In travel, some moments transcend sightseeing—they connect us to something deeper. This journey took us, along with two friends, to the breathtaking Azores, a chain of volcanic islands in the Atlantic Ocean. It was another reminder of how travel can weave together personal stories and ancestral ties—something I strive to create for my clients at AMG Inspired.

With its volcanic landscapes and rich maritime history, the Azores hold a special allure not only for travelers seeking natural beauty but also for those tracing their Portuguese roots. Many families in the United States, Canada, and Brazil have ancestral ties to these islands, making them an inspiring destination for heritage travel.

Inspired by our family’s heritage trip to Italy, our friend Jeff shared his dream of visiting the volcanic island that had captured his imagination as a child—the mythical place of family stories. “Let’s go,” I said. “I can make it happen.” With great honor, I crafted an itinerary centered on his heritage, blending personal interests and discovery on mainland Portugal with the stunning landscapes of the Azores.

Our journey began in Lisbon and took us to Horta to explore the tranquil charm of Faial Island before crossing the channel to Pico Island. After Faial, we would continue to São Miguel Island, the largest of the Azores, before wrapping up our adventure in Porto and Lisbon.

As the morning light broke, our ferry from Horta arrived at the Madalena port on Pico Island. Jeff stood still, swept by emotion—a sense of connection to a man he had never met but whose choices had profoundly shaped his life. For Jeff, this wasn’t just a trip; it was a homecoming.

The day before, we had stood together at a lookout point on Faial, gazing across the channel at Pico Island. Its towering volcano was shrouded in clouds, as though veiling the stories of the past—stories tied to Jeff’s great-grandfather, who had left this very place more than a century ago for San Francisco. Jeff was the first in his family to return to Pico since his great-grandfather’s departure. Though the reasons behind his ancestor’s emigration remained unclear, the significance of standing on ancestral soil was profound.

Jeff reflected on the courage and hope that define so many immigrant stories—a universal thread woven into countless families. For most of us, no matter how far removed, our roots trace back to lands we may only know through stories. Some feel a strong bond, while others are simply curious. But here on Pico, the connection was palpable, as though the island itself remembered and welcomed Jeff home.

At a café near the port, we met Andrei, our guide, whose enthusiasm for Pico’s volcanic history and culture was infectious. As he drove us along narrow roads bordered by black volcanic stone walls, the island’s fiery origins were unmistakable. We stopped at a historic windmill overlooking a vast grid of ancient stone enclosures, built to shield grapevines from the salty ocean breeze. Unlike trellised California grapes, Pico vines run along the ground, spanning over volcanic rock, enclosed by black basalt stone walls. These UNESCO World Heritage vineyards hold a history as rich as the wine they produce.

Once celebrated as the drink of Russian Czars and European nobility, Pico’s wine industry came to an abrupt halt in the 19th century. Imported American vines brought invasive aphids called phylloxera, which destroyed the vine roots along with the profitable industry. Forced to adapt, many locals turned to the perilous occupation of whaling. Today, sperm whales are only watched, and a revival is underway as a new generation works to restore the historic vineyards, rekindling a nearly lost tradition.

Our journey then took us to Lajes do Pico, a charming seaside village that once thrived on whaling. For Jeff, this stop held a deeply personal significance—it was his great-grandfather’s birthplace, where he had worked as a whaler before emigrating to California. Walking along narrow cobblestone streets lined with basalt rock walls and whitewashed buildings, Jeff felt the gravity of stepping into his ancestor’s world. The life his great-grandfather had left behind was one of risk, resilience, and ultimately, sacrifice.

From Lajes, we ascended the slopes of Pico’s towering volcano, a dense mist enveloping the landscape. Along the way, we encountered a quintessential “Pico traffic jam”—a local herding cows down the road, moving them along with ease and familiarity in his shorts and rain boots, his truck left idling behind. Later, while hiking toward some lava tubes, we passed more cows grazing peacefully in misty pastures. These small moments reflected the island’s agrarian traditions and its deliberate pace of life.

Andrei guided us into a labyrinth of lava tubes—dark, twisting passageways that shimmered on the rocky surfaces with highly fragile iridescent bacteria, which we took great care not to touch. These underground formations, carved by molten rivers of lava, stood as a powerful reminder of the forces that shaped this land and its people. The volcanic conditions that forged these tubes also contribute to Pico’s distinctive vineyards. 

As such, no visit to Pico would be complete without wine tastings. As the day drew to a close, we arrived at a strikingly modern winery set amid basaltic vineyards. Here, we sampled iconic local wines, including Verdelho, the island’s signature varietal. Its crisp mineral notes and subtle hints of salinity captured the essence of Pico’s volcanic terroir and ocean breezes. Each sip told a story of resilience, renewal, and the enduring spirit of the island—a fitting reflection of Jeff’s journey to reconnect with his roots.

Time to return to the ferry port, we pulled off at a natural swimming pool framed by black basalt rock, a common sight in the Azores and one of the things to do in Pico. Overlooking the pool was an architectural gem of a wine bar, designed to resemble a wine barrel. I imagined returning one day to take a dip in this water before watching the sunset over Faial Island with a glass of wine.

As we bid farewell to Pico, Jeff turned for one last look, sensing the hidden volcano rising above the sea, even cloaked within the clouds. Its powerful presence seemed to symbolize the strength, mystery, and enduring ties of family.

But for now, it was time to leave. As the ferry pulled away, Jeff turned back for one last look at Pico’s volcano rising above the sea. Though still cloaked in clouds, its presence was a powerful reminder of the strength, mystery, and enduring ties of family.

As we sailed back to Faial, we felt excited for the next leg of our journey to São Miguel, the largest island in the Azores. While Lisbon offered a glimpse into Portugal’s vibrant urban culture and Pico revealed the raw, volcanic heart of the Azores, São Miguel promised lush crater lakes, geothermal wonders, and verdant landscapes with a different perspective on Azorean beauty and culture. Each stop along our journey added a distinct layer to the story we were uncovering.

For Jeff, this trip was more than a vacation—it was a pilgrimage. It was a return to the roots that had nourished his family tree, a chance to honor the legacy of those who came before him. The stories of whaling, though bittersweet, echoed the ingenuity and perseverance of the island’s people.

Heritage travel offers a unique opportunity to walk in the footsteps of ancestors, to feel the weight of their choices, and to bridge the past with the present.

It’s experiences like these that inspire our work at AMG Inspired Travel. We specialize in creating personalized heritage journeys, weaving together history, culture, and personal discovery. Whether it’s exploring ancestral villages, savoring local flavors, or walking in the footsteps of your ancestors, we design trips that honor your unique story.

Ready to explore your roots? Contact us to craft your personalized heritage adventure today.

Copyright Photo Credit: Note “Image by Ali Giaudrone via AMG Inspired.” All rights reserved. Contact AMG Inspired for more permissions.

Lindblad Expeditions

Islands of The Azores – Basalt Peaks to Volcanic Vineyards (9 Days)

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