From Lisbon to Porto: A Two-Week Itinerary Through Portugal

Portugal is a treasure trove of cultural, historical, and natural delights, offering a unique blend of old-world charm and contemporary luxury. This itinerary is tailored for discerning travelers seeking to delve into Portugal’s rich heritage while indulging in the finest accommodations and exclusive experiences the country has to offer. From the artisanal traditions of Lisbon to the wine-soaked terraces of Porto, every step of this grand tour is designed to enchant, educate, and inspire. Join us as we uncover the timeless allure of Portugal, where luxury meets tradition in the heart of Western Europe.

Day 1-3: Lisbon’s Lively Lure

Your journey begins in Lisbon, the charismatic capital of Portugal, known for its vibrant culture and picturesque streets. The city is built on a series of seven hills, each revealing a different chapter of Lisbon’s rich history. Stay at the Four Seasons Hotel Ritz Lisbon, which combines art deco charm with modern luxury, providing a perfect haven of relaxation after a day of exploration.

Lisbon Portugal

Lisbon is a city best explored on foot or by tram. Begin your exploration in Alfama, the oldest district, where narrow cobblestone streets lead to hidden courtyards and quaint cafés. A private guided tour can enhance your experience, bringing to life the stories behind historic sites such as São Jorge Castle and the panoramic viewpoints of Miradouro de Santa Luzia.

Culinary delights are an integral part of the Lisbon experience. Dine at a Michelin-starred restaurant, where traditional Portuguese dishes are reimagined with contemporary flair. A must-do is a private Fado dinner where the poignant sounds of Portugal’s traditional music form the perfect backdrop to a night of gastronomic indulgence.

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Day 4-5: Sintra’s Royal Sanctuaries

Just a short drive from Lisbon lies Sintra, a UNESCO World Heritage site that feels like a page taken out of a fairy tale. Your residence here will be the Tivoli Palácio de Seteais, an 18th-century palace turned luxury hotel, offering spectacular views over Sintra’s lush landscapes.

Sintra Portugal

Sintra’s palaces and gardens are breathtaking. The most iconic, Pena Palace, stands atop a hill encased in mist, its vivid colors striking against the greenery. Spend a morning exploring this royal sanctuary with a private guide who unveils its romantic history and architectural intricacies. Don’t miss the Moorish Castle and the enigmatic Quinta da Regaleira, a gothic estate steeped in mystique with its deep wells and hidden tunnels.

Day 6-7: The Alentejo’s Undulating Charm

Heading eastward, enter the Alentejo, a vast region of rolling plains and vine-covered hills, dotted with medieval villages. Your accommodation, São Lourenço do Barrocal, is a masterfully restored farm estate in the heart of this serene landscape, blending rustic charm with five-star amenities.

Alentejo Portugal

Explore the medieval town of Évora, a UNESCO World Heritage site, with a knowledgeable local guide. Visit the Roman Temple, the Cathedral, and the chilling Chapel of Bones. The region is also renowned for its wine, and no visit would be complete without a private tasting session at a local vineyard, where you learn about the Alentejo’s distinct wine varietals and savoring some of the finest selections.

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Day 8-9: Coastal Algarve’s Luxurious Leisure

Travel to the Algarve, known for its stunning coastlines and luxury resorts. Check into Vila Vita Parc, a resort famed for its clifftop views and lush gardens. The resort offers a variety of leisure activities including golfing at world-class courses, spa days designed to pamper and rejuvenate, and gourmet dining experiences that feature ocean-fresh seafood and international cuisine.

Algarve Portugal

A private yacht excursion is a splendid way to see the Algarve’s famous caves and secluded beaches. Discover hidden coves accessible only by water, and perhaps stop at a secluded beach for a bespoke picnic lunch, prepared just for you.

Day 10-11: Coimbra’s Academic Aromas

Continue north to Coimbra, a city renowned for its historic university, one of the oldest in continuous operation in the world. The University of Coimbra is a UNESCO World Heritage site, famous for its Baroque library, the Biblioteca Joanina, and the stunning Royal Palace of Alcáçova.

Coimbra Portugal

Stay at the Quinta das Lágrimas, a luxury hotel with a storied history, linked to the tragic love story of Pedro and Inês. Explore the city’s rich academic and religious history with a private guide, and spend an evening enjoying traditional Coimbra Fado, a more melancholic and refined variant of the Lisbon style.

Day 12-13: Porto’s Wine Wonders

Your Portuguese adventure culminates in Porto, a city that has become synonymous with its namesake port wine. The luxurious Yeatman Hotel in Vila Nova de Gaia offers sweeping views of the Douro River and Porto’s historic center. A private tour of the wine cellars, guided by a sommelier, provides insight into the age-old techniques of port wine production.

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Porto Portugal

A river cruise on the Douro offers a serene way to appreciate the terraced vineyards and tranquil scenery. Visit a traditional wine estate to see firsthand how the region’s wines are made, complete with tastings and a rustic Portuguese lunch.

Day 14: Departure

As your two-week journey through Portugal concludes, take a leisurely morning to reflect on the myriad experiences and the lush tapestry of history, culture, and natural beauty you’ve encountered. Portugal leaves an indelible mark on all who travel through it, ensuring memories that linger and beckon for your return.


From the sunlit alleys of Lisbon to the historic cellars of Porto, this two-week itinerary not only unveils the best of Portugal but also wraps you in the lap of luxury. Engaging tours, sumptuous accommodations, and immersive experiences ensure that every moment spent is a testament to Portugal’s warm hospitality and rich heritage. This journey through Portugal promises not just a vacation, but an enriching adventure that is both luxurious and deeply touching.


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