Updated October 2026 • 8 min read
We asked the travel advisors on our team, all based in the Azores, to share a trip they have taken themselves and loved. Five of them turned it into a package: João picked São Jorge and São Miguel by car, Daniela slow days on Graciosa before São Miguel, Marina the hidden side of São Miguel on foot, Carolina the food and wine of Pico and São Miguel, and Mariana the wild western islands of Flores and Corvo. Each one includes flights from North America, hotels and either a rental car or guided experiences.
Every trip can be adjusted to your dates, departure city and travel style by our travel advisors.
How These Trips Were Chosen
Most visitors to the Azores see São Miguel and leave. Our team lives here, and when we travel between the islands ourselves, we head for the places that rarely make it into first-time itineraries: the fajãs of São Jorge, the quiet villages of Graciosa, the vineyards of Pico, the waterfalls of Flores. Each Team Pick is built on a trip one of us has made, and most pair one of those islands with São Miguel, so you get the highlights and something most visitors miss, planned by someone who has been there.
João's Choice: São Jorge & São Miguel by Car
6 nights | 3 on São Jorge, 3 on São Miguel | rental car on both islands
São Jorge is a long, narrow ridge of an island, with cliffs that drop to the sea and fajãs, small flat strips of land at their foot where villages, vineyards and natural pools sit. It is also known for its cheese. With a car on both islands, this trip starts with São Jorge's coast and finishes with the crater lakes and hot springs of São Miguel.
JOÃO'S CHOICE
"From São Jorge's cliffs and hidden fajãs to the crater lakes and hot springs of São Miguel, this is a trip for travelers who want to see the Azores beyond the usual stops. With a rental car on each island, you can reach the lava-rock pools of Pontinha do Topo and the black-sand shore of Mosteiros at your own pace." João M., Local Travel Crafter
See João's trip →Best for: independent travelers who like to drive, coastal walks and quiet villages.
Daniela's Choice: Slow Life on Graciosa & São Miguel
7 nights | 3 on Graciosa, 4 on São Miguel | rental car on both islands
Graciosa is one of the smallest and quietest of the nine islands, and the one where the pace of Azorean life is slowest. Its villages are whitewashed, its windmills still stand, and inside its caldera is the Furna do Enxofre, a volcanic cave with a lake at the bottom. Four nights on São Miguel then add the island's best-known sights.
DANIELA'S CHOICE
"Two different rhythms of Azorean life in one trip. Graciosa is small and quiet, with whitewashed villages, windmills and the Furna do Enxofre cave inside its caldera. São Miguel brings crater lakes, tea plantations and geothermal hot springs. With a rental car on both islands, you explore at your own pace, and we, your local team, are a call away." Daniela C., Local Travel Crafter
See Daniela's trip →Best for: couples, second-time visitors and anyone who wants to slow down.
Marina's Choice: São Miguel Off the Beaten Path
6 nights on São Miguel | airport transfers and 4 guided experiences
This is the only single-island pick, and it replaces the rental car with airport transfers and four guided experiences. Marina built it around the São Miguel she knows: a farmers' market, the Sanguinho and Moinho do Félix trails to waterfalls in the east of the island, a pineapple plantation and a fado dinner.
MARINA'S CHOICE
"Experience the soul of São Miguel beyond the typical tourist spots. Explore a local Farmers' Market, hike the breathtaking trails of Sanguinho and Moinho do Félix, and savor authentic flavors from fresh pineapples to a soulful fado dinner. Discover the magic of my home place and create memories that will stay with you long after you leave." Marina F., Local Travel Crafter
See Marina's trip →Best for: first-time visitors who prefer not to drive, hikers and travelers interested in local culture.
Carolina's Choice: Pico & São Miguel Food and Wine
7 nights | 3 on Pico, 4 on São Miguel | rental car on each island
Pico's vineyards, planted inside black lava-stone walls, are a UNESCO World Heritage landscape, and the island's wines and cheeses are some of the best in the Azores. This trip includes a six-course dinner paired with five Pico wines, then a pineapple farm tour, a wine tasting and a dinner on São Miguel.
