Off the Beaten Paths of Basque Country & Alentejo Itinerary

A 8 day trip to Portugal & Spain 
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Stepping away from the beaten path offers a sense of tranquility and rich discovery during your custom tailored Spain and Portugal tour. Indulge in the exquisitely fresh flavors of the sea in a private cooking course. Stroll along historical homes crafted out of marble. Sip enchanting wines while basking in the view of rolling vines and bordering mountains. Witness captivating contemporary architecture and fascinating ancient ruins. From San Sebastian in Spain to Evora in Portugal, you will experience the pleasures that can only be found away from the familiar worn path. 

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Most tours are customized for private travel.

General Information

Detailed Itinerary

Places Visited 

Bilbao, Rioja, San Sebastian, Lisbon, Elvas, Borba, Monsaraz, Vila Viçosa, Estremoz, Evora, Marvao

Departure Dates 

Dates are flexible and customizable for private departures.

Detailed Itinerary 

Day 1: San Sebastian – In the Pleasures of San Sebastian

San Sebastian is a city of sophistication and relaxation, Old World charm and modern luxury, cobbled lanes, and golden beaches. Your flight arrives at San Sebastian Airport, where your private transfer greets you upon your arrival. The city fills with the aroma of the sea. Michelin Star restaurants open their doors along the cobbled lanes and boulevards, offering an array of scents from sautéing garlic to aromatic fennel, with each fragrance complementing the sea breeze. Surfers carve the waves rolling over Plaza de Gros. Elegant boutique shops line the lanes of Area Romantica, named for the 19th-century buildings connecting Playa de la Concha to the banks of the Urumea River.

You take the time to settle into the comforts of your luxury hotel overlooking the turquoise waters and verdant patches of forest along the Bay of Biscay. For an unforgettable introduction to the seaside city, you make your way to the summit of Monte Igueldo, located west of the town. A funicular travels up to the summit. The mountain reaches a height of nearly 525 feet above sea level, providing a perfect panorama of the rolling verdant mountains, graceful shoreline, and relaxed beachgoers along Playa de la Concha.

What’s Included: airport transfer, accommodation

Day 2: San Sebastian – In the Depths of San Sebastian

The morning light washes over the three 19th-century bridges crossing over the Urumea River. The water flows to the edges of the bay and splashes against the rocks, erupting in scattered white foam. The aroma of cappuccino layered with foam and dusted with chocolate emanates from the cafes in Old Town. The scent of pastries stuffed with cream and topped with cinnamon-sugar drifts through the streets of the El Centro, which circles the dramatic cathedral. Your guide greets you after breakfast intent on introducing you to the unforgettable sites of San Sebastian beginning with a stroll through Old Town.

In the morning, the fish market brims with life near Plaza de la Constitución. Fishmongers call out to passersby to check on the tables brimming with mussels, marlins, and sea basses. The 16th-century Church of San Vicente contains Gothic architectural style and remains the city’s oldest church, first erected in the late 16th century. Restaurants serve pintxos, the Basque version of tapas, filling the cobbled streets with the aroma of fried cod and handmade croquettes amongst the colorful balconies and bordering trees. In the afternoon, you meet a chef in a private kitchen.

The ingredients for producing a traditional Basque meal are displayed along the counter. Your chef greets you with open arms and an excitement deriving from teaching you the staples of Basque cuisine and San Sebastian flavors. In spring, locals enjoy Idiazabal cheese and green caviar. In autumn, locals cook mushrooms and sausage. Your guide introduces you to the colorful sweet peppers and green beans of summer. You begin to smoke the red peppers over small embers to impart the depth of flavor in the Pimientos de Piquillo, a dish of peppers stuffed with salt cod.

What’s Included: breakfast, dinner, tour, accommodation

Day 3: San Sebastian – Exploring La Rioja

The aroma of fresh orange juice accompanies the delicious scent of eggs with goat cheese in the morning. Cafes provide a relaxed pace to begin the day, with rich espresso helping to energize patrons to tackle their day. Your guide greets you in the hotel after breakfast and escorts you into the Basque division of the Rioja wine region. You begin in the town of Haro, which is renowned as the capital of La Rioja wines. The Old Quarter contains cobbled lanes and a series of taverns traveling in a horseshoe with Santo Tomas Church at the center.

A former church hidden behind a stone archway now offers a series of local pintxos, with the aromas of peppers and marinated olives drifting through the wooden doorways. The gothic Church of Santo Tomas contains 16th-century charm in the intricate sculptures along the south portal and baroque organ pipes towering over the choir loft. In the valley around Haro, you discover a sea of vines sweeping towards the bordering foothills. The first winery you visit opened in the 1890s and continues to produce wine with traditional and contemporary methods.

The vineyards encompass nearly 1,000 acres. While walking amongst the vines, you can touch the arid soil and dig your fingers into the pebbles protecting the roots from over saturation during the wet season. The landscape helps fortify the flavors of the grapes that become the wine. In the tasting room, your guide pours a sample of the Tempranillo and Graciano blend. The ruby hues fill the glass. You find notes of cinnamon, vanilla, and hints of chocolate drifting upwards from the wine, discovering an enjoyable balance and lasting flavor of cedar, caramel, and cherry on your palate.

What’s Included: breakfast, lunch, tour, accommodation

Day 4: Bilbao – A Brief History of Bilbao

The fishing boats return to the harbor after sunrise with fishermen carrying boxes of their daily catches to the marketplace. Surfers return to the waters along the quiet beach of Zurriola. Chocolate brioches fill the display windows of cafes across the promenade of La Concha. Your private transfer greets you at the hotel and leads you away from the stylish streets and golden beaches of San Sebastian, bound for the chic urban lifestyle of Bilbao. Images of the historical industrial port town have shaped the art and cuisine of the city, crafting in a dazzling display of architecture and culture embodied in the Guggenheim Museum. After checking into your hotel, you make your way with your private guide to view the galleries of the world-renowned museum.

