Portugal

The Wild Beauty of the Azores

Explore the rugged heart of the Atlantic while enjoying the finest flavors, landscapes, and hospitality

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Overview

Far removed from the crowds of mainland Europe, the Azores remain one of the Atlantic’s best-kept secrets. Over nine days, we’ll explore the islands of São Miguel and Terceira, discovering the people, flavors, and traditions that define island life, from visits to historic tea and pineapple plantations to a family-run cheese farm and a tasting of distinctive volcanic wines shaped by the islands’ rugged terroir. We'll venture beneath the earth's surface through an ancient lava tube, cruise along the coastline by boat, and experience landscapes sculpted by volcanic forces over millennia. What makes the Azores so compelling is the balance between wild natural beauty and a way of life that remains refreshingly genuine. Throughout our journey, we’ll enjoy exceptional local cuisine, meaningful cultural encounters, and access to places that many travelers never discover. For those seeking a destination that feels untouched and wonderfully off the radar, this journey offers an opportunity to experience the Azores in depth and perhaps fall a little in love with them along the way.

Highlights

Head out to sea in search of whales and dolphins

Head out to sea in search of whales and dolphins

Soak in a iron-rich thermal bath in the lush Terra Nostra Park

Soak in a iron-rich thermal bath in the lush Terra Nostra Park

Taste the sweetest pineapple at a local plantation

Taste the sweetest pineapple at a local plantation

Sample local cheeses and volcanic wines, two specialties of the islands

Sample local cheeses and volcanic wines, two specialties of the islands

Descend into a dormant volcanic chimney

Descend into a dormant volcanic chimney

Visit Europe's oldest tea plantation and sip fresh brews

Visit Europe's oldest tea plantation and sip fresh brews

Kayak through two bright blue volcanic crater lakes

Kayak through two bright blue volcanic crater lakes

Stroll the charming cobblestone streets of Ponta Delgada and Angra do Heroísmo

Stroll the charming cobblestone streets of Ponta Delgada and Angra do Heroísmo

Itinerary

Here's a day-by-day itinerary of the trip. Press the "<" and ">" buttons below to scroll through each day.

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Welcome to Ponta Delgada

Day 1: Friday, June 4, 2027

After an overnight flight, most likely from Boston, New York, or Newark, you’ll arrive in Ponta Delgada on the lush island of São Miguel and transfer to the beautiful Octant Hotel. With its contemporary design and excellent location, it provides the perfect plush place to settle in after our journey.

To conquer jet lag, we've scheduled spa treatments for everyone at the hotel's eco spa. When it's time for your appointment, let yourself completely relax during a hot stone back massage and a rejuvenating facial.

Once we've been properly pampered, we'll climb aboard a tuk-tuk to explore the hidden gems of Ponta Delgada. It's a fun, breezy way to discover the city's highlights while our guides share their favorite local spots. 

We'll stop for lunch at Cafe Central before wandering through the bustling Mercado da Graça, where we can taste the island's famous sweet pineapples and artisan cheeses. We'll wrap up the afternoon with a leisurely stroll along the harbor's iconic black-and-white basalt sidewalks.

Tonight, dinner is at Alcides, a beloved Ponta Delgada eatery and the island's finest steakhouse, just a short walk from the hotel. Raise a glass, our Azores adventure has begun!

Included

Lunch & Dinner

All activities & tours

Not Included

Airport transfer

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Sete Cidades

Day 2: Saturday, June 5, 2027

Today promises to be one of the highlights of our journey. After breakfast, we’ll set off with our guide for a full-day exploration of the western side of São Miguel, beginning at the breathtaking Vista do Rei viewpoint. From this dramatic vantage point, we’ll take in one of the Azores’ most iconic landscapes: the twin crater lakes of Sete Cidades, their brilliant blue and green waters nestled within the rim of an ancient volcanic caldera.

Then we're off to the lakeshore for a kayaking adventure, paddling across the tranquil waters beneath towering volcanic walls. Surrounded by the serenity of the crater and some of the island’s most spectacular scenery, it’s a great opportunity to experience this remarkable landscape from a completely different perspective.

We’ll pause to enjoy lunch in the village, taking time to relax and soak in the atmosphere before continuing our day. This afternoon, we’ll visit Ponta da Ferraria, one of the Azores’ extraordinary natural wonders. Here, geothermal springs emerge from beneath the ocean floor, warming the Atlantic waters and creating a naturally heated sea pool among the volcanic rocks. 