CAROLINA'S CHOICE
"Sip bold Pico wines paired with tangy local cheeses, sit down to a 6-course feast on Pico and a dinner on São Miguel, and toast among sweet pineapple plantations. With a car on both islands, the vineyards, villages and viewpoints are all within easy reach. Vamos!" Carolina D., Local Travel Crafter
See Carolina's trip →Best for: food and wine lovers and couples. Pico is also the island for climbing Portugal's highest mountain and for whale watching.
Mariana's Choice: The Wild Islands of Flores & São Miguel
7 nights | 4 on Flores, 3 on São Miguel | airport transfers and 5 experiences
Flores, the westernmost island of the Azores, is the one our team mentions most when asked where to go to disconnect: waterfalls pouring down green cliffs, crater lakes and almost no crowds. From Flores, a boat crosses to Corvo, the smallest island of the archipelago. Read more in our guide to Flores.
MARIANA'S CHOICE
"Flores is the island that always leaves me speechless: it is wild, untouched, and feels like something out of a movie. Pairing it with a boat ride to Corvo, that tiny, magical dot, and the iconic trails and crater lakes of São Miguel creates a once-in-a-lifetime trip. Truly disconnect and let the islands do the rest." Mariana P., Local Travel Crafter
See Mariana's trip →Best for: nature lovers, hikers and travelers who have already seen São Miguel or want somewhere truly remote. Flights to Flores are more often affected by weather, so allow some flexibility.
The Five Team Picks at a Glance
| Trip | Islands | Nights | Getting around |
|---|---|---|---|
| João's Choice | São Jorge, São Miguel | 6 | Rental car |
| Daniela's Choice | Graciosa, São Miguel | 7 | Rental car |
| Marina's Choice | São Miguel | 6 | Transfers, 4 guided experiences |
| Carolina's Choice | Pico, São Miguel | 7 | Rental car, food and wine experiences |
| Mariana's Choice | Flores, Corvo, São Miguel | 7 | Transfers, 5 experiences |
All five include flights from North America and, on the two-island trips, the inter-island flights, hotels, taxes and fees, and an expert trip manager. Every pick can be adjusted: more nights, a different hotel or another island.
When to Go
All five work from May to October, when the weather is most settled and boat trips run most reliably. The two-island picks with Flores, São Jorge and Graciosa depend on inter-island flights, which are more often delayed by weather in winter. Marina's São Miguel trip is the most flexible for a winter visit. See our month-by-month guide.
Plan your trip
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Tell our local travel advisors which islands, dates and experiences you want and we build the itinerary around you.
Start your custom trip →Limited time
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Book now →Azores Team Picks: FAQ
What are Azores Getaways Team Picks?
Vacation packages designed by members of our Azores-based team around trips they have taken themselves. Each combines flights, hotels and a rental car or guided experiences.
Do the Team Picks include flights from the US and Canada?
Yes. All five include international flights, plus the inter-island flights on the two-island trips. Departures are available from several North American cities, including Boston, New York and Toronto.
Which Team Pick is best for a first trip to the Azores?
Marina's Choice for a first trip without driving, or João's Choice if you want a car and a second island.
Can I customize a Team Pick?
Yes. You can add nights, change hotels or swap islands with our travel advisors.
Which Team Pick is best for food and wine lovers?
Carolina's Choice, on Pico and São Miguel, with a six-course dinner paired with Pico wines, a wine tasting and a pineapple farm tour.
.jpg "Sete Cidades Caldera Lakes in São Miguel Island, Azores")
.jpg "Jeep tour through Cumeeiras, Sete Cidades, São Miguel Island")
.jpg "Scenic View of Tea Plantations in São Miguel, Azores")
.jpg "Pico Island’s Longitudinal Road (IS1) – Scenic Drive Through the Heart of the Island")
