2-Week Guided Itinerary Through Portugal

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Your Two Week Portugal Tour Plan

Unveil the mysteries and marvels of Portugal on this two-week, driver-guided itinerary. From the bustling streets of Lisbon to the medieval charm of Óbidos, the sun-kissed beaches of the Algarve to the terraced vineyards of the Douro Valley, every corner of Portugal beckons with stories, flavors, and sights that captivate the senses.

Navigate the nation’s vast landscapes with the expertise of a seasoned guide, ensuring not a single gem goes unnoticed. Whether you’re a history enthusiast, a beachcomber, a wine aficionado, or someone seeking the soul of Portugal, this carefully crafted itinerary promises an immersive experience into the country’s rich tapestry of culture, tradition, and natural beauty.

Prepare to embark on an unforgettable voyage through the heart and soul of Portugal!

Destinations On Our 14-Day Portugal Itinerary:

Day 1: Lisbon: Dive into the Capital's Rich Heritage

Jeronimos Monastery in Lisbon, Portugal
Jeronimos Monastery in Lisbon, Portugal

Lisbon, the capital city of Portugal, greets visitors with its magnificent balance of history, culture, and contemporary vibrance. Nestled across seven hills, the city offers an enticing blend of architectural wonders and modern urban flair.

Your private driver will collect you from the airport and deliver you to your accommodation in the center of Lisbon in style with our deluxe air-conditioned vehicle as you prepare to experience your first day in the Capital.

Belém Tower: Guardian of Lisbon's Legacy

Embark on a guided exploration of Belém Tower, a majestic emblem of Lisbon’s coastal heritage.

This monumental guardian, crafted in the glory days of Portugal’s Age of Exploration, stands tall, recounting tales of maritime ventures and global discoveries. With each stone and battlement, relive the era when Portugal unfurled its sails to chart unknown territories.

Jerónimos Monastery: Manueline Majesty and Maritime Legends

Just a brief walk from the tower, immerse yourself in the grandeur of Jerónimos Monastery.

This architectural masterpiece, carved in the distinctive Manueline style, narrates tales of monastic devotion and maritime adventures. Within its hallowed halls, pay homage to the legendary Vasco da Gama, whose final resting place is beautifully nestled in this historical gem.

Historic Tram Ride and Alfama District

Board the famous Tram 28 for a ride that takes you through the heartbeat of the city.

It winds through various iconic neighborhoods, with the ancient Alfama district standing out. Its narrow alleyways resonate with the melodies of Fado music and exude the tantalizing aroma of traditional Portuguese dishes.

Lisbon's Culinary Scene

End the day immersed in Lisbon’s rich culinary landscape. Relish the creamy texture of the renowned ‘pastel de nata’ and savor the fresh seafood dishes served at the bustling local eateries or vibrant food markets.

Day 2: Lisbon to Sintra: Fairy-tale Palaces and Gardens

image of colorful Pena Palace in foreground with city of sintra in background
Pena Palace, Sintra, Portugal

The journey from the bustling streets of Lisbon to the enchanting realm of Sintra, where fairy-tale palaces and lush gardens await. Dive into a world of regal splendor and natural beauty, found just 30 minutes away from the CapitalCapital, with your private driver and vehicle.

Private Guided Experience at Pena Palace

Accompanied by your private guide, immerse yourself in the vibrant hues and diverse architecture of Pena Palace.

Perched on a hilltop, this gem blends Moorish, Manueline, and Gothic influences, creating a unique aesthetic wonder. Wander further into its captivating gardens, uncovering hidden trails, decorative statues, and an array of exotic plants, all while your guide unveils the palace’s tales and secrets.

Historic Heart of Sintra

With your guide leading the way, descend into the heart of Sintra. Navigate the intertwining lanes, where Moorish history lingers at every corner. Listen closely as your guide brings to life the legends and stories that have shaped this ancient town.

The Moorish Castle: A Journey to Sintra's Past

Experience the majestic ruins of the Moorish Castle with your private guide. As you traverse its stone pathways, ancient towers, and crumbling battlements, be treated to unrivaled views, with the colorful Pena Palace dotting the landscape.

Your guide will weave tales of the castle’s past, giving voice to the stones beneath your feet.

Return to Lisbon in the evening.

Day 3: Evora: UNESCO Heritage and Roman Roots

Cloister of the Evora Cathedral, the largest cathedral in Portugal_
Evora Cathedral, Portugal

Your journey to the historical heart of Évora starts with a comfortable pick-up from your Lisbon accommodation by a private driver for the 1.5-hour journey.

