Proposal Destinations: A Trip to Portugal & Spain
A Custom Journey Designed for Two
Trip Highlights
- Historical Walking Tours in Portugal
- Douro Valley Sailing Experience
- Gastronomic Society Experience
- Regional Tastings in the Basque Country
“The detail and care put into the itinerary were noteworthy. Traveling can be a very stressful experience. I felt zero stress on this trip.”
Let us take you there by highlighting some of their unforgettable, custom experiential moments that highlight our ability to craft custom travel:
Historical Walking Tours in Lisbon, Toledo, and Bilbao
There’s no better way to know a place than by walking it, and this couple experienced this step after step through centuries of history. While in Lisbon, the scent of pastéis de nata drifts from neighborhood bakeries as trams rattle along steep cobbled streets. Toledo, a city of three cultures, they were immersed in layers of Moorish, Jewish, and Christian history within its medieval walls. In Bilbao, sleek modernity met the old-world charm of the Casco Viejo, where the Guggenheim’s shimmering curves contrast with the historic bridges arching over the Nervión River. At each stop, our guides offered the stories that bring these places to life.
Douro Valley Vineyards & Private Sailing
Terraced vines cascade down the hillsides of the Douro Valley, where this couple savored winemaking traditions that stretch back over 2,000 years. Here, the rhythm of the river set the pace as they embarked on a private cruise along the Douro. This part of their journey allowed for an intimate view of the UNESCO-listed landscape, with glasses of port in hand and the sun casting golden light over the hills. Visits to small, family-run estates introduced them to the art of port production, where time and patience yield rich, complex flavors. The many beautiful moments of this trip culminated in their proposal here—surrounded by vineyards and history. It was like something out of a dream.
San Sebastián’s Gastronomic Societies
Still floating from their new engagement, their next stop was San Sebastián where food is more than sustenance—it’s ritual, tradition, and identity. Few experiences capture this better than a night inside a private txoko, or gastronomic society. With a local chef guiding the way, the couple joined in the preparation of Basque specialties, slicing jamón ibérico, stirring pots of velvety pil-pil sauce, and grilling txuleta over hot embers. There were no menus, just an understanding that good food and great company are all that’s needed. To cook, to toast, to eat at leisure—this is the rhythm of Basque dining at its most authentic.
Exploring the Small Villages of the Basque Country
As the finale of their beautiful destination engagement, they traveled beyond San Sebastián, where winding roads led to the villages where Basque traditions are fiercely preserved. In Getaria, the salty sea breeze carried the scent of freshly grilled turbot from waterfront asadores. At a small txakoli winery, crisp, slightly effervescent white wine was poured high into glasses, the traditional Basque way. Time seemed to slow in these hamlets, where centuries-old cider houses and family-run pintxos bars still follow the customs of generations past. These moments—simple, unhurried, deeply rooted—were what made the trip unforgettable.
Your Adventure Awaits
Custom travel—like this trip to Portugal and Spain—is about the memories you make and not just the passport stamps you collect. No two travelers experience a place the same way. That’s why our Custom Travel team tailors every detail to your preferences, from choosing the right mix of structure and spontaneity to ensuring the most meaningful moments happen seamlessly. Whether you dream of a private sailing through the Douro Valley, a behind-the-scenes look at Basque cuisine, or a leisurely winetasting ending in a surprise proposal, we’re here to craft an itinerary that’s uniquely yours.
Start Your Journey Here