Published: 9/10/2023

Our Epic 8 Day Azores Itinerary

This 8 Day Azores itinerary was truly a dream come true.

I know I say that a lot, but honestly, for years I’ve been trying to convince pretty much everyone I know to take a trip with me to Portugal‘s subtropical islands in the middle of the north Atlantic Ocean.

Despite gaining popularity in recent years thanks in part to some airline advertising campaigns, many people aren’t familiar enough with the Azores to gamble their precious vacation time on this seriously underrated destination.

But I’m here to change that!

Now that I’ve been lucky enough to explore these beautiful European islands with my friends Jenny and Leah, I can tell you wholeheartedly that the Azores absolutely deserve a spot on your travel bucket list.

In this post, I’ll share our full 8-day itinerary, explain the logistics of getting to and around the Azores, how we booked our hotels (hello Azores Getaways!), and all the best things to do in the Azores including hikes, restaurants, scenic spots, tours, and more.

By the end of this post, you’ll be all set to book your own trip to Portugal’s Azores!

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Three travel friends on the Azores’ Sao Miguel Island, the largest island in the nine island archipelago.

What are the Azores?

Often referred to as Europe’s Hawaii, the Azores are located in the middle of the North Atlantic Ocean. These nine volcanic islands sit between 950 – 1400 miles west of Portuguese mainland. You can get there with an approximately 4.5 hours flight from both Boston and Frankfurt, Germany. There’s some speculation that these remote islands are the Atlantis of ancient mythology.

The Azores operate as an autonomous region of Portugal. While Azoreans identify as Portuguese, they have their own government, accent, and cultural identity. In many ways, they are to Portugal what an American state is to the United States.

The islands were uninhabited until trade winds blew Portuguese sailors into Angra do Heroismo’s harbor on Terceira Island in the 1400s. Because of their strategic position in between the Americas and Europe, the Azores played an important role in the days of ocean exploration and trade.

US Air Force jets on the tarmac at Lajes Airfield on Terceira Island.

The Azores can also make a convenient meeting point for American and European leaders. Did you know the decision to invade Iraq in 2003 was made in the Azores?!

Historically, the Azores were very poor. Residents mainly farmed and whaled. Many, looking to escape a subsistence lifestyle immigrated to the Boston area. (If you’re ever looking for Azorean cuisine in the U.S., check out Boston!)

These days, the islands’ main industry is tourism. In addition to pimping out their gorgeous landscape, the Azores are still known for agriculture, especially cattle and dairy. Because of their unique temperate climate, you can grow just about anything in the Azores including tropical fruits and tea.

Mosteiros Beach on Sao Miguel’s West Coast is known for its gorgeous black sand.

Why You Should Visit the Azores

You’ll often hear that the Azores feel like Hawaii and Ireland’s love child. Since both Hawaii and Ireland have special places in my heart, I can assure you that this description is very accurate!

The island hopping and the distinct personalities of each Azorean Island definitely reminded me of Hawaii. While the gulf stream allows tropical plants like palm trees to grow in the Azores, the actual appearance of the Azores, with its the rugged coastline and pastoral hillsides, more closely resembles Ireland.

The Azores’ unique position in the world in and of itself attracts visitors, but the islands offer a lot more than just travel bragging rights.

For outdoor enthusiasts, all nine of the major Azores offer extensive hiking opportunities. As you might expect, you can also expect excellent fishing and whale watching.

The Azores’ unique geography offers endless dramatic vistas perfect for amateur and professional photographers. With geothermal energy literally oozing out of the islands, you’ll find lots of unique bathing opportunities, including ocean pools warmed by geothermal springs. (I’ll admit geothermal travel is a weird niche, but I did go on another geothermal adventure in Alaska . . . .)

Culture lovers will enjoy the Azores’ rich human history. Those escaping persecution in Europe sometimes ended up in the Azores which contributes to the islands’ distinctive culture and cuisine.

And if you want to sip some of the most unique wine in the world, you need to get to the Azores. Because the Azores (like other places on the Atlantic) can experience hurricanes, the grapes must be harvested early to avoid crop destruction. The result is a very dry, slightly salty wine. Although Azorean wine is somewhat maligned, especially when compared with wine from mainland Portugal, I loved it!

Seriously, the Azores offer so much that one visit really isn’t enough to do this special corner of the world justice.

On these primarily Catholic islands, the Holy Spirit is especially important. You’ll find adorable little Holy Spirit Chapels scattered all over the Azores.

What To Know Before Visiting the Azores

Before we jump into our complete Azores itinerary, here’s some need-to-know information to help you plan your trip.

How To Get to the Azores

Unless you own a yacht (I do not . . . but the Azores are a popular destination for yachters!), you’re probably get to the Azores via either a cruise ship or an airplane. If you want the most control of your time in the Azores, your best bet is to fly. 

You’ll find direct flights to the Azores’ largest city – Ponta Delgada on Sao Miguel Island – from New York City, Boston, and Toronto. You get a lot more flight options from the European side of the pond. Various airlines offer direct flights to the Azores from Frankfurt, Lisbon, London, Manchester, and Porto.

