Day 1 – Lisbon, Portugal

Arrive in Lisbon, the capital of Portugal. Perched on seven hills, Lisbon welcomes travelers with its laid-back charm. As arrival times will vary, there is no scheduled sightseeing today. Spend the day as you wish, exploring the city independently. At a local restaurant, meet your fellow travelers for a welcome dinner to officially kick off your adventure.

Day 2 – Lisbon

Good morning, Lisboa! Start your day like a local with a walk to the Metro. Meander through historic neighborhoods, hearing stories that bring the city and its colorful neighborhoods to life. Begin in Lisbon’s chic Chiado district, learning about the 1755 earthquake and the 1974 Carnation Revolution. Continue to Praça do Comércio for views over the Tagus River and a tasting of traditional ginjinha. The city tour ends around noon, followed by free time until dinner in the evening. Over dinner, experience an Impact Moment, learning how this inspiring restaurant empowers individuals experiencing homelessness through culinary training and social reintegration.

Day 3 – Lisbon

It’s your day to experience Lisbon at your own pace. With plenty of free time in the capital city, you may wish to check out its famous culinary scene or venture downtown to do some shopping. If you’d prefer, you may opt to join an excursion to visit the colorful Pena Palace, one of Portugal’s most iconic landmarks, before continuing to the picturesque seaside town of Cascais, where you’ll have time to explore at your leisure.

Day 4 – Lisbon – Tomar – Porto

Depart Portugal’s capital city and head to Tomar, home to some of the country’s historical jewels, including the Templar Castle and Convent of Christ (UNESCO). Explore the octagonal Templars’ Rotunda and imagine the day-to-day life of a warrior monk. Next stop: Porto! Take in the landscape of wild pine trees as you leave Tomar and embark on a two-and-a-half-hour drive to Portugal’s second largest city.

Day 5 – Porto

Today, an extensive walking tour of Porto reveals its many charms. See the São Bento railway station, which opened in 1916 and is one of Portugal’s most striking architectural gems. Visit the Bolsa Palace (UNESCO) — known as the Stock Exchange Palace, a 19th-century neoclassical masterpiece, and finish your morning crossing the river to Vila Nova de Gaia for a visit and a taste of the port wine production scene. Later in the afternoon, head just outside Porto for a home-hosted experience. Join your host family to prepare a beloved local dessert and share a warm, authentic dinner together.

Day 6 – Porto – Douro Valley

Today, say tchau to Porto and set out for the Douro wine region, where the Douro Valley blends natural beauty with rich history, culture, and a renowned food scene. On the way, stop at one of Portugal’s most famous wineries for a tasting and a visit to its stunning Baroque palace. This afternoon, embark on a relaxing boat ride along the Douro River, passing terraced vineyards and dramatic landscapes. Then settle into your winery hotel in the heart of the Douro Valley for the next two nights. This evening, enjoy dinner featuring traditional Portuguese cuisine.

Day 7 – Douro

Spend a relaxed morning enjoying the picturesque grounds of your winery hotel, nestled in the heart of the Douro Valley. This UNESCO World Heritage site is known for its breathtaking landscapes and long tradition of winemaking. After soaking in the serene atmosphere, roll up your sleeves for a hands-on cooking class where you’ll prepare and savor a light lunch of petiscos, the Portuguese style of small, shared plates. Enjoy the end of the day on your own.

Day 8 – Douro – Salamanca, Spain

Depart the Douro wine region and cross the border into Spain. Head to an olive grove and learn about this family-owned business, known for its dedication to traditional methods of olive cultivation and oil production. During your visit, sample high-quality olive oil, renowned for its rich taste and health benefits. The tasting will be accompanied by a light lunch featuring local dishes that perfectly complement the olive oil. End your day in Salamanca with an orientation walk to help you find your preferred spot for dinner on your own.

Day 9 – Salamanca

In Salamanca, step back in time on a walking tour with your local guide as you discover the city’s rich history. Visit the Cathedral of Salamanca, which is actually two churches joined together from the 12th–13th and 16th centuries, and stroll through the historic University of Salamanca, the oldest university in Spain, imagining student life through the ages. Afterward, enjoy free time to explore Salamanca at your own pace. With more than two thousand years of history and beautiful sandstone architecture, this charming city is a true hidden gem.

Day 10 – Salamanca – Burgos – La Rioja

Today, leave for the famous Rioja wine region. On your way, stop in Burgos and set out on a walking tour, discovering the city’s pedestrian-friendly riverside to the historic Plaza Mayor. As you make your way back to Rioja, stop at a local winery nestled in the center of Spain’s beautiful Basque Country. Taste some of the wines and walk through the vineyards before heading to your hotel. Arrive in La Rioja, your home for the next two nights.

Day 11 – La Rioja (Option to Pamplona)

Today is yours to enjoy at leisure. Stroll into the historic center to see the Concatedral de Santa María de la Redonda, or visit the renowned Bodegas Franco-Españolas if you would like to sample local wines. You might also explore Logroño’s Camino de Santiago heritage with a walk across the medieval Puente de Piedra. Or perhaps you’ll choose to join an optional excursion to Pamplona, the capital of Navarra and home to the famous San Fermín festival and its legendary Running of the Bulls.

Day 12 – La Rioja – Vitoria – Bilbao

Begin your adventure with a visit to Vitoria, the capital of the Basque Country. Embark on a walking tour through its enchanting old town, where you’ll encounter a tapestry of historic buildings and bustling squares. The charm of this area is unmistakable, with every corner offering a glimpse into the city’s rich past. Continue to Bilbao, a city where tradition meets cutting-edge design. End your day with an immersive audio-guided visit to the iconic Guggenheim Museum, a striking symbol of modern architecture and contemporary art.

Day 13 – Bilbao

Put on comfortable walking shoes and get ready for a day of discovery. This morning, it’s your choice! Explore the glimmering Spanish coastline during a guided tour of the coastal villages of Mundaka and Bermeo -OR- take a leisurely hike along the Camino de Santiago, “the Way of Saint James” for a scenic experience along this world-famous route. Then, set off for an extensive walking tour of Bilbao, a city known for its avant-garde architecture and rich history. Wander through the old town, Casco Viejo, with its charming streets and vibrant atmosphere, alongside a local expert.

Day 14 – Bilbao – San Sebastián – Bilbao

Set off for San Sebastián, beginning the morning with views of the city’s beautiful coastline. Wander through the Old Town as the aroma of freshly prepared pintxos fills the air, setting the stage for a guided food tour through the heart of Basque cuisine. Visit iconic bars and local favorites while sampling a variety of traditional and inventive pintxos, each highlighting the region’s rich culinary traditions. Later, you may wish to take a leisurely walk along La Concha Beach, where golden sands and sweeping views of the Bay of Biscay offer the perfect way to end your time in San Sebastián before returning to Bilbao. Tonight, toast to a wonderful trip with your fellow travelers.

Day 15 – Bilbao – Tour Ends

Today, your tour of Portugal and Spain comes to a close — may your memories be your favorite souvenirs.