This 12-day itinerary takes you on an epic journey through Portugal's cultural highlights and compelling history. Check off the major cities and iconic sites while seeking out a bounty of lesser-visited gems in between. Climb the towering, tiled staircase of Lamego, cruise down the Douro River in a traditional rabelo boat, cross the legendary bridge of Amarante, sip fortified wine in the riverside cellars of Porto, and gaze out over Lisbon's colorful rooftops from the medieval Castelo de S. Jorge.


  • Experience 2,000 years of history on a walking tour of Évora
  • Go wine tasting among the steep hillsides and winding rivers of the Douro Valley
  • Climb the Baroque Clérigos Tower for sweeping views across Porto
  • Hop on a yellow tram to explore the steep streets of Lisbon
  • Discover the fairy-tale palaces & mysterious Masonic towers of Sintra

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Lisbon, Transfer to Évora via Arrábida Natural Park Évora
Day 2 Walking Tour of Évora  Évora
Day 3 Transfer to Coimbra via Fátima Coimbra
Day 4 Self-Drive to the Douro Valley via the Bairrada Wine Region & Lamego Peso de Régua
Day 5 Douro Valley Guided Tour Peso de Régua
Day 6 Self-Drive to Porto via Minho & Amarante Porto
Day 7 Walking Tour of Porto Porto
Day 8 Day Trip to Braga & Guimarães Porto
Day 9 Transfer to Lisbon via Óbidos and Batalha Lisbon
Day 10 Walking Tour of Lisbon, Evening Dinner & Fado Show Lisbon
Day 11 Day Trip to Sintra, Cabo da Roca, Cascais & Estoril Lisbon
Day 12 Depart Lisbon  

Detailed Itinerary

Day 1: Arrive in Lisbon, Transfer to Évora via Arrábida Natural Park

Enjoy a scenic drive along the coastline of Arrábida Natural Park
Welcome to Portugal! Upon arrival at the Lisbon Airport, your driver will be waiting to pick you up for the 1.5-hour drive to Évora. Before turning east, you can skirt the coast for a while and pass through the breathtaking landscapes of Arrábida Natural Park.
Stop in the busy fishing village of Setúbal for a memorable lunch of fresh seafood and fried squid before continuing into the rolling fields of the Alentejo province and its historic capital of Évora. After some downtime at your hotel, head out to get your bearings and enjoy dinner and drinks in the bustling city square of Praça do Giraldo.

Day 2: Walking Tour of Évora

Évora Cathedral rising above the ruins of the Templo Romano
Wear your comfortable shoes today and meet your guide for a three-hour walking tour of Evora's abundant architectural wonders. With narrow streets of Moorish origin contrasting with light-filled squares, this World Heritage Site is one of Portugal's oldest cities and dates back over 2,000 years. Stroll the medieval walls, visit the grand Évora Cathedral, see the ancient Roman ruins of Templo Romano, and experience the macabre 16th-century Capela dos Ossos (Chapel of Bones).

In the afternoon, you'll have free time to explore the city at your own pace and do some shopping. The Alentejo region is famous for its cork forests and products, and you'll find an incredible selection of cork shoes, bags, umbrellas, jewelry, and clothing among the local shops and boutiques.

Day 3: Transfer to Coimbra via Fátima

Transfer to the historic university town of Coimbra

It's time to head north! Meet your driver this morning for the three-hour drive to Coimbra. Along the way, stop to stretch your legs and discover the famous pilgrimage site of Fátima. Take a walk around the site's monuments and shrines, then stop for lunch before getting back on the road and continuing to Coimbra for the evening.

