Curator’s statement
Portugal is quickly emerging as one of Europe’s most sought-after destinations, blending its rich history, warm hospitality and striking landscapes. What sets Portugal apart is not just its scenic beaches and world-class wine, but the warmth and kindness of its people. Known for their genuine friendliness, locals often go out of their way to make visitors feel at home, whether in vibrant cities like Lisbon and Porto or quaint coastal towns.
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Day 1: Lisbon and the Tagus River
Morning: private tuk-tuk tour of Lisbon
Your tuk-tuk guide will pick you up from your hotel. Begin the tour with a scenic ride through Alfama, the oldest district of Lisbon, where you’ll explore the narrow cobblestone streets, colorful houses and the majestic Lisbon Cathedral. Head up to Miradouro da Senhora do Monte for panoramic views of the city. Your guide will give you a brief history of Lisbon’s iconic skyline, and you can snap some incredible photos. Drive past the Baixa district, where you can admire the grand Praça do Comércio, before heading to the stylish Chiado neighborhood for a glimpse of Lisbon’s charming boutiques and cafes. Continue your journey to Belém, the historical district famous for its maritime heritage. Visit the Jerónimos Monastery, a stunning example of Manueline architecture, and the Belém Tower, a UNESCO World Heritage site that once guarded Lisbon’s harbor.
Enjoy lunch at one of the trendy restaurants near the river, such as Rio Maravilha or Ponto Final across the river for a waterfront view.
Evening: sunset boat tour on the Tagus River
Head to the dock for a private sunset boat tour along the Tagus River. Board a luxurious sailboat or yacht, and start the leisurely cruise as the city’s golden hour begins. Sail under the impressive 25th of April Bridge. Enjoy breathtaking views of the Lisbon skyline, including the Christ the King statue and iconic landmarks along the waterfront.
As the sun sets over the Atlantic, sip a glass of local wine while passing by Belém Tower and Monument to the Discoveries, now beautifully illuminated by the evening light.
Day 2: Enchanting town of Sintra
We invite you to explore the enchanting town of Sintra, known for its breathtaking palaces and stunning landscapes. Discover the magic that has inspired kings, poets and dreamers for centuries. Visit the Pena Palace or the beautiful gardens. Afterward, experience the fresh, blue embrace of the Atlantic Ocean at Cabo da Roca, the westernmost point of continental Europe. Finally, we’ll guide you to the charming coastal towns of Cascais and Estoril, often called the Portuguese Riviera. Here, elegance and beauty meet the ocean in perfect harmony.
Day 3: Lisbon to the Algarve
Embark on a scenic journey from Lisbon to the Algarve, filled with picturesque stops along the way. Your day begins with a visit to Évora, a UNESCO World Heritage site renowned for its well-preserved Roman temple and charming medieval streets. Stroll through the town, soaking in the blend of ancient history and local culture.
Continue south, stopping in the quaint town of Alcácer do Sal, nestled along the Sado River. Here, enjoy a leisurely coffee while taking in the views of the river and the old castle perched above the town.
As you drive further, pause in the coastal town of Sines, birthplace of the famous explorer Vasco da Gama. Explore the historic fort and take in panoramic views of the Atlantic, with its rugged cliffs and sandy beaches.
Finally, you’ll arrive in the Algarve, where golden beaches, dramatic cliffs and azure waters await. Finish your day with a sunset view over Praia da Marinha or explore the charming old town of Lagos, ending with a relaxing dinner overlooking the sea. This journey offers a perfect balance of history, culture and natural beauty on your way to the Algarve’s stunning coastline.
Day 4: Cliffs of Ponta da Piedade
Start your day in the Algarve by immersing yourself in the region’s natural beauty, beginning with a sunrise walk along the iconic cliffs of Ponta da Piedade. The dramatic rock formations, golden cliffs and turquoise waters create an unforgettable backdrop, perfect for a peaceful morning of reflection or photography.
Next, head to a secluded beach like Praia do Camilo, where you can relax on soft sands or take a dip in the crystal-clear waters. As the morning unfolds, explore hidden coves by kayak or boat, getting up close to the unique grottos and sea arches that make the Algarve so distinctive.
For lunch, indulge in world-class cuisine at one of the region's Michelin-starred restaurants.
In the afternoon, take a scenic drive to the charming town of Carvoeiro. Here, you can visit the stunning Benagil Cave, one of the most photographed natural landmarks in Portugal. Continue your journey to Cabo de São Vicente, Europe’s southwesternmost point, where sheer cliffs rise dramatically above the ocean. As the sun sets, enjoy the breathtaking views over the vast Atlantic Ocean. A perfect end to a day of exploring the Algarve’s unique combination of world-class food, stunning cliffs and captivating charm.
Day 5: From the Algarve to Porto
After a short, scenic flight from the Algarve to Porto, you’ll arrive in one of Portugal’s most vibrant cities, where history and modernity blend seamlessly. Begin your afternoon by wandering through the charming Ribeira district, a UNESCO World Heritage site with narrow, winding streets, colorful buildings and the stunning Douro Riverfront. As you explore, stop by the iconic Luís I Bridge, offering panoramic views of the city and the river below.
Next, visit the magnificent Livraria Lello, often considered one of the most beautiful bookstores in the world, with its neo-Gothic architecture and intricate wooden staircase. Nearby, the Clerigos Tower awaits those ready to climb its 200 steps, rewarding you with sweeping views of Porto’s terracotta rooftops and the Douro Valley.
For a taste of the city’s world-renowned wine, cross the river to Vila Nova de Gaia, home to centuries-old Port wine cellars. Enjoy a private tour and tasting at one of the historic wineries, savoring the rich flavors of this iconic Portuguese wine.
End your afternoon with a stroll along the riverfront promenade, perhaps with a leisurely boat ride to see the city from the water. As the sun sets, the vibrant atmosphere of Porto comes alive, setting the perfect stage for a relaxing evening of exploration.
Additional days: Douro Valley and beyond
Discover the beauty and heritage of Portugal’s premier wine region, the Douro Valley, on this immersive full-day tour from Porto. Accompanied by a knowledgeable private guide, explore several key locations that showcase the region’s rich history and winemaking traditions. Begin your journey with a visit to Peso da Régua, the heart of the Douro’s wine production, where you’ll learn about the area’s deep connection to viticulture.
Continue to Pinhão, a charming riverside village surrounded by terraced vineyards, and take in breathtaking views of the valley from a scenic lookout. Here, you’ll enjoy a relaxing boat ride on the Douro River, offering a unique perspective of the region’s stunning landscape.
Next, head to Lamego, a picturesque town known for its baroque architecture and the iconic Sanctuary of Nossa Senhora dos Remédios. Stroll through its historic streets before stopping at two renowned wineries for exclusive wine tastings. At each stop, you’ll have the opportunity to sample the valley’s celebrated wines. From robust reds to sweet Ports, while learning about the unique terroir and winemaking techniques that make Douro wines so distinctive.
Need to know
All tours can be done in a small group or completely private.
You can also do the drive from Algarve to Porto with some scenic stops along the way.
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Sarit Rothschild
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This itinerary is part of our ongoing series on travel to Portugal. Looking for more travel inspiration? Check out my itinerary, How to See Japan in Luxury.