Evora's Roman Temple: A Glimpse of the Past with an Expert Guide

Upon arrival in Évora, your knowledgeable guide leads you to your first stop, the iconic Roman Temple or the Temple of Diana.

Marvel at its Corinthian columns that once graced a thriving Roman city in the 1st century AD. With a wealth of knowledge, your guide paints a vivid picture of Évora’s ancient Roman significance, allowing you to immerse yourself in a bygone era.

Chapel of Bones

Delve deeper into Évora’s history with a visit to the evocative Chapel of Bones. Your guide explains the significance of this unique chapel, adorned with human bones and skulls.

As you take in the weighty inscription, “We bones, lying here, for yours we wait,” reflect on life’s transience and the historical context behind this architectural marvel.

The Bustle of Giraldo

As the day progresses, your guide brings you to the heart of Évora’s lively culture: Giraldo Square.

Admire its Renaissance fountain and surrounding arcaded buildings that echo tales from the past. However, it’s not just the structures that captivate. The square pulses with life, and with the guidance of your expert, you navigate the bustling market scene.

Explore stalls that showcase the best of local craftsmanship, fresh produce, and sumptuous delicacies, gaining insight into the daily life and traditions of the people of Évora.

Return to Lisbon

Rejoin your driver for the ride back to your accommodation.

Day 4: Monsaraz & Alentejo: Wine Tasting and Hilltop Views

Old vineyards with red wine grapes in the Alentejo wine region near Evora, Portugal Europe
Alentejo Vineyards, Portugal

Journeying towards Monsaraz, the horizon reveals a village perched atop a hill overlooking the expansive Alqueva Dam. Monsaraz, with its narrow streets paved in schist, feels like a step back in time.

The castle walls provide a vantage point, offering panoramic views of the Alentejo plains and the waters below. Each corner of this ancient village tells tales of Moorish knights and battles of yore.

Alentejo: The Vineyards' Call

As the afternoon sun casts a golden hue over the vast Alentejo plains, you’re introduced to one of Portugal’s best-kept secrets – its wines.

In the heart of Alentejo, expansive vineyards roll into the horizon, beckoning oenophiles and enthusiasts alike. Here, traditional wine-making methods blend seamlessly with modern techniques.

Wine Tasting Experience

At a renowned local winery, be greeted by local experts who have preserved wine-making traditions passed down through generations.

Delve into the wine-making process, from vine to bottle, culminating in a tasting session. As you swirl, sniff, and sip, the complex notes of Alentejo wines reveal themselves, from bold reds to crisp whites. Accompanied by local cheeses and charcuterie, it’s a sensory journey like no other.

End your day with a serene walk through the vineyards. As rows of vines stretch in every direction, there’s a palpable sense of peace, with only the whisper of the wind and a glass of wine in hand, embodying the spirit of Alentejo.

We booked with Emily solely after reading these reviews for a 2 week trip to Portugal and southern Spain. Never met her prior. She and her team exceeded our expectations. Every detail of the trip went smoothly and her planning was perfect for our group. Lots of guided tours intermingled with just the right amount of free time. We challenged Emily and her team with 3 generations of travelers from 18 months to upper 60's and she handled our group perfectly with details such as baby seats in cars and cribs in hotel rooms. Our trip included Lisbon, Porto, Sevilla, and Madrid with day trips to Cordoba, Rhonda and and a small "white city." All in, we would highly recommend Emily and her team for any travel in Spain and Portugal. She also does Morocco but we didn't have time for that.
Gene Petrie (US)
★★★★★

Day 5: Setúbal and Troia Peninsula: Coastal Retreat

Comporta Beach at the Troia Peninsula in Portugal
Comporta Beach at the Troia Peninsula in Portugal

Discover the serene beauty and rich history of Setúbal and the Troia Peninsula on this day tour. Journey through picturesque coastal landscapes, exploring charming towns, ancient ruins, and pristine beaches in one of Portugal’s most captivating regions.

Setúbal’s Dolphin Haven

The morning sun glimmers over the Sado Estuary as your day begins with a promise of a rare spectacle – the resident bottlenose dolphins playfully swimming in their natural habitat.

Climb aboard the boat we have rented with your private captain and cruise through the estuary, with your captain pointing out these magnificent creatures, making for a truly magical experience.

Troia's Unspoiled Beauty

A short ferry ride takes you to the Troia Peninsula, where miles of golden sand await.

Time seems to slow as you walk along the pristine beaches, the waves gently lapping at your feet. It’s a haven for those seeking tranquility away from the bustle.

Seafood Delights in Setúbal

As evening approaches, return to Setúbal to indulge in its culinary offerings. Known for its seafood, the town’s restaurants serve dishes fresh from the ocean. From grilled sardines to cuttlefish stew, every meal is a testament to the region’s rich marine bounty.