The exterior architecture shimmers in the passing sunlight, with soft, curving lines seen as groundbreaking 20th-century architecture spanning nearly 258,335 square feet. Natural light pours into the central gallery. The white walls and halls shine bright circling layers of the upper stories. Paintings and sculptures are displayed alongside the walls of the galleries, contrasting the neutral tones for an extra burst of artistic color. Your guide leads you to the painting, The Raft of Medusa, by Jose Manuel Ballester. The piece focuses on the interpretation of space and light, reducing the former master painting of the same name to an image of a single raft.

What’s Included: breakfast, transfer, tour, accommodation

Day 5: Evora – The Splendors of Portuguese History

The San Anton Bridge crosses the river with double arches connecting to the more contemporary neighborhood of Ensanche. The Church of San Nicolas shimmers with gold stone and a soaring decadent cupola. The aroma of churros dusted with powdered sugar emanates from the café, which locals repeatedly return for the handmade pastries, rich espresso, and dark, gooey hot chocolate meant for the most ardent chocolate fan. Your private transfer greets you in the hotel and leads you to Bilbao Airport for your flight to Evora, Portugal. The city highlights the layers of history in the country, from the medieval town center to the Roman ruins, along with evidence of Neolithic monuments beyond the former town walls.

The city stands atop a small hill overlooking the Alentejo plains. Your private transfer greets you at Evora Airport and escorts you to a gorgeous hotel at the heart of the city, combining historical elegance with modern luxury. Meet your guide in the lobby to begin your tour of the charming streets, starting with the Templo Romano. The 3rd-century pillars stand atop a pediment in what was once the Roman Forum. The 14 Corinthian pillars with marble tops add to the uniquely and best-preserved Roman colonnade in Portugal. You continue to the Church of Saint Francis to find the remarkable Chapel of Bones, known for its décor of the former monks’ skulls and skeletons adorning the vaults and walls like mosaics.

What’s Included: breakfast, transfer, tour, accommodation

Day 6: Evora – Strongholds and Marble

After breakfast, you venture to the town of Elvas, located less than eight miles from the Spanish border. The ramparts of the 17th-century military town rise above the plain with flickers of golden sandstone. Cobbled streets weave through Old Town leading to Republica Square. The nave of Church of Nossa Senhora da Assunçao shimmers with blue and yellow tiles. Your guide points to the four metal hooks along the marble pillory in the square of Largo Santa Clara, which the local government would once shackle prisoners. From the outer ramparts of the historic city, you can see the Amoreira Aqueduct running more than four miles across the valley.

The layered archways reach more than 100 feet tall, numbering nearly 845 in total. Enter into a small ceramic workshop under the domed castle structure to discover ceramic tubes covered with a taught skin. The traditional musical instrument produces a humming sound similar to a cicada. The villages around Elvas flicker with bright-white stone, lending to their collective name as “Marble Towns.” You reach the town of Estremoz, whose 13th-century castle crowns the summit along the upper ridge. A marble statue of Queen Saint Isabel decorates the castle terrace, visible when visiting the 13th-century keep. The scent of the stone has a rich, earthiness, combining with the plum and caramel aromas drifting out of the charming taverns.

What’s Included: breakfast, lunch, tour, accommodation

Day 7: Evora – Alentejo at Leisure

The renaissance fountain at the center of the Moorish Plaza continues to trickle with water along the spherical design. The sun shed light on the arched colonnade of the 16th-century university adorned with sky blue ceramic tiles. The interior contains decorative tile panels representing the subjects taught inside the classrooms over time, including depictions of Aristotle and Plato. After breakfast, the day is yours to enjoy the region of Alentejo at your preferred pace, basking in the sunlight around the serene cafes or venturing to Lisbon for a day tour amongst the historical neighborhoods and lavish architecture. Continue your exploration of the region inside the majestic medieval village of Monsaraz.

The historic walls wrap around the village first fortified by the Knights Templar. Outdoor stairways and wrought iron balconies adorn the ancient houses steeped in white stone. Wandering along the main cobbled street of Rua Direita provides a view of the 16th and 17th-century whitewashed architecture leading to the parish church. A sphere representing the universe tops a pillar inside the plaza. Enchanting cafes offer fresh cappuccinos and pastries stuffed with citrus cream offering a scent of orang. The visions of storybook castles continue in Vila Viçosa, where orange and lemon trees offer a touch of color and citrus aromas to the whitewashed marble houses along the medieval lanes.

What’s Included: breakfast, accommodation

Day 8: Evora – Returning to the Beaten Path

The bakeries of Evora present Pastel de Tentugal, thin pastries dusted with powdered sugar, in their display cases, set against the bright yellow slices of pineapple promising sweet, exotic flavors. The walls of a lost 14th-century castle of the Palace of the Dukes of Cadaval continue to frame the private gardens decorating the museum. The galleries offer insight into the history of the region with illuminating 15th-century manuscripts and weaponry dating back to the 16th century. The aroma of roses blends with the scent of lemons blossoming in the garden. Your private transfer greets you at the hotel when you are ready, before escorting you to Lisbon Portela Airport for your flight home.

What’s Included: breakfast, airport transfer 


Starting Price 

This trip is customizable for your private travel.

What's Included 

  • Accommodations
  • In-country transportation
  • Some or all guided tours and activities (dependent on season)
  • Expert trip planning
  • 24x7 support during your trip
The starting price is based on travel during the low season for a minimum of two travelers staying in shared 3-star accommodations. Please inquire for a custom trip quote based on your travel preferences and travel dates.