After some time to relax and refresh back at the hotel, we'll wrap up the day over tapas and cocktails at a local favorite, Louve Michaelense.

Included

All meals

All activities & tours

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Tea Plantation, Caldeiras das Furnas, & Terra Nostra Park

Day 3: Sunday, June 6, 2027

There's no shortage of gorgeous scenery on this island, and today we'll head north to soak it all in. 

Our first stop is the Gorreana Tea Plantationthe oldest tea plantation in all of Europe, which feels utterly magical. We'll walk through endless rows of tea plants with the Atlantic shimmering below, then sample freshly brewed teas in the café before continuing east.

We'll time our arrival at the Caldeiras das Furnas to catch one of the Azores' most extraordinary rituals: restaurant staff unearthing the pots of Cozido das Caldeiras. This hearty traditional stew has been slow-cooking underground in the volcanic soil since early morning, and watching the steaming pots emerge from the earth is something you simply won't find anywhere else in the world.

After indulging in a one-of-a-kind meal, the rest of the afternoon is devoted to Terra Nostra Park, where we'll soak in the famous orange, iron-rich thermal pools set within one of the world's most beautiful botanical gardens. It's genuinely restorative and will leave you feeling even more connected to this beautiful place.

Back at the hotel, we'll gather for a meticulously crafted dinner at A Terra, savoring the vibrant flavors of local delicacies.

Included

All meals

All activities & tours

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Flavors of São Miguel

Day 4: Monday, June 7, 2027

We'll indulge our senses around the island today, starting with a visit to Augusto Arruda Pineapple Plantation after breakfast. We'll learn how São Miguel grows its legendary greenhouse pineapples, a centuries-old tradition quite unlike anything found in the tropics. Sample a few pieces of their sweet fruit and take a look through the gift shop, the homemade pineapple liqueur is fantastic.

Then, we're off to revisit Mercado da Graça for a guided tour through its plentiful stalls. This market is a local staple for meat, fruit, and Azorean specialties that we'll taste as we go along. 

The Azores produce lovely, unique wines from grapes grown in volcanic soil and exposed to the ocean breeze. We'll sit down for a tasting of a few wines paired with locally-made cheese and learn more about what makes these vinos so special. 

Back at the hotel, take the rest of the evening to relax. Maybe dip into the pool, head out for a stroll around the neighborhood, or book into the spa circuit for some well-deserved self-pampering. Dinner is on your own tonight or with new friends, your guide would be happy to point out a few local favorites.

Included

Breakfast & Lunch

All activities & tours

Not Included

Dinner

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Angra do Heroísmo, Terceira

Day 5: Tuesday, June 8, 2027

This morning, we'll say a fond farewell to São Miguel and board our short inter-island flight to Terceira, arriving around midday. This island, known affectionately as the Lilac Island, has an entirely different personality that's quieter, steeped in history, and impossibly charming.

We'll transfer to the UNESCO World Heritage town of Angra do Heroísmo to check in at Torel Terra Brava, our home for the next four nights. A leisurely lunch awaits us at the hotel's wonderful restaurant, Três, with sweeping ocean views to welcome us to the island.

This afternoon, we'll step out on the town to explore the colorful colonial architecture and storied harbor that were once a vital crossroads for ships traveling between Europe and the Americas. We'll pause to try a Donas Amelia, the island's most loved sweet treat in honor of Queen Amélia's first royal visit to the Azores.

To wrap up the tour, we'll walk up Monte Brasil for a breathtaking panoramic view of the city and its ancient fortified walls. The path is gradual and perfectly manageable; just be sure to wear comfortable shoes.

Dinner this evening is at Mercatto di Osteriaa cozy local restaurant right in the heart of Angra serving delicious Italian fare.

Included

Flight to Terceira

All meals

All activities & tours

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Terceira - Whale Watching & Cooking Class

Day 6: Wednesday, June 9, 2027

We're heading out to sea after breakfast this morning. A whale watching excursion takes us into waters that are among the finest in the world for cetacean encounters including sperm whales, dolphins, and with a little bit of luck, the magnificent blue whale. Few experiences rival the sight of these gentle giants in the wild, and we'll get to experience them from the luxury of our private charter boat.

