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

$4,600 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 208 reviews

Portugal Travel Review: Porto, Douro Valley, Alentejo, Lisbon, Lagos, 11-Day Trip

I'd make this 4.5 stars if I could. We had a five-star experience with a few glitches, but they were addressed quickly and kindly.

Zicasso’s travel specialist is a gem. She goes out of her way to clearly communicate what to expect, who you'll be with, and the times for meets and activities. She made us feel special, as though we were her personal guests rather than just clients. We had a luggage issue that she went out of her way to help resolve.

We asked to stay in nice places with AC and king-size beds, and she delivered. All places were great and a bit different from what we're used to and from each other. Most of the drivers were also a lot of fun to be with and spoke at least reasonably good English.

I offer two suggestions for those who use this service. One, always verify meet times and contact info that you receive. Two, don't pre-book two meals in a day if you're staying at a place that offers breakfast. It's just too much food too close together.

We had an 11-day vacation. We chose variety rather than immersion, so went from Porto to Douro Valley to Alentejo to Lisbon to Lagos in the Algarve area, with some stops in between and drivers who brought us everywhere. Next time, we'd likely choose two or three places for a more immersive experience.

I highly recommend this travel company and the travel specialist in particular.

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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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Portugal Travel Review: Sao Miguel, Porto, Lisbon, Douro Valley, Guides, Local Cuisine, Wine Tasting, 12 Days

Our trip to Portugal, via an itinerary planned and executed by Zicasso’s travel specialist, was perfect. We spent a significant amount of telephone time with the travel specialist prior to the trip and he was able to transform our travel wants into a program that aligned with our style and pace.

We were able to have three wonderful experiences—São Miguel, Porto, and Lisbon. He gave us just enough time in each location to see and feel, and eat and drink, the particular flavor of that region. The hotels were very nice and in great locations, and in some cases exceptional. The guides and drivers were all committed to making sure we were comfortable and having the experience we hoped for.

We cannot say enough about the quality of the local partners. All were of a very high standard of customer service.

Our guides in São Miguel made sure we had the true feeling of the islands.

Our guide in Porto was a force that we were able to enjoy. We loved her dedication to the local communities, especially the fishing villages. It was special spending that time with her.

Our guide was inspirational in the Douro Valley.

And in Lisbon, many thanks to our guide for bringing us close to his heart and sharing so much with us. He was very educational and fun. At the same time, no one could surpass our other guide. We loved her style and energy. We had such a wonderful experience with both of them. We would love to travel with them again.

Thank you for helping us make wonderful memories and we will spread the word about you to all of our traveling friends.

We will be back in touch for our next trip!

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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 Family Tour Review: Lisbon, Sintra, Evora, Porto, Algarve, Madeira, Douro Valley, Cooking Class, Tile-Painting Workshop, 13 Nights

The travel agent from Zicasso's tour company planned for my family of four the most spectacular and luxurious two-week trip around Portugal. We traveled to and enjoyed the highlights of Lisbon, the romantic architecture in Sintra, the incredible history of Évora, the beautiful coastline of the Algarve, the laid-back atmosphere and gorgeous scenery of Madeira, the beautiful, historical, bustling city of Porto, and the stunning scenery of the Douro Valley. 

The travel agent's suggestions and bookings were all perfectly aligned with what we envisioned and the accommodations booked were all beautifully appointed and family-oriented – five-star hotels that catered to the entire family, with indoor pools and kids greeted with backpacks and toys at the door, and nightly treats on pillows.

The tour guides booked were all very knowledgeable and kind. They were patient with my two- and four-year-olds, and taught us all so many new, amazing things.

Every day was a highlight, but I would say my girls really enjoyed the tile painting as well as the pastel de nata-making workshops.

My husband and I really enjoyed Évora and Sintra, and truly seeing the beauty and history of it all.

We absolutely fell in love with Portugal, the culture, and the food. My only regret is not having more time so we could’ve seen the Azores as well and stayed even longer. 

We so look forward to this travel agent planning us another perfect vacation in the near future!