Portugal's former medieval capital is also home to one of Europe's oldest centers of learning—the 13th-century University of Coimbra. Get settled into your hotel, then spend some time exploring the atmospheric streets of its historic center, which tumble down a hillside to a picturesque setting along the Rio Mondego

Day 4: Self-Drive to the Douro Valley via the Bairrada Wine Region & Lamego

Stop in Lamego to climb the Shrine of Nossa Senhora dos Remédios
Pick up your rental car this morning to start the self-drive portion of your adventure—setting out on the two-hour drive northeast to the Douro Valley. En route, take your time and explore the Bairrada wine region, visiting a winery and tasting the local vintages. With its seaside location and variable temperatures, this region's unique climate and terroir create a renowned freshness in its wines.
Stop next in Lamego, an ancient city influenced by Moorish, Christian, and Muslim occupations. Considered one of the most beautiful cities in northern Portugal, it's located at the base of an immense blue and white tiled flight of steps leading to the Shrine of Nossa Senhora dos Remédios. Finally, you'll enter the terraced hillsides and winding river valleys of the Douro Valley and make your way to your accommodations for dinner and some downtime.

Day 5: Douro Valley Guided Tour

Terraced vineyards along the Douro River
Spend today visiting the famous wine country of the Douro Valley. This UNESCO-listed region has been producing wine for over 2,000 years, with lush vineyards carved by hand into the rugged valleys and hillsides along the winding Douro River. Along with your knowledgeable guide, you'll stop at one of the many quintas (wine estates) to taste some of the valley's finest wines—including the area's famous sweet port. 
In the afternoon, see more of the valley from a breathtaking perspective with a cruise down the Douro River on a traditional rabelo boat—ancient wooden vessels once used to navigate the region's winding waterways.

Day 6: Transfer to Porto via Minho & Amarante

Self Drive from Douro Valley to Porto with the Green region & Amarante
Amarante's historic Ponte de São Gonçalo
Today, it's time to say goodbye to the enchanted valley and hit the road toward Porto, heading north first through the vineyards of the Minho region and the home of northern Portugal's famed Vinho Verde. These refreshing "green wines" are known for their crisp, aromatic flavors and low alcohol content.

Turn south again to spend some time in Amarante, a city full of history and tradition. Make sure to stop for a stroll across its iconic bridge, the Ponte de São Gonçalo. During the Peninsular War of the early 19th century, the bridge played a significant role in helping the Portuguese army to defend the city against the French. Take lunch at one of the many bistros lining the Tâmega River and enjoy views across the Serra do Marão mountains. Continue to Porto in the afternoon, where you can drop off your rental car and get settled into your hotel. 

Day 7: Walking Tour of Porto

Porto's colorful Foz neighborhood

Enjoy breakfast at your hotel this morning before embarking on a guided tour of Porto. Start at the São Bento Station, famed for its atrium lined with over 20,000 blue azulejo tiles. Nearby you'll find the Romanesque Porto Cathedral and the Clérigos Tower, a Baroque bell tower worth the climb for its expansive views over the city.

Don't miss Livraria Lello, a 19th-century bookstore that inspired parts of Harry Potter. Then pop into Café Majestic for a rest and a cup of coffee while admiring its ornate interior. Continue to the neighborhood of Ribeira, navigating the steep steps and medieval streets to reach café terraces and picturesque corners. After lunch, take a walk along the banks of the Douro River, or cross to the opposite bank to visit one of the city's historic port wine cellars for a tasting.

Day 8: Day Trip to Braga & Guimarães

The beautifully-tiled Chapel of St Francis in Guimarães 
Today's adventure is all about Portugal's incredible history. In the morning, your driver will transfer you northeast to the city of Guimarães, known as the birthplace of Portugal and the country's first king. A walk around the atmospheric UNESCO-listed Old Town and its well-preserved medieval buildings feels like a trip back in time. Highlights include climbing the 10th-century hilltop Guimarães Castle and visiting the grand Dukes of Bragança Palace.

After lunch in Guimarães, continue north to Braga, one of the oldest cities in Portugal. Braga or "Bracara Augusta" was the capital of the province of Gallaecia under the Roman Empire. Braga’s Cathedral, built between the 11th and 13th centuries, is the oldest in the country and has been revered as an iconic religious symbol for many centuries. Don't miss the Braga Tower, the Archbishops' Court, and the Baroque Palácio do Raio before heading back to Porto for the evening.