Day 6: Algarve (Lagos): Beaches, Cliffs, and Cultural Heritage

Private tour of Coves and cliffs at Ponta da Piedade in the Algarve region.
Ponta da Piedade the most famous spot of Algarve region, in Portugal

Begin your day in Lagos with a visit to the breathtaking cliffs of Ponta da Piedade. Marvel at the dramatic limestone formations carved by centuries of sea erosion, creating secluded beaches and grottoes.

A guided boat tour offers an intimate view of this natural wonder, letting you navigate through arches and caves.

Lagos' Historical Tapestry

The charm of Lagos extends beyond its natural beauty.

Stroll through its historic center, where the cobbled streets echo tales of seafarers and explorers. The ancient city walls, the Forte da Ponta da Bandeira, and the ornate Santo António church collectively narrate a tale of a city steeped in history.

Evening By the Sea

End your day by the seafront promenade.

As the horizon turns orange and pink, the ambient sounds of Fado music emanate from local bars, and the aroma of Algarvian cuisine fills the air, making for a perfect culmination to your day in Lagos.

Overnight in Lagos.

Day 7: Algarve (Sagres & Cape St. Vincent): The Edge of Europe

Drone image of Cape St. Vincent, Portugal, Algarve
Cape St. Vincent, Portugal, Algarve

Your day begins in Sagres, where legends of explorers and navigation schools come to life. Its towering cliffs have watched over centuries of maritime history. The town’s atmosphere, steeped in stories of seafarers, is palpable as you stroll through, with the sea breeze carrying tales of ancient maritime adventures.

Fortaleza de Sagres: Sentinel of the Seas

Perched dramatically on cliff edges, the Fortaleza de Sagres offers panoramic vistas of the fierce Atlantic.

While its stone walls and battlements have withstood pirate attacks and time itself, the real allure lies in the expansive horizon it overlooks. At Fortaleza de Sagres, you’re not merely observing a landmark; you’re witnessing the confluence of history and nature.

Cape St. Vincent: Europe's Dramatic End

A short drive brings you to Cape St. Vincent, the continent’s southwesternmost tip.

Known as the ‘End of the World’ in ancient times, the sheer cliffs plunge dramatically into the roaring waves below. The lighthouse, standing tall, is a beacon to ships and offers views that are a feast for the eyes.

Return to Lagos in the evening.

Day 8: Algarve (Faro): Nature, History, and Gastronomy

Faro, Old Town, Portugal
Faro, Old Town, Portugal

Dive into Faro’s rich tapestry, starting with the Cidade Velha (Old Town). Encircled by ancient city walls, its labyrinthine cobbled streets, Gothic cathedrals, and stately squares whisper tales of its Moorish and Roman past. Every corner turned unveils a new piece of Faro’s intricate historical puzzle.

Ria Formosa Natural Park: A Haven for Nature Lovers

Escape the city’s confines as you venture into Ria Formosa Natural Park. This series of islands and lagoons is a sanctuary for migratory birds and a diverse marine life.

Whether you’re kayaking through its calm waters or observing the myriad of bird species, nature’s symphony plays in the background.

Return to Lagos.

Day 9: Portimão and Silves: Riverfront Elegance and Moorish Castle

Village of Silves, Alrgarve, Portugal
Village of Silves, Alrgarve, Portugal

Begin your journey in the bustling coastal town of Portimão.

Its modern marina is a testament to the town’s maritime traditions, with elegant yachts dotting the water, reflecting the golden hues of the sunrise.

Stroll along the promenade, feeling the gentle ocean breeze as you admire the juxtaposition of contemporary luxury against the town’s historic backdrop.

Arade River: A Tale of Adventure

The Arade River, weaving its way through Portimão, provides an avenue for aquatic adventures. Whether you choose a peaceful boat ride or opt for more exhilarating water sports, the river ensures a splash of excitement to your day.

Silves: Echoes of the Moors

Journey into the heart of Silves, a city that once thrived as the Moorish Capital of the Algarve.

Dominating its skyline is the formidable Silves Castle. This red sandstone fortress, with its robust battlements and towers, is a window into the city’s storied past. As you navigate its walls, tales of Moorish rulers, Christian conquerors, and ancient battles come alive.

Day 10: Lisbon Private Day Tour: Hidden Gems and Cultural Riches

skyline of alfama at lisbon, portugal at dawn
Lisbon, Portugal

Return to Lisbon with your private driver as you dive deep into Lisbon’s lesser-known treasures with this immersive day tour, crafted to unveil the city’s hidden gems and cultural heart.

