Portugal is a land of endless discovery, a destination that intertwines ancient history with modern vibrancy, boasts sun-dappled coastlines alongside cobbled medieval streets, and reveals stories at every turn. At TourTailors, our Portugal Tour immerses you in the country’s rich tapestry of traditions, scenic wonders, and cultural gems.
For travelers captivated by the soulful fado of Lisbon, the medieval romance of Óbidos, or the magnificent vineyards of the Douro Valley, our itinerary promises a seamless, enriching travel experience. Embark on a journey across Portugal’s most captivating regions and let its history, culture, and coastal beauty spark your next adventure.
Day 1 & 2: Lisbon – A City of Tradition and Innovation
Your journey begins in Lisbon, a city that perfectly blends the old with the new! Wander through the historic Alfama district, where narrow, winding streets lead to hidden viewpoints over the city’s terracotta rooftops. In the heart of Lisbon’s history, you will marvel at Belém’s iconic monuments, the exquisite Jerónimos Monastery and the legendary Belém Tower, each reflecting Portugal’s Age of Discovery.
In addition to exploring these cultural landmarks, you can join an engaging walking tour through the bustling Baixa and chic Chiado districts. As evening falls, surrender to the soulful sounds of a live fado performance, an intimate experience that captures the very essence of Portuguese melancholy and passion. These two days are about absorbing Lisbon’s dynamic spirit, its blend of tradition and innovation setting the stage for the diverse experiences that await you.
Day 3: Óbidos, Nazaré & Alcobaça – Timeless Treasures
On day three, your adventure begins as you rent a car in Lisbon and set off northward to explore Portugal’s storied locales. Start with a visit to the picturesque village of Óbidos, a living postcard of medieval charm. Stroll along its ancient cobbled streets lined with whitewashed houses and vibrant bougainvillea, and let the centuries of history etched into every corner ignite your imagination.
Next, drive along the surfing haven of Nazaré, a seaside town celebrated for its colossal waves and traditional fishing culture. Beach enthusiasts will find its inviting shores irresistible, while admirers of nature's raw power can marvel at the dynamic energy of the ocean.
Your third stop would be at the awe-inspiring Monastery of Alcobaça, a monument steeped in history and Gothic grandeur. Its serene cloisters and towering arches offer a moment for reflection, blending romance, tradition and cultural heritage. This diverse itinerary weaves together scenic landscapes, ancient streets, and monumental wonders to narrate Portugal’s rich past.
Day 4: Porto – Portugal’s Riverside Gem

On this day, immerse yourself in the captivating city of Porto, where the charm of a UNESCO-listed historic center meets a vibrant riverside culture. Begin your exploration on a guided walking tour through Porto’s scenic streets and timeless landmarks, including the iconic Livraria Lello and the Clérigos Tower. Uncover layers of history reflected in the colorful facades, ancient bridges, and bustling marketplaces.
A key highlight awaits in Vila Nova de Gaia with an authentic Port wine tasting experience. Enjoy the region's celebrated wine while discovering the meticulous production process, a craft refined over centuries. With each sip, admire panoramic views of the Douro River gracefully winding through the cityscape. This carefully curated day in Porto offers a rich blend of cultural heritage and culinary indulgence, ensuring a memorable and fully immersive urban adventure.
Day 5: Douro Valley – A Wine Paradise
The adventure continues into the heart of Portugal’s wine country with a visit to the breathtaking Douro Valley. Upon arrival, endless vistas of rolling vineyards, terraced hillsides, and the shimmering Douro River carved through the landscape greet you. The region stands as a living canvas painted with nature’s most vibrant hues and offers an intimate encounter with rural charm and traditional winemaking.
Enjoy a relaxing river cruise that provides a fresh perspective on the valley’s scenic beauty. As the boat glides along the river, captivating scenes unfold: lush vineyards stretching to the horizon, quaint quintas displaying centuries-old techniques, and rustic villages adding a rich cultural dimension. Enhance your journey with a visit to a local winery for a guided tasting session, complete with fascinating insights into the production of world-renowned Port wine. This immersive day promises relaxation and a deep connection to Portugal’s agricultural heritage and winemaking legacy.
Day 6: Viseu & Belmonte - Hidden Historic Gems
Venture off the well-trodden tourist paths on day six, with two hidden treasures in Portugal awaiting exploration. Start in Viseu, a city celebrated for its elegant streets, artistic heritage and lively cultural scene. In Viseu, centuries-old buildings and modern artistic expressions coexist, offering a fascinating glimpse into Portugal’s evolving identity. Wander through pleasant squares, explore quaint galleries, and sample local delicacies in traditional eateries.
Next, travel to Belmonte, a town carrying a fascinating Jewish legacy and a proud history that distinguishes it among Portugal’s lesser-known destinations. Roam ancient streets and visit historic landmarks that chronicle a rich tapestry of cultural influences. Additional highlights include local craft markets, the stunning castle, and a museum dedicated to Jewish culture, all contributing to an immersive experience. This day offers an in-depth dive into local traditions and a storied past that have quietly shaped the nation’s identity.
Day 7: Castelo de Vide & Marvão - Enchanting Villages

