Experience the very best of Portugal on this thoughtfully crafted 6-day small-group journey. From the vibrant streets of Lisbon and the fairytale landscapes of Sintra to the medieval towns of the Alentejo, you’ll discover the country’s rich heritage, spectacular scenery and authentic local traditions.
Designed for travellers who value comfort, connection and unforgettable experiences, this tour combines hand-picked accommodation, exceptional local cuisine and expert guides to showcase Portugal beyond the obvious. Every day is carefully balanced to blend iconic landmarks with hidden gems, creating memories that will last long after your journey ends.
Price Includes
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’ll step aboard a traditional boat for a peaceful cruise along the Douro River. It’s a wonderfully relaxing experience, offering a unique perspective of the valley’s spectacular terraced vineyards.
Following our time on the water, we visit a nearby quinta to enjoy a curated tasting of exceptional Douro wines. You’ll then have free time to explore Pinhão and enjoy lunch at your own pace before we continue to Porto, a vibrant riverside city that captures the hearts of all who visit.
As we arrive in Porto, your unforgettable journey through Portugal comes to an end. It’s time to say farewell to your guide and the fellow travellers who have shared this adventure with you—many of whom have become lasting friends along the way. The evening is yours to enjoy at leisure, whether you choose to stroll along the picturesque Ribeira waterfront, discover Porto’s lively neighbourhoods, or raise one final glass to an incredible Portuguese adventure.
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.
