Seven Island Portugal Escape: Azores and Madeira Vacation

Lighthouse Ponta da Ferraria San Miguel, Azores

What to expect on this itinerary

Madeira and the Azores are islands of volcanic wonder that abound with natural drama in the midst of the Atlantic Ocean. Escapist and expressive, the islands bring nature, history, culture, wildlife, lava trails and languid beaches all at once, and this luxury vacation tour visits the most inspiring seven islands.  Look forward to a private journey across spectacular landscapes and remote destinations for the very best of the Portuguese archipelagos.

Countries Visited

Portugal

Places Visited

Madeira, Azores, Funchal, Camara de Lobos, Cabo Girao, Paul da Serra, Porto Moniz, Sao Vicente, Horta, Faial, Capelinhos Volcano, Pico Island, Pico Volcano, Terceira, Angra de Heroismo, Monte Brasil, Praia de Vitoria, Porto Judeu, Sao Sebastiao, Algar do Carvao, Altares, Doze Ribeiras, Sao Miguel, Ponta Delgado, Lagoa, Vila Franca, Sete Cidades, Flores, Ponta da Faja, Fajazinha, Rocha dos Bordoes, Corvo

Suggested Duration

14 Days

Customizable Itinerary

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Day 1

Madeira (Funchal) – Relaxed Welcome to Portugal’s Islands

A lush green landscape will greet you on Madeira as the multitude of tones tumbles down the mountains to the ocean.  The blue of the Atlantic stretches out just a few hundred meters from your hotel, and the view will be stunning. You will be greeted at the airport and transferred to the old harbor city of Funchal, the capital of the archipelago. Gothic and Romanesque styles mix on the streets, most spectacularly in Funchal Cathedral as gardens stretch out behind the promenade and wine cellars provide an easy introduction to the wine of the region. Settle in for a day at your leisure with many avenues to explore in the city. A quiet beach is close by and captures Madeira’s feel as an island getaway.

What's Included:

Transfer
Accommodation
Breakfast
Day 2

Madeira (Funchal) – Free Day on the Beaches

Day 3

Madeira (Funchal) – The Best of Madeira in One Day – Private Tour

Day 4

Madeira to Faial (Horta) – Whale and Dolphin Watching Around Faial

Day 5

Faial (Horta) – Ash and Lava Fields of Capelinhos Volcano

Day 6

Faial (Horta) – Private Day Trip to Pico Island, an Atlantic Natural Wonder

Day 7

Terceira (Angra do Heroismo) – A World Heritage Village and a Magnificent Volcano

Day 8

Terceira (Angra do Heroismo) – Fishing Villages and Natural Wonder of the Azores

Day 9

Sao Miguel (Ponta Delgada) – Outdoor Adventure Around the Sete Cidades Volcanic Crater

Day 10

Sao Miguel (Ponta Delgada) – Viewpoints, Tea Plantations, Botanical Gardens and Thermal Pools

Day 11

Flores (Santa Cruz) – The Astonishing Nature of Westernmost Europe

Day 12

Flores (Santa Cruz) – Private Day Tour of Flores

Day 13

Flores (Santa Cruz) – Day Trip to Remote Corvo Island

Day 14

Flores to Sao Miguel – Departure

Trip Highlights

  • Savor the decadent atmosphere of Madeira, an island of wine and beaches that provides an indulgent start to your vacation
  • Spend several nights in the old whaling village of Hotra on Faial, the perfect base for coming face to face with Capelinhos Volcano
  • Enjoy a day on tiny volcanic Pico island, where lava trails lead you towards vineyards and whales seen from the shore
  • Immerse yourself in the 16th-century UNESCO World Heritage Angra do Heroismo, a base for a couple of days of culture and adventure on the island of Terceira
  • Marvel at the landscapes of Sao Miguel, a single day including tea plantations, botanical gardens, thermal springs, bubbling mud pools, and innumerable viewpoints
  • Engage with the Azores as they are an archipelago of natural wonder and nowhere is this better epitomized than Sete Cidades, volcanic crater lakes on the west of Sao Miguel
  • Explore Flores, the remarkable island to the west of the Azores, where the days are filled with lakes and waterfalls and unimaginable shades of green
  • See whales and dolphins as part of the scenery in the Azores as you will get chance to see some from the shore and many more on a boat excursion
  • Visit some of the most unique cultures in Europe as you visit Corvo, a unique destination unseen by most travelers

