Combining equal parts history, culture, and gastronomy, this nine-day itinerary is the perfect introduction to Portugal. Start in the captivating city of Évora before moving on to Porto and Lisbon—discovering the plentiful highlights and hidden corners in between. Marvel at the ancient ruins of Templo Romano, refine your palate with a day of wine tasting in the Douro Valley, get lost in the medieval walls of Óbidos, and save room for an unforgettable food tour through Lisbon's most authentic neighborhoods.


  • Tour Évora's Roman ruins & medieval cathedral
  • Sip your way through the vineyards & quintas of the Douro Valley
  • Discover the beautiful walled city of Óbidos
  • Experience the mournful beauty of a live fado show
  • Taste the best of Portuguese cuisine on a food tour of Lisbon

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Lisbon, Transfer to Évora & Private Tour Évora
Day 2 Explore the Alentejo Region  Évora
Day 3 Transfer to Porto via Coimbra Porto
Day 4 Discover Porto  Porto
Day 5 Day Trip to the Douro Valley, Wine Tasting & River Cruise Porto
Day 6 Transfer to Lisbon via Óbidos, Evening of Fado Lisbon
Day 7 Get to Know Lisbon, Evening Culinary Experience Lisbon
Day 8 Day Trip to Sintra, Cascais & Estoril Lisbon
Day 9 Depart Lisbon  

Detailed Itinerary

Day 1: Arrive in Lisbon, Transfer to Évora & Private Tour 

Évora's spectacular medieval cathedral
Welcome to Portugal! Upon arrival at Lisbon Airport, a driver will be waiting to take you to Évora, the cultural capital of the Alentejo region. After settling in, discover Évora's most impressive treasures with a private guided tour. Explore the UNESCO-listed city's historic center and visit its main monuments, including the ruins of the Templo Romano and many landmarks of the golden age of Portuguese maritime discoveries. You'll gain a fascinating overview of the city's major events, which have always been linked to the most significant moments in Portuguese history.

Day 2: Explore the Alentejo Region

Vineyard in Alentejo
Rolling vineyards in the Alentejo
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Today you have a free day to explore the Alentejo region, where the pace of life slows amid the area's iconic golden plains. This sparsely populated yet vast swath of land between the Algarve and Lisbon offers scenic rolling hills, olive groves, vineyards, and charming fortified towns with a number of walking trails, Neolithic monuments, rustic wineries, and cork production facilities. 

Day 3: Transfer to Porto via Coimbra

Coimbra's Largo da Portagem Square
Meet your guide this morning for a transfer toward Porto. About halfway through the trip, you'll stop in Coimbra to walk around and have lunch. Coimbra is the medieval capital of Portugal and the site of the University of Coimbra, established in 1290. The city's historic core cascades down a hillside creating a lovely setting along the east bank of the Rio Mondego. When you're ready, get back on the road and continue to Porto, where you'll check into your hotel and have the rest of the day free to relax and explore on your own. 

Day 4: Discover Porto

Porto's colorful riverfront

Get to know more of Porto today with a private guided excursion, where you'll learn about the city's history, heroes, and battles as you make your way through the trendiest and most culturally-rich areas of town. Start in the UNESCO-listed city center to admire its renowned Romanesque, Gothic, and Baroque monuments and sites, including the São Bento Railway Station, Clerigos Tower, Church of St. Francis, Lello Bookshop, Sta. Catarina Street, Majestic Café, and Bolhão Market.

After visiting the imposing Porto Cathedral and its surroundings, you'll finish the tour along the banks of the immense Douro River for sweeping views over the city from the Miradouro da Vitória. The rest of the afternoon is free to spend at your leisure. Consider visiting the Museum of Contemporary Art in Serralves Park to admire modern masterpieces in a peaceful setting, or head to the seaside nearby to see how Portugal's famous gourmet-quality tinned fish is made with a small-scale factory tour.

