Hiking the Azores  2026

September 20 – 28, 2026 * 9 Days * 

$4,595 

 

Optional Portugal Mainland Extension

September 28 – October 5, 2026 * 7 Days *

$4,395  

-Flight to Lisbon included  

Far out in the Atlantic Ocean, roughly one-third of the distance between southern Europe and the East Coast of the USA, lies a nine-island archipelago called the Azores. Here, the tips of some of earth’s tallest mountains rise above the ocean surface from the bottom of a deep sea, at the junction of three major tectonic plates. The depth of the surrounding waters—nearly four miles—and the moderating influence of the Gulf Stream attract a wealth of marine life, including an extraordinary array of cetaceans: whales, dolphins, and porpoises that gather in these rich feeding grounds.

The latitude of the islands, combined with the Gulf Stream’s tempering embrace and nutrient-rich volcanic soil, produces a Garden-of-Eden effect where luxuriant vegetation blankets hillsides and valleys in every shade of green. Emerald pastures dotted with prolific dairy cows roll across the landscape, while black lava beaches meet the pounding of starkly contrasting, crystal-blue surf. Mysterious lava caves wind through ancient geology, and a fascinating variety of lagoons and lakes shimmer beneath volcanic peaks—all connected by a well-developed system of trails and dirt roads perfect for exploration on foot.

Six hundred years ago, Prince Henry the Navigator’s mariners—pioneers of blue-water sailing—stumbled upon the Azores en route to the East. Remote yet Portuguese, the islands remain autonomous today, where island calm meets continental culture.

After immersing ourselves in the natural wonders and slower rhythms of island life, we continue our adventure on the Portuguese mainland, where history, culture, and landscape intertwine in captivating ways. From Lisbon’s grand monuments and clifftop palaces to Porto’s riverside charm and the terraced vineyards of the Douro Valley, this extension offers a rich contrast to our island exploration—medieval castles and Moorish gardens, port wine cellars, coastal fishing villages and fertile wine country. Together, the Azores and Portugal mainland create an unforgettable journey through landscapes shaped by the sea, centuries of exploration, and the enduring warmth of Portuguese hospitality.

Plus, it’s a tasty journey curated by our local expert partners—authentic flavors, unforgettable meals, and the right places at the right time. Step into a different dimension and join us on this island-hopping odyssey in search of the heart of the Azores—and discover the soul of Portugal!

Adventure Pace
Tour Pace: 1 2 3 4 5
Walk Challenge: 1 2 3 4 5

How much Adventure do you want? Here are a few features to help gauge the following factors on each tour.

Tour Pace: On a scale of 1 (slowest pace) to 5 (fastest pace), we’ve rated the following factors: number of 1-night hotels; driving miles per day; fullness of schedule; mid-tour airline flights; high elevation setting; and average amount of walking per day.

Walk Challenge: This number represents an average walk difficulty rating for the tour using a scale of 1 (easiest) to 5 (hardest).

Join Us for this New Adventure

Spaces are limited and filling quickly — registrations are confirmed in the order received

Click “Book Now” and select your preferred departure date in the dropdown menu. If a date doesn’t appear, it means that departure is full. If you’d like to join the waiting list, just email us at fun@walkingadventures.com.

HIGHLIGHTS

  • Four Island Adventure – Our Azores exploration takes us to four distinct islands: the green island of São Miguel, known for its deep woods and productive dairy farms; the purple island of Terceira, celebrated for its lilacs, wisteria, and UNESCO World Heritage town of Angra do Heroísmo; the blue island of Faial, with its strong seafaring heritage and hydrangea-lined roads; and the gray island of Pico, home to Portugal’s tallest mountain and UNESCO-listed vineyards planted in dramatic volcanic terrain. 
  • Geothermal Wonders & Botanical Gardens – Experience the otherworldly landscape of Furnas Valley, where bubbling fumaroles and thermal springs steam from volcanic earth. Stroll through the bicentennial botanical gardens of Parque Terra Nostra, guardian of a renowned camellia collection, and taste the famous “Cozido das Furnas,” a traditional stew cooked underground using only the earth’s natural heat. 
  • UNESCO World Heritage Sites – Discover Angra do Heroísmo on Terceira Island, impeccably preserved since the Age of Discovery, and explore Pico’s unique vineyards, where vines grow protected by intricate lava stone walls—a testament to generations of ingenious viticulture. In Portugal, visit Lisbon’s magnificent Jerónimos Monastery, a masterpiece of Manueline architecture. 
  • Maritime Heritage & Island Culture – Learn about the Azores’ deep connection to the sea, and explore volcanic caves and dramatic coastal viewpoints. Take a scenic ferry ride between islands, walk among UNESCO-protected vineyards, and taste local wines and liqueurs crafted from the islands’ tropical bounty. Visit historic whaling stations (optional activity).
  • Portuguese Mainland Discovery (Optional Extension) – From Lisbon’s grand avenues to the fairytale palaces of Sintra, from the colorful moliceiro boats of Aveiro’s canals to Porto’s riverside wine cellars, the Portugal Extension reveals the country’s rich cultural tapestry. Enjoy the Douro Valley’s terraced vineyards and savor traditional cuisine in charming historic towns across the northern regions. 
  • Authentic Portuguese Cuisine & Curated Dining Experiences – You’ll notice this tour is exceptionally generous with included meals—and there’s a reason. Rather than tourist restaurants, our expert local partners take us to the places they go: family-run tascas serving traditional recipes passed down through generations, quinta estates where lunch is paired with wines from the surrounding vineyards, and regional eateries where locals gather for authentic flavors. From the famous “Cozido das Furnas” stew cooked underground by volcanic heat to Pico’s Verdelho wine paired with local delicacies, from Pastéis de Belém’s legendary custard tarts to fresh seafood in coastal Nazaré, from Azorean pineapple and fruit liqueur tastings to Douro Valley wine cellars and enchidos, from Europe’s only tea plantation at Chá Gorreana to a celebratory dinner in historic Ponte de Lima, each meal reveals Portugal’s rich culinary heritage—both island and mainland—and the warm hospitality that makes every table feel like home.

