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The Ultimate Adventure Release..

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We’ve really done it this time, a brand new adventure for the ages. Join us next year on our inaugural journey throughout Picturesque Portugal & the Awesome Azores! High on our bucket list for years, this meticulously crafted itinerary is in a word: diverse. From the opulence and world-class wine of Porto, to the timeless villages nestled on the mountainsides of the Serra do Açor, to Aveiro; the “Venice of Portugal”, to the historical capital of Lisbon, and so many hidden gems in between!  BUT, the adventure is far from over as we continue to the volcanic archipelago of the Azores with gigantic calderas, beautiful beaches, charming villages, & gorgeous landscapes begging to be photographed.

More trip overviews below

Picturesque Portugal & the Awesome Azores

September 4th-18th, 2023

E-mail us at for the daily itinerary!

  • 14 nights/15 Days
  • Private, Local English Speaking Guide(s) Throughout
  • 3 Domestic Flights INCLUDED ($500+ Value!)
  • Breakfast Everyday
  • 1 Lunch, 3 Dinners (Including Welcome & Farewell Dinner Celebrations)

Part 1: Mainland Portugal (8 Nights/9 Days)

“Portugal’s 1,000 miles of shore and California-style climate are attracting travelers in record numbers. Beyond the glorious beaches, this ancient nation is crammed with heritage ranging from Stone Age graffiti to villages clustered beneath medieval castles and forests filled with romantic palaces. Its lifestyle is laidback; its food and wine fabulous. Five hundred years ago, Portuguese explorers opened up the world; now it’s time to discover this little land of many wonders.”  – Frommer’s

Porto & the North (3 Nights)

“Craggy mountain wilderness, towering medieval castles and hilltop vineyards with jaw-dropping views are among the many attractions awaiting you on a day trip from Porto. Whether you’re seeking a nature escape with rugged trails and waterfalls or want to explore some surprisingly amorous elements of village life in the Minho, Porto makes an ideal gateway to the wonders of northern Portugal.” – Lonely Planet

– Privately guided walking tour: Discover & photograph the impressive D. Luis Bridge, City Hall, & Clérigos Tower while learning about the city’s fascinating history. Other highlights include visits to the Stock Exchange Palace, Music Hall, & Oporto’s Cathedral.

– The most colorful & lively district:  In the heart of the old town along the riverbank we’ll discover Ribeira, the most picturesque part of the city. Capture stunning photographs of the colorfully decorated facades reflecting off the Douro River. Did we mention it’s here where they produce the world-famous port wine?

– Delicious food & even better wine:  Visiting Porto is not complete without tasting her delicious cuisine and drinking world-class wine. Let’s eat and drink like a local, with a local!

Douro Valley
“The Douro Valley could as easily be called the enchanted valley, such is the beauty and magic that its landscapes offer.” – Visit Portugal
– Wine tasting while exploring the valley: We’ll start our road trip along the route that offers the best vistas, stopping for photos as we go. A visit to Douro is not complete without tasting the “fruits” of her rich & fertile lands: the delicious wine!

– Cruise on the Douro: We’ll relax on a sail through the lush landscapes of the Douro Valley along the river of the same name.

Central Portugal & Her Mountain Villages (1 Night)

“Finding hidden treasures in Central Portugal is the feeling one embodies after walking amidst the mountains and rivers that lead to the mountain Villages of Portugal. A world of secular trails connecting each unique village to another, where centuries of history, tradition, and landscape remain preserved.” – Portugal A2Z

Piódão, the Ultimate Mountain Village
This “small village nestled up in the mountains of the Serra do Açor looks like it is out of a fairytale. Piodão is one of 12 classified as Aldeias Históricas de Portugal – Historical Villages of Portugal and has been featured in historical accounts since the 14th century. It was probably used by medieval fugitives hiding in the wild Portuguese mountains. Indeed, on a rainy day you should look from the other side of the mountain to see the village coming out of the fog.” – The Guardian
– Exploring Foz d’Égua: This moderate hike begins in Piódão and takes us to an idyllic and unforgettable little village. Take in the historic architecture and well-maintained schist houses. The “iconic” spot to capture is near the two stone bridges that cross the village streams, giving way to a picturesque river beach
The Schist Villages: Talesnal & Casal de São Simão
“The 27 schist (shale) villages that have been beautifully preserved in the center of Portugal are scattered across the countryside, with the most crucial cluster in the Lousã Mountains. Talesnal is considered the prettiest example, with much loved Ti Lena restaurant at its heart. Try the goat, baked with chestnuts from the surrounding mountains, or stop at one of the village shops for a talasnico, a pastry made with local honey, chestnuts, and almonds.” – CN Traveler | “The stone houses of (Casal de São Simão) are built side by side and imbue a special character of belonging and a strong sense of community. The village was built by men who derived their sustenance from the land: in the valley bathed by Ribeira do Fato, vegetable gardens were sown, while in Ribeira de Alge, stone millstones ground cereals to make bread. Today, simple tales of this occupation are an important part of the local villager’s identity.” – From