Day 5: Day Trip to the Douro Valley, Wine Tasting & River Cruise

Douro Valley traditional boat
Vineyards overlooking the Douro River

Today your private driver will be waiting to whisk you into the mountains and valleys of the famous Douro Valley wine region, where you'll visit traditional wineries accompanied by your expert guide. After a wine tasting, you'll enjoy a traditional lunch at one of the valley's famous quintas (estates).

Next, you'll hop aboard a riverboat for an hour-long cruise down the tranquil Douro River. Relax and admire the beautiful scenery of the valley and the rolling hills along the riverbanks. At the end of the day, your guide will return you to Porto, where you can spend the evening at leisure in the city's lively Ribeira area.

Day 6: Transfer to Lisbon via Óbidos, Evening of Fado

Charming side streets in the medieval village of Óbidos

Meet your driver for the journey south today, stopping first at the charming town of Óbidos to see the narrow cobblestone streets and white-painted houses of this classic Portuguese walled city. Historically, Óbidos was recaptured from the Moors and presented to the Queen of Portugal on her wedding day—a long-lasting tradition that continued until the 19th century. This royal patronage left a legacy of pride within the town, which you'll notice as you explore the medieval castle and wander alleys adorned with bougainvillea and honeysuckle.

After some time exploring Óbidos, your driver will be waiting to continue your journey to Lisbon. Upon arrival, check in to your hotel in the city center. In the evening, you'll head into the Bairro Alto to enjoy a night at one of the city's best fado restaurants, where good food, the perfect setting, and the melancholic tones of the fado come together for a truly authentic night in Lisbon.

Day 7: Get to Know Lisbon, Evening Culinary Experience

Traditional trams climb Lisbon's hilly streets

First things first, you'll get your bearings on a privately guided tour of the city's most happening neighborhoods as you hop on board an iconic tram and head into the Bairro Alto. Continue onto Chiado and discover a cultural enclave where the great writers and philosophers of the 20th century used to gather to hone their ideas. Next up is the picture-perfect neighborhood of Alfama. Here, you'll get a feel for traditional Lisbon with its narrow cobblestoned streets and the stunning 12th-century Sé de Lisboa Cathedral.

As evening falls, you'll take part in a small group gourmet food tour. Wear a good pair of walking shoes because you, along with your English-speaking guide, will meander through a series of authentic winding alleys tasting the incredible flavors of Portuguese gastronomy and exploring the neighborhoods that set Lisbon's cultural and culinary trends. You'll visit several delicious spots throughout the afternoon that brilliantly link tradition with modernity.

Day 8: Day Trip to Sintra, Cascais & Estoril

Sintra's hilltop setting near Lisbon
Sintra's hilltop setting near Lisbon

After breakfast, your private driver will pick you up to start today's adventure in Sintra. Located just half an hour east of the city, this resort town in the Sintra Mountains is known for its forested hills, upscale villas, and Moorish palaces. Start with a visit to the Palacio Nacional da Pena (Pena Palace). This 19th-century romanticist castle mixes Moorish and Portuguese late-Gothic architectural styles with distinct features like gargoyles, ornate battlements, and colorful terraces.

After touring the palace, you'll have a break for lunch, at which point you can also stroll through the historic village of Sintra and do some shopping and/or sightseeing. Then it's off to Sintra Cascais Natural Park. Some can't-miss locales in this area include the dramatic coastal cliffs of the Cabo de Roca, the wide and inviting Guincho Beach (a popular surf spot), and the glamorous towns of Cascais and Estoril. After the tour, you'll private transfer will take you back to your hotel in Lisbon.

Day 9: Depart Lisbon

Sunset over Lisbon's Abril Bridge

After a final leisurely breakfast, your driver will be waiting to transfer you back to the Lisbon Airport to catch your departing flight. Safe travels and boa viagem!

More Great Portugal Itineraries

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Map of Explore Portugal's Culture & Cuisine:  Évora, Porto & Lisbon - 9 Days
Map of Explore Portugal's Culture & Cuisine: Évora, Porto & Lisbon - 9 Days