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Sandra is an Azorean native who has researched and written the first . Here she shares a one-week itinerary for first-timers to São Miguel, Terceira, and Pico.

I was born and raised on the Azores Islands, and these are the questions people ask me the most: Is it always raining? Which islands should I visit?

The first one is easy: it’s not. As for the second one, sometimes answering involves me printing out a map of the archipelago, marking spots with a pen, and asking lots of follow-up questions. 

This one-week itinerary covers the three largest islands: São Miguel, Terceira, and Pico. I’m sure you’ll want to return to explore the other six.

• When to arrive: The best time to visit the Azores is between June and August. The weather is warmer; it’s beach season; it’s the best time for whale watching; and you’ll find more cultural events and festivals. 

• How to get to/from the airports: Driving is the best option to travel between the airports and the islands’ main cities – public transit on the islands is hit-and-miss, plus understanding each network is confusing and time-consuming. 

• What to pack: A light, waterproof jacket is your best friend in the Azores. Although it's not always raining, the weather can shift quickly throughout the day. In summer, pack swimwear – there's always a spot for an ocean dip somewhere.

• Planning tip: To travel between islands, optimize your time by choosing the earliest flights possible and the ones with the least layovers. Research and book flights using the multi-city option on .  

Day 1: Start your Azores experience in São Miguel

Most international flights land in Aeroporto João Paulo II (PDL) on the largest island, São Miguel. I call it the “gateway island”, a great way to ease into the Azores experience – not too remote to feel isolated, but far enough from the mainland.

How to spend the day: Day one calls for a slow start. Explore the main city, Ponta Delgada, and get accustomed to urban life by the ocean. Shake any jet lag or long-flight drowsiness with a walk in the historic center. Take in black-and-white pavements, the deep blue Atlantic, and the aroma of sea air.

Dinner: is a great place for your first taste of traditional Azorean cuisine, with local fish served grilled.

Day 2: Soak up postcard-perfect views in Sete Cidades and Mosteiros 

Morning: Hire a taxi or drive from Ponta Delgada to Sete Cidades (30km/ 18 miles). Most travelers head straight to Miradouro da Vista do Rei for the views over the blue and green lakes – although stopping here is a must, after seeing São Miguel’s most famous landscape, drive down the winding road that leads to the center of the quiet lakeside village.

Take a break: Head to for a light lunch. Weather permitting, ask to pack your meal and have an impromptu picnic by the lake.  

Afternoon: One of the top beaches in São Miguel, Praia dos Mosteiros, is a 10km-drive from Sete Cidades. A well-known spot for experienced surfers, it's also a family's favorite in the summers. Whether it's a good day for a swim or relaxing by the shore, stick around for the sunset.

Dinner: Ponta Delgada’s artistic district O Quarteirão has some of the best restaurants in town, including the local institution , one of the city’s first vegan and vegetarian restaurants.

In the evening: If you still have the energy, wrap up your day with a cocktail at Résvés Street Bar.

Day 3: Spend a relaxing day in Furnas

How to spend the day: Start early and take the scenic road EN1-1A towards Furnas. It’s a long and curvy trip (approx. 45km/27 miles), so I suggest a stop mid-way in Vila Franca do Campo to stretch your legs and see the islet from Miradouro Ilhéu da Vila. 

Take in the view, but hit the road soon, so you reach Furnas around mid-morning. You’ll want to explore the walking paths of and soak in their pool of naturally heated water and visit the caldeiras (puddles of scalding water in the village center) before lunch. The shallow pools at are safer for non-swimmers.

Take a break: After lunch, whether you had the traditional cozido (meat-and-potatoes stew cooked underground in volcanic steam) or not, stop by Padaria Glória Moniz for coffee and get a few bolos lêvedos (traditional Furnas sweet bread) for the road.

Dinner: Head to the fishing town Rabo de Peixe for an early dinner at .

Planning tip: For cozido das Furnas, make reservations at least one week in advance. is one of the best spots in town to try this local dish.

Day 4: Reach Terceira and walk around Angra do Heroísmo

How to spend the day: After landing on Terceira Island, head straight to Angra do Heroísmo (about 20km/12 miles from the airport). Drop everything at the hotel and set out to get lost in the streets of the city’s historic center, a UNESCO World Heritage Site since 1983 where colorful buildings line narrow cobblestoned streets and picturesque squares. Depending on the weather, either hike to Monte Brasil to see the views from Miradouro do Pico das Cruzinhas or learn about Terceira’s rich history at .

Take a break: Grab a coffee or a glass of wine, and unwind at cozy, dog-friendly family-owned bookstore, cafe, and cultural venue . With a busy calendar, you'll likely stumble upon some event with local artists.

Dinner: You can’t leave Terceira without trying alcatra (stew in a clay pot). Boca Negra is one of the best places to have it.

Day 5: Take a road trip to some of the top sights of Terceira

How to spend the day: Drive from Angra do Heroísmo to to learn about one of the volcanoes that formed Terceira Island. Take in the views from Miradouro de Santa Bárbara and then head north to Biscoitos. One of the busiest beach destinations in the summer, this town is also known for its wine. 

Dinner: Drive along the coast to Praia da Vitória to grab dinner at , a traditional seaside restaurant known for fish dishes.

In the evening: A post-dinner walk along the promenade by the beach before driving back to Angra is a great way to start saying goodbye to Terceira. 

Day 6: First day in Pico, explore the island’s vineyards

How to spend the day: On a short trip, you're unlikely to have time to climb Mount Pico (it's at least an 8-hour roundtrip). You won’t be able to miss the mountain, though. Upon arriving, and after a recognition walk in Madalena, get to know Pico’s wine industry history at . Afterwards, head to Porto da Areia Larga – the starting point of a hiking trail leading to the vineyards at Criação Velha. 

Take a break: When walking back to Madalena, stop by for petiscos (food to share) and local wine by the glass.

Dinner: Make reservations for one of the tasting menus paired with selected local wines served at Azores Wine Company – or choose one of the smaller menus with petiscos. 

Day 7: Visit historic whalers’ towns

How to spend the day: The whaling industry was a crucial source of income in the Azores and is strongest in Pico. Head to one of the whalers’ towns, São Roque, through the scenic road EN-3, to visit and see the view of São Jorge Island. Then, drive south to Lajes do Pico, and if you’re visiting during peak season, book a half-day afternoon whale-watching tour with .

Dinner: Have a sushi dinner made with local products at the Japanese restaurant with a view , about 5km/ 3 miles from Lajes.

In the evening: A trip to Pico isn’t complete without a visit to . Order the Cella Wine Tasting to bid the Azores farewell.