Azores Island-Hopping Hiking Adventure

Please note that the following information is meant to provide a general overview of your tour. The specifics of your trip will be contained in a pre-trip letter you will receive prior to your confirmed departure.

Important Trip Details: 

MEETING PLACE: Ponta Delgada, São Miguel Island, at the hotel in the city center. Specific hotel details will be provided prior to departure.
MEETING TIME: Guests should aim to arrive by the afternoon. The welcome dinner will take place in the evening.
RETURN TIME:  Transfer to the airport in the morning for departure on Day 10. 
TRIP LENGTH: 10 days
AGE LIMIT:   Minimum age is 18
NEAREST AIRPORTS: Ponta Delgada Airport (PDL) on São Miguel Island, where you will arrive and depart.

Day 1 - Arrival in Ponta Delgada, São Miguel Island

Welcome to the lush, volcanic archipelago of the Azores! Upon arrival in Ponta Delgada, settle into your hotel in the heart of the city. This evening, the group will gather for a welcome dinner at a local restaurant known for its commitment to sustainable practices. Here, you enjoy your first taste of authentic Azorean cuisine—fresh seafood, locally grown produce, and the unique flavors of the islands.

If you arrive early, there’s time to explore at your own pace. Take a gentle stroll through the Antonio Borges Botanic Gardens, serene green spaces filled with exotic plants. You might also visit a nearby pineapple plantation, Plantacao de Ananas dos Acores to learn how this tropical fruit thrives in volcanic soil. Just across from the hotel, step into history at Forte de São Brás, a 16th-century military fort, or wander the halls of the Museu Carlos Machado, where taxidermy, natural history, and local artifacts are housed in a former convent.

Activity: Optional gentle stroll Antonio Borges Botanical Gardens

MEALS INCLUDED: Dinner

Day 2 - Sete Cidades Adventure

Today, we set out to explore one of the most iconic landscapes in the Azores: Sete Cidades, a vast volcanic caldera on the island of São Miguel, famous for its vivid twin lakes and lush scenery. Our morning begins with a scenic hike along lush ridgelines overlooking the twin lakes — one green and one blue — nestled within an ancient volcanic crater.

After working up an appetite, we pause for a picnic lunch at the water’s edge, savoring fresh local fare while taking in the peaceful beauty of this extraordinary setting.
In the afternoon, the pace picks up with a guided e-bike ride, allowing us to cover more ground and uncover hidden corners of this magical area. Weather permitting, we finish the day with a visit to Ponta da Ferraria, where natural volcanic hot springs meet the Atlantic Ocean — a unique opportunity to soak in geothermal waters while waves lap gently against the rocks.

We return to Ponta Delgada for the night to rest up for tomorrow’s adventure.

Activity: Hiking in Serra Devassa

• Distance: 5 km (3 miles)
• Est Time: 2 hrs
• Elevation Gain/Loss: Relatively moderate with minimal elevation changes
• Difficulty: Moderate

Activity: E-bike ride

• Distance: 12–15 km (7.5–9 miles)
• Est Time: 2–3 hrs
• Elevation Gain/Loss: Moderate elevation changes with some gentle climbs
• Difficulty: Easy to moderate – suitable for most people, even those with minimal biking experience

MEALS INCLUDED: Breakfast, Lunch, Dinner

Day 3 - Terceira Island — Traditions & Volcanic Wonders

After a short flight to Terceira Island, it’s time to explore Angra do Heroísmo, immersing ourselves in its rich cultural heritage. The island’s main city was the first in Portugal to be designated a UNESCO World Heritage Site, celebrated for its historical architecture and role in Atlantic history. We have the opportunity to explore its cobblestone streets, admire colorful buildings, and visit landmarks such as the 16th-century Cathedral of Angra do Heroísmo.

Free time for lunch at a place of your choosing.

In the afternoon, we delve into Terceira’s volcanic heart with a visit to Algar do Carvão (or an alternative cave if closed), a rare opportunity to descend into an ancient volcanic cave.

