Immerse yourself in Portuguese history and food on this comprehensive 12-day tour. Start in the hilly capital of Lisbon to explore local markets, see numerous medieval castles, and catch more than one breathtaking sunset. Then, head north to Porto and the Douro Valley, where rolling hills and glistening rivers will greet you as you drink your way through wineries and visit some of Portugal's oldest historic towns.


  • Catch a Lisbon sunset aboard a vintage sailboat
  • Drive along the coast to Cape Roca, the westernmost point in Europe 
  • Try port wine at a legacy vineyard in the Douro Valley
  • Explore Porto on a vintage motorcycle sidecar
  • Ride a traditional boat in Aveiro, the Portuguese Venice

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Lisbon & Sunset Sailing on a Vintage Boat Lisbon
Day 2 Private Half-Day Tour of Old Lisbon Lisbon
Day 3 Day Trip to Sintra Castles & the Lisbon Coast Lisbon
Day 4 Culinary Lisbon Tour With Food & Wine Tasting Lisbon
Day 5 Day Trip to Monsaraz & Évora in Alentejo Lisbon
Day 6 Transfer from Lisbon to the Douro Valley Douro Valley
Day 7 Douro Valley Wine Tasting Tour Douro Valley
Day 8 Douro Valley to Porto & Sidecar Tour Porto
Day 9 Private Guided Tour of Porto with Wine Tasting Porto
Day 10 Northern Portugal Day Trip: Guimarães, Braga & More Porto
Day 11 Aveiro & Óbidos via Lisbon Lisbon
Day 12 Depart Lisbon  

Detailed Itinerary

Day 1: Arrive in Lisbon & Sunset Sailing on a Vintage Boat

Cable car in Lisbon
Cable car in Lisbon

Welcome to Portugal! Upon arrival, a driver will greet you and transfer you to your hotel in Lisbon. The Portuguese capital boasts hilly waterfront neighborhoods dotted with pastel-colored buildings. For a perfect introduction, head to one of Lisbon's famed miradouros (lookout points), which provide breathtaking panoramic views.

In the afternoon, a driver will pick you up at your hotel and transfer you to the Port of Lisbon. Board a beautiful vintage sailing boat for a two-hour sunset tour on the Tagus River. Enjoy Lisbon from the water as you sail between the two river banks, passing by iconic monuments like the emblematic bridge Ponte 25 de Abril and the Cristo Rei, a Christ statue that overlooks Lisbon. 

Day 2: Private Half-Day Tour of Old Lisbon

Panoramic view of Lisbon
Panoramic view of Lisbon

Begin the day with a private walking tour to explore Old Lisbon. Stroll the alleys and narrow streets of the old quarter, as well as the trendy upscale downtown. Uncover the history of this vibrant city as you visit neighborhoods like Alfama and Baixa. The former is a maze of ancient buildings with an irresistible crumbling charm. And the latter is the heart of Lisbon, filled with magnificent plazas and grand avenues.

Walk through important landmarks like Castelo de S. Jorge (St. George Castle), a medieval castle in the middle of the city. Occupied from the 8th century, this large fortification is easily accessible by foot and is one of the most iconic symbols of Lisbon. Because of its privileged position on the highest hill, the castle also provides a glimpse of the capital that is sure to leave you speechless.

Day 3: Day Trip to Sintra Castles & the Lisbon Coast

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

Get away from the bustle of the capital on a visit to the town of Sintra. Its highlight is the colorful Pena Palace, considered one of the most beautiful in the world. Located on the top of Sintra Hill, this 19th-century landmark symbolizes Romanticism in Portugal. After the castle visit, walk around and shop in the historic village center.

Then, head along the coast to Cape Roca, the westernmost point in continental Europe. Get views of the lighthouse atop the cliff and stop by a fresh seafood restaurant for lunch. Continue south along the coast on your way to Cascais. The beaches and seaside rock formations in this charming resort town have made it a popular getaway with the rich and famous. As the sun goes down, return to Lisbon.

Day 4: Culinary Lisbon Tour With Food & Wine Tasting

The delicious and addictive pasteis de nata or Portuguese tarts
The delicious and addictive "pasteis de nata" or Portuguese tarts

Take advantage of a free morning to experience Lisbon at a slower pace. Stroll around the pleasant Jardim do Principe Real (Royal Prince Garden), known for its peaceful atmosphere and beautiful trees. Or visit the Museu Nacional do Azulejo (National Portuguese Tile Museum). Dedicated to azulejos (Portuguese-style tiles), the museum provides a look into this local art style.

In the afternoon, go on a private gastronomy tour of Lisbon. Stopping at seven bars and restaurants, you'll taste your way around the city. Besides trying authentic local fare, your guide will explain the country's history, culture, and traditions. Must-try dishes include cod, sardines, and açorda, a simple soup. But the most emblematic food in the country is the pastel de nata, or Portuguese egg tart.

Day 5: Day Trip to Monsaraz & Évora in Alentejo

Monsaraz, Portugal
Monsaraz, Portugal

Get excited for a day trip to the beautiful Alentejo region, west of Lisbon. Stop in Évora, a UNESCO-listed medieval city and base of the Portuguese Franciscan Order. Visit the Igreja de São Francisco (Church of St. Francis), whose famous Capela dos Ossos (Chapel of Bones) has walls covered in human bones. The Évora Cathedral and the Roman Temple are other highlights of this city.

Stop at a small artisanal pottery town on your way to Monsaraz, close to the Spanish border. Once in the city, go to the astonishing Monsaraz Castle, a medieval knight templar castle with a village inside. From the top, take in views of the Alqueva Dam, the biggest artificial lake in Europe. Return to Lisbon for one last night in the capital and head to a bar for fado, a hauntingly beautiful Portuguese music genre.

