Lisbon & Azores Highlights - 5 Days
Highlights
- Buzz around Lisbon's historic Pombalin architecture in a tuk-tuk
- Experience the soul-stirring melodies of fado music over dinner
- Soak in thermal hot springs in the Azorean village of Furnas
- Witness the largest mammal on earth on a whale watching tour
Brief Itinerary
| Day | Highlights | Overnight |
|---|---|---|
| Day 1 | Arrive in Lisbon, Discover the Portuguese Capital | Lisbon |
| Day 2 | Lisbon Walking & Food Tour, Explore Belém by Tuk-Tuk, Fado Dinner | Lisbon |
| Day 3 | Fly to São Miguel Island, Kayak at Sete Cidades, Tour Western São Miguel | São Miguel Island |
| Day 4 | Whale Watching Excursion, Tour Eastern São Miguel | São Miguel Island |
| Day 5 | Walking Tour of Ponta Delgada, Depart São Miguel |
Detailed Itinerary
Day 1: Arrive in Lisbon, Discover the Portuguese Capital
Welcome to Portugal! You'll touch down in Lisbon, known for its sunny weather and hilly streets and often called the "City of Light" for its gorgeous golden-hour hues. A private driver will be waiting at the airport to take you to your accommodation for the next two evenings, and then it's time to explore! There's no set itinerary for your first day, which gives you free rein to indulge in whatever you like. Go on the hunt for Portugal's famous azulejos (blue tiles), stroll the sweeping Praça do Comércio, or even take a nap to ward off jet lag.
Tomorrow, you'll be walking the city and buzzing around the Belém neighborhood, so you should spend today exploring the other corners of Lisbon and simply becoming familiar with Portugal. Tram 28 provides a scenic way to get up and down the hills, and a walk along the Tagus River is never a bad idea. Cap off the day with a traditional dinner of bacalhau (cod) or grilled sardines and the classic Portuguese dessert, pastéis de nata (egg custard tarts). Whatever you do, don't miss the sunset at Miradouro do Monte Agudo.
Day 2: Lisbon Walking & Food Tour, Explore Belém by Tuk-Tuk, Fado Dinner
Your second day in Lisbon is packed full of interesting and fun experiences. Start with a private walking tour. Guided by an expert, you'll explore some of the most iconic sites as well as hidden gems, transporting you through centuries of history. After working up an appetite among the city landmarks, you'll finish off with a visit to Lisbon Winery for a wine tasting, complete with cheese pairing and other local bites.
In the afternoon, it's time to zoom around the city on another private tour with your trusty tuk-tuk driver. You might be wondering what a Southeast Asian vehicle is doing in Lisbon, but once you've walked the steep hills, you'll understand why they've become so popular. See the best of the Belém neighborhood, one of the most historic areas of Lisbon, from your funky set of wheels. Notable sites include the Torre de Belém and the Jerónimos Monastery, all with views of the iconic 25 Abril Bridge. As evening falls, you'll end the day in style with dinner and a fado performance.
Day 3: Fly to São Miguel Island, Kayak at Sete Cidades, Tour Western São Miguel
Chat with a local specialist who can help organize your trip.
Today begins with a quick flight from Lisbon to the largest island in the Azores, São Miguel. Your private driver will drop you off and pick you up at both airports. Drop off your bags at your accommodation and kick off the day with your very first adventure on the island—kayaking the Sete Cidades. If you've seen those quintessential photographs of the Azores from a clifftop overlooking a chain of turquoise lakes, you'll be familiar with this iconic natural wonder. Spend the morning gliding along these peaceful lagoons and soaking in the sweeping scenery.
Later on, you'll hop in a car for a private tour of the western side of São Miguel. This might be the largest island in this volcanic archipelago, but it only takes 1.5 hours to drive across it. A stroll through the storybook village of Ribeira Grande is up first, followed by a deep dive into the island's lush interior at Salto do Cabrito waterfall and Lagoa do Fogo and a well-deserved meal to fuel your adventures. You'll get a bird's-eye view of Sete Cidades before ending with a grand finale at the island's westernmost point in the seaside village of Mosteiros, known for its lava rock tide pools.
Day 4: Whale Watching Excursion, Tour Eastern São Miguel
Start your last full day in Portugal with a bucket list experience. The ocean off the Azores is known for its biodiversity—and for being a sanctuary for whales and dolphins. This is one of the only places in the world where sperm whales and blue whales (the largest mammals on earth) are found year-round. You'll hop on a boat for a group tour and head out into the open ocean to track down these gentle giants, observing them from a safe and respectful distance. If you're extra lucky, you might even get to see them breach!
Head to the eastern end of São Miguel next, driving your way through the rolling landscape on a private tour. This excursion highlights São Miguel's volcanic activity, with your first stop dedicated to sweeping ocean views at Miradouro de Santa Iría. Then speed your way toward the town of Furnas for a glimpse of the volcanic activity the Azores are known for. Tucked inside a volcanic caldera, Furnas is known for its thermal baths, burbling mud pits, and a local delicacy cooked underground called cozido das Furnas (a meat and vegetable stew cooked using geothermal heat).
Day 5: Walking Tour of Ponta Delgada, Depart São Miguel
Squeeze in one last walking tour this morning before your departure. You'll stroll around Ponta Delgada, where you've been based these last few nights, with a private guide. Ornate churches, cobblestone streets, and the island's traditional Micaelense architecture are all on display, and you'll learn about both its significance and the history of this far-flung, seafaring city.
More Great Azores Itineraries
Looking for more inspiration for your trip to the Azores? Check out these other Azores itineraries, explore different ways to spend five days in the Azores, or discover the best time to visit the Azores.
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