• Portugal: Azores Islands Explorer

Discover one of the world's "best-kept secrets," off the coast of Portugal.

The Azores Islands are a wild and otherworldly archipelago that only recently emerged as a trending destination. The Azores consist of nine islands: Sao Miguel, Santa Maria, Terceira, Faial, Pico, Sao Jorge, Graciosa, Flores, and Corvo. Each island is distinctly different, and locals claim a lifetime isn’t long enough to fully explore the mysteries and hidden forces shaping the landscapes here.

On our 8-day journey through the Azores, we visit four of the archipelago’s most scenic and dynamic islands, hike along volcanic calderas, and take to the sea for a whale watching excursion. Along the way, we sample the Azores’ extensive culinary bounty, visit with local artisans, enjoy a wine tasting at a UNESCO World Heritage Site vineyard, and relax in thermal springs and warm, oceanic pools.

With barely 5% of its land developed, the Azores are a must-see locale for nature lovers.

What Our Guests Have To Say About This Tour

Good combo of all aspects

5 5 1
The Boundless Journey's home office and guides find the best hikes and deal with all aspects such as transportation, lunches, accommodations and language communications, which results in providing good value by making excursions timely and cost effective.

Write a Review

Review Title
Review Content
Itinerary &

Itinerary & Accommodations

Day 1

Arrival in Sao Miguel, Sete Cidades

  • Activity Overview: Hiking
  • Activity Level: Easy
  • Activity Length: 4 hours, 7 miles

Welcome to the Azores! We meet our fellow travelers and local guide in the hotel lobby for an informational session and a preview of our activities in the days to come.

On our first excursion together in this lush archipelago, we head to Sete Cidades. These two jewel-colored lakes in the heart of Sao Miguel - one bright blue, the other green - are nestled inside a dormant volcano crater. Hiking along their western edge, we learn about the region's flora and fauna, history, volcanic formation, and the legendary love story behind Sete Cidades' creation. We enjoy a picnic lunch on the shore, taking in the sparkling waters, and steep, verdant slopes.

Later in the day, we take a dip at Ponta da Ferraria, a therapeutic spring and bathing site renowned since the 15th century for its healing powers.

This evening, we dine together at one of our favorite restaurants in town.

Grand Hotel Azores Atlantico

Grand Hotel Azores Atlantico
Ponta Delgada, Sao Miguel, Portugal

With 123 modern rooms overlooking the surrounding ocean, the five-star Hotel Azor boasts an award-winning restaurant and rooftop bar, gym, and panoramic outdoor swimming pool.

Day 2

Sao Miguel to Pico

  • Activity Overview: Walking and wine-tasting
  • Activity Level: Easy
  • Activity Length: 2 hours walking

After breakfast, we take a scenic 40-minute plane transfer to Pico Island, famous for its towering, long-dormant volcano - the highest point in Portugal. Our day of exploration begins with a visit to the famed Gruta das Torres lava tube, with a length of nearly 17,000 feet. It is estimated that the tube was formed about 1,500 years ago, during an eruption originating from Cabeco Bravo volcano. With flashlights in hand, an expert guide takes us through part of the tube and teaches us about its unique geology.

Next, we transfer to the town of Madalena on the western coast, where we enjoy a short walk around Criacao Velha vineyards, part of a 2,400-acre UNESCO World Heritage Site. Wine has been an important export for the Azores since the 17th century, but the islands' volcanic terrain makes viticulture a unique challenge. Over the centuries, wine growers have adapted, creating rock wall wind breaks, known as currais, which protect and cultivate the grapes.

Later today, we have the opportunity to taste the wine produced from Azorean grapes - from fresh and saline whites, to reds with spicy notes, and intensely colored liquor wine.

Dinner this evening will be en route to Aldeia da Fonte, our home for the next three nights.

Aldeia da Fonte

Aldeia da Fonte
Pico, Portugal

Passionately built, the Aldeia da Fonte hotel is part of the magnificent and stunning Nature of Pico Island. With six volcanic stone houses perched on the cliffs overlooking the Atlantic Ocean, this eco-friendly resort is set amidst lush gardens.

Day 3

Calheta de Nesquim Hike

  • Activity Overview: Hiking and whale watching
  • Activity Level: Moderate or a strenuous option with 3,700' elevation gain/loss
  • Activity Length: 3.5 hours, about 4 miles, 3-hour whale watch; or 6.5 hours, about 6 miles

Today, we lace up our boots for circular hike around Calheta de Nesquim and its surroundings. This traditional settlement is located in a remote area of the island, where the first official Azorean whaling company was founded. Fortunately, whaling is now forbidden. But nevertheless, the whaling heritage is an important part of the local community identity.