Day 6: Transfer from Lisbon to the Douro Valley

Douro Valley vineyard
Try local wines in the sprawling Douro Valley

On your last morning in Lisbon, enjoy a hearty breakfast before your private transfer to the Douro Valley. This UNESCO World Heritage-designated area is the oldest demarcated wine region in the world. The libation shapes the landscape, as rows of grapes paint the hills with soft vertical lines. On your journey, you'll encounter the Douro River, which gives this region its name.

Upon arrival, use your free time to relax, take in the simple beauty of the landscape, and try some local wine.

Day 7: Douro Valley Wine Tasting Tour

Douro valley
Vineyards in the Douro Valley with the Douro River

Spend the day discovering the amazing Douro Valley, where you will visit some of the best and most exclusive family-owned wineries. During your visit to wine estates, learn about—and, of course, taste—Douro wines, from reds and whites to famous ports.

To wrap up the winery experience, enjoy lunch in a traditional quinta (winery). But this tour is not just about drinking wine. It's also about taking in the beautiful vineyard landscapes as you drive through mountain backroads. You'll have the rare experience of sailing along the Douro River on a traditional rabelo, a style of vessel distinctive to this region.

Day 8: Douro Valley to Porto & Sidecar Tour

Houses in Porto's Ribeira district
Houses in Porto's Ribeira district

A private driver will transfer you to Porto, Portugal's second city, known for its colorful old quarter. Enjoy your free time by hitting up landmarks like the Palácio da Bolsa (Old Stock Market). This 19th-century national monument is a fine example of neoclassical architecture and boasts lavishly-decorated interiors. The 15th-century Gothic Igreja de São Francisco (Church of St. Francis) is beside it.

In the afternoon, you'll have the option of doing a unique tour of Porto on a vintage motorcycle sidecar. Your guide will pick you up for a whirlwind adventure. Breeze through the old neighborhoods of the historic center, then follow the Douro River to the ocean, stopping at beautiful viewpoints. Afterward, ride uphill to see the city from above, visiting a traditional Portuguese café.

Day 9: Private Guided Tour of Porto with Wine Tasting

Ribera district in Porto
Ribeira district in Porto

This morning, enjoy a private half-day tour of Porto. The first stop will be the famous Lello Bookshop, nicknamed "the Harry Potter bookstore" for its aesthetic. Then, climb the 225 steps of Torre dos Clérigos (Clérigos Tower) for breathtaking panoramic views. See the Old Jewish Quarter and the Railway Station of Saint Bento, where you'll learn about the city's history.

Continue to the Sé do Porto (Porto Cathedral), an elaborate 12th-century monument. Make your way along the winding medieval Escada das Verdades (Stairway of Truth), heading south until you reach Ribeira. Discover the iron Bridge of Luís I and historic UNESCO-listed houses in Porto's most famous district. Throughout the tour, stop for petiscos (snacks) and wine. Spend your free afternoon at one of Porto's famed vintage wine cellars like Ramos Pinto, Graham's, and Taylor's.

Day 10: Northern Portugal Day Trip: Guimarães, Braga & More

Landscaped gardens in Braga
Landscaped gardens in Braga

Today is devoted to a full-day tour of the historic cities of Guimarães and Braga. Inhabited for over a millennium, Guimarães is one of Portugal's oldest settlements and is considered the birthplace of Portuguese identity. Get insight into its vivid history as you visit the mighty medieval Castelo de Guimarães (Guimarães Castle) and the Palace Duques de Bragança

From there, head to Braga, which boasts the towering Cathedral of Braga, and the Sanctuary of Bom Jesus do Monte, a grand Catholic shrine in nearby Tenões. On the way back to Porto, you can visit Ponte de Lima, the country's oldest town, and Viana Do Castelo, crowned by its Basilica of the Sacred Heart of Jesus. Alternatively, conclude your trip with a visit to one of the region's amazing wine estates.

Day 11: Aveiro & Óbidos via Lisbon

waterfront town in Portugal called Aveiro
Colorful "moliceiros" in Aveiro

A driver will pick you up for a private road transfer back to Lisbon. On the way, stop in Aveiro and Óbidos, two of the most beautiful villages in Portugal. Known as the Portuguese Venice, Aveiro is intersected by canals, streets of water along which float the brightly colored boats known as moliceiros. Embark on one for a genuine local experience. Don't leave without trying the famed local egg pastries, ovos moles.

Get back on the road for the medieval town of Óbidos. Once gifted to Queen Isabel of Portugal by her husband, King Dinis, the town's fortified castle is impressively well-preserved. Stroll along the maze of streets and squares within the walls, passing by traditional white houses decorated with Manueline (rich and lavish style of architectural ornamentation) porticoes and colorful windows. Then, continue to Lisbon.

Day 12: Depart Lisbon

Praça do Comércio in Lisbon
Praça do Comércio in Lisbon

It's time to say goodbye to Portugal. At the appointed time, a private driver will pick you up at your hotel to transfer you to the airport, where you will take your flight back home.

More Great 12-Day Portugal Itineraries

Looking for more inspiration for your trip to Portugal? Check out these other 12-day Portugal itineraries, which include culinary tours, self-driving adventures, and visits to historic sites.


Map of Portugal Food, Wine & Castles: Lisbon, Douro Valley & Porto - 12 Days
Map of Portugal Food, Wine & Castles: Lisbon, Douro Valley & Porto - 12 Days