Back on land, the afternoon takes a delicious turn with a hands-on Azorean cooking class, where we'll learn to prepare traditional island dishes from scratch before sitting down to enjoy everything we've created. This is the perfect way to bring the flavors of Terceira home with you to share with friends and family.

The evening is yours to wander and dine at your leisure, a great opportunity to explore some of the unique dining options in town.

Included

Breakfast & Lunch

All activities & tours

Not Included

Dinner

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Terceira - Farm & Walking Tour

Day 7: Thursday, June 10, 2027

Terceira is an island shaped by its land, and today we'll experience that firsthand. The morning begins with a visit to a local dairy farm, where traditional cheese-making has been passed down through generations. Our tour is a warm, authentic glimpse into the rhythms of island life and the importance of local producers.

From there, lace up your shoes for a scenic walking trail through the lush countryside, with an open-air picnic lunch waiting to be savored amidst the endless rolling green pastures.

Late afternoon is yours to enjoy. Perhaps you'll pop into a local shop to pick up some last minute souvenirs, or simply sit at the hotel bar with a glass of Azorean wine in hand. 

Tonight, dinner is at Restaurante Caneta, a celebrated steakhouse where the cattle are raised right on the property. It doesn't get more farm-to-table than that.

Included

All meals

All activities & tours

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Algar do Carvão & Mistérios Negros

Day 8: Friday, June 11, 2027

For our final full day, Terceira saves its most dramatic experience for last. After breakfast, we'll drive about 20 minutes towards the lush, verdant middle of the island. There, we'll descend into Algar do Carvão, one of the only places on earth where visitors can walk inside a dormant volcanic chimney. The vast cathedral of ancient lava will leave you completely speechless. 

Later in the day, we'll walk the Mistérios Negros trail that winds through centuries-old lava flows and endemic Azorean vegetation, offering an intimate, hands-on encounter with the island's extraordinary geological history. Lunch will be served along the way.

We have the perfect finale in store this evening: dinner at Oficina da Esquina. As one of the most iconic restaurants in Angra, Chef Vítor Sobral's kitchen focuses entirely on fresh, seasonal produce, prepared with flaming hot charcoal grills. What a gorgeous way to toast our final evening on the islands.

Included

All meals

All activities & tours

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Departure Day

Day 9: Saturday, June 12, 2027

Our final morning calls for a leisurely coffee at a harbor-side café in town, watching the boats, savoring the last few magical moments, and letting the beauty of these islands wash over you one last time.

When the time comes, call a taxi to the Lajes Airport for your departure flight. On Saturdays, there are direct flights to Boston and San Francisco, as well as Lisbon and Zurich, if you want to continue your European adventure. Until next time, Azores. You have completely stolen our hearts. 

Included

Breakfast

Not Included

Airport transfer

You'll Be Staying Here

Octant Hotel

Octant Hotel

Set right on the Ponta Delgada marina, the cosmopolitan Octant Hotel maintains a strong sense of place with much of the interior architecture honoring natural materials found around the volcanic island. The rooms are sleek and plush, many with endless views of the North Atlantic Ocean. 

Torel Terra Brava

Torel Terra Brava

Occupying a historic 18th century building nestled within the winding cobblestone streets of Angra do Heroísmo, Torel Terra Brava is the perfect base for exploring Terceira. Take a dip in the outdoor pool, sip a carefully crafted cocktail at the on-site bar, or relax in one of their 44 colorfully designed rooms and soak in the sprawling views of Angra and the sea.

Hosts

L. Leigh Rhoads

L. Leigh Rhoads

Leigh Rhoads is your guide for this journey, bringing both a wealth of experience and an adventurous spirit. She hails from the scenic Blue Ridge Mountains of Virginia, where Southern charm and warmth come naturally to her. A Civil Rights attorney by profession and a yoga enthusiast at heart, Leigh thrives on finding balance between her career, raising lively twin children, and exploring the world. 


Her travels have been fueled by a desire to connect with people, uncover new perspectives, and create unforgettable memories. Leigh can’t wait to welcome you on this adventure and make it truly special. 

Price

Private Room

Private Room

Everyone gets their own fabulous room!

$10,995

Shared Room

Shared Room

Share a room with a friend or family member

$9,595

Add Ons

Arrive June 3, 2027 - Private Room

Arrive June 3, 2027 - Private Room

Includes one night and breakfast at the Octant Hotel in Ponta Delgada

PRICE$599.00

ADD THIS
Arrive June 3, 2027 - Shared Room - Price is per person. Each guest must book individually.