 

Trip Details

Azores Islands


Including:

  • Three inter-island flights (São Miguel to Terceira, Terceira to Faial, Faial to São Miguel)
  • Round-trip ferry service from Faial to Pico Island
  • All land travel as outlined by motorcoach (smaller buses on narrow roads)
  • Superior tourist-class hotel accommodations on four islands
  • 16 meals: all breakfasts, 4 lunches, and 4 dinners as denoted (BLD)
  • 7 walk routes as listed
  • Walking fees for those collecting walk credit, if sanctions approved
  • Two WAI tour leaders throughout
  • Cultural and historical expertise of a national WAI team throughout
  • All tipping for local guides, coach drivers, and group meals

Pricing is based on double occupancy. A limited number of single rooms are available during the hotel portion of tour for a supplement of $985. We also provide a roommate matching service for those interested.

Visits to/admission fees

  • Parque Terra Nostra Bicentennial Botanical Garden – São Miguel
  • Lagoa das Furnas with geothermal cooking demonstration
  • Angra do Heroísmo UNESCO World Heritage Site – Terceira
  • Capitães-Generais Palace – Terceira
  • Amélia’s pastries with baking demonstration – Terceira
  • Monte Brasil Natural Reserve – Terceira
  • Algar do Carvão volcanic cave guided tour – Terceira
  • Whaling Museum in Porto Pim – Faial
  • Monte da Guia viewpoint and historic fortifications – Faial
  • Pico Island wine cellar and Verdelho wine tasting – Pico
  • Pico vineyards UNESCO World Heritage Site walk
  • Pineapple plantation tour and tasting – São Miguel
  • Lagoa das Sete Cidades – São Miguel
  • Azorean fruit liqueur tasting – São Miguel
  • Chá Gorreana tea plantation – São Miguel
  • Coastal walks and hikes on all 4 islands
  • More fun and educational stops than we can list!

Optional Excursion:

  • Whale watching cruise from Ponta Delgada (Day 1 in the morning for those arriving for the Day 0 pre-night) – Price: $129 per person

 

Portugal Mainland Extension


Including:

  • Flight from Nordela Airport (PDL) in Ponta Delgada to Lisbon (LIS)
  • Transfer from Lisbon airport to hotel on first day of the tour
  • Superior tourist-class hotel accommodations in Lisbon
  • 10 meals: all breakfasts, 3 lunches and 3 dinners as denoted (BLD)
  • Multiple walking routes in historic cities and scenic regions
  • Walking fees for walks for those collecting walk credit (if BWF approved)
  • Two WAI tour leaders throughout
  • All tipping for local guides, coach drivers, and group meals

Visits to/Admission Fess (Mainland Extension):

  • Jerónimos Monastery – Lisbon
  • Pastéis de Belém tasting – Lisbon
  • Pena Palace – Sintra
  • Moliceiro boat ride through the canals – Aveiro
  • Wine tasting and dinner experience in the Douro Valley 
  • Local products tasting – Ponte de Lima region
  • Historic town walks in Nazaré, Aveiro, Porto, and Ponte de Lima
  • Scenic drives through Portugal’s diverse landscapes

Pricing is based on double occupancy. A limited number of single rooms are available during the hotel portion of tour for a supplement of $1129. We also provide a roommate matching service for those interested.

Optional Excursion:

  • Fado Dinner Experience in Lisbon (Day 1 of the Mainland Extension) – Price: $129

IMPORTANT INFO

Group Size

24 travelers maximum

Accommodations

Strategically located Tourist Class accommodations or better

Meals

Breakfasts included with 4 lunches and 4 dinners on the Azores Islands tour, and breakfasts included with 3 lunches, and 3 dinners on the Portugal Mainland Extension. Letters BD indicate which meals are included.

Airfare

Not included. Travelers will fly into and out of Nordela Airport (airport code PDL) in Ponta Delgada, on the Azores island of São Miguel.

For those continuing to the Portugal Extension, airfare Ponta Delgada and Lisbon is included in the price of the Extension and we will book this flight on your behalf. Departure will be from Porto Airport (airport code OPO) in northern Portugal.

Transportation

Transportation Azores: Included: 3 inter-island flights, 1 round-trip inter-island ferry, motorcoach on each island (smaller buses due to narrow roads). Portugal Extension: Flight from Azores to Lisbon and Private motorcoach throughout.

