travelers who enjoy scenic views—from river cruises to coastal cliffs—and like a blend of cultural, natural, and culinary discoveries. If you’re traveling with family or a small group, the private nature of this tour ensures a personalized experience tailored to your interests and pace.

FAQ

Is this tour suitable for all ages?
Yes, most travelers can participate, and the private setup makes it adaptable for different physical capabilities. However, some attractions, like palace visits, may involve walking or waiting in lines during peak seasons.

How flexible is the itinerary?
The tour offers options like skipping certain activities (e.g., palace interior visits) and choosing where to eat or take additional photos. The guide, David, is known for customizing experiences based on your preferences.

Are meals included?
No, all meals are not included, but you’ll have opportunities to enjoy local specialties like Ginjinha, regional cheeses, and pastries. The focus is on sightseeing and tasting rather than full meals.

What’s the transport like?
A private, air-conditioned vehicle with WiFi ensures a comfortable ride and smooth transitions between stops. Parking fees and tolls are included, removing typical travel headaches.

Are there any extra costs?
Entry to some attractions like the Pena Palace or wineries is not included, so you might want to budget for those if you choose to go inside. The wine estate tour is optional.

Can I bring kids or older relatives?
Yes, the tour is suitable for most ages, but consider the walking involved at some sites, especially in Sintra and Porto.

What’s the significance of the Douro River cruise?
It offers a peaceful hour on the water with stunning views of the vineyards and landscape—a real highlight for many guests.

How professional are the guides?
Reviews praise guides like David for their enthusiasm, local knowledge, and flexibility, making the tour both informative and enjoyable.

What is the cancellation policy?
Full refunds are available if you cancel at least 24 hours in advance, giving peace of mind if your plans change.

This 5-day private tour offers a well-rounded, authentic journey through Portugal’s most beloved regions—perfect for curious travelers seeking comfort, cultural depth, and unforgettable scenery. Whether you’re a wine lover, history buff, or adventure seeker, this experience is designed to leave you with lasting memories and plenty of stories to tell.