– Fragas de São Simão Walkway: The wooden paths embrace dramatic granite landscapes, steep hills, an enchanting valley, and also vestiges of laurel forest. We’ll encounter a “Hobbit-like” hermitage and river beach, where the Alge stream rips through the rocky massif and follows its path towards the river Zêzere. The “hike” starts and ends in yet another beautiful village

Coimbra & the Coast (2 Nights)

Rising scenically from the Rio Mondego, Coimbra is an animated city steeped in history. It was Portugal’s medieval capital for more than a century and it’s home to the country’s oldest and most prestigious university. Its steeply stacked historic center dates to Moorish times and is wonderfully atmospheric, with its dark cobbled lanes and monumental cathedral. On summer evenings, the city’s old stone walls reverberate with the haunting metallic notes of the guitarra (Portuguese guitar) and the full, deep voices of fado singers.” – Lonely Planet

Aveiro, “Little Venice”
Situated on the edge of an extensive coastal lagoon system, Aveiro (uh-vey-roo) is a prosperous town with a good-looking center and a youthful, energetic buzz. It’s occasionally dubbed the Venice of Portugal thanks to its small network of picturesque canals. But where the Italian city has gondolas, Aveiro has moliceiros – colorful boats traditionally used for seaweed-harvesting but now used for canal cruises.” – Lonely Planet
– A Serene Float: It would be a sin to visit Aveiro and not take a serene ride on the canals via a Moliceiro. These slender and colorful boats were originally used to harvest moliço, a type of algae used as agricultural fertilizer.
Óbidos, a Fairytale Town
Surrounded by a classic crenelated wall, Óbidos’ gorgeous historic center is a labyrinth of cobblestoned streets and flower-bedecked, whitewashed houses livened up with dashes of vivid yellow and blue paint. It’s a delightful place to pass an afternoon”

– The Walled Labyrinth: Privately guided walking tour: Enclosed in unique medieval walls with a castle watching over, explore the maze of cobblestone pathways and learn about the significance of Óbidos’ “nooks and crannies”.

Lisbon, City of Hills (2 Nights)

“Seven cinematic hillsides overlooking the Rio Tejo cradle Lisbon’s postcard-perfect panorama of cobbled alleyways, ancient ruins and white-domed cathedrals, a captivating scene crafted over centuries.” – Lonely Planet

– Guided Tuk-Tuk Adventure in the capital: Exploring this world-class city by tuk-tuk is a real treat. The historic center of Lisbon is the city’s most atmospheric district, but its narrow lanes and steep hills can be tiring to navigate on foot. We’ll cover ground in style with less hill climbing and more sites, sounds, & photos

Mystic Sintra
“With its rippling mountains, dewy forests thick with ferns and lichen, exotic gardens and glittering palaces, Sintra is like a page torn from a fairy tale. Its Unesco World Heritage-listed center, Sintra-Vila, is dotted with pastel-hued manors folded into luxuriant hills that roll down to the blue Atlantic.” – Lonely Planet

– The Stunning Palace & Her Marvelous Town: On top of São Pedro de Penaferrim, the palace sits on top of lush hills, painted in striking yellows & reds and cloaking the skyline of Sintra. Combining Romanesque, Neo-Manueline, and a pinch of Moorish architecture, Pena Palace is the pinnacle of Romanticist design in Portugal. We’ll explore the grounds and tour the castle getting incredible photos inside and out.