Traveler Age

Our travelers usually range from 50–75 years of age. All ages welcome!

Azores Islands

Itinerary

Day 1 – SAT (September 19) – Ponta Delgada - Furnas, São Miguel Island (D)

Welcome to the Azores Islands! This surprisingly diverse Portuguese archipelago promises a mesmerizing and magical 9-day adventure exploring four of its most scenic and colorful islands.

We begin and end our exploration on the green island of São Miguel, known for its deep woods and verdant pastures where productive dairy cows roam freely. 

For those arriving a day early, we recommend an optional whale-watching excursion on the morning of Day 1. The Azores are known worldwide as an oceanic magnet for cetaceans—of the 81 total whale and dolphin species existing on the planet, 28 of them appear in these waters. A morning spent sailing toward the deep ocean in the company of a marine biologist offers the chance to witness migratory and resident whales and dolphins. Since wildlife is wild and not scripted, we cannot guarantee sightings, but the experience of being on these rich waters is unforgettable in itself. Optional Whale Watching Excursion: approximately 3 hours. Price: $129 per person

This rainbow-themed road trip begins with an afternoon group transfer from São Miguel’s main airport in Ponta Delgada to the geothermally active region of Furnas, where bubbling terrain and steaming fumaroles create an otherworldly landscape. Here, in this sleeping volcanic crater, we settle into our hotel—ideally positioned near the thermal pools and hot springs that make Furnas a restorative haven. This evening, we gather for a welcome dinner, toasting the beginning of our island adventure and the promise of discoveries ahead.

Day 2 – MON (September 21) – Activities on São Miguel Island (BL)

Lagoa das Furnas Town and Lakeside Walk – 7 km, rated 2B

On São Miguel Island today, we lose ourselves in the steam and sulfurous scent of Furnas Valley. On our morning walk through this remarkable volcanic landscape, we encounter bubbling terrain, vaporous fumaroles, and thermal running waters. The setting unfolds around us: immense vegetation backdropping the emerald, crystal-like Lagoa das Furnas—the first of numerous lagoons that will enchant us throughout this journey. The steam breathing from the ground is used by locals to cook the famous “Cozido das Furnas,” a hearty stew made with different vegetables and meats, left underground for 6 to 7 hours to cook slowly using only the earth’s natural heat. We taste this unique culinary tradition during our lunch break, experiencing firsthand the intimate connection between the land and local cuisine.

During the afternoon, we discover the softer and more delicate side of Furnas as we stroll through the bicentennial botanical garden of Parque Terra Nostra, guardian of a highly regarded camellia collection and home to an English oak tree planted in the 18th century by Thomas Hickling, a North American consul in the Azores. The garden’s lush pathways, exotic plantings, and thermal pools create a soothing retreat. We finish our day exploring the southeast part of the island and its lovely little towns such as Povoação, with amazing coastal viewpoints running along the rugged shore.

Day 3 – TUE (September 22) – São Miguel to Angra do Heroísmo, Terceira Island (BD)

Monte Brasil Walk – 8 km, rated 2B

This morning we bid farewell to São Miguel and fly to Terceira, the purple island. After arrival, we explore Angra do Heroísmo, considered a UNESCO World Heritage Site for its impeccable preservation as a Renaissance town. We absorb its colonialist ambiance, imagining the buzzing port life, arriving settlers, and Jesuit monks as we visit the town’s vibrant streets, baroque churches, and the Capitães-Generais Palace—a magnificent testament to the islands’ strategic importance during the Age of Discovery.

Color and religion are both prominent features in Terceira’s architecture, which we witness at the “Impérios,” modest chapel-like buildings decorated in strong contrasting hues, where the Brothers of the Holy Spirit perform their religious practices. Our education in this town’s history and culture continues at the charming Town Hall while tasting D. Amélia’s pastries, small confections made in honor of the queen and bearing her name. Before tasting, we witness how these precious treats are made, learning the traditional techniques passed down through generations.

In the afternoon, we enter the vibrant and verdant nature reserve of Monte Brasil, a remnant of an extinct volcano. Here we explore one of the oldest fortifications on the island, walking among historic ramparts while enjoying remarkable vistas overlooking Angra do Heroísmo and the azure sea beyond. This evening, we gather for dinner, reflecting on our first impressions of Terceira’s unique character.

Day 4 – WED (September 23) – Activities on Terceira Island (BL)

Agualva Bay Walk – 4 km, rated 3B

During the morning, a journey to the north of the island offers up a coastal walk to the dramatic cliffside views, rock columns, and pebble beach of Agualva Bay. The trail winds along rugged headlands where the Atlantic crashes against ancient lava formations, creating a symphony of sound and spray. We remain alert for numerous bird species, including the Rock Dove, Azores Wood Pigeon, and perhaps even the Common Tern wheeling overhead. This lovely coastal hike works up an appetite for a tasty local lunch featuring the flavors of Terceira.

In the afternoon, we make our way to the volcanic cave of Algar do Carvão, one of the rare places in the world where you can descend into the interior of a volcano. This volcanic chimney contains a pool of water and two amazing rocky domes decorated with enormous stalactites, resembling a stone-carved theater. The cave is explored on guided walks with an expert who reveals the secrets hidden in the heart of this island, explaining the geological forces that shaped this extraordinary subterranean cathedral. The play of light and shadow on the volcanic rock creates an ethereal atmosphere, making this one of the most memorable experiences of our Azores adventure.