Many people opt to visit the Azores as a stopover on a larger European itinerary. Alternately, you might find more affordable flight options by flying first to Lisbon or Porto and having a mainland Portugal stopover before continuing to the Azores.

We opted to book our trip through Azores Getaways, a travel agency that offers flight and lodging packages. For the best rate, we booked separate flights to Boston where we caught our flight to Ponta Delgada. After a six-hour layover in the Azores’ capital city, we finally made it to our final destination: Terceira Island.

The Azores offer endless scenic overlooks . . . until the fog rolls in.

Weather in the Azores

Azoreans are fond of saying they have “all four seasons in one day.” As a Minnesotan, I strongly disagree with the sentiment, but their point is taken.

Don’t expect tropical weather on the Azores. While the gulf stream keeps the islands warm year-round, it also means the islands never really get hot. You can expect temperatures to stay above 50 degrees and below 80 degrees year-round.

During our March visit, we found the weather very similar to Ireland’s spring weather: think gusty winds and frequent rain showers followed by rainbows. While you might be absolutely buried in fog at the island’s high points, you often only need to drive 10 minutes to find blue skies.

Moral of the story: always wear layers and have a rain jacket within reach!

In the tea fields at Cha Gorreana on Sao Miguel Island. 

About the name “Azores”

In English, “Azores” looks an awful lot like “Azure.” For a long time, I assumed Azore was the Portuguese word for this blue color. I mean, it seemed like a fitting enough name for islands in the middle of the wide blue ocean . . .

But when you’re in the Azores, you’ll quickly realize that the islands’ name is actually Açores. Because we don’t use cedillas in English, the islands’ name is Anglicized to “Azores.” Instead of the harsh “A-zoar-s”, you pronounce Açores like “A-sores,” with a little extra “z” sound on the “s.”

In Portuguese, an açor is a northern goshawk. When the Portuguese reached the Azores, they saw a raptor soaring above the islands and decided to name the islands for it. However, they misidentified the bird. (There are absolutely zero goshawks on the Azores.) They probably spied a buzzard or kite.

Despite the mistake, the name stuck. You’ll even find a goshawk on the Azorean flag. The popular Azores distillery, Goshawk, continue to honor the islands’ misnomer name.

Cow traffic jams are par for the course when driving on the Azores. We were caught in two of them during our visit to Sao Miguel Island.

Getting Around the Azores

To get around the Azores, we depended on planes and cars. During the summer months, you also have an option to take a ferry between the Azores’ nine major islands. Since we visited in the early spring, flights were our only way to get from island to island.

Driving in the Azores

Once you’ve arrived on the island of your choice in the Azores, you’ll want a car.

If you don’t have a set of wheels during your time on the islands, you’re seriously going to miss out or be very beholden to tour bus itineraries. The Azores are pretty rural and there’s really no public transportation.

Happily, our Azores Getaways package also included a car rental on both Terceira and Sao Miguel Islands.

While I can’t speak from personal experience since Jenny drove us everywhere, driving in the Azores seemed pretty straightforward. While the endless roundabouts are no joke (Jenny even got us through an interesting triangle roundabout in Angra!), compared to driving in Hawaii, the traffic was very manageable. We often had the roads to ourselves.

How to Choose Which Island To Go to in the Azores

Just like with Hawaii, which islands you visit in the Azores will have a dramatic impact on your experience and impressions of the region.

For example, Pico Island is the island best known for producing wine. Terceira Island is home to the oldest city in the Azores – Angra do Heroismo. Sao Miguel is both the largest and most populous island in the Azores. If you only visit one island in the Azores it will likely be Sao Miguel, if only for a flight connection.

The islands are often divided into the three groups: Eastern, Central, and Western.

We took the easy route when it came to choosing which of the Azores to visit. Instead of hemming and hawing over the merits of each island, we simply accepted the itinerary presented by Azores Getaways. We ended up with three nights on Terceira and four nights on Sao Miguel.

While I would have loved to have seen Pico and Faial Islands, this itinerary was the perfect introduction to the Azores. Read on to learn what exactly we got up to on this epic first-time Azores itinerary!

Eastern view of Monte Brasil in Angra do Heroismo, Terceira Island

Our Entire 8 Day Azores Itinerary

Day One: Arrive to the Azores

Our plane touched down in Ponta Delgada right at sunrise. Unfortunately, Sao Miguel Island wasn’t our final destination. We were booked on the 1 p.m. flight to Terceira Island. We briefly considered hopping on the earlier flight, but after realizing there would be $100 change fee per ticket, we decided to stick with our original plan.

The week before, I’d become nervous about our six-hour layover and after a little research about the Ponta Delgada airport (FYI: it’s teeny), booked a private room in the nearby Azores Youth Hostel.

If your Azores itinerary also presents you with a long layover in Ponta Delgada, I highly recommend this option. Ponta Delgada is a 10-gate airport with very limited amenities. If you do spend a long layover here, I recommend at least going out of the secured area for a little more shopping and food.

