Hiking in the Azores

Adventures in a Breathtaking Archipelago


Discover an island world of traditional villages, lake-filled calderas, and ancient vineyards—the Azores! On this volcanic archipelago just a five-hour flight from Boston, we explore the four enchanting islands of Sâo Miguel, Faial, Sâo Jorge, and spectacular Pico, each with its own personality and terrain. We’ll hike along crater rims, cross rugged moorlands above a deep blue sea, and follow ancient canadas (pathways) that link farms and villages. Complementing our hikes, we’ll head out for whale watching, dine on catch-of-the-day fish at cozy local spots, and relish the unhurried pace of Azorean life. Our accommodations include a refurbished 16th century fort, a 17th century townhouse, and an Art Deco hotel with thermally heated bathing pools.

Itinerary at a Glance

Days 1-3
Sâo Miguel Island / Faial Island

On Sâo Miguel Island, we hike up to the twin crater lakes of Sete Cidades, then fly to Faial Island, known as “the blue island” for its long rows of hydrangea hedges and famed as a stopping-off point for yachts on trans-Atlantic crossings. Our hike across the volcanic landscape brings us to Ponta dos Capelinhos for spectacular coastal views.

Hotel Talisman
Ponta Delgada, Portugal
Day 1 (1 night)
Grand Hotel Açores Atlântico
Ponta Delgada, Portugal
Day 1 (1 night)
Pousada Forte Hotel
Horta, Portugal
Days 2 to 3 (2 nights)
Days 4-7
Pico Island / Wine Tasting / Whale Watching / Sâo Jorge Island

On Pico Island, crowned by a dormant 7,713-foot volcano, Portugal’s highest point, we explore vineyards where wines have been produced since the 17th century. Whale watching is one of our delights at the town of Lajes do Pico, once a whale-hunting hub and now a major whale-watching destination. While on Pico, we’ll offer the option of a challenging hike up to Picos’ summit. A ferry ride brings us to Sâo Jorge Island for a hike along the island’s spine through high heather, past a series of ancient villages, and along a panoramic trail to charming Fajã dos Cubres on the coast. São Jorge produces the best cheese of all the islands and we’ll visit a family creamery to sample some.

Hotel Caravelas
Madalena, Portugal
Days 4 to 6 (3 nights)
Hotel S. Jorge Garden
Velas, Portugal
Day 7 (1 night)
Days 8-10
Sâo Miguel Island / Furnas / Ribeira Quente / Terra Nostra Gardens

Returning to Sâo Miguel Island, we visit the Chapel of Nossa Senhora da Paz, with its beautiful Portuguese azulejos (painted tiles), and explore the 19th century spa village of Furnas, nestled inside a huge caldera. In the fishing village of Ribeira Quente, our traditional Azorean feast of cozido nas caldeiras (beef slow-roasted on geothermally heated stones!) is a special treat. Depart on Day 10 via Ponta Delgada.

Terra Nostra Garden Hotel
Furnas, Portugal
Days 8 to 9 (2 nights)



Hike and explore four lush volcanic islands, each with a unique culture and landscape
Taste Pico Island’s white wines from age-old vineyards
Search for whales and dolphins in one of the world’s largest whale sanctuaries
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: $7295  
Arrive: São Miguel Island, Azores
Depart: São Miguel Island, Azores
Lodging: 9 nights hotels
Meals: All meals included except 1 dinner as indicated in the Detailed Itinerary (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

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