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
Soak in a iron-rich thermal bath in the lush Terra Nostra Park
Taste the sweetest pineapple at a local plantation
Sample local cheeses and volcanic wines, two specialties of the islands
Descend into a dormant volcanic chimney
Visit Europe's oldest tea plantation and sip fresh brews
Kayak through two bright blue volcanic crater lakes
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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You'll Be Staying Here
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
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
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.
Add Ons
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.
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
What's Not Included
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
What airport should I fly into?
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.
When should I arrive?
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.
What airport should I depart from?
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.
What is the weather like in the Azores in June?
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.
What should I pack?
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.
What are the new travel requirements for entering Europe?
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!
What is the activity level of this trip?
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.
Is there anything else I should know?
Visit our Frequently Asked Questions (FAQ) page to see answers to most other questions about traveling with Girls' Guide to the World.