Activity: Cave exploration

• Distance: 1–2 km (0.6–1.2 miles)
• Est Time: 1.5–2 hrs
• Elevation Gain/Loss: Minor elevation changes, mostly flat terrain with some uneven surfaces inside cave
• Difficulty: Moderate – walking on uneven terrain, sometimes slippery surfaces

MEALS INCLUDED: Breakfast, Lunch, Dinner

Day 4 - Luxurious Forests & Dramatic Coastline

Today, we lace up our boots for a full-day hike along the Rocha do Chambre trail. This scenic route winds through the island’s lush interior, highlighting Terceira’s diverse flora and volcanic origins. After the hike, we visit the island’s dramatic coastline, shaped by rugged basalt formations.

The afternoon leads us to the north of the island, where we will see the local vineyards close to the ocean, in the area of Biscoitos.

Activity: Hiking in the center of the island

• Distance: 8.8 km (5.5 miles)
• Est Time: 3 hrs
• Elevation Gain/Loss: Some moderate elevation changes and uneven terrain, but no significant climbing
• Difficulty: Moderate – requires a moderate level of fitness

MEALS INCLUDED: Breakfast, Lunch, Dinner

Day 5 - Arrival on Pico Island — Wine & Heritage

Today, we fly to Pico Island, home to Portugal’s highest peak and a landscape rich with volcanic history. Known as the "Black Island" for its striking volcanic soils, Pico offers a deep dive into its culture and winemaking traditions. Our first day focuses on exploring its historic vineyards, where black volcanic stone walls cradle the vines in a dramatic contrast of green against the dark basalt.

We visit charming villages and museums that showcase the island’s cultural heritage and seafaring past. Later, we visit a local wine cooperative to learn about the resilient vines that produce the island’s celebrated wines. As the day winds down, we enjoy a wine-paired dinner at the esteemed Azores Wine Company.

Activity: Vineyard walk in Vinhas da Criação Velha

• Distance: 7 km (4.3 miles)
• Est Time: 1.5–2 hrs
• Elevation Gain/Loss: Mostly flat terrain, slight elevation changes through vineyards
• Difficulty: Easy to moderate

MEALS INCLUDED: Breakfast, Lunch, Dinner

Day 6 - Mount Pico Summit

Today’s highlight is a guided ascent of Mt Pico, Portugal’s highest peak. Standing at 2,351 meters (7,713 feet), Mt Pico is the third-highest peak in the Atlantic Ocean. The summit reveals a vast crater and a dramatic volcanic cone—Pico Pequeno—rising from its center.

If weather conditions prevent the summit hike, we will choose an alternative mountain trail on Pico Island.

For those not seeking the challenge of the summit hike, you’re welcome to stay in town and enjoy local offerings, such as exploring charming villages, visiting museums, or relaxing at a café by the sea.

Activity: Mount Pico ascent (optional)

• Distance: 8 km (4.4 miles)
• Est Time: 6–7 hrs (3–4 hr ascent & 3–4 hr descent)
• Elevation Gain: 1150 m (3743 ft)
• Start Elevation: 1200 m (3970 ft)
• End Elevation: 2351 m (7713 ft)
• Difficulty: Challenging – steep terrain, significant elevation gain, best for experienced hikers

MEALS INCLUDED: Breakfast, Lunch

Day 7 - Caldeira Hike & Volcanic Landscapes on Faial

Today, we take a ferry to nearby Faial Island. Our first adventure is a hike along the rim of Faial’s vast Caldeira. From the summit, enjoy views of lush forests, rolling fields, and the Atlantic Sea.

After lunch at Genuino, a restaurant run by a local sailor who has circumnavigated the globe twice, we visit the Capelinhos Interpretation Centre to learn about Faial’s 1957 eruption.

• Activity: Caldera hike
• Distance: 7 km (4.3 miles)
• Est Time: 2.5–3 hrs
• Elevation Gain/Loss: Moderate elevation changes with some uphill sections
• Difficulty: Moderate

MEALS INCLUDED: Breakfast, Lunch, Dinner

Day 8 - Return to São Miguel & the Geothermal Charm of Furnas

This morning, we return to São Miguel by air. We visit one of Europe’s only tea plantations, nestled in the hillsides. Learn about the traditional process and enjoy a tasting.

In the afternoon, travel to Furnas, a town known for its geothermal activity. A walking tour will take us past steaming fumaroles and to the Terra Nostra Botanical Garden, with naturally heated thermal pools.