Day 5 – THU (September 24) – Terceira Island to Horta, Faial Island (BD)

Entre Montes Walk – 5 km, rated 3C

Bidding farewell to Terceira, we fly this morning to our next island destination: Faial, the blue island. Upon arrival, we begin exploring the town of Horta, where our first visit takes us to Peter’s Sports Café, a world-famous institution that is far more than just a café. With well over 100 years of history under its belt and a bright blue façade with an orange sign, Peter’s has served as a place for currency exchange, a yachting club, a post office, and even a place of charity on occasion. On its upper floor, we find the most striking scrimshaw collection on the island, bearing witness to Faial’s long whaling history—intricate carvings on whale bone and teeth that tell stories of the men who once hunted these giants of the deep.

We further explore the island’s relationship with large aquatic mammals when we visit the Whaling Station in Porto Pim, where captured whales were once processed into various products. This museum offers a sobering yet fascinating look at an industry that shaped island life for generations, and its eventual transformation as attitudes toward whales evolved from exploitation to conservation.

In the afternoon, our introduction to Faial continues as we enjoy a walk to Monte da Guia, one of the most beautiful viewpoints on the entire island. Because of its strategic location, this peninsula was vital in the development of telecommunications between Europe and the United States—in 1893, the first underwater telegraphic cable was installed here. This cable proved crucial during both World Wars and remained operational until 1969. All along our trail, several fortifications dating from the 16th and 17th centuries stand as reminders of the need for maritime protection in these strategic waters. When evening comes, we enjoy a relaxed dinner in the beautiful marina of Horta, the town where we spend the next two nights. The harbor is famous worldwide for the tradition of visiting sailors painting colorful murals on the marina walls, creating an ever-evolving outdoor art gallery.

Day 6 – FRI (September 25) – Day Trip to Pico Island (BL)

Pico Vineyards Walk – 6 km, rated 2A

Today we take a scenic ferry ride from Faial across the narrow channel to our fourth island: Pico. Rising dramatically from the sea, Pico Mountain—Portugal’s tallest peak at 7,713 feet —dominates the landscape with its perfect volcanic cone. The island’s terrain reveals the raw power of volcanic geology in shades of black and gray lava, contrasting beautifully with the green vines that somehow thrive in this harsh environment.

Pico is home to a UNESCO World Heritage Site unlike any other: vineyards planted in a unique way, protected from the harsh Atlantic winds by small lava stone walls called “currais.” These intricate stone corrals create a spectacular landscape of sandy browns, dark gray walls, and light green foliage—a testament to generations of patient, back-breaking labor. We walk among these vast vineyards, soaking up the rare beauty and marveling at the ingenuity required to cultivate grapes in such challenging conditions. The wines produced here, particularly the famous Verdelho, have been prized for centuries.

While on Pico, we also discover a most impressive maritime viewpoint located atop a rocky cliff where waves constantly crash and fashion the rock into what some say resembles a dog’s head—a natural sculpture carved by the relentless Atlantic. We head to a traditional wine cellar where we learn more about rural life on the island and see how the cellar maintains its centuries-old production methods, including a cooper’s workshop. We absorb this uniquely regional wine culture while tasting Pico delicacies accompanied by Pico’s wine (Verdelho) and other liqueurs produced in the cellar.

Even though our time on Pico is relatively short compared to the other islands, we should have time to visit Lagoa do Capitão, a small lagoon in the center of the island and one of the best places to observe Pico Mountain in all its glory—especially if the weather cooperates and the summit emerges from the clouds that often shroud it. Following this perfect day on Pico, we board our ferry for the short 30-minute ride back to Faial for one last night in Horta.

Day 7 – SAT (September 26) – Faial Island to Ponta Delgada, São Miguel Island (BL)

Vista do Rei Sete Cidades Walk – 7.5 km, rated 2B

During the morning, we fly back to the island of São Miguel, returning to where our adventure began. Following lunch, we make our way to the most impressive lagoon on the entire island: Lagoa das Sete Cidades. We start at the Vista do Rei viewpoint, where a breathtaking panorama unfolds—this strange body of water appears part luminous green and part deep blue, nestled within an enormous volcanic crater. Legend says the lagoon formed after a blue-eyed princess and a green-eyed shepherd, who shared a forbidden love, cried together and created a symbol of their love: something that, even though separated by color, can never be apart. As we contemplate this romantic legend, we also observe green pastures rolling toward the coast and, in the distance, Mosteiros—a proud little fishing town with black sand beaches where natural pools have formed in the volcanic rock.

A couple of afternoon stops bring us to stunning viewpoints of the twin volcanic lakes, each offering a different perspective on this geological wonder. Before we finish the day, we visit a pineapple plantation and packaging center—a uniquely Azorean agricultural tradition. The owner greets us and guides us through several stages of pineapple cultivation in the characteristic greenhouses found across São Miguel. We play our part in the growth process by learning about the careful tending required for these tropical fruits to thrive in a temperate climate. In the end, we delight ourselves with the final product, tasting fresh pineapple along with other pineapple-based treats such as liqueurs and jams.

