Lighthouse Ponta da Ferraria San Miguel, Azores

Seven Island Portugal Escape: Azores and Madeira Vacation

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Customizable Itinerary

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

Countries Visited


Places Visited

Madeira, Azores, Funchal, Camara de Lobos...

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Suggested Duration

14 Days

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.

Customizable Itinerary

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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

$3,635 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.

Reviews of Zicasso's Referral Service

4.93 stars based on 1029 reviews.

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