Detailed Description

Crafted from volcanoes and surrounded by dolphins, Portugal’s islands are Europe’s natural Edens. Lava trails lead you through vineyards and subterranean landscapes as crater lakes are perfect for hiking and kayaking adventures.  The beaches are empty, and there is always another viewpoint found over the next hill. Madeira and the Azores are not uninhabited islands, as while the wilderness abounds, there is also remarkable history and culture to discover.  From remote civilizations to whaling villages and ports from a forgotten era, when a day of private touring comes to an end, you will never be far from deserted sand or an uninterrupted view of the sunset. While these are archipelagos made for adventure, the islands will also feel like a getaway to soothe your soul and relax your mind.

This unique itinerary visits seven islands in two weeks.  Handcrafted to blend the best of Madeira and the Azores, your private tour will bring a little of everything. Whale watching, volcano hiking, wine tasting, village encounters, beach days, kayaking, biking, and the contemporary cuisine of the Atlantic. You will spend most nights in historical villages or port towns where your boutique hotel may be just a few minutes from the beach, and the sense of old allure will keep you company at all times. Most of the islands are connected by plane, and you will be based on five of the islands. The other two islands are visited by boat, as tiny Pico and Corvo are the perfect sizes for a relaxed day trip.

Madeira is a relaxed, but also opulent, island to start on with a couple of free days to begin your handcrafted tour with some relaxation. You will soon explore the best of the island and find a mishmash of vineyards, cliffs, plantations, natural swimming pools and villages from the past. The day will end at the second highest sea cliff in the world, Caba Girao just one of the many impressive sights you will see over these two weeks. Fly to Faial in the Azores next, your base for several nights being the old, yet new, whaling village of Horta. Spend a day to admire the drama of Capelinhos Volcano as you walk over the ash and lava fields that tumble down from an iconic summit. Then enjoy a day trip to Pico Island for another volcanic wonder that rises high from the Atlantic Ocean.

UNESCO World Heritage site Angra do Heroismo is your base on Terceira, an island which exemplifies the atmosphere of your vacation. There will be a lot to see and discover, but the pace is leisurely, and you will never feel rushed. Sao Miguel is the largest island in the Azores archipelago, where the landscapes are both dramatic and soothing. Spend a day in the west at Sete Cidades for an adventure on land and water that brings you closer to nature. The next day will mix the complete range of landscapes with a remarkable profusion of green and blue that stretch across this lost island in the Atlantic.

With its rugged cliffs and bountiful volcanic lakes, Flores is the most celebrated of all of Portugal’s islands. You will cross vast stretches of hydrangea hedges, stand beneath gushing waterfalls, explore bizarre lava formations and enjoy insatiable views across the lakes. It will be an island once famous for whaling, and a boat trip will reveal just how many dolphins and whales inhabit the surrounding waters. Visit tiny Corvo Island on your final day, where less than 500 residents keep their culture alive and speak in a language with its roots in the 16th century. Every day, there will also be the chance to drink local wine, dine of fresh seafood, and gaze out over the solitude of the Atlantic.  Don’t take just our word for it - consider reading some of our travelers’ reviews of Portugal, and see how you can customize your own dream vacation.

Starting Price

$3,700 per person (excluding international flights)

Your Zicasso trip is fully customizable, and this sample itinerary is a starting place for your travel plans. Actual costs are dynamic, and your selection of accommodations and activities, your season of travel, and other such variables will bring this budget guideline up or down. Throughout your planning experience with your Zicasso specialist, your itinerary is designed around your budget. You can book your trip when you are satisfied with every detail. Planning your trip with a Zicasso travel specialist is a free service.

