Portugal Castles, Beaches & Vineyards: Lisbon to the Algarve - 13 Days

Day 1: Arrive in Portugal & Lisbon

Welcome to Portugal! Upon arrival, a driver will greet you and transfer you to your hotel. You'll have a couple of free hours to rest or explore Lisbon on your own.

The Portuguese capital boasts hilly waterfront neighborhoods dotted with pastel-colored buildings. Old cable cars lurch up winding cobbled roads, and medieval castles sit perched atop the highest points in the city. For a perfect introduction to this beautiful destination, head to one of Lisbon's famed miradouros or lookout points, which provide panoramic views.

Day 2: Private Half-Day Tour of Old 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 crumpling 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 CE, 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: Private Tour of Sintra Castles & the Lisbon Coast

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 is a symbol of Romanticism in Portugal. After the castle, walk around, and shop in the historic village center.

Then, head to the coast to see Cape Roca, the westernmost point in continental Europe. Get views of the lighthouse perched 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: Transfer from Lisbon to the 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 5: Douro Valley Wine Tasting Tour & Boat Ride

The Douro Valley could easily be called the enchanted valley, with terraced fields undulating on both sides of the Douro River. A private guide will take you around hidden areas only locals know about. Then, visit a local winery, and taste the famous port wines. Strong and sweet, port is the region's cultural treasure, attracting international wine lovers since the 18th century. 

Enjoy lunch at the winery—with local wine, of course—before heading down to the river to embark on a semi-private boat tour. As you cruise down the calm waters of the Douro, take in the exquisite softness of the landscape from a unique perspective. Afterward, a driver will transfer you to Porto. Stop on the way at the Casal de Loivos viewpoint, famous for its unmatched outlook onto the valley.

Day 6: Guided Tour of Porto with Wine Tasting

This morning, enjoy a private half-day tour of Porto. The first stop will be the famous Lello Bookshop, nicknamed "the Harry Potter Bookshop" 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. In Porto's most famous district, discover the iron Bridge of Luís I and historic UNESCO-listed houses. Throughout the tour, stop for local snacks, or petiscos, and wine. Spend a free afternoon at a Porto vintage wine cellar like Ramos Pinto, Graham's, or Taylor's.

Day 7: Transfer from Porto to Évora in Alentejo

A private driver will transfer you from Porto to Évora in south-central Portugal. After checking in, use your free time to walk around this historic city that dates back to Roman times. The center is famous for its whitewashed homes with yellow accents that create a light and airy atmosphere. As the capital of the Alentejo region, Évora has plenty to offer.

Go to the Museu de Évora to understand why this city is a UNESCO World Heritage Site. You can also visit numerous 14th and 15th-century palaces that once housed the Portuguese royal court. The Paço dos Duques de Cadaval (Palace of the Dukes of Cadaval), and the Paço dos Condes de Basto are two of the most impressive.

Day 8: Private Guided Tour of Évora & Monsaraz

Spend the day exploring the charming Alentejo region, starting with a private tour of Évora. Visit the Igreja de São Francisco (Church of St. Francis). Here, go into Capela dos Ossos (Chapel of Bones), famous for its walls covered in human skulls and bones. Other landmarks include the impressive Évora Cathedral, and the 2,000-year-old Templo Romano built for Diana, the goddess of the moon. 

From Évora, stop at an artisanal pottery village on the way to Monsaraz. Located near the Spanish border, this medieval town is known for its sizeable Knights Templar fortification. From Monsaraz Castle, you can get views of the town and the Alqueva Dam, the biggest artificial lake in Europe. After walking around, return to Évora for the night.

Day 9: Transfer from Évora to the Algarve Region

Today, a driver will take you from Évora to the Algarve, Portugal's southernmost region. After checking in at your hotel, you will have a free afternoon for some fun self-guided adventures in Carvoeiro. This small town is considered one of the prettiest in the area.

The Algarve is known for its stunning limestone cliffs and rock formations. Search for an elevated lookout point from where to see the forceful Atlantic Ocean crashing into the rocks. Then, head down to the beach. You can spend the day splashing in the water if the weather is good, or enjoy the astonishing scenery if it's too cold. Either way, end the day treating yourself to delectable fresh seafood at a local restaurant.

Day 10: Algarve Wine & Food Experience

Get excited for a day of culinary adventures in the Algarve. A driver will pick you up in the morning and take you to Tôr, a traditional village with a rich wine-making heritage. After a short tour through town, go to a local winery. Learn about the production process, and taste premium Algarvian wines. Enjoy the mountainous landscape as you sample delicious regional tapas. 

Once the tour finishes, transfer back to Carvoeiro. This evening you have the option of embarking on a luxury dining experience at Bon Bon, a one-star Michelin restaurant. Serving traditional Portuguese fare with a modern twist, the establishment boasts magnificent vistas of the Monchique Mountains. Gastronomy-focused travelers will appreciate the opportunity to dine at one of the best restaurants in the Algarve.

Day 11: Guided Tour of Algarve Villages & Beaches

Discover the most beautiful towns in the Algarve on a private tour. Stop in Lagos, a small fishing village with two thousand years of history. It was from here that many of the country's famed explorers departed. Get some sun or play in the water at Meia Praia, a popular Lagos attraction. 

Then, head west to Sagres, a must-see destination for its beaches and the immensity of its landscapes. Sagres Fortress is the town's highlight. Built in the 15th century, it is now a National Monument. Finally, go to Cape St. Vincent, the most southwesterly point in mainland Europe. Its iconic lighthouse overlooks one of the busiest trade routes in the world—the views are nothing to scoff at either!

Day 12: Transfer from the Algarve to Lisbon via Costa Vicentina

After breakfast, head out to Lisbon. But, don't worry! You'll still get to see the ocean as you drive along the Costa Vicentina. Considered Europe's last wild coast, strict environmental laws limit development along it. Gaze out to see the pristine beaches and small fishing villages as you pass.

Stop at the coastal village of Zambujeira do Mar. Stretch your legs by walking around the quiet, pretty town. Have lunch on your own at a typical seafood restaurant by the beach. Then, continue to Lisbon for one last night in the capital. Once there, head to a bar for fado, a hauntingly beautiful Portuguese music genre.

Day 13: Depart from 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.

Looking for more inspiration for your trip to Portugal? Check out these other Portugal itineraries, explore more 13-day trips in Portugal, or discover the best time to visit Portugal.