5-Day Portugal Discovery: Lisbon, Sintra & Historic Strongholds

Overview

Welcome to Portugal! This private five-day journey has been thoughtfully designed for your party of four, combining Lisbon's storied monuments and picturesque old quarters with the romantic castles of Sintra, the dramatic Atlantic coastline, medieval strongholds, and the sun-drenched a vineyard of the Alentejo. Traveling in the comfort of a dedicated Mercedes-Benz vehicle with your private driver/guide, you will discover the authentic spirit, rich traditions, and remarkable heritage of this captivating country at a refined and seamless pace.

Highlights

• Wander through the atmospheric streets and storied alleys of the historic Alfama quarter
• Enjoy a riverside stop by Belem Tower and learn about Portugal's Age of Discovery
• Admire the intricate Manueline stonework of Jeronimos Monastery along the Tagus waterfront
• Take in the expansive panoramic views over downtown Lisbon and the river from Parque Eduardo VII
• Visit the colourful Pena Palace standing high above the lush forested hills of Sintra
• Stroll through the cobblestone streets and artisan shops of Sintra's historic village
• Take in the dramatic clifftop ocean vistas at Cabo da Roca, Europe's westernmost point
• Explore the charming coastal streets and traditional fisherman harbor of Cascais
• Experience the peaceful ambiance and monumental architecture of the Sanctuary of Fatima
• Admire the sweeping clifftop ocean panoramas and maritime character in authentic Nazare

Day by day

1. Day 1 — Best of Lisbon & Monumental Belem
   Begin your Portuguese adventure with an immersive private introduction to Lisbon, starting in the historic quarters before journeying to the monumental riverside district of Belem. Admire the architectural wonders of Jeronimos Monastery and Belem Tower, taste warm pasteis de Belem fresh from the oven, and take in the sweeping panoramic vistas over the Tagus River from Eduardo VII Park.
2. Day 2 — Sintra, Cabo da Roca & Cascais
   Journey into the enchanted Serra de Sintra to discover the vivid fairy-tale architecture of Pena Palace and the romantic charm of Sintra's historic village. Later, stand on the wind-swept clifftops of Cabo da Roca, the westernmost point of continental Europe, before following the dramatic Atlantic coastline into the elegant old fisherman village of Cascais.
3. Day 3 — Fatima, Nazare & Medieval Obidos
   Travel north into Portugal's heartland to experience the profound serenity of the Sanctuary of Fatima, one of the world's most venerated pilgrimage sites. Continue to the Atlantic coast to admire the colossal ocean cliffs and historic fisherman traditions of Nazare, concluding your day inside the preserved medieval walls of Obidos with a taste of traditional ginjinha liqueur.
4. Day 4 — Knights Templar: Tomar & Almourol
   Step back into the realm of medieval crusaders with a journey dedicated to the legendary Knights Templar. Explore the monumental UNESCO World Heritage Convent of Christ in Tomar, marveling at the famous Manueline Window, before visiting the evocative island fortress of Almourol Castle rising dramatically from the waters of the Tagus River.
5. Day 5 — Evora, Monsaraz & Alentejo Wine Country
   Venture southeast across the 25th of April Bridge into the sun-drenched plains of the Alentejo to uncover the UNESCO-listed treasure of Evora, home to the ancient Roman Temple and the intriguing Chapel of Bones. Conclude your journey in the fortified hilltop village of Monsaraz, where whitewashed lanes overlook the shimmering Alqueva reservoir, followed by a curated Alentejo wine tasting at a traditional regional estate.

What is included

• Private English-speaking driver-guide
• Black Mercedes-Benz vehicle (E-Class, V-Class, or Sprinter based on group size)
• All ground transport between cities and on tour days
• Door-to-door pickups and drop-offs at hotels and airports
• Bottled water and Wi-Fi in the vehicle
• Personalized planning by Portugal Magik travel designers

Not included

• Hotel accommodation (we recommend properties on request)
• Flights to and from Portugal
• Meals and drinks (suggestions provided by your driver)
• Museum and monument entrance fees
• Travel insurance

Who this trip suits

Travellers who prefer a private, fully planned Portugal journey with a driver-guide handling every transfer.

Frequently asked questions