Part 2: The Azores (6 Nights/7 Days)

“In the realm of legend, some associate the Azores to the Atlantis, the mythical island kingdom quoted by Plato. 9 naturally surprising islands, with hotels and restaurants in complete harmony with the environment, the no. 1 archipelago in sustainability awaits you. The lakes of São Miguel, the Mountain of Pico, the Capelinhos Volcano of Faial, the waterfalls of Flores, and the Caldeirão of Corvo are unmistakable features. To travel throughout the Azores is to get to know nine islands where the same genetic code generated profiles that are distinct from one another.” – Visit Azores

São Miguel: The Green Isle (2 Nights)

“São Miguel is the largest island of the Azores archipelago and wears its elder status proudly, with an enviable landscape of forest-wrapped volcanic peaks, azure lakes, and improbably perfect calderas.” – Lonely Planet

“The Furnas Valley is a volcanic caldera that has lain dormant since 1630, and it’s one of São Miguel’s most intriguing and otherworldly geothermal spots where mud pots bubble and fumaroles steam amid the lush green landscape.” – Lonely Planet– Thermal Waters abound: We find 32 different kinds of thermal water activity in this region, some sulfurous, others calcareous; either hot, warm, or cold. The variety is fascinating; some are muddy while others have clear water. They can also take the form of sulfurous steam vents.

– Thermal Waters abound: We find 32 different kinds of thermal water activity in this region, some sulfurous, others calcareous; either hot, warm, or cold. The variety is fascinating; some are muddy while others have clear water. They can also take the form of sulfurous steam vents.

Sete Cidades
“A real jewel of the archipelago, this small “city” and its lakes offer the postcard view most commonly seen around the world. “The Azores are full of places that stop visitors dead in their tracks and cause a sharp, involuntary intake of breath. But the first glimpse of this enormous caldera with its sparkling twin lakes might just be the most eye-popping of them all.” – Lonely Planet

– Giant Caldera Hike: Embark on the most beautiful trail in the Azores. We’ll walk along the best section of the crater rim in awe, to photograph and imprint this mouth-dropping scene into our memories.

Faial: The Blue Isle (2 Nights)

“From the lookout of Cabeço Gordo, the ground seems to slide softly until it levels out by the seaside, where a profusion of hydrangeas brings to land the color of the sea, as if materializing a romance between the blue of the flowers and the green of the vegetation and pastures. The same happens along the road leading to the Caldeira, in the center of Faial, and on other roads, justifying the nickname of Blue Island. But there is a complete change at the Capelinhos Volcano, with its arid and rough landscape proving that grey can also be charming…” –

Capelinhos, the volcano that came from the sea…
“The Capelinhos volcano that surged up from the seabed off Faial in 1957 is one of the best-documented sites in the world and the interpretation center beneath its now abandoned lighthouse does a superb job of explaining the Earth’s convulsions” – Valise Travel Concierge
“The Caldeira is both literally and figuratively the highlight of Faial. The crater sits in the center of the island and towers above everything else.”  – Wapiti Travel

Pico: The Mountain Island (Day Trip)

“Named after its imposing mountain, (Pico) is one of the most beautiful and underrated islands of the Azores. Only second to S. Miguel in size the ‘Mountain Island’ stands majestically in the middle of the Azorean central group” – “If you are looking for a getaway filled with unspoiled nature and vegetation, volcanos, lava stone landscapes, coastline views, and exquisite vineyards, Pico is the place to go.”  – We Are Travel Girls

– Cachorro Rocks: A photo stop reveals unique volcanic rock formations.

– Museu dos Baleeiros: While the factory museum focused on the manufacturing of lucrative whale byproducts, the Whalers Museum houses many expositions reflecting the greater Azorean Whaling industry that only ended in the early 1980 ́s. Spread throughout a set of three whaling houses from the 19th century, the museum is a homage to the old whaling tradition, still visible in the local ambiance and lifestyle.

Flores: The Flower Island (2 Nights)

Calling Flores the Azorean Jurassic Park would not be completely honest because it is so much more; natural pools with turquoise waters, filled with fish of a thousand colors, imposing waterfalls, colorful lagoons surrounded by a thousand shades of green, and orange sunsets, accompanied by a gin & tonic in hand to welcome the evening and awe-inspiring milky way soon overhead.

– The great fajãs: This Portuguese term describes the beautiful coastal formation of a small flat land on the ocean below giant cliffs, caused by lava deltas from the penetration of lava flows into the sea. Flores has some of the most beautiful fajãs with small towns claiming the arable land. We’ll visit and photograph the stunning landscapes of Fajãzinha and Fajã Grande, where countless streams of water running down the cliff form impressive waterfalls.