Activity: Furnas walking tour

• Distance: 3–4 km (1.9–2.5 miles)
• Est Time: 2–3 hrs
• Elevation Gain/Loss: Minimal
• Difficulty: Easy

MEALS INCLUDED: Breakfast, Lunch, Dinner

Day 9 - Cooking, Cycling & Thermal Relaxation

Our final full day begins with a hands-on culinary experience, learning to prepare Cozido das Furnas, a stew cooked underground using volcanic heat. We deliver it to the cooking pits by e-bike, then enjoy a relaxed ride through Furnas.

In the afternoon, choose an optional hike or soak in the warm, iron-rich thermal waters of Terra Nostra’s pools. In the evening, we enjoy the Cozido we prepared together.

Activity: E-bike tour

• Distance: 12 km (7.5 miles)
• Estimated Time: 2–3 hrs
• Elevation Gain/Loss: Moderate with gentle climbs
• Difficulty: Easy

Activity: Optional hike

• Distance: 3 km (1.9 miles)
• Estimated Time: 1–1.5 hrs
• Elevation Gain/Loss: Minimal
• Difficulty: Easy

MEALS INCLUDED: Breakfast, Lunch, Dinner

Day 10 - Farewell to the Azores

Transfer to the airport for your departure, with a final farewell to the beautiful Azores.

MEALS INCLUDED: Breakfast

Travel to the Azores (Ponta Delgada, São Miguel Island)

The Azores are accessible by air, with direct flights to Ponta Delgada (PDL) from several North American cities.

Azores Airlines offers direct service from:

• Boston (BOS)
• New York (JFK)
• Newark (EWR)
• Toronto (YYZ)

United Airlines offers direct from:

• Newark (EWR)
• Direct flights from Denver and Boston begin in July 2025.

Most travelers will arrive into and depart from Ponta Delgada (PDL) on the island of São Miguel, which serves as the main hub for this trip.

We recommend arriving at least one day before the trip begins to allow time for any unexpected travel delays and to settle in before the adventure starts.

Passport & Visa Requirements

U.S. citizens can visit Portugal, including the Azores, for up to 90 days without a visa. However, starting in the last quarter of 2026, travelers from visa-exempt countries, including the U.S., will need to obtain an ETIAS (European Travel Information and Authorization System) travel authorization before entering Portugal and other Schengen Area countries. ETIAS is not a visa but a mandatory pre-travel authorization that involves a simple online application and a small fee. Once approved, it is valid for multiple entries over a period of three years or until your passport expires, whichever comes first.

Ensure your passport is valid for at least six months beyond your planned departure from the Schengen Area.

The Azores enjoy a mild, maritime climate year-round, but conditions can vary depending on the season. Spring (April–June) and fall (September–October) offer comfortable temperatures in the mid 60s to low 70s°F (18–22°C), with a mix of sun and light showers. Summer (July–August) is the warmest and driest time to visit, with highs reaching the upper 70s°F (24–26°C) and longer stretches of sunshine — ideal for hiking and ocean activities. Winters (November–March) are cooler and wetter, with daytime temps in the upper 50s to low 60s°F (15–17°C), and frequent passing rain.

Weather in the Azores is famously changeable no matter the season, so it’s best to dress in layers and always pack a light rain jacket.

This journey through the Azores is an active, multi-island adventure, designed for travelers who enjoy exploring on foot and by bike, with a mix of cultural experiences and time in nature. You’ll hike along volcanic ridgelines, explore lush calderas, cycle through pastoral landscapes, and (optionally) summit Mount Pico — the highest peak in Portugal. Daily activities range from relaxed walks and vineyard strolls to more strenuous hikes, with distances typically between 1.5 and 7 miles (2.5 to 11 km). The Mount Pico ascent, while optional, is a challenging 8 km (5 mile) hike with significant elevation gain.

You don’t need technical hiking or biking experience, but you should be in good physical condition and comfortable with several hours of activity most days. Activities involve uneven terrain, stairs, moderate climbs, and occasional exposure to wind, sun, or rain. E-bikes help make the cycling days more accessible, but a basic level of biking comfort is helpful. Guides will provide full support throughout the trip.

If you have any medical concerns or limitations, please let us know ahead of time so we can help determine if this trip is a good fit. As with any active travel, we recommend checking with your doctor if you have questions about your readiness for this style of trip.