Day 8 – SUN (September 27) – Activities on São Miguel Island (BD)

Praia da Viola Walk – 7.5 km, rated 2A 

Chá Gorreana Tea Plantation Walk – 1 km, rated 1B

Today on São Miguel, we drive to the northern part of the island for a delightful walk in the charming little town of Ponta de Maia and along the elevated shoreline. The coastal path offers great ocean views, abundant hydrangeas in season, and photogenic watermills that once ground grain for island communities. A bonus waterfall at the turnaround point provides a perfect spot for photos and contemplation. Following our morning walk, we head to the picturesque town of Porta Formosa for a lunch break, enjoying the relaxed pace of island life.

In the afternoon, the calming fragrance of tea leaves guides us through our visit to Chá Gorreana, the only existing tea plantation in Europe. Producing both black and green tea since 1883, this family-run business doesn’t use any chemicals and maintains century-old artisanal cultivation methods that have been passed down through generations. The splendid green plantation runs along a 79-acre field bordered by views of the Atlantic Ocean, creating a uniquely scenic agricultural landscape. We learn about the tea-making process from leaf to cup, witnessing traditional methods that have remained largely unchanged for over a century. At the end, we reminisce about our wonderful day as we sip a freshly brewed cup of Azorean tea together.

On our way back to the hotel, we stop at a coastal town where we try some of the famous fruit liqueurs that the Azores have to offer. The archipelago’s tropical climate, moderated by the Gulf Stream, is perfect for cultivating exotic fruits, and local distillers have perfected the art of transforming these fruits into distinctive liqueurs. We celebrate our final night together with a lovely farewell dinner in Ponta Delgada, sharing stories and memories of our island-hopping adventure—the volcanic landscapes, the vibrant island culture, the welcoming people, and the natural wonders we’ve experienced together.

Day 9 – MON (September 28) – Departure from Ponta Delgada or Continue to Portugal Extension (B)

No group activities are scheduled for this morning. Following breakfast, those concluding their journey today are free to share taxis for the short 10-minute ride to the airport. With some reluctance, we leave this storied green archipelago, carrying with us memories of a world seemingly forgotten by time—where volcanic forces still shape the land, where communities maintain centuries-old traditions, and where the rhythm of life is guided by the sea and the turning of seasons.

For those continuing to the Portugal Extension, today marks a transition from island life to the vibrant culture and history of mainland Portugal, where new adventures await.

Mainland Portugal Extension

Itinerary

Extension Day 1 – MON (September 28) – Ponta Delgada to Lisbon (B)

Those joining the Portugal Extension depart São Miguel this morning, flying to Lisbon, Portugal’s captivating capital where seven hills meet the Tagus River and centuries of exploration have left an indelible mark. After settling into our well-located hotel in the heart of the city, the afternoon is yours to begin discovering Lisbon at your own pace. Perhaps stroll through the nearby Baixa district with its grand plazas and elegant shops, or simply find a café terrace where you can watch the famous yellow trams rattle past while savoring a bica (Portuguese espresso) and a pastel de nata.

This evening is free to explore Lisbon’s vibrant dining scene on your own. Your WAI guides can provide recommendations for traditional tascas serving authentic Portuguese cuisine, or perhaps you’d like to join our Optional Dinner Experience at a fado venue where Portugal’s hauntingly beautiful traditional music fills intimate tavernas with soulful melancholy and celebration. Price $129 per person.

Day 2 - TUE (September 29) - From Belem to Sintra (BD)

Lisbon Historic Walk – approximately 8 km, rated 2A

Today we discover Lisbon’s golden age of exploration and its remarkable recovery from the devastating 1755 earthquake. Our walking tour begins in the Belém district, where Portuguese caravels once set sail to chart unknown waters and discover new worlds. We visit the magnificent Jerónimos Monastery, a UNESCO World Heritage masterpiece of Manueline architecture—a uniquely Portuguese style that incorporates maritime motifs and exotic influences from far-flung corners of the empire. The intricate stone carvings, soaring vaulted ceilings, and peaceful cloisters embody the wealth and ambition of Portugal’s Age of Discovery.

Adjacent to the monastery, we stop at the iconic Pastéis de Belém, a café and bakery that has been crafting Portugal’s most famous pastries since 1837 using a secret recipe guarded by a select few. These warm custard tarts dusted with cinnamon and powdered sugar are a Portuguese institution—creamy, flaky, and utterly irresistible. With our sweet tooth satisfied, we continue past the Monument to the Discoveries, which honors Prince Henry the Navigator and the explorers who expanded the known world, before reaching the Belém Tower, a fortress that once guarded the entrance to Lisbon’s harbor.

Then we depart to Sintra, a fairytale town nestled in the pine-covered hills of the Serra de Sintra. Long favored by Portuguese royalty as a summer retreat from Lisbon’s heat, Sintra enchants visitors with its microclimate of mists and mystery, its Romantic-era palaces, and its lush gardens.

The highlight of our day is a visit to Pena Palace, one of Europe’s most extraordinary royal residences. Perched atop a rocky peak with commanding views across the forested hills to the Atlantic beyond, this flamboyant 19th-century palace combines Moorish, Gothic, Manueline, and Renaissance elements in a riot of color and architectural imagination. Bright yellows and deep reds cover its walls and towers, creating a structure that seems pulled from a storybook. We explore its lavishly decorated rooms and walk through the surrounding park, where exotic trees and hidden grottoes add to the romantic atmosphere.

