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 four enchanting islands—Sâo Miguel, Faial, Sâo Jorge, and spectacular Pico, each with its own personality and terrain. We’ll hike along crater rims and cross rugged moorlands above a deep blue sea, and follow ancient canadas (pathways) that crisscross the islands linking farms and villages. Complementing our hikes, we’ll head out for whale watching, dine on catch-of-the-day fish at delightful 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
São Miguel Island / Faial Island

In Ponta Delgada on São Miguel Island, we hike up to the twin crater lakes of Sete Cidades, and on Faial Island, known as “the blue island” for its long rows of hydrangea hedges, we’ll visit the native botanical garden and hike from Cabeço do Fogo to Ponta dos Capelinhos for coastal views. On our walk to dinner along the marina in Faial, we’ll pop into a café to sample the local passion-fruit-flavored gin. Overnights are in a restored 16th century fort, now a welcoming hotel.

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 4-5
Pico Island / Wine Tasting / Whale Watching

Ferrying to 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 and 18th centuries, and go whale watching from the ancient town of Lajes do Pico. Once a whale-hunting hub, Lajes do Pico is now a major whale-watching destination, with 26 species of cetaceans documented in the deep waters offshore. We’ll have a choice between a moderate hike along the Caminho dos Burros, with fabulous views of Pico Mountain, or a challenging hike up to Picos’ summit at 7,713 feet.

Hotel Caravelas
Madalena, Portugal
Days 4 to 5 (2 nights)
Days 6-7
São Jorge Island

On São Jorge Island, we hike the island’s spine through high heather and past a series of ancient villages, and along a panoramic trail to charming Fajã de São João on the coast. While we’re here, we’ll sample the island’s own cheeses and locally grown coffee.

Hotel S. Jorge Garden
Velas, Portugal
Days 6 to 7 (2 nights)
Days 8-10
São Miguel Island / Furnas / Ribeira Quente / Terra Nostra Gardens

Returning to São Miguel Island, we visit the 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. In the village of Ribeira Quente, with its colorful small houses and busy fishing harbor, we enjoy a traditional Azorean feast of cozido nas caldeiras (beef slow-roasted on geothermally heated stones!). Overnights in Furnas are at the Terra Nostra Garden Hotel, with its thermally heated pools. 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 crisp 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: $6995  
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 (for luggage or if you wish to skip a day's hike)

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