From the historic, sun-drenched streets of Lisbon to the breathtaking terraced vineyards of the Douro Valley and the soulful heart of Porto, this carefully curated 8-day journey captures the very soul of the country. Travel in ultimate style and comfort alongside an intimate group of like-minded travelers, guided by our world-class local experts who bring history, culture and flavor to life.
This is not just a vacation, it is an immersive, high-quality experience designed to take you behind the scenes of Portugal’s most iconic, timeless destinations.
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Price Excludes
No driving today
Your Portuguese adventure begins in the mid-afternoon in the heart of Lisbon. Here, you’ll meet your expert local guide and connect with your fellow travelers, a group of strangers who will soon feel like lifelong friends. We’ll set off straight into the energy of Portugal’s capital with an introductory walking tour. Feel the pulse of the city as we navigate its historic, winding neighborhoods and hop aboard one of Lisbon’s famous vintage trams for a classic, nostalgic ride through history.
Afterward, take the evening to explore and dive into Lisbon’s incredible food scene. The night is yours to enjoy at leisure, though you may well wish to head out and dine with your new travel companions to kick off the trip’s camaraderie over some fantastic local petiscos and wine.
Accommodation – Hotel Lumen Lisbon (or similar)
Total driving time: 3 hours, excluding stops
Today we head to the hills of Sintra to visit the famous, colourful Pena Palace, wandering through its distinctive architecture and expansive gardens. Afterward, you’ll have some free time to explore Sintra’s historic centre before we drive to Cabo da Roca, the westernmost point of continental Europe, for some incredible ocean views and a breath of fresh Atlantic air.
Our return journey to Lisbon takes us along the scenic coast through Cascais, an elegant seaside town known for its beautiful architecture and coastal charm. Enjoy a relaxed stroll by the water and perhaps grab a gelato to cool down, just keep an eye out for the local seagulls, who are known to have a bit of a sweet tooth!
Accommodation – Hotel Moon & Sun Lisboa (or similar)
Total driving time: 4 hours, excluding stops
Leaving the capital behind, watch the scenery shift into the rolling plains, golden fields, and cork forests of the beautiful Alentejo region. Our first stop is a traditional, family-run olive oil estate for a private farm tour and tasting experience. Afterward, we arrive in historic Évora for a leisurely lunch.
In the afternoon, your guide will lead you through the city’s ancient Roman Ruins. We will also visit the famous Chapel of Bones (Capela dos Ossos), a truly moving experience that offers a unique glimpse into the region’s spiritual past. The evening is then yours to enjoy at leisure, giving you plenty of time to wander and soak up the atmosphere of this beautiful historical town.
Accommodation – Hotel M’Ar de Ar Muralhas (or similar)
Total driving time: 4 hours 30 minutes, excluding stops
Today is a longer travel day, but the incredible destinations ahead make it entirely worth the journey. This morning, we transfer north to the historic town of Tomar, where we will enjoy lunch before visiting the stunning Convent of Christ, a magnificent stronghold once home to the legendary Knights Templar.
From Tomar, we make our way to the historic riverfront city of Coimbra. As evening falls, prepare for an emotionally stirring cultural highlight: an intimate, live performance of traditional Coimbra Fado. Let the soulful melodies introduce you to the true heart of Portuguese music before heading to your hotel.
Accommodation – Vila Gale Coimbra (or similar)
Total driving time: 2 hours 40 minutes, excluding stops
We begin the morning with a guided tour of the prestigious University of Coimbra, including the magnificent, gold-leafed Joanina Library—a masterpiece of Baroque design that is genuinely something to behold. After some free time for lunch in the old town, we make our way to the spectacular Douro Valley.
Frequently rated by our past guests as a highlight of the trip, this region features endless hillsides carved into dramatic, terraced vineyards. Check into our gorgeous valley hotel, kick back, and spend the afternoon relaxing while soaking in the unforgettable views.
Accommodation – Hotel Vila Gale Vineyards (or similar)
Total driving time: 2 hours 40 minutes, excluding stops
This morning we head to the riverside village of Pinhão, where you will step aboard a traditional boat for a peaceful cruise down the Douro River. It is an incredibly serene, relaxing experience that allows you to take in the terraced slopes from a completely new perspective.
Following our time on the water, we visit a nearby quinta to enjoy a curated tasting of excellent Douro table wines. You will then have some free time for lunch to explore and dine at your own pace in Pinhão. Afterward, we depart for Porto, a vibrant, colorful city that completely steals the heart of those who visit. The evening is yours to wander its riverside paths and lively neighborhoods.
Accommodation – Fontinha Hotel (or similar)
No driving today
Enjoy a slightly later, relaxed start this morning before setting out on a guided walking tour of Porto’s most famous landmarks and hidden gems. In the afternoon, we will cross the river to visit the world-renowned historic wine cellars. Here, you’ll hear the fascinating history of the region’s shipping legacy and enjoy a premium Port wine tasting—a rich and delightful treat.
Following our cellar visit, the evening is completely yours to explore the city at leisure and soak up the last of Porto’s positive vibes. For a perfect end to your journey, we highly recommend catching the sunset from Jardim do Morro, where you can watch the sun dip below the horizon with panoramic views over the Douro River.
Accommodation – Fontinha Hotel (or similar)
No driving today
Your Portugal adventure draws to a close this morning after a delicious breakfast. As you bid farewell to your guide and your group, you’ll realize that the people who started as strangers on Day 1 are leaving as lifelong friends. Take the memories, stories and spirit of Portugal home with you!
Portugal is a country of cobbled hilltop streets, sweeping terraced vineyards and historic neighbourhoods full of character and our tours take you right into the heart of all of it. Guests should be comfortable with a moderate level of walking and navigating hilly, uneven terrain throughout the tour.
Please also note that our itineraries are not currently wheelchair accessible, as many of the destinations and historic properties we visit are not yet equipped with the facilities to accommodate this.
Jessica is your perfect link to Portugal. As a travel expert, Jessica loves turning our customers’ bucket lists into reality. With her deep local knowledge and global perspective, she ensures our international guests have the trip of a lifetime. Her warm nature and passion for adventure will make your Overland Portugal journey truly unforgettable.