After descending from Pena’s heights, we explore Sintra’s historic center, wandering its narrow lanes lined with pastry shops offering travesseiros and queijadas—local sweets that have been made here for centuries. The town’s UNESCO World Heritage status recognizes it as an outstanding example of Romantic architecture and landscape design. 

Extension Day 3 – WED (September 30) – Sintra to Aveiro via Nazaré (BL)

Nazaré Coastal Walk – approximately 5 km, rated 2B

This morning we depart Sintra and head north along Portugal’s Atlantic coast, stopping first in Nazaré, one of Portugal’s most traditional fishing villages. Nazaré is famous worldwide for its massive winter waves—some of the largest ever surfed—but it’s equally captivating for its authentic Portuguese character. Women in traditional seven-petticoat skirts still sell fish in the market, and colorful boats line the beach. We walk from the lower town up to Sítio, the clifftop neighborhood reached by a funicular, where a viewpoint offers stunning perspectives along the coast and down to the crescent beach below. The contrast between the white-washed houses and the deep blue Atlantic is quintessentially Portuguese.

After lunch featuring fresh seafood in Nazaré, we continue north to Aveiro, often called the “Venice of Portugal” for its network of canals plied by colorful moliceiro boats. Once used to harvest seaweed for fertilizer, these traditional boats with their curved prows and vibrant painted decorations now offer leisurely cruises through the city’s waterways. We settle into our hotel in Aveiro and take a late afternoon moliceiro boat ride, gliding beneath Art Nouveau bridges and past graceful buildings that reflect in the calm waters, learning about the city’s history as a salt and fish trading center.

Extension Day 4 – THU (October 1) – Aveiro to Porto (BL)

Porto Riverside and Historic Center Walk – approximately 7 km, rated 2B

Today we journey to Porto, Portugal’s second city and the heart of the port wine trade. Upon arrival, we begin exploring this UNESCO World Heritage city, where medieval lanes tumble down steep hillsides to the Douro River and the colorful Ribeira district crowds the waterfront. Our walk takes us through Porto’s historic center, where centuries of history are layered in the architecture—from Romanesque churches to Baroque palaces to Art Nouveau treasures.

We continue to the Ribeira, the riverside quarter where medieval houses painted in warm ochers and blues crowd narrow lanes, and outdoor restaurants spill onto the quayside. Crossing the iconic Dom Luís I Bridge—a double-deck metal arch bridge designed by a student of Gustave Eiffel.

We visit one of the historic wine cellars for a tour and tasting, learning how port wine is produced, aged, and classified. In the dim, cool cellars, rows of ancient barrels hold ruby, tawny, and vintage ports developing their complex flavors. Lunch together gives us time to savor Porto’s culinary traditions—perhaps sampling a francesinha, Porto’s famous and indulgent sandwich, or fresh grilled sardines when in season.

Extension Day 5 – FRI (October 2) – Porto to Douro (BLD)

Douro Valley Quinta Walk – approximately 4 km, rated 2B

Today brings one of the extension’s most scenic experiences: a journey through the Douro Valley, one of the world’s oldest demarcated wine regions and a UNESCO World Heritage landscape. Leaving Porto, we follow the Douro River as it winds between terraced hillsides where vineyards have been cultivated for over 2,000 years. The landscape is simply breathtaking—steep slopes covered with geometric patterns of vines supported by ancient stone walls, whitewashed quintas (wine estates) perched on hilltops, and the silvery river threading through the valley below.

We stop at a family-run wine estate where tradition meets hospitality. Here we enjoy a tasting of regional wines accompanied by local enchidos (smoked sausages and cured meats), learning about the unique microclimate and schist soils that give Douro wines their distinctive character. A gentle walk through the quinta’s vineyards offers intimate views of the terraces and the valley, with photo opportunities at every turn.

Continuing up the valley, we reach another quinta for lunch featuring regional specialties—perhaps roasted kid, octopus rice, or other traditional dishes paired with excellent local wines. The afternoon brings us to Quinta da Avessada, where we experience a memorable dinner in this spectacular setting. As the sun sets over the terraced vineyards, casting golden light across the valley, we dine on authentic Portuguese cuisine, celebrating the day’s journey through one of Europe’s most beautiful wine regions.

Extension Day 6 – SAT (October 3) – Douro Valley to Ponte de Lima via Gerês National Park (BD)

Gerês Roman Road Walk – 7 or 11 km, rated 3C

This morning we depart the Douro Valley and journey north into the rugged beauty of Peneda-Gerês National Park, Portugal’s only national park and a UNESCO Biosphere Reserve. Today we follow in the footsteps of Roman legionnaires along the remarkably preserved Via Nova, an ancient road that once connected Braga to Astorga in Spain.

The path is paved with original Roman stones, worn smooth by two millennia of travelers, and marked by ancient milestones still standing where Roman engineers placed them. We pass through traditional granite villages where stone houses with slate roofs seem unchanged by time, and see old granary structures (espigueiros) raised on stone pillars—testaments to centuries of rural ingenuity. The landscape is spectacular: rolling hills covered in heather and gorse, rocky outcrops framing distant mountain views, and ancient oak trees providing dappled shade along cobblestone paths.