Our trail begins in a fishing harbor, where old whaling boats are docked. Along the way, we pass by a traditional whale lookout, nowadays used for the whale and dolphin watching experiences, natural pools, ancient paths and houses, gardens, forests, and fields.

Our last stop today is the 15th-century Lajes do Pico, where we enjoy a conservation talk and tour of the town's whaling museum with a local marine biologist. We then board a RIB boat and head out to sea for a chance to spot more than 25 species of whales, dolphins, and porpoises.

If you prefer a more challenging trail (weather-permitting), your hike will begin at Casa da Montanha, or "Mountain House," located at an elevation of nearly 4,000 feet. This steep, rocky climb proceeds to the summit of Pico Mountain, where your efforts will be amply rewarded with a picnic lunch and, if skies are clear, views of the Atlantic and the four surrounding islands.

This evening we celebrate our day with dinner together.

Aldeia da Fonte

Aldeia da Fonte
Pico, Portugal

Passionately built, the Aldeia da Fonte hotel is part of the magnificent and stunning Nature of Pico Island. With six volcanic stone houses perched on the cliffs overlooking the Atlantic Ocean, this eco-friendly resort is set amidst lush gardens.

Day 4

Faial Caldeira, Capelinhos

  • Activity Overview: Hiking
  • Activity Level: Moderate
  • Activity Length: 3.5 hours, 4 miles

This morning, a short ferry ride brings us to Faial, known as the "blue island" for its long rows of blue hydrangea plants. The island has long been a favorite and convenient stopping point for yachts on trans-Atlantic crossings. Our guide highlights the island's volcanic history and the 1957 eruption of Capelinhos, which lasted for 13 months and added nearly a square mile of new land.

Our hike begins at the impressive Faial Caldeira, more than a mile wide in diameter and 1,300 feet deep. Overlooking the surrounding villages, Sao Jorge, and Pico, our path leads around the crater rim, where stop for a picnic lunch along the way.

From here, we continue to the lunar-like landscape of Capelinhos, which ejected more than 30 million tons of ash and lava extending the island of Faial further into the sea and partially burying a lighthouse.

Upon our return to the lively port town of Horta, we board our ferry to Pico, arriving in time for dinner at Ancoradouro, a renowned seafood restaurant offering panoramic views of Faial.

Aldeia da Fonte

Aldeia da Fonte
Pico, Portugal

Passionately built, the Aldeia da Fonte hotel is part of the magnificent and stunning Nature of Pico Island. With six volcanic stone houses perched on the cliffs overlooking the Atlantic Ocean, this eco-friendly resort is set amidst lush gardens.

Day 5

Sao Jorge

  • Activity Overview: Hiking
  • Activity Level: Easy to moderate
  • Activity Length: 1.5 hours, 2 miles

Today, another ferry brings to Sao Jorge, our base for the next two days. Long and narrow in shape, the island's rugged topography is the result of volcanic activity, which created its tall, surrounding cliffs and coastal erosions known as fajas. The fertile plains and unique microclimates created by these fajas make for excellent growing conditions, including some of the best coffee in Portugal.

We arrive in the town of Velas, known for its picturesque cobbled streets, renovated square, and 17th-century church. Here, we stop for lunch at one of the town's quaint restaurants before proceeding to Cafe Nunes, in the village of Faja dos Vimes. At this renowned coffee plantation arabica coffee is made from beans grown in the village. Above the cafe, we visit a small weaving center where Senora Nunes and her sister make woven woolen bedspreads.

Our short hike this afternoon skirts the coast on our way north to Portal. Afterwards, we are treated to a lesson in Sao Jorge's most iconic export: cheese. Known as the best in all of Portugal, the island's cheddar-style queijo - made using milk from the thousands of happy cows that call São Jorge home - was created out of necessity for the island's sailors, who needed a hearty food staple that could survive for months at sea. We sample the acclaimed cheeses before returning Velas for a short rest before a delicious dinner and another restful evening in the Azores.


Hotel Sao Jorge Garden
Sao Jorge, Portugal

The Sao Jorge Hotel offers a quiet and relaxing atmosphere with beautiful views of an expansive garden, outdoor seawater pool, and the Atlantic Ocean.

