Off-the-Beaten-Path Azores: São Miguel & Pico Island - 5 Days

Day 1: Arrive on São Miguel Island, Tour Eastern São Miguel

Bem vindo aos Açores! You'll arrive on São Miguel, the largest of the Azores' string of nine volcanic islands, nicknamed the "Pearl of the Atlantic.". As your first introduction to Portugal's far-flung isles, get a lay of the land in Ponta Delgada, the unofficial capital of the Azores and the city you'll be calling home for the next two nights. Its quaint center is wreathed in Baroque architecture, basalt trimwork, and çalcada à Portuguesa, white and black tiled mosaics. 

It might be your first day, but it's already time to hit the ground running. Your guide will be waiting outside your accommodation this afternoon to take you on a tour of São Miguel's most famous natural landmarks. Head to the eastern end of the island, with a stop for sweeping ocean views at Miradouro de Santa Iría. Then speed your way toward the town of Furnas for your first glimpse of the volcanic activity the Azores are known for. Tucked literally inside a volcanic caldera, Furnas is famous for its thermal baths, burbling mud pits, and a local delicacy that's cooked underground, cozido das Furnas.

Day 2: Whale Watching Excursion, Tour Western São Miguel

Over 20 different kinds of whales and dolphins, including blue whales, the largest mammals on earth, can be seen year-round in the Azores—and you're off to find them this morning! Grab a quick breakfast of Azorean queijadas (Portuguese cheesecake) and head out on a group cruise for the possibility to see these gentle giants. The ocean surrounding the Azores is known for its astonishing biodiversity, and there's no better way to experience it than from the water. 

This afternoon, get better acquainted with the western side of São Miguel on a private tour. The historic city of Ribeira Grande is up first, followed closely by a deep dive into the island's jungle interior at Salto do Cabrito waterfall and Lagoa do Fogo. If you've been inspired by pictures of the Azores before your trip, you'll be excited about your next stop. Lagoa das Sete Cidades and its turquoise lagoons are truly postcard-worthy on a clear day. You'll end your trip at the island's westernmost point in the seaside village of Mosteiros. Stroll along its black-sand beaches before tracing the coast back to Ponta Delgada.

Day 3: Fly to Pico Island, Wine Tasting Experience

Part of the adventure today is reaching your second island of the trip—Ilha Pico (Pico Island). You'll fly from São Miguel's main airport in Ponta Delgada to Madalena, the island's largest town. You'll notice right away that Pico is a smaller and even more remote island than São Miguel—but this is what makes it so special. As you might have seen out your plane windows, this little isle is dominated by a large dormant stratovolcano, Montanha do Pico, which happens to be the tallest point in all of Portugal at over 7,713 feet (2,351 m). 

Pico's fertile, volcanic soil mixed with a maritime, subtropical climate is a difficult albeit ideal environment for growing grapes. Get to sipping and sampling Azorean wine today, often rated as the best white wine in the entire country, on a guided tour. You'll notice that each vineyard is contained within volcanic rock walls called currais. These help to protect the fragile vines from harsh winds and salt air. But the gastronomic tour doesn't end there. You'll also have the chance to taste Azorean cheese and its distinctly sulfuric notes alongside traditional bread and, of course, more wine.

Day 4: Full-Day Jeep Adventure: Lagoons, Lunch & Lava Caves

Bring your bathing suit and a sense of adventure today on today's tour. Your last full day of the trip is the perfect blend of exhilaration, jaw-dropping views, and delicious cuisine. Hop in a fleet of Jeeps headed out of your base in Madalena for an expedition with the Pico Lagoons as stop number one. The lush landscape—and the imposing peak of Montanha do Pico—are reflected in the crystalline water. This is where you'll have the option to pull out your swimsuit and take a dip, with an incredible backdrop to boot. 

After working up a sweat on a short hike through the rolling landscape, you'll stop for a traditional lunch. No trip to the Azores is complete without trying the locally-raised steak, cavaco (local lobster), and polvo grelhado (grilled octopus). Afterward, climb back in the Jeep for an exhilarating ride through Pico's rugged terrain with panoramic views to match. Last but not least is a pit stop at Gruta das Torres, the largest lava tube cave in Portugal.

Day 5: Depart Pico Island

Whether you're headed to another island in the Azores, back to mainland Portugal, or home, you'll never forget your time exploring this volcanic chain of islands. Transportation will be waiting to whisk you away to the Aeroporto do Pico. Don't forget to grab a culinary souvenir straight from the Azores, like pineapple jam or Chá Gorreana tea. Boa viagem!

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