We have two route options: a 7-kilometer walk covering the main highlights (with an opt-out point at approximately 3 km), or an 11-kilometer extended route for those wanting more time in this beautiful wilderness. Both routes traverse the same terrain—Roman paving stones, dirt roads, and rural paths—with cumulative ascents of 350 or 600 meters respectively.

Following our walk, we continue to Ponte de Lima in the Minho region, where we spend our final night. This charming riverside town, one of Portugal’s oldest, sits along an ancient Roman bridge that has spanned the Lima River for two millennia. This evening, we gather for dinner together, celebrating our journey through Portugal’s diverse landscapes and the friendships forged along the way.

Extension Day 7 – SUN (October 4) – Ponte de Lima to Porto Departure (B)

Ponte de Lima Historic Walk – approximately 3 km, rated 1A

Our final morning unfolds in Ponte de Lima, a town that seems suspended in time. After breakfast, we take a leisurely walk through the historic center, crossing the medieval bridge and exploring the riverside parks and traditional architecture. The weekly market (if our timing coincides) brings the town to life with vendors selling local products, handicrafts, and regional foods.

We transfer to Porto Airport for departures. As we bid farewell to Portugal, we carry with us a rich tapestry of memories: the wild beauty of the Azores, the grandeur of Lisbon, the fairytale palaces of Sintra, the maritime heritage of Porto, the terraced vineyards of the Douro, and the timeless charm of Portugal’s historic towns. From volcanic islands to wine-covered valleys, from Age of Discovery monuments to Roman bridges still standing strong, this journey has revealed Portugal in all its diversity—a land shaped by the sea, enriched by centuries of exploration, and blessed with enduring beauty.

BEFORE YOU BOOK

How Do I Lock in My Place on This Adventure?

To register, a non-refundable $500 deposit is required to hold your spot. If you’ve already pre-registered for this tour ($200), all that is required is an additional $300 to lock in your place.

A second non-refundable $500 deposit is due 6 months before departure. Final payment is due 90 days before departure and is non-refundable after the due date. You will receive a prompt email from us 2 to 3 weeks in advance of each payment deadline.

Soon after registration, an “Adventure Advice” email will be sent with critical information on flight arrangements as well as important steps to take in the months before your trip. Please do not buy your airline tickets until you review this Adventure Advice email.

Please follow this link to read our full General Tour Conditions

Unique Aspects of This Tour

Azores Islands Adventure is unique in that we visit 4 islands using inter-island flights and ferry. The temperate, sub-tropical climate of the Azores can produce abundant rain at any time of the year, but we have planned the itinerary for one of the drier periods. We highly recommend booking an optional pre-night in Ponta Delgada to take full advantage of the geothermal hot springs and thermal pools in Furnas—a restorative experience that allows you to begin your adventure fully relaxed and acclimated.

Portugal Extension offers a comprehensive journey through Portugal’s diverse landscapes and cultural treasures, from cosmopolitan Lisbon to the wine country of the Douro Valley, with carefully selected accommodations that place you in the heart of each destination.

Curated Culinary Experiences – You’ll notice this tour is exceptionally generous with included meals, and there’s a reason. Rather than tourist restaurants, our expert local partners take us to the places they go: family-run establishments serving traditional recipes, quinta estates pairing lunch with local wines, and regional eateries where locals gather. From “Cozido das Furnas” cooked underground by volcanic heat to Pico’s Verdelho wine tastings, from Pastéis de Belém’s legendary custard tarts to Douro Valley wine cellars, from Azorean pineapple liqueurs to Europe’s only tea plantation, each meal reveals Portugal’s authentic culinary heritage and warm hospitality.

What is a Classic Curated Tour?

With help from local experts and walking guides, these itineraries are crafted with extensive on-site planning by WAI tour planners.

When designing Classic Curated Tours, our objective is to capture the essence of destination—the history, culture, and natural wonders unique to that part of the world. We then build activities and walks that take us inside these characteristics.

Yes, these tours are educational, but they are also interactive and immersive; walking gets us off the bus and penetrates local cultures to not only see, but also touch, smell, and feel these special spaces.

Along the way, interactions with locals amplify the experience by sharing insights into the magic of that particular location.

Walk Ratings

We generally walk at a pace of 2 to 3 miles per hour. A few walks on this trip are oriented more towards education, and therefore take longer due to stops for guide commentary.

Nature walks, on the other hand, generally continue at a steadier pace because we’re stopping less to talk. Many of our walks on the Channel Islands are nature hikes.

In most cases, we are not “strolling.” We are walking at a relaxed but steady pace. Your experience will be significantly affected by your level of physical fitness. If not walking regularly at home, we strongly recommend that you make a priority of “training” beforehand in order to both enjoy the trip and avoid medical issues due to overexertion. If you have questions about your ability to participate, please call our office at 1.360.260.9393.