From panoramic vistas to culinary delights and soulful melodies, embark on a journey that bypasses the usual tourist trails, revealing the true essence of Portugal’s radiant Capital.

Miradouro da Senhora do Monte

Start your day at one of Lisbon’s highest points. With your personal guide, watch the city come alive with the sunrise from this vantage point, offering sweeping views of Lisbon’s hills, the Tagus River, and iconic landmarks.

LxFactory Tour

Located in a transformed industrial complex, LxFactory is a testament to Lisbon’s modern renaissance. Wander through quirky boutiques, innovative art studios, and lively cafes.

Your guide will share tales of this area’s transformation from a manufacturing site to a contemporary cultural hub.

Estrela Basilica – Baroque Brilliance

Explore the grandeur of the Basilica da Estrela, a stunning Baroque and neo-classical church. Your guide will highlight its ornate features, from detailed mosaics to its imposing dome. Outside, the adjacent Estrela Garden provides a serene spot for a stroll.

Time Out Market, Culinary Journey

Dive into Lisbon’s gastronomic scene at the Time Out Market. Your guide will introduce you to local flavors and traditions, recommending stalls offering the best Portuguese cuisine, from fresh seafood to pastries.

Museu Nacional do Azulejo

Discover Portugal’s love affair with tiles (azulejos) at this dedicated museum. With your guide elucidating, witness the evolution of design and style over centuries, and understand the cultural significance of this art form.

Fado Experience at A Tasca do Chico

Round off your day soaking in the soulful strains of Fado, Portugal’s traditional music, in the intimate setting of A Tasca do Chico. While the melodies serenade, your guide will decode the deep-rooted emotions and stories embedded in each song.

Amazing! Great vacation, great time. They handled everything for us. All transfers and tours were taken care of. We didn’t wait in lines. Whenever any issues arose. They solved them before we even knew about them. Can’t say what a pleasure it was to work with them, and to visit these beautiful countries! Worth, every penny! Priceless memories that even the beautiful pictures can’t describe enough. Especially loved the dinner we made at the cooking class in Barcelona and the balloon ride in Segovia. But everything was wonderful!
Todd Runyan (US)
★★★★★

Day 11: Full-Day Guided Tour: Fátima and Óbidos from Lisbon

Private tour at the Basilica of our Lady of Fatima.
The Basilica of our Lady of Fatima, Portugal

Begin your day with a comfortable ride in a private vehicle as your knowledgeable guide sets the stage for a day of historical discovery and spiritual reflection.

The scenic 1 hour and 15-minute drive from Lisbon sets the mood for the beautiful destinations awaiting you.

Óbidos: A Medieval Gem

Enter the town through the ornate gates, and immediately you’ll be transported back in time. Encircled by formidable walls, Óbidos’ narrow, cobbled streets and whitewashed houses adorned with vibrant flowers offer a postcard-perfect setting.

Your guide will lead you through the town’s labyrinthine alleys, pointing out historically significant sites and sharing tales of the town’s rich tapestry of history.

Ascend the medieval castle walls and walk along them to get panoramic views of the town and surrounding vineyards. The castle, a testament to different civilizations that once occupied the town, also offers insights into Óbidos’ historical significance.

Fátima: Sanctuary of Faith

Upon arriving in Fátima, one of the world’s most venerated Marian shrines, you’ll immediately sense its unique ambiance of tranquillity and reverence.

The vast plaza surrounding the shrine sees millions of pilgrims every year, each drawn by their faith and the stories of the apparitions of the Virgin Mary to three shepherd children in 1917.

Chapel of the Apparitions

Step onto the hallowed grounds where, over a century ago, the Virgin Mary is believed to have manifested before three shepherd children.

As you stand on this revered spot, take a moment to light a candle in remembrance or in prayer. With every flicker, feel the weight of countless pilgrims’ hopes and pleas. The ambient tranquility surrounding the site encourages introspection and offers an enveloping sensation of peace felt by believers and non-believers alike.

Basilica of Our Lady of the Rosary of Fátima

Moving onwards, the grandeur of the Basilica of Our Lady of the Rosary of Fátima stands as an imposing tribute to the apparitions and their spiritual legacy.

Marvel at its impressive neoclassical architecture, a testament to the artistic and devotional aspirations of those who built it. Venture inside to explore its intricately adorned interiors. The tombs of the three shepherd children, Lucia, Francisco, and Jacinta, now canonized saints, find their eternal resting place here.

As you stand before their tombs, reflect on their profound journey from simple shepherds to pivotal figures in Catholicism.