Day 9: Transfer to Lisbon via Óbidos & Batalha

The ornate Gothic monastery of Batalha
Your driver awaits this morning to transfer you south to Lisbon, stopping en route to explore some of the many highlights along the way. Start with a visit to the magnificent Batalha Monastery, a masterpiece of late Gothic architecture constructed in 1386 in honor of Portuguese independence against the powerful Kingdom of Castille.
You'll have some free time to have lunch before continuing to Óbidos. This delightful town of white houses adorned with bougainvillea and honeysuckle is one of the most picturesque and well-preserved in Portugal. Inside its medieval walls, you can soak up the cheerful ambiance of winding streets, Manueline porticoes, colorful window boxes, and small squares. Take your time to walk around, take pictures and do some shopping. When you're ready, get back on the road and continue to Lisbon and your accommodation for the evening.

Day 10: Walking Tour of Lisbon, Evening Dinner & Fado Show

Yellow trams climb Lisbon's hilly streets

After breakfast, join your guide for a walking tour of Lisbon, the "City of Seven Hills." One of the best ways to truly see the city is by strolling its streets—made with Portugal's world-famous cobblestone—and exploring its characterful neighborhoods. Start with the historic Alfama and Castelo districts, two of the city's oldest areas. Ride the quintessential yellow trams up to the Graça, Santa Luzia, or Portas do Sol scenic vistas, where you can gaze over the sea of red roofs to the Tagus River.

Check out Lisbon Cathedral, the 17th-century National Pantheon, and the 11th-century Castelo de S. Jorge. On your way down, pass the National Theatre of São Carlos and grab lunch near the riverfront at the Time Out Market, where you'll find an entire floor devoted to international food stalls. After lunch, walk toward Belém, home of the Torre de Belém and the Jerónimos Monastery. Then meander into the bohemian Chiado and Bairro Alto districts for more steep streets, the ornate Church de Sao Roque, and the ruins of Carmo Church.

In the late afternoon, return to your hotel for a little relaxation. As evening falls, head back into the Bairro Alto to enjoy a night at one of the city’s best fado restaurants. Enjoy traditional Portuguese fare with a live soundtrack of the melancholy, haunting tones of Portugal's distinctive fado music.

Day 11: Day Trip to Sintra, Cabo da Roca, Cascais & Estoril

The mysterious inverted towers of Quinta de Regaleira

Today takes you to magical Sintra, also known as the "Mountain of the Moon." Located just half an hour east of the capital, this resort town in the Sintra Mountains is known for its forested hills, upscale villas, and Moorish palaces. Visit the Palacio Nacional da Pena (Pena Palace), a fantastical 19th-century castle that mixes Moorish and Portuguese late-Gothic architecture, or take a tour of the mystical Quinta da Regaleira, an impressive estate whose grounds hold countless secrets like dizzying inverted towers used in Masonic initiation rites. 

Afterward, explore Sintra's historic center to see more examples of 19th-century romantic architecture surrounded by the lush gardens and forests of the area. On the way back to Lisbon, stop at Cabo da Roca, the westernmost point of mainland Europe, where you can breathe in the sea breeze at the 18th-century cliffside lighthouse. The day will end in Cascais and Estoril, two beachside resorts that are known as some of the most cosmopolitan places in Portugal. Stroll around town and take in the panoramic sea views before returning to Lisbon to enjoy your final night in the city.

Day 12: Depart Lisbon

The red rooftops of Lisbon's Alfama district

It's time to say goodbye to charming Portugal. Enjoy a final morning in the city before meeting your driver and transferring to the airport for your departing flight. Adeus!

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Map of Historic Portugal: Évora, Coimbra, Douro Valley, Porto & Lisbon - 12 Days
Map of Historic Portugal: Évora, Coimbra, Douro Valley, Porto & Lisbon - 12 Days