Seven Island Portugal Escape: Azores and Madeira Vacation

Over these two weeks, you will explore seven different islands and travel between unique destinations and dramatic landscapes. Before all of this beings, you will have a completely free day in Madeira for a chance to settle into the rhythm of the islands and get over any travel fatigue. There are many beaches within easy reach of Funchal, including those surrounded by cafes, as well as those where very few people will be around. For cultural exploration, try the Contemporary Art Museum and for a spectacular sunset on the road that leads away from Funchal and into the verdant mountains that dominate so much of Madeira.

Madeira may have changed since its days as a pirate retreat, but the island is still packed with myth and fable. Fishing villages like Ribeira Brava and Camara do Lobos exude color and charm, as well as the scent of fresh oceanic catches. Continue along the remote southwest coast, and you will climb into the mountains for breathtaking plateaus that bring endless views. Descend into the north of the island, and volcanic rock swimming pools hide in the verdant landscapes as the road is dramatically cut into the cliffs of the north. Stop for lunch somewhere on route, and then return to Funchal on the eastern side of the island, where the second highest sea cliff in the world is just one of the sights. It will be a lot to fit into one day, but you will be entirely immersed in Mother Nature as you explore an island that can fill an entire memory card on your camera.

Faial has quite a history, and the once-timbered village of Horta has been a sailing hub for centuries. In the 21st century, you will find super yachts lulling in the harbor while centuries ago, it used to be explorers, pirates, whalers, and armadas. Fly here in the morning and go on a walking tour of Horta to listen to a history that sounds fictional but is as real as they come. After lunch in town, you will head out on a two-hour whale and dolphin watching tour and discover why whalers were so obsessed with this little island. Spotted and bottlenose dolphins jump clear of the surface, as humpback and sperm whales crash their tails into the water and seabirds dive like arrows into the ocean. Fin and sei whales are also in abundance around here, spiraling out of the water with a grace that defies their size.

Capelinhos Volcano looms large over Horta and is much younger than the whaling community. The volcano exploded dramatically in 1958, rising from the Atlantic depths to add new landmass to Faial Island. Blackened lava fields ripple towards the shore, and extensive ash fields are slowly turning into nutrient-rich soil, the process of which will take many more hundreds of years. Cross the mountains to the Valley of Flamengos and enjoy the view from Caldeira, an iconic crater that feels like the top of the world. Move next to explore the remnants of Capelinhos with the beauty and brutality of nature all around. Return to Horta for an afternoon at leisure for a perfect time to settle in at any one of the beaches close to town.

Nearby Pico is unmissable as a volcano that rises over two kilometers into the blue Atlantic sky. Pico erupted long before Capelinhos, and its ash has turned to fertile soil that is perfect for grape wines. Take a boat journey in the morning and follow a walking trail along ancient lava rock, weaving through the vineyards and villages of a past century. Verdelho is the primary grape, and you will go tasting in one of the cellars with winemakers giving you a chance to taste the difference between Azores wine and those from mainland Portugal. It will be a beautiful half-day hike that will be interspersed with food and wine before a stop at the whaling museum to show how Pico has been transformed over recent decades.

The harmonious buildings of Angra de Heroismo will make you feel as though you have landed on the streets of the 16th century. This UNESCO World Heritage Site was where New World explorers would dock on route back to Europe with their ships laden with riches. Wealth has always dominated the town, and your local walking tour will reveal historical tales from the Age of Discovery. Savor lunch at a legendary seafood restaurant, and then climb the hill behind Angra de Heroismo for an insatiable view across the third largest island in the Azores. Monte Brasil rises in the distance and the red rooftops glimmer in the afternoon sun as a symbol of how the archipelago mixes history with nature.