Museum of Sacred Art and Ethnology

To delve deeper into the rich tapestry of Fátima’s religious history, the Museum of Sacred Art and Ethnology stands ready to illuminate.

Each artifact, whether a delicate chalice or a centuries-old scripture, tells a tale of devotion, artistry, and tradition.

Overnight in Coimbra.

Day 12: Coimbra: Portugal's Medieval Capital

Coimbra City Viewpoint, Portugal
Coimbra City Viewpoint, Portugal

Your exploration of Coimbra must commence at its renowned university. Established in the 13th century, the University of Coimbra stands as one of the world’s oldest institutions of learning. Its grand buildings, like the Joanina Library, with intricately carved wood and gold leaf, hold centuries of academic achievements within their walls.

Roman Ruins and Architectural Wonders

Unearth Coimbra’s layered history as you stumble upon remnants of Roman occupation.

These ancient structures, coexisting with Gothic cathedrals and Baroque churches, paint a mosaic of the city’s rich past. Every alleyway and square in Coimbra speaks of epochs gone by, ensuring a deeply immersive historical experience.

River Mondego: Coimbra’s Lifeline

Running through the city, the Mondego River has been an eternal witness to Coimbra’s evolution. A stroll along its banks provides both serenity and scenic beauty, with the city’s landmarks reflecting off its shimmering waters.

As the day draws to a close, the riverside lights up with local life, making it a perfect spot to soak in the ambiance and reflect upon your journey through Portugal’s medieval heart.

Overnight in Porto.

Day 13: Porto: Riverside Beauty & Port Wine

Porto city skyline at Porto Ribeira and Douro River and Dom Luis I Bridge
Dom Luis I Bridge, Porto, Portugal

As your feet touch the cobbled streets of Porto’s historic Ribeira District, you’re instantly transported to another era.

This UNESCO World Heritage site, with its narrow alleyways, ancient buildings, and lively squares, offers a tapestry of Porto’s rich past. Overlooking the Douro River, the district provides stunning views, particularly during sunset when the golden rays bathe the cityscape.

Luis I Bridge: Architectural Majesty

Spanning the Douro River, the iconic double-deck iron bridge, Dom Luís I, stands as a testament to Porto’s architectural prowess.

As you traverse this engineering marvel, either on its lower or upper decks, you’re treated to breathtaking views of the city and its riverside beauty.

Port Wine Cellars: A Taste of Tradition

Porto’s soul lies not just in its historic edifices but also within its wine cellars.

Visit one of the renowned cellars nestled along the riverbanks to delve deep into the world of Port wine. Let expert sommeliers guide you through a tasting journey, where each sip tells a story of tradition, terroir, and time.

Emily is absolutely fantastic! She is super accommodating to our needs and comes up with wonderful itineraries tailored to our liking. Most importantly, she is flexible to last minute changes and requests, as we all know things can change duration vacation. We will recommend them to all our friends and will use them in the future! Also, the guides she works with are all fantastic! The best part of her tours!
Mona Ascha (US)
★★★★★

Day 14: Douro Valley: Terraced Vineyards and River Cruise

Porto city skyline at Porto Ribeira and Douro River and Dom Luis I Bridge
Dom Luis I Bridge, Porto, Portugal

Begin your day amidst the mesmerizing terraced vineyards of the Douro Valley. These meticulously maintained terraces, cascading down the valley’s slopes, present a stunning visual spectacle, especially during harvest season. The very land here seems to be in symphony with the region’s winemaking traditions.

Douro River Cruise

Board a traditional Rabelo boat for a serene journey along the Douro.

As the boat gently glides on the river, you’re surrounded by undulating hills adorned with vineyards and punctuated with Quintas (wine estates). This leisurely cruise offers unparalleled views of the valley and a sense of tranquility that only nature can bestow.

Wine Estates

No visit to the Douro Valley is complete without stepping into one of its quintas.

These wine estates, often housed in grand manors with histories spanning centuries, offer more than just wine tasting. They provide an immersive experience – from understanding the nuances of grape cultivation and wine production to savoring gourmet meals that celebrate local flavors. As the day concludes, lift a glass to the valley’s bounteous beauty and the memories you’ve garnered.

Emily owner of guided spain tours

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Over two weeks, we’ve traversed the diverse landscapes of Portugal, from the bustling streets of its cities to the serene expanses of its countryside, from coastal havens to terraced vineyards.

Yet, this journey only scratches the surface of what Portugal has to offer. If you’re inspired to uncover more or wish for an experience tailor-made to your desires, our dedicated team awaits your call. Dive into a bespoke Portuguese adventure crafted just for you. Contact us, and let’s curate your perfect journey together.

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