What's Included

  • Accommodations
  • In-country transportation
  • Some or all activities and tours
  • Expert trip planning
  • 24x7 support during your trip

Your final trip cost will vary based on your selected accommodations, activities, meals, and other trip elements that you opt to include.

4.9

Verified Traveler Reviews

Based on 223 reviews

Portugal Family Travel Review: Lisbon, Sao Miguel, Sao Jorge, Faial, 12-Day Trip

Our travel agent made this an extraordinary, unforgettable, and wonderful trip for our family! The events and tours she arranged were exactly what we were looking for. The tour and transportation companies she contracted were on time, flexible, knowledgeable, and provided outstanding value for the cost.

Our agent provided an incredible, complete package at a cost much less than competitors. We highly recommend our agent and her team to anyone looking for a memorable trip to Lisbon and/or the Azores.

-Glen

Five Stars!

Loved all the service and tour guides.

Most enjoyable was the Azores. Doing the trip again I would focus more time on the Azores. Lisbon is nice but a whole different world. Thanks for a great trip.

-Tony

5 Stars.

The guides made this trip most enjoyable. They shared their knowledge willingly and always with a smile.

The only thing I would do differently is make the trip longer.

-Mary

My star rating is 5. We had a wonderful trip without a concern over logistics thanks to this travel company. With 9 of us, it was a challenge to get the itinerary we all wanted but our agent did a great job. I was also impressed by the low cost, given all that we did, and the quality of the hotels and tours. I will absolutely recommend and in fact, plan to write a review on TripAdvisor.

The highlight was seeing my grandmother’s house in Santa Luzia on our free day in Pico. I enjoyed the Azores more than the mainland. Every one of our tour guides was excellent. I especially liked the coffee plantation in Sao Jorge, the volcano museum on Faial, and the whaling museum on Pico. Ponta Delgado was a great place to stay. I didn’t much like Madalena though with two ferry trips on the itinerary it was the best option.

What I would change, in retrospect, is less time in Lisbon, perhaps substituting a fifth island. The crowds were a problem in Lisbon and we found it a little frustrating to be pressed for time at each destination. Maybe offer Sintra or Cascais but not both, and pick two of the Batalha/Nazare/Obidos options. It’s a shame to not see it all, but also a shame to have only 45 minutes in a place like Nazare.-Susan

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Portugal Tour Review: Horta, Terceira, Volcano, Tea Production, Hiking, Winery, 10 Nights
"The accommodations on all three islands ranged in quality, but were comfortable and centered in the main cities."

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Portugal Travel Review: Lisbon, Sintra, Nazare, Coimbra, Douro Valley, Azores, Porto, 16-Day Tour
"We thoroughly enjoyed our trip. Zicasso’s travel agency did a great job of arranging gorgeous hotels and top-notch tour guides."

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Luxury Portugal Trip Review: Azores Islands, Canoeing, Views, Exploration & Local Cuisine
I cannot say enough about how amazing our trip was to The Azores. The islands are magical and it feels as if we barely scratched the surface of the overall beauty of the islands, the culture and the food. It was the type of trip that leaves you craving for more and it just wraps you up. There were moments in looking at the Hydrangeas and then gazing at the ocean and the volcanoes that you completely forgot about any worries. To enhance the experience even more, we were blessed to have the guides that showed us around the three islands we toured (Pico, Faial and Sao Miguel). Each island had its own character and feel. Just thinking about the trip makes me want to go back, learn Portuguese and move our families there. Which all leads to the incredible, world class and phenomenal service that this travel company provided. From the first phone call with our travel planner, he fully understood what my wife and I would enjoy and was able to enhance what I had already thought was an exceptional trip. Our Sao Miguel guide was kind enough to give us a brief tour during a layover. We arrived in Pico and our guide was an absolute joy. She drove us to so many beautiful places and set the tone. So many wonderful little places on the newest island. Our guide in Faial was equally great as he took us to the caldera and gave us a brief glimpse of the hidden beauty in Faial. Then 4 days in Sao Miguel which honestly was not enough. Actually the 2 days in Pico and 1 day in Faial were not enough. Our guide did his best even on rainy days to make the best of the trip. We discovered so many little spots on the island that left us speechless. The canyoning, the views, the lakes, the ocean, the trees, the food, the personal service that our guide provided was above and beyond what my wife I expected.Thank you travel planner and this travel company for a trip that my wife and I truly cherish.