Spend the day exploring Terceira with a full-day tour on an island that is rich in both natural and cultural splendor. Fishing hamlets sit in secluded bays, colorful churches date to the 15th century, vast green pastures are divided by hedges of hydrangeas, and the town of Praia da Vitoria makes a delicious lunch spot. Spend the afternoon discovering lava tubes, wandering through them to find stalactites and stalagmites that sparkle in the gloom. On the northern coast, you can swim in natural lava pools and then change the focus with a tasting at the wine museum. A succession of lovely villages mark the route back to Angra de Heroismo, and each will be able to hold you captive if you stop for more than one drink.

Lakes of green and blue stand proudly on the west of Sao Miguel Island, hypnotically framed by forested slopes and endemic flora. Stand at Vista do Rei and soak up the panorama, the beauty of the old volcanic craters so postcard perfect from this point. Savor the adventure as you can choose to hike or mountain bike down the slopes towards the lake. There are different routes, all lined with exotic Azorean flora. Take lunch at one of the Sete Cidades villages before getting closer to the lakes colors on a kayaking tour if you would like as no kayaking experience is necessary, and the serenity of paddling is perfect for touring the Azores most iconic natural site. Earlier in the day, you will have flown into the west of Sao Miguel. After the day’s adventure, you will pass through pineapple plantations and cattle fields to Ponta Delgado, the capital city of the archipelago and where your hotel is located in the heart of the historical center.

Landscapes collide on the island of Sao Miguel as a tea plantation covers swathes of the interior for an idyllic sight for the morning. Botanical gardens are lush and almost overgrown, the volcanic soil and continual sun allowing thousands of species to flourish. Hot springs create swimming pools of soothing waters, full of minerals that once made them a 19th-century spa resort. As part of the private tour, you will have a classic lunch of cozido nas caldeiras, a meat and vegetable stew that will have been stewing underground for seven hours, heated by volcanic steam. Throughout the day, you will enjoy incredible viewpoints as Sao Miguel is an island with such rich and unusual landscapes.

Flores is the westernmost and wildest of the Azores, an island where nature takes over, and whales are seen continually from the shore. This great Eden is a paradise of cliffs and craters, lakes and leisurely strolls to remote beaches. Hydrangeas add shocks of blue to a rainbow of green, while scenic lookouts gaze upon the waterfalls that make up the Flores postcards. After your flight, you will be transferred to the small town of Santa Cruz. The day will be at your leisure, and there are many unguided options you could take. Relax in the sun, hike the trails into the hills, and try some of the local wine. Flores is the ideal island for a quiet day, with the sound of the surf your accompaniment regardless of what you do.

Spend the day on a private guided tour to pass vertical lava formations and the endlessly lush landscapes of nature. Most of this Azorean island feels like a wilderness, and with so many viewpoints, it often feels like you have the whole of the Atlantic archipelago to yourself. You can swim beneath waterfalls, trek through the overgrown foliage to hidden caves, sail across volcanic lakes and discover an island cast adrift in the Atlantic. Your guide will discuss various options the day before so that the itinerary can be adjusted to your interests and energy levels. Dozens of exceptional hikes can be completed, from 20 minutes long to four hours. You can also stick to a four-wheel drive vehicle and bump into the wilderness with so many natural wonders ready to make up your day.

Remote Corvo has an unusual history. Civilization has thrived here for more than 500 years, the oldest evidence found at the 16th-century church. But the language the locals speak is not Portuguese, and the culture they follow is unlike the rest of the Azores. Kept alive by less than 500 residents, Corvo is home to one of Europe’s most unique cultures and lifestyles. Take the ferry here in the morning to spend a relaxed day connecting with the story of Corvo as you meet the locals and muse over a lifestyle that has been kept distinct from the rest of the world. Corvo will be the seventh and final of the islands you will visit on this luxury tour and one that will also offer some wonderful natural scenery and viewpoints. Perhaps on the boat back to Flores, you may even pass one of the migratory whales that navigate through the Azorean channels.

From Flores, you will take the early flight back to Sao Miguel to connect with your departing flight back home.