– The 7 Lagoas: We’ll explore this lush area with a number of serene lakes throughout the valleys. Each lake is named after its unique features: Lagoa Funda (Deep Lake), Lagoa Branca (White Lake), Lagoa Seca (Dry Lake), Lagoa Comprida (Long Lake), Lagoa Rasa (Shallow Lake), Lagoa da Lomba (Crest Lake) and Lagoa Negra (Black Lake). This last lake is 300 ft deep!

Corvo Day Trip: The Black Isle

“A charming, honest, and unique community in Europe. This island may be small in size, but it has a huge heart.” – Geeky Explorer” | “Corvo literally means “the Island of the Crow”, and is the smallest and the northernmost island of the Azores archipelago. It has a population of approximately 384 inhabitants (as of 2021) making it the smallest single municipality in the country, let alone the archipelago” – Wikipedia | Though small, Corvo Island attracts the intrepid and most seasoned travelers for many reasons: beauty, mystery, and isolation to name a few.

– Caldeirão, The Crater: This ancient crater is responsible for the epic landscape of the extinct volcano that gave rise to the island. One thousand feet deep and occupying nearly 15% of the entire island, this high point of our trip is special because most travelers never even come here. As we learn about the geological history that made the landscape what it is today and its importance to the nearby sole village of the island, amazing panoramic photographs must be taken in every direction!

Travel Club Update: COVID-19 

PhotoFly Travel Club takes our current global pandemic extremely seriously. As such, a number of our 2020 and 2021 adventures have had to be cancelled & postponed like most in our travel industry. We want nothing more than all of our members to stay healthy & happy during these trying times. We hope everyone is playing their part by social distancing as much as possible. The more people who properly follow this crucial tactic in our country, and everyone around the world, the faster we will conquer and come out stronger & better prepared when this happens again.

As of today, we remain hopeful that travel will become feasible and safe again for most travelers early next year. In fact many countries, including most of Europe, have been on the decline for months now.  It’s important to acknowledge that these are mainly countries that have enacted strict social distancing measures much sooner and in a more timely manner than the USA has been able to. Good news is most of the countries on our upcoming calendar fit this description! For more details about the predictions and scientific modeling in each state AND many countries around the world go here: (you can select any state or country for the location specific predictions)

Enhanced Procedures & Safety Measures

As we get ready to explore the world with you again soon, our travel club has begun to implement new guidelines and practices for the “Post-Covid World”. Some of them are listed below. Safety is #1 and the ability to experience a destination without limitations due to the pandemic is #2

1. Country Specific Qualifications must be met to run the tour. Some of these include:
a. Daily infection incidence must show stable or decreasing trends for at least 30 days
b. Population Infected must be equal to or lower than .007% per 100K people
c. Hospital resources in country must be sufficient for predicted modeling at least 3 months after the start date of said trip.
3. PhotoFly Enhanced Safety Practices Including:
a. Masks for everyone in vehicles and other enclosed spaces
b. Sanitizer available at all times/ Surface Cleanings done constantly
c. Social distancing practices as much as possible & no contact health/temperature checks
d. Small Groups Only = Lower Risk. Only time will tell and we’re following the situation very carefully. Our pledge is to share nothing but scientific evidence and advice given by the CDC and World Health Organization (WHO). We will base our decisions in the coming months solely on these two sources. 

We know this is going to be a difficult time for all of us, in a myriad of ways. PhotoFly Travel Club is committed to building amazing experiences for years to come. We will get through this together and come out on the other side with even more amazing trips.

We wish everyone nothing but the best navigating this crisis. Our thoughts and prayers are with you all to remain healthy and persevere until we overcome. 

Much love and gratitude to all of our members,

Steve, Andrew, Catalin, Michelle, Raya, & the rest of our PhotoFly Team!


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Spread the word about our travel clubs! If you know any friends, colleagues, or family that love to travel invite them to join! It’s free and all are welcome! The larger we get the more trips we can plan each year…

Any questions feel free to contact us anytime as always!

Travel Club Organizer: Steve Juba
978 479 4527

*Please always review our cancellation and refund policy located at the bottom of every trip page before making payments. Don’t hesitate to ask if you have any questions.

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