Day seven transports you to the heart of the Alentejo region, beginning in Castelo de Vide, celebrated as the “Jewish Village.” This town offers labyrinthine streets, an ancient castle, and panoramic views that evoke mystery and nostalgia. Castilian stone walls and centuries-old architecture provide a fascinating glimpse into Portugal’s multifaceted history and cultural fusion.
Continuing the day, travel to Marvão, a hilltop village perched above the surrounding plains. Marvão boasts well-preserved medieval fortifications, cobblestone lanes, and wonderful vistas extending toward Spain. Narrow lanes wind past historic churches and traditional houses, while local artisans display their crafts in small boutiques. Opportunities to savor regional cuisine in a rustic setting and discover local legends add even more depth to the journey. In addition, interactive experiences with local historians and scenic stops along the route enrich your understanding of the region’s heritage. Both villages combine to create a remarkable day that highlights the romance, history and authentic charm of Alentejo.
Day 8: Évora – A Journey into Portugal’s Past

Embark on a journey through history in Évora, a city whose every stone unveils a tale. As you wander through this well-preserved medieval town, immerse yourself in a historical narrative that spans millennia. The Roman Temple of Diana stands proudly as a reminder of the ancient past, and the eerie yet captivating Chapel of Bones prompts reflection on life’s transience. A guided walking tour leads you through Évora’s narrow lanes, uncovering hidden squares, charming cafés, and centuries-old structures that embody the city's enduring spirit. Discover additional treasures such as the imposing Évora Cathedral and local artisan workshops offering traditional crafts.
A visit to a nearby vineyard provides an opportunity to appreciate the robust wines crafted in the region. Évora transforms a simple visit into an immersive journey into the soul of Portugal, blending history, art, and gastronomy in cherished harmony.
Day 9: Arrábida Nature Park - Exploring the Untamed Beauty

Your final day unfolds in the wild and unspoiled landscapes of Arrábida Nature Park. This natural paradise is defined by rugged limestone cliffs, lush Mediterranean forests, and pristine turquoise waters. The park’s network of trails invites exploration, leading to spectacular viewpoints that reveal hidden coves and secluded beaches. The crystal-clear waters create an ideal setting for kayaking, snorkeling, or simply unwinding by the shore.
Amidst the natural beauty, discover historical sites such as the serene Convento da Arrábida, a 16th-century monastery tucked into the hills. Sample regional delicacies in the nearby town of Azeitão, known for its delectable cheese and locally produced wines. As the day winds down, return to Lisbon, carrying with you the memorable sights, flavors, and moments that have made this journey through Portugal truly special.
Ten Days, Endless Memories: Your Perfect Portugal Getaway
In just ten days, our Portugal Tour unveils the country’s most captivating landscapes, vibrant cities, and rich traditions. Wander through the soulful streets of Lisbon, marvel at Porto’s historic charm, and cruise past the terraced vineyards of the Douro Valley. Explore medieval villages steeped in legend, savor world-renowned wines, and immerse yourself in the breathtaking coastal scenery of Arrábida Nature Park.
Each detail is carefully designed to offer a seamless balance of history, culture, and natural splendor. With expert local insights and personalized touches from TourTailors, your journey promises an unforgettable adventure through Portugal’s most iconic and hidden treasures.
Are you ready to experience Portugal’s history, flavors, and stunning landscapes? Let TourTailors design your perfect escape.