Day 6

Serra do Topo to Faja dos Cubres

  • Activity Overview: Hiking
  • Activity Level: Moderate to strenuous
  • Activity Length: 5 hours, 5 miles

Our hike today is one of the highlights of our journey, bringing us along the spine of the island from Serra do Topo to Faja dos Cubres. The dramatic scenery here alternates from dense woodlands and high heathers to deep ravines. We pass by a series of now-abandoned faja villages, traveling mostly downhill while enjoying views of the coast and the Terceira and Graciosa islands.

Our efforts on the trail this morning are rewarded with a refreshing dip in a natural lagoon and a picnic lunch along the route to our destination.

Tonight, you are free to explore Velas and enjoy dinner on your own at one of the town's delightful restaurants.


Hotel Sao Jorge Garden
Sao Jorge, Portugal

The Sao Jorge Hotel offers a quiet and relaxing atmosphere with beautiful views of an expansive garden, outdoor seawater pool, and the Atlantic Ocean.

Day 7

Return to Sao Miguel

  • Activity Overview: Walking
  • Activity Level: Easy
  • Activity Length: Variable

A late-morning flight brings us back to Sao Miguel, the largest island in the archipelago. Upon arrival, we transfer to the lakeside town of Furnas, a 19th-century spa village nestled in a huge caldera. The active landscape here houses many fumaroles and several hot springs known for their medicinal waters.

This afternoon, you may have time to relax and explore Furnas and its attractions on your own, including Terra Nostra, one of Portugal's most beautiful parks featuring a thermal swimming pool and more than 2,000 species of trees.

Furnas contains a plethora of mini-geysers, hot springs, and other geologic wonders sprinkled around the village. Among them are thermal pockets used to make Furnas's famous, cozido - a slow-cooked stew made in pots heated in the ground by volcanic steam.

This evening, we have the chance to try cozido de Furnas at our farewell dinner, where we raise a glass to our time together and our magnificent adventure here in the Azores.


Octant Furnas
Furnas, Portugal

The 4-star Octant Furnas is located in Sao Miguel Island, in Vale das Furnas, site of the largest concentration of thermal waters in Europe. The tranquil property was renovated in 2015 and features swimming pools and a Spa & Wellness center.

Day 8


After breakfast, you will be transferred to the airport in time for your departing flight home.

Please note that this is a typical itinerary, and actual activities may vary due to weather conditions, local events, and to allow serendipity to play a hand in your experience. Accommodations are as outlined in the itinerary, although we reserve the right to change these or the order visited should the need arise.

Back To Top
Dates &

Dates And Prices

Trip Length

8 Days

Trip Dates

May 22-29, 2023

Sep 24-Oct 1, 2023

2023 Land Cost

From $6,195 Per Person

Single Supplement

First two reserved:$295


See single supplement policy below.

Pricing Notes


9+ Guests: $6,195 per person

5 to 8 Guests: $6,695 per person

Make it Private price is based on Land Cost only, and a guarantee of the specified number of guests in double occupancy. For groups smaller than the numbers shown, or those requiring single occupancy, we reserve the right to adjust the per person price. Additionally, some trips have minimum group sizes. Please call 1-800-941-8010 for details.

What's Included

  • Expert leadership
  • All accommodations
  • All meals from lunch on Day 1 to breakfast on Day 8, except dinner on Day 6 and lunch on Day 7
  • Local wine and beer with included dinners
  • Entrance fees and local guide fees
  • Activities as noted in the itinerary
  • All on-tour transportation
  • Internal flights, Sao Miguel to Pico and Sao Jorge to Sao Miguel
  • All gratuities except for those for your guide and driver, which are at your discretion
  • Explorers Club savings on your next scheduled, small-group trip (conditions apply)
Single Supplement Policy

Accommodations (hotels, tents, cruise cabins) are based on double occupancy. A single supplement is paid by participants who specifically request single accommodations, subject to availability. If you reserve at least 120 days prior to departure, you may be eligible for a reduced or free single supplement.* This is generally limited to the first one or two solo travelers to reserve, and the reduction is outlined in the pricing for each trip. Please note, free or reduced single supplements are not combinable with other offers or promotions.