We had no trouble snagging a taxi from the line outside the airport. Our competent taxi driver Karla was up to the challenge of finding the hostel (which has no street number – it’s the only building on the street) and with a little help from Google Translate, we arranged for her to pick us up three hours later to return us to the airport.

Azores Youth Hostel in Ponta Delgada was the perfect spot for us to catch some shut-eye during our long layover. Located in an old monastery, the hostel offers both private and dorm style rooms. Our private room even had its own bathroom. The hostel abuts Antonio Borges Botanical Garden.

At long last, we landed on the east end of Terceira Island. A 20-minute car ride delivered us to Terceira Mar Hotel. The view of Monte Brasil rising above the crashing Atlantic Ocean from our hotel room made all the jet lag well worth it.

Stay: While I generally consider myself too old for youth hostels, the Azores Youth Hostel in Ponta Delgada was one of the best travel decisions I’ve ever made.

After our no-frills hostel naptime, Terceira Mar Hotel was a dramatic contrast. Every room in this beautiful 4-star hotel has an ocean view. The hotel features indoor and outdoor pools, an onsite bar and restaurant, and racquet ball courts. Honestly, it’s kind of “the” place to stay on Terceira Island.

Eat: We briefly considered making a reservation at the onsite Terceira Mar Hotel restaurant, but an early bedtime beckoned. Instead, we grabbed a light bite (and my first Azorean gin!) in the Fanal Bar well before the European dinner hour. 

Day Two: Angra do Heroismo

The oldest city in the Azores, Angra do Heroismo on Terceira Island, as seen from Memória a D. Pedro IV. In the distance, Monte Brasil rises up and Fortress of São João Baptista overlooks the city’s historic quarter.

The historic city of Angra do Heroismo deserves a full day of exploration.

We gave it just that, starting our day with a climb to the top of Monte Brasil. This ancient volcano juts into the Atlantic Ocean and offers a panoramic view of the historic city. On our way up to Miradouro do Pico das Cruzinhas, we passed the Fortress of São João Baptista. After taking in the Miradouro’s view, we visited the mountain’s cat colony as well as an old whaling signal station.

Part of an old whaling station at the top of Monte Brasil in Angra do Heroismo on Terceira Island 

The Cathedral of Angra do Heroismo.

The entire city of Angra do Heroismo is a UNESCO World Heritage site. Largely destroyed by a deadly earthquake in 1980, the historic quarter’s buildings have all been meticulously rebuilt. We ended up doing a self-guided tour of the historic quarter after lunch.

During our walk-through Angra, we took in City Hall, the town square, the Cathedral of Angra do Heroismo, and the Captain-General’s Palace. You definitely don’t want to miss the beautiful Duke of Terceira Garden. Be sure to hike up the hill in the garden to reach the Memoria a Di Pedro IV for a fantastic overlook of the city and Monte Brasil.

We also ducked into a few shops, including Bordado dos Açores, a lace and local handicrafts shop. If you’re looking for an authentic Azorean souvenir, a piece of lace is an excellent choice. In addition to offering wares, the shop included several interpretative panels that explain the history and importance of lace making in the Azores.

Stay: Terceira Mar Hotel, Angra do Heroismo

Eat: I’d forgotten how spectacular European hotel breakfast spreads are. The breakfast buffet at Terceira Mar Hotel set us up for a full day of exploring in the historic city.

We had a great lunch at Verde Maca in downtown Angra. Check them out for fresh, “brunch-y” options. 

My biggest culinary regret of the trip is how hard I pushed to eat dinner at Quinta dos Açores, the ice cream factory just north of Angra. You can’t deny their great dining room view, but everything about our experience here was just okay.  

Day Three: Dairy Farm Tour and Exploring Terceira

Yes, those mugs are full of milk we milked ourselves on a quirky Dairy Farm Visit tour on the east side of Terceira Island.

We hopped straight in our rental car this morning and drove to the eastern end of Terceira Island to Praia da Vitoria. There we meet up with our tour guide, Vitor of Islanders Azores, for a dairy farm visit and wine tasting.

I assumed we’d be part of a larger tour group, but nope, it was just the three of us and Vitor tootling around eastern Terceira in his cherry red van.

Weather (sideways rain to be exact) curtailed the dairy farm visit, but not before we all milked Frenchie the cow. Instead, our tour evolved into a driving tour where we took in Lajes Airfield, the American military base, and various scenic viewpoints. The tour concluded with an Azorean wine and cheese tasting at Vitor’s home. Along the way we learned about the Azorean Holy Spirit chapels, the islands’ impressive dairy production (30% of Portugal’s milk comes from the Azores), and Terceira’s bull running tradition.

If there was a word to describe this tour, it would be awkward, but I do recommend it. Vitor was an absolute wealth of knowledge. I wish we’d done the tour first thing upon arriving in Terceira so we could have taken full advantage of his local knowledge and restaurant recommendations.

The natural pools of Biscuitos are enjoyable in any weather, but they’re particularly dramatic in rough seas.