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Travel Review: Portugal Couples Trip, Azores, Sao Miguel, Faial, Pico & Sao Jorge, Terceira, 2-Week Tour

My husband and I recently spent 2 weeks in the Azores in Portugal.  We had the pleasure of working with our travel specialist. She is in a class by herself! She is extremely knowledgeable and a pleasure to work with.  From beginning to end everything was planned perfectly.  What was especially nice is that she took the time to understand what we were looking for and then tailored a trip to our personal interests. We visited 5 islands- Sao Miguel, Faial, Pico & Sao Jorge and Terceira. Our travel specialist booked all the tours, hotels, flights and ferries between the islands. She even provided us with a mobile hotspot should we need to reach her for any reason. We truly felt that all our personal needs were attended to. For anyone thinking of doing this on their own, I would say “forget it!” Working with a travel agent within the country truly made the difference.  From beginning to end, this was a trip of a lifetime! I would highly recommend our travel specialist and would certainly call upon her for our next trip.

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Portugal Review: Luxury 3-Week Tour, Algarve, Douro Valley, Lisbon, Peneda Geres National Park, Piodao, History & Culture

            This past October my wife and I took a comprehensive three-week guided tour of Portugal, starting out in the Algarve, traveling north through the interior as far as the Douro valley and Geres National Park, then heading south down the coast, ending in Lisbon.  When we initially chose Portugal as our destination, friends remarked “Three weeks in Portugal!  Will there be enough to do?”  I confess that when we originally chose Portugal as our destination, we had only a vague idea of the cultural and scenic riches in store.  We can now attest that Portugal has it all.  Small in area, it nonetheless offers amazing variety–gorgeous beaches, beautiful mountains studded with medieval walled villages, breathtaking vistas of river valleys, arid land with expanses of cork and olive trees, lush wine estates, unusual and sometimes quirky World Heritage sites, and two fabulous cities.  Looking back, three weeks was barely enough time to accomplish all we had hoped to do.

I. The Plan. As return clients of Zicasso, we have come to expect that they will put us together with top-notch tour directors, and the company that designed our tour of Portugal was no exception.  This company is first rate in every respect.  The travel planner, co-owner and director, was first in touch by email, offering a preliminary itinerary based on the general specifications we had given. We then had an extended, very productive chat by phone.  The travel planner’s charm and enthusiasm came through instantly, and it was evident that she knows Portugal like the back of her hand.  She is a great listener, and picked up right away on our interests and touring style.  We were less interested in relaxing at the beach or in wine tastings, and much more in visiting museums and exploring picturesque villages and historic sites. We are generally driven to squeeze in as much as possible in the allotted time, and presented her with a sizable list of towns we would like to include. The travel planner was back in touch the next day with a thoroughly revamped itinerary that incorporated virtually everything we had wanted to do (excluding just a few places that were not feasible due to time and distance).  On tour this plan proved to be extremely well constructed, ambitious but do-able, keeping an energetic pace and having an occasional long day.  This plan was ideally suited to us, and we loved every minute. 

II. The Tour. When we arrived at the Lisbon airport, the travel planner and co-owner were there to greet us.  The travel planner had prepared a very handy comprehensive guidebook that included the complete itinerary, descriptions with historical background, maps, vouchers, and pertinent details such as hotels and times for pick-ups.  She also provided a portable wi-fi hotspot that was a real boon throughout the tour.  Although the itinerary was charted out in great detail, it was still flexible, and guides introduced additional attractions based upon our interests.  