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Portugal Tour Review: Lisbon, Porto, Obidos, Coimbra, Azores, Jeep Tour, 10-Day Trip

Good Afternoon,

We are reaching out regarding a review request for our recent trip. Recently, we booked a 10-day trip to Portugal through Zicasso. This is our third trip booked through Zicasso, and we chose Zicasso because the previous two trips were fantastic; they were well organized, and we had very enjoyable experiences in two countries we had never visited. The previous agents built our itinerary based on their vast knowledge of the country, confirmed all logistics, were communicative, and provided us with a great and luxurious experience in line with the cost. 

Unfortunately, we cannot say the same about our recent experience with this travel company. We approached the collaboration with the travel company and agent similarly to our past two vacations. Based on the provided itinerary and our conversations with the travel agent, we understood, as before, that the itinerary items that required guides, reservations, and transport details had been worked out with the respective parties. However, on our trip, there were many miscommunications between the agency, ourselves, and our guides and drivers. The itinerary listed many places we thought we would be shown on the tours, but in reality, we did not visit many of them, they were just listed as options for us to explore ourselves, which was unclear from how the itinerary was initially presented to us in the planning stage. When the tours started, the tour guides were often asking us what we would like to see instead of having a list of stops to take us to. As this was our first trip to Portugal, we were not informed enough to provide that input and did not expect to have to do so. The guides were very good, they were knowledgeable, often kind, and tried to help us, but it was clear that they had also not received proper communication from our travel agent, which was upsetting and made the experience feel very disorganized. Additionally, the private transport drivers were not clear as to where they were taking us, again due to miscommunication from the travel agency. For example, when we traveled from Lisbon to Porto, as per the itinerary, we were supposed to stop at Obidos and Coimbra along the way for specific sightseeing and tours. Our driver was not aware that we were meant to make those two stops along the way. Luckily for us, we found out the previous day that the same driver would be taking us to Porto, and our guide worked with him to figure out the stops and timings for our scheduled activities on that trip. However, it was stressful to learn that our driver was not aware that we had a stop at Obidos, he did not know that we were going to have a tour guide in Coimbra who he had to coordinate with regarding pickup and drop-off. Additionally, we were meant to have lunch at a restaurant where the agent was supposed to have made a lunch reservation. However, when we went there, they had no reservation on record but they were nice enough to accommodate us. As this was happening and we reached out to our travel agent to request that she communicate with the driver, we just received a text message back saying that the driver was already aware, which was clearly not the case.

In the Azores, because of the weather, our whale tour was cancelled, which we completely understand due to safety, but we still had a jeep tour portion of the excursion. The guide for this jeep tour did not provide a good experience at all. He did not stop at a lot of viewpoints though we saw other jeep tours stopping at them, and he spent a lot of the trip complaining about tourists. The jeep ride was very uncomfortable as they made several of us sit in the back rear facing seats, even though we had specifically mentioned to the agent during planning that my mother is 70 years old and cannot easily climb in and out of some of these types of vehicles. As part of the itinerary for this day, a lunch was also included but the tour guide was not aware of it, and when he learned about it, he said he could not arrange the lunch because he needed to go to his next tour. We ultimately left and had lunch on our own. When planning, our agent said that although this was a jeep tour it would be comfortable and that the tour the next day would be in a minivan. However, the next tour was also in a jeep. The tour guide was very good but the ride was uncomfortable, and again did not accommodate the mobility issues we had identified with our agent previously. 

On the last day, we were supposed to be picked up for our transport to the airport for our flight home. The driver did not show up and the hotel staff tried to help us by calling the travel company’s emergency number. It was surprising that instead of helping us they were being very rude to the hotel staff who were actually going out of their way to help us. We found out that the agency communicated the wrong time to the pick-up driver and finally the hotel arranged for a taxi to take us to the airport, otherwise we would have been late for our return flight. 

Overall, the trip was not on par with the level of quality we have come to expect from a Zicasso identified travel agency. In addition to the general logistical issues we experienced, the agent never checked on us at any time to see if all was well. Whenever we had a question and we reached out to her, we received unclear responses via text, and nothing further. We wanted to provide this feedback as we know Zicasso takes pride in providing luxury travel experiences to their customers, and we have experienced that first hand in previous trips. As return customers, I would not recommend this agent/company to anyone who wants a Zicasso experience.

 Sincerely,

Jyotsna R.

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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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