If you are traveling alone and wish to share accommodations, we will try to match you with a roommate of the same gender. If you reserve at least 120 days ahead and a roommate is not available, you will only be charged a “forced” single supplement in the amount of 50% of the standard single supplement* (unless otherwise noted in the detailed itinerary). Single accommodations are limited so you are encouraged to reserve early!

*This may not apply to certain trips with unique accommodation arrangements. Please see specific trip information for more details.

What To

What To Expect

Physical Activity

Boundless Journeys' trips are designed for energetic and flexible individuals who like to be active, have a spirit of adventure, and a positive attitude. The Azores Islands Explorer is rated a 3, moderate, on a scale of 1-5 (with 5 being the most strenuous). The fertile landscapes, rolling hills, and coastal paths offer a range of beautiful scenery and a mix of easy walks to strenuous hikes - 1.5 to an optional 6.5 hours and 2 to 7 miles, on trails with some rocky and steep sections, paved or cobblestone streets, and dirt paths. If choosing to hike to the summit of Pico Mountain, there is a 3,700' elevation gain and loss.

Meeting Point

At the Hotel Azor in Ponta Delgada at 9 a.m.

Departure Point

After breakfast at Ponda Delgada airport.

Traveling To and From

If you will be arriving from North America, it is possible to arrive on Day 1 as most flights land around 5 or 6 a.m. However, we recommend arriving the night before to have plenty of time to recover from jet lag and allow a buffer should there be delays. If you are arriving from mainland Portugal, you will most likely need to arrive the night before.


Average high temperatures range from upper 70's in the summer to low 60's in the winter, while the average low temperatures range from mid-60's to low 50's. Perhaps most notable is the unpredictability of the islands' weather, as it can change quickly and drastically from warm sunshine to a windy rainstorm. Most days see some rainfall, which gives the islands their lush, verdant landscapes. You may obtain more detailed information at www.weatherbase.com.



High: 66
Low: 56


High: 75
Low: 64


High: 71
Low: 61

When to Go

The islands of the Azores are characterized by a maritime subtropical climate, with temperate weather year-round. April through October are the best times to visit, for slightly warmer weather and longer, sunnier days.


Portuguese cuisine is all about simple, delicious cooking and fresh ingredients, themes that are present across all geographic regions of the country - including the islands of the Azores.

In general, the expansive, fertile soil and mid-Atlantic location mean that grilled seafood, smoked meats, sun-ripened fruit, and other fresh produce are commonplace. Portugal consumes more rice (arroz) than any other European nation, and its lesser-known savory dishes fall somewhere between a Spanish paella and Italian risotto. Fish is a staple, and you're likely to find everything from cod and octopus to tuna and grilled sea bass - prepared simply with lemon, garlic, and the country's famed olive oil - on most menus.

You'll also see plenty of stews and soups, including alcatra, a traditional beef stew with warm spices; and the unique cozido das Furnas - cooked underground with the steam of the earth. Local cheeses, desserts, and wines are ubiquitous. For dessert, traditional favorites such as egg tarts (pastel de nata) and Madeira honey cake (Bolo de mel da Madeira) can be found at most pastry shops. Oenophiles should be certain to try wine from Pico Island's rare, World Heritage vineyards.


Featured Guides

About Our Guides

With a Boundless Journeys guide, your experience is that of friend and local adventurer. We believe strongly in working with local guides, experts in the areas to which we travel, and they hold the keys to unlocking the hidden delights of your chosen destination. Although you will never know they are at work—the mark of a truly great leader—our guides make magical things happen and add a dimension to your trip that you could not experience on your own. Over the years we have forged bonds with some of the best guides in the world, and we typically work with a small team of guides in each region. You will be informed of the guide for your trip one month prior to your departure.

From $6,195 / person* *airfare not included
8 Days
Reserve This Tour
  • Departure Dates: May 22-29, 2023
    Sep 24-Oct 1, 2023
Activity Level 3 Moderate

Walking and hiking 2-5 hours and whale watch. Optional strenuous hike to Pico summit.

Read about our Activity Levels
  • Group Size: 4-16 Guests

Make it Your Own!

This trip can be your own adventure by taking over one of our scheduled dates, or we can request a fresh one.

Prefer a Custom Tour?


Our dedicated team of travel experts are here to help.


Travel + Leisure World's Best Award

Top 5 World's Best Tour Operators
Multi-year Recipient

National Geographic Traveler

50 Tours Of A Lifetime
Multi-year Recipient

National Geographic Adventure Magazine

Best Adventure Travel Company Winner

ATTA member since 2006