The travel planner and her staff were at the ready to address any questions or concerns that arose.  When we decided at the last minute that we wanted to tour the amazing caves off the coast at Lagos by speedboat, even though a kayak adventure had already been booked, the travel team made sure that happened.  And they were always happy to attend to special arrangements and details. When I wanted to make a reservation at a fine restaurant for my wife’s birthday, they secured a reservation at one of the top spots in Lisbon.  The staff there was thoroughly aware of the occasion and gave us a table in a special alcove.  I sensed the travel team's guiding hands in making this evening so memorable.  These are just two examples of the great care and responsiveness of the travel planner and her team.

III.  The Guides.  Although the travel planner offered the possibility of a self-guided tour with rental car, we opted to have a driver-guide with us from start to finish, a luxury that we consider well worth the added cost.  The travel planner ensured that all the transition points were seamless; without fail every guide was waiting for us at the appointed time.  We had a total of six driver-guides during the tour, each a local in the area we were touring.  Each was a unique and charming individual.  All were polished professionals who loved their country and wished to share its history and beautiful sights with the visitors.  All had a perfect command of English and were wonderful people with whom we have formed lasting friendships.  Our experiences with these people were indeed the very heart of this tour.  We feel intimately acquainted with the Portuguese people, their history, and their culture. 

Our first guide introduced us to the prehistoric menhirs outside Évora, a fascinating cork factory, a very authentic Taberna, and the lovely family pottery makers of Sao Pedro do Corval.  We also explored the wonders of Évora itself, with its narrow winding streets, aqueduct, beautiful churches, and the famous chapel of bones.

The next focused on Portugal’s rich history, from the Neolithic rock art at Foz Côato Roman ruins at Mértola and Ammaia, with marvelous museums explicating their significance.  He took us to fortresses and castles built as bulwarks against the Spanish at Mértola, Castelo de Vide, Marvão, and we walked castle walls and climbed up many a keep; he led us through picturesque medieval villages, often perched on a mountaintop, and greeted his friends in these sites. The town of Piódão, built entirely of schist, was unforgettable, especially with its lights at night.  A wine making tour was very educational, and followed by a tasting.  At the end of our stay, he took us to an unforgettable evening of fado music and dinner.

Our next guide played recordings of fado music during our travels, and we became enamored of the legendary Amalia Rodrigues and other performers.  We cruised the Douro Valley with its lovely vineyards, took a gondola ride in Aveiro, toured the sumptuous library and tiled rooms of the University of Coimbra, and explored the city of Porto, with its impressive Casa de música and a wonderful museum.  It seemed that everyone was a friend of our guide!

The next guide led us through the breathtakingly beautiful Geres National Park, where he lives.  He gave a botanical tour during a hike, and also stopped at a little stone village with a population of 15.

Our next guide took us to lovely churches, such as that in Batalha, and the polygonal oratorio of the Templar Knights in Tomar.  We toured the huge palace of Mafra, the deserted Roman ruins and museum at Conimbriga. and the picturesque villages of Óbidos and Nazaré. 

And our last guide gave us a wonderful overview of Lisbon, with highlights the Jerónimos Church and Monastery, the National Tile Museum, and the best pastel de nataof Portugal!  On another day we ventured out to the Palace of Queluz with its lovely gardens, and the impressive National Palace of Sintra, her home town.

IV.  Hotels and transportation.  The hotels were excellent and varied—the luxury resort-spa in the Algarve, a wonderfully located hotel in the center of Porto, an intimate little hotel situated among the vineyards of the Douro, a former convent transformed into a lovely hotel, and modern lodging with a gorgeous view of the city of Lisbon.  We were presented with alternatives for every town and had a part in choosing our hotels. All of the cars used were spacious, air-conditioned, spotless, and new.

V. Summary. This was one of the best tours we have ever taken, perhaps the best.  Everything, from start to finish, was perfect.  We would love to return, and, if we do, we would hope to book the tour again with this great company! 

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Customizable Itinerary

This is a sample itinerary to inspire a personalized trip designed with your travel specialist.

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