Clothing

• Base Layers: Quick-drying, moisture-wicking shirts (short and long-sleeved)

• Mid-Layers: Lightweight fleece or merino wool sweaters

• Outer Layers:

  • Waterproof and windproof jacket

  • Waterproof pants

• Bottoms:

  • Hiking pants (convertible to shorts)

  • Comfortable leggings or activewear

• Footwear:

  • Sturdy, waterproof hiking boots

  • Lightweight sandals

  • Casual walking shoes

  • Comfortable socks (preferably merino wool)

• Accessories:

  • Hat and gloves (for higher elevations)

  • Sunglasses with UV protection

  • Sun hat or cap

  • Buff or neck gaiter

• Swimwear: For hot springs and coastal areas

Gear & Essentials

• Daypack: For daily excursions

• Reusable water bottl

• Sun Protection:

  • High-SPF sunscreen

  • Lip balm with SPF

• Headlamp or flashlight: With extra batteries

Toiletries & Personal Items

• Toothbrush and toothpaste

• Biodegradable soap and shampoo

• Personal hygiene items

• Hand sanitizer

• Wet wipes

• Small first aid kit

• Prescription medications (if any)

Documents & Miscellaneous

• Valid passport (ensure it has at least six months validity)

• Travel insurance details

• Emergency contact information

• Credit/debit cards and some cash (in euros)

• Plastic or dry bags for wet clothing

• Notebook and pen

Weather Tip: The Azores are known for their unpredictable weather. It's not uncommon to experience multiple seasons in a single day. Always be prepared for sudden rain showers, especially during hikes.

Falling in Love with the Azores by Lucy H. Beech (2015)
A deeply personal travel memoir that captures the enchantment of the islands through lived experience. Beech blends rich observations with cultural and environmental insights, offering both emotional resonance and a grounded sense of place.

Azores: Nine Islands, One History by Susana Goulart Costa
A thoughtful and accessible overview of the shared past that binds the nine islands together. Costa weaves cultural, political, and geographic threads into a cohesive narrative that enriches any visit to the archipelago.

Saudade by Miriam Winthrop
A poetic and evocative novel that captures the essence of longing so central to Azorean identity. Through its characters and settings, it offers a literary window into the emotional landscape of the islands.

The Tenth Island by Diana Marcum
A heartfelt memoir blending humor and introspection, this book traces the author’s discovery of the Azores and how the islands’ rhythms and people helped her reframe her own life. A gentle, personal entry point into Azorean life.

The Nature of the Azores by Nuno Palmeirim (2019)
A stunning celebration of the islands' natural world—from volcanic peaks to lush forests and marine life. Palmeirim’s eye for detail makes this a must-read for anyone wanting to understand the ecological richness of the Azores.

Azores by Jean E. McCauley (2005)
More than just a guidebook, this beautifully illustrated work delves into the heart of Azorean life. McCauley paints a vivid portrait of the islands’ cultural traditions and daily rhythms, perfect for travelers seeking more than just the highlights.

Island at the End of the World: A Personal Journey to the Azores by David Greenberg (2009)
A reflective and intimate memoir that uncovers the layered social and cultural fabric of the islands. Greenberg brings the Azores to life through stories of encounters with locals, class distinctions, and the quiet drama of island living.

The Women of the Azores by Maria Luísa Maluf (2008)
An insightful exploration of the often-overlooked roles women have played in shaping Azorean society. Maluf combines history and personal narrative to challenge stereotypes and spotlight resilience and change.

The Geology of the Azores by João Duarte (2011)
An in-depth look beneath the surface—literally. Duarte breaks down the islands’ volcanic origins and ongoing geological evolution in a way that’s both scientific and compelling, ideal for those fascinated by earth sciences.

Official Azores Tourism Website
This site offers detailed travel information about the islands, including things to do, places to visit, events, and other resources for travelers.

Weather in the Azores
For accurate and up-to-date weather forecasts, it’s good to know what to expect, especially since the weather can change quickly on the islands. - Search "Azores" for specific forecasts.

Local Cultural Events and Festivals
This site lists cultural events and festivals taking place across the Azores, helping your guests plan activities during their visit.

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