We have adopted a walk difficulty rating system which contains a numeric indicator for trail incline and an alpha indicator for trail terrain. The explanation for this system is presented on the table below:

INCLINE

1. Minimal hills or stair climbing. Cumulative elevation gain: <200 feet.

2. Some moderate hills and stair climbing. Cumulative elevation gain: 200-1000 feet.

3. Some significant hill or stair climbing. Cumulative elevation gain: 1000-2000 feet.

TERRAIN

A. Almost entirely on pavement.

B. A significant part of the route is on well-groomed trails with very few obstacles.

C. A significant part of the route is on somewhat difficult terrain (rocky / rooted paths or soft sand).

How Is Airfare Arranged?

Travelers will fly into Nordela Airport (airport code PDL) in Ponta Delgada, on the Azores island of São Miguel. Those taking only the Azores portion will also depart from PDL. Those continuing to the Portugal Extension will depart from Porto Airport (airport code OPO) in northern Portugal. The flight between Ponte Delgada and Lisbon is included in the extension price. 

Air travel to the Azores is available via direct flights from limited East Coast USA cities and by flying through Lisbon, Portugal. The Azores air transport situation is unique due to their location in the middle of the Atlantic. The islands are roughly two-thirds of the distance to Europe measured from the East Coast of the USA.

More details about flight arrangements and travel agent contact information will be provided in an Adventure Advice PDF by email after you register for the Adventure. Please do not book your airfare prior to receiving these flight details from us!

Once you receive the Adventure Advice memo, we recommend that you contact Laura Pfahler, the travel agent we work with, to help book your flight arrangements. In this age of airfare complications and airport uncertainty, using a travel agent is a good investment!

Laura Pfahler: 503.434.6401 or llp@wtpdx.com

Travel Insurance

WAI recommends travel insurance for financial and medical protection from any number of unforeseen circumstances that can arise before departure or during your Adventure. Many travel insurance providers are available for you to consider. Laura Pfahler and Sharon Mitchell of World Travel Inc. can provide travel insurance options for your WAI tour, as well as for your airfare. For those who purchase airfare through Laura, purchasing your travel insurance from her colleague, Sharon Mitchell, may be the simplest option.

Be aware that some travel insurance policies contain time-sensitive provisions (i.e. some benefits, such as coverage of pre-existing conditions, are available only if the policy is purchased within a certain number of days of the purchase of the travel package). In addition, remember that airfare is not covered by any travel insurance policy you may have purchased for the tour.

Check out Insurance Tips from World Travel for a short introduction to travel insurance.

To contact Sharon Mitchell:

Phone: 971.261.2091

Email: smitchell@wtpdx.com

Other options include:

Allianz

Betins

Travel Guard

Travel Insured International 

Using the www.SquareMouth.com  website can be an easy way to compare pricing.

We suggest purchasing from a reputable, well-established insurance company (avoid buying insurance from an unknown company found only online). Travelers interested in purchasing “cancel for any reason” insurance coverage should be careful to check pricing and terms BEFORE they register for a tour. Recent changes in the international travel landscape has caused changes in the policies of some insurance companies, and made the purchase of this particular type of policy even more time-sensitive. 

NOTE: WAI receives no commission or financial remuneration from World Travel Inc. In addition, WAI bears no responsibility for travel insurance benefits advertised by various credit card companies. If you are relying on this type of benefit for insurance, we advise you to verify coverage types and limits and that your purchase does in fact qualify you for this insurance.

What if WAI Cancels the Tour

Walking Adventures International reserves the right to cancel this tour departure with fewer than 15 participants, in which case registered participants will receive a 100% refund of payments received.

This refund policy contains one exclusion. Many suppliers require non-refundable deposits as a condition of booking services. Though it is rare, unforeseen circumstances can force us to cancel a tour. In cases where supplier’s non-refundable policies are imposed, WAI attempts to retrieve as much of these deposits as possible but cannot guarantee a 100% refund. In cases where full refunds cannot be obtained for a cancelled tour, we will do our best to transfer unrefunded money as traveler credits to be applied to a future tour to that destination.

Wellness Procedures for This Tour

Our approach to wellness on tour has traditionally been to encourage travelers to:

Focus on health before the tour so you start healthy.

Pace yourself while on tour; travel is inherently stimulating and can produce adrenalin boosts that mask energy drain. Guard your energy reserves and consider the length of the trip and whether to opt out of some activities and/or walks.

Be self-aware. If you feel yourself tiring or feel a bug coming on, take precautions to block it (e.g. extra rest, extra doses of vitamin C, etc).

If you feel a bug coming on or if you take ill, distance yourself from others when possible.

If you feel ill, isolate yourself towards the back of the bus and away from others.

Click WAI Wellness on Tour Policy to view the WAI policy on Wellness on Tour.

What Happens Next?

Soon after registration, an “Adventure Advice” email will be sent with critical information on flight arrangements as well as important steps to take in the months before your trip.

Please do not buy your airline tickets until you review this Adventure Advice email.

Afinal payment is due 90 days before departure (early June 2026) and is non-refundable after the due date. You will receive a prompt email from us a week or two in advance. Please see our General Tour Conditions for the full terms and conditions for participation in this Adventure.

Around 2-3 weeks before departure, you will receive a final email packet with details of the program, including hotel names and contact information, a list of fellow travelers, and a more detailed daily schedule.

We look forward to enjoying this beautiful and remote slice of Portugal together as we explore the Azores Islands and mainland Portugal!

CONTACT US

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