Adventures in a Breathtaking Archipelago with Skye McDonald


Discover an idyllic world of seaside villages, lake-filled calderas, and ancient vineyards—this is the island paradise of the Azores! Our new WT Expedition with phenomenal Trip Leader Skye MacDonald brings you deep into the culture and  beauty of this volcanic archipelago 800 miles west of Portugal (and just a 5-hour flight from New York). Our journey explores four islands—Sâo Miguel, Faial, Sâo Jorge, and spectacular Pico, with its 7,713-foot volcano—each with its own personality and terrain, along with traditional white-walled Portuguese architecture. We’ll hike along crater rims, cross rugged moorlands and meadows above a deep blue sea, and follow ancient canadas (pathways) that crisscross the islands to link farms, villages, and towns.  To complement our hikes, we’ll head out for whale watching (the surrounding seas support 26 species of cetaceans), taste wines grown in rich volcanic terrain, sample each island’s unique cheeses, dine on catch-of-the-day fish, soak in thermal waters, and relish the unhurried pace of Azorean life. In this farthest outpost of western Europe, our accommodations are as unique as the Azores themselves, including a refurbished 16th century fort, a 17th century town house, and an Art Deco hotel with vast gardens and thermally heated bathing pools.

Itinerary at a Glance

Days 1-3
São Miguel Island / Faial Island

In Ponta Delgada on São Miguel Island, hike up to the twin crater lakes of Sete Cidades. On Faial Island, visit the native botanical garden and take a beautiful hike from Cabeço do Fogo to Ponta dos Capelinhos, with phenomenal views. Overnights in Faial are in a restored 16th century fort-turned-hotel.

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Days 4-5
Pico Island / Wine Tasting / Whale Watching

Ferry to Pico Island, crowned by a dormant 7,713-foot volcano, Portugal’s highest point. Explore the wine-growing area, where wines have been produced since the 17th and 18th centuries. Go whale-watching from the ancient town of Lajes do Pico (a remarkable 26 species of cetaceans have been documented in the deep waters offshore here). Hike the Caminho dos Burros, with fabulous views of Pico Mountain, enjoy a refreshing dip in rock pools along the coast, and explore a giant lava tube full of stalactites.

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Days 6-7
São Jorge Island

Ferry to São Jorge Island for a hike along the island’s spine through high heather and past a series of ancient villages. Taste the local cheeses, sample Azores’ locally grown coffee, and hike a beautiful trail to charming Fajã de São João on the coast.

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Days 8-10
São Miguel Island / Furnas / Ribeira Quente / Terra Nostra Gardens

Return to São Miguel Island to visit the charming Chapel of Nossa Senhora da Paz, with its beautiful Portuguese azulejos (blue painted tiles), and explore the 19th century spa village of Furnas, nestled inside a huge caldera with active fumaroles. Hike to the village of Ribeira Quente, with its colorful small houses, picturesque church, and busy fishing harbor, and enjoy a traditional Azorean feast of cozido nas caldeiras. Overnights in Furnas at the Terra Nostra Garden Hotel, with its vast 19th century garden and thermally heated pools. Depart via Ponta Delgada on Day 10.

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Hike and explore four lush volcanic islands, each with a unique culture and landscape
Taste Pico Island's deep red wines from age-old vineyards
Go whale- and dolphin-watching in one of the world's largest whale sanctuaries
Dine on fresh-caught fish and the famous local 'cozidos nas caldeirias,' cooked in thermally heated ground
Stay in a converted 16th century fort, a 17th century townhouse, and the Art Deco grandeur of Terra Nostra Garden Hotel


Length: 10 days
Cost From: $6795  
Arrive: São Miguel Island, Azores
Depart: São Miguel Island, Azores
Lodging: 9 nights hotels and inns
Meals: All meals included except 1 dinner (B=Breakfast, L=Lunch, D=Dinner)
Activity: Hiking / Trekking
Trip Level:

8 hiking days on moderate trails (some steep sections), 3-5 hours a day, van support (for luggage or if you wish to skip a day’s hike).