Arrive June 3, 2027 - Shared Room - Price is per person. Each guest must book individually.

Includes one night and breakfast at the Octant Hotel in Ponta Delgada

PRICE$299.00

ADD THIS

Untamed, unspoiled, and unforgettable.

Awe-inspiring Azores

Sitting atop a geothermal hotspot in the North Atlantic Ocean, the Azores offer a striking diversity of landscapes dotted with charming cobblestoned colonial towns. The perfect place for an adventurous traveler with a taste for the finer things in life, São Miguel and Terceira are filled with natural beauty, once-in-a-lifetime experiences, and delicious cuisine that will capture your heart. 

Awe-inspiring Azores

What's Included

What's Included

All meals (except where indicated), including beer, wine, or cocktails with dinner

All transportation during the trip (except where otherwise indicated)

Tour and pineapple tasting at Augusto Arruda Pineapple Plantation

Tour and geothermal-cooked lunch at Caldeiras das Furnas

Accommodations at unique 4-star (or better) hotels

Walking tour of Angra do Heroísmo and Monte Brasil

Guided walk and picnic through Terceira countryside

Wine and cheese tasting at an Azorean winery

Soak in the thermal pools of Terra Nostra Park

Tour and tasting at Gorreana Tea Plantation

Jet lag spa treatment at Octant Hotel spa

Guided tour of Algar do Carvão lava tube

Azorean cooking class with a local chef

Guided walk on Mistérios Negros trail

Tasting tour through Mercado da Graça

Everything specified in the itinerary

Kayaking excursion on Sete Cidades

Visit and tasting at a local dairy farm

Expert guides and trip leaders

A small group experience

Tuk-tuk tour of Ponta Delgada

Visit to Vista do Rei viewpoint

Visit to Ponta da Ferraria

Domestic flight to Terceira

Whale watching cruise

Round-trip airfare to the starting location of the trip

Additional wine, beer, and/or spirits beyond what’s offered at meals

Travel and medical insurance (required)

All personal souvenirs

Airport transfers

FAQs

Fly into the João Paulo II Airport (PDL) in Ponta Delgada on the island of São Miguel. There are frequent flights there from New York, Boston, and San Francisco.

The trip officially begins mid-morning on Friday, June 4, because most arriving flights land early in the morning. Plan to arrive by 10 am on June 4. 


If you're traveling across an ocean to get to the Azores, consider arriving one night early to rest and acclimate to the new time zone. You can purchase this option in the Add-on section of this page, and we will ensure you're kept in the same hotel room once the trip begins. 

The trip officially ends on Saturday, June 11 in Terceira, so plan your onward travel from Lajes Airport (TER). On Saturdays, there are direct flights to Boston and San Francisco, as well as Lisbon and Zurich, if you want to continue your European adventure.

June is one of the most beautiful times to visit the Azores, with mild temperatures, blooming landscapes, and long daylight hours. Expect daytime highs of around 68–75°F (20–24°C) and cooler evenings in the 59–64°F (15–18°C) range. The islands are famously green thanks to occasional passing showers, but these are often brief and interspersed with sunshine.

We'll have a Zoom call about 8 weeks before the trip starts to discuss important logistics and give you packing guidance. In the meantime, here is a great website that we love that will help you with packing and travel tips.

Beginning in late 2026, travelers from visa-exempt countries - including the U.S., Canada, and Australia - will need an ETIAS permit to visit most of Europe. No action is needed just yet. 


As we get closer to the launch date, likely several months in advance, we’ll share all the details on how to apply. Feel free to reach out with any questions!

We require that everyone traveling with Girls' Guide be able to comfortably walk 3–5 miles per day unassisted, and without difficulty, can navigate stairs, uneven streets or paths, and occasional steep terrain. Most of our trips require this level of physical mobility and fitness, especially when visiting historic towns and landmarks where vehicle access is limited and walking often offers the best experience.


Additionally, some of the 4 and 5-star boutique or historic hotels we stay in do not have elevators and may require climbing stairs to get to your room or access other facilities in the hotel.

Visit our Frequently Asked Questions (FAQ) page to see answers to most other questions about traveling with Girls' Guide to the World.  

Inquire about this trip

The Wild Beauty of the Azores

Portugal· Departs on June 4, 2027 · 9 Days

$10,995/pp