From Bustling Streets to Island Retreats. Unveiling the Magic of Lisbon and The Azores

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Advisor - Wendy Ritter
Curated By

Wendy Ritter

  • Lisbon

  • Azores

  • Active Travel

  • Nature Escapes

  • Islands

  • History

  • Sightseeing

Islands with dramatic landscapes.
Curator’s statement

Embark on an unforgettable journey that blends the allure of Lisbon’s vibrant streets with the enchantment of the Azores’ breathtaking islands. Explore historic landmarks and savor local delicacies in Lisbon and then transport yourself to the gorgeous Azores which promises an immersive and awe-inspiring vacation that will leave you with cherished memories and a deeper connection to the wonders of Portugal that will have you planning your next trip back.

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Day 1: A lay of the land

Elevador de Santa Justa (Santa Justa Lift) is a transportation service in Lisbon, Portugal

After checking onto the charming Heritage Avenida Liberdade Hotel, get freshened up and just start wandering around town. Our wanderings led us to the Elevador de Santa Justa, the views are not to be missed! By now you will be starving. You can pick just about anywhere for lunch around there and you won’t be disappointed. After lunch we walked through Rossi Square and then to the waterfront. Next find the funicular and ride to the top where you will find a lively area to sip mojitos and listen to music while gazing out over the Alfama district.

Find a tapas restaurant such as Grau Douro Tapas & Wine Bar before headed back to the hotel after a long day.

Day 2: Sintra & Balem

Moorish Castle is a medieval castle in Sintra, Portugal.

Today take the train to Sintra. We prearranged a TUk TUk tour, which I highly recommend as our guide effortlessly bypassed the traffic, courtesy of the left lane reserved for such nimble vehicles.

In 40 minutes we found ourselves ready to explore the magnificent Peña Palace and the awe-inspiring Moorish Castle. After Sintra, we hopped in a taxi and headed towards Balem. Our first stop was the monastery and then made our way towards the towering Torre de Balem. We made a quick stop back at the hotel to freshen up and then embarked on an evening stroll to the Bairro Alto area. We ate at Rosa Da Rua which we all enjoyed .

Day 3: Alfama region

Pizzaria Lisboa is a restaurant with nice ambiance and good food.

On day three, we embarked on a delectable journey through the Alfama region. After a quick Uber ride, we met our walking food tour guide ready to explore the hidden culinary gems in this charming neighborhood. The tour meandered through narrow alleyways steeped in history and our taste buds were treated to unique and delicious dishes along the way.

After our tour we wandered through the local shops trying to work off some of the food we ate and stopped for a drink or two along the way. For dinner we had the pleasure of visiting Pizzaria Lisboa. Be sure to make reservations in advance to secure a spot at this popular establishment.

Day 4: Ponta Delgada, Azores

Ponta Delgada is the largest municipality in Azores with a lively economic and cultural life.

Today we began with an early start, catching a taxi to the airport to Ponta Delgada. After landing we picked up our rental car and got to exploring this captivating island.

Our first stop was Tuka Tula, a delightful restaurant situated right on the water’s edge. After a delicious lunch we continued our adventure to Dona Beira Thermal Springs. We changed onto our swimsuits in the well-appointed locker rooms ready to immerse ourselves in all of the 5 hot springs and their the rejuvenating waters. Afterwards we made our way to the lovely Grand Hotel Acores Atlantico, our haven for the evening. Dinner was a delight as we indulged in a scrumptious meal at the hotel’s restaurant.

Day 5: Azores adrenaline

The travel advisor looks like she enjoyed canyoning in Azores.

Day 5 of our Azores adventure was filled with adrenaline pumping thrills as we drove to our meeting spot for a thrilling day of canyoning. Our expert guide equipped us with all the necessary gear including wet suits and prepared us to conquer the cascading waterfalls. It was an unforgettable experience, a blend of thrill and nature that I will not soon forget. Afterward we took a leisurely stroll through the beautiful park. We stumbled upon a hidden gem indulging in the best grilled cheese sandwiches and ice-cold beer we had ever tasted! Back to the hotel we went stopping along the way for a casual dinner and then grabbing a nightcap at the hotel bar.

Day 6: Exploring the island

Termas Da Ferraria is a geothermal pool located in an ocean lagoon.

Today we embarked on a self guided exploration of the island. Our first stop was Vista Do Rei Miradouro, a breathtaking viewpoint that offered panoramic vistas of unparalleled beauty. Continuing our journey we made our way to Sete Cidades. We were spellbound by the vivid hues of the twin lakes. With appetites calling, we stumbled upon a charming restaurant called Quiros. We savored the local flavors while enjoying the cozy atmosphere. We hit the road again and headed towards Ferrier, the western point of the island. There we discovered the mesmerizing Termas da Ferraria, a geothermal oasis nestled amidst dramatic cliffs and crashing waves. We took a dip in the geothermal pools, taking in our stunning surroundings. We then embarked on a picturesque drive back to the hotel stopping along the way for a casual dinner and another nightcap at the hotel bar.

Day 7: Pico island

Two boats on water going to Pico island.

Today we checked out of our hotel and took a short flight to the enchanted island of Pico. We picked up our rental car and drove to Villa Da Madalena, our base for the next leg of our journey. We ate at Ancoradouro, a restaurant not to be missed while on Pico! Early to bed since we have a very early day tomorrow!

Day 8: Mt. Pico

Views from the top of Mt. Pico.

On day 8 of our Azores expedition our knowledgeable tour guide picked us up bright and early as we embarked on a thrilling adventure to conquer the majestic Mt. Pico. The hike to the summit proved to be an awe-inspiring challenge, pushing our physical limits and testing our endurance. Finally after a grueling full day of hiking we stood atop Mt Pico! The panoramic views stretched before us as the sense of accomplishment washed over us. The climb down was just as hard as the climb up. Exhausted and sore we we mustered the strength to enjoy dinner and a well deserved bottle of wine.

Day 9: Wine tasting

A winery in the Azores.

Day 9 our tour guide, a knowledgeable local picked us up from the villa setting the stage for an unforgettable all day adventure. We started our journey through renowned vineyards where we indulged on wine tastings. As our appetites grew our guide led us to a charming cafe in town where we enjoyed a delectable lunch. After lunch was the highlight of the day when we went on a mesmerizing whale watching excursion. The sheer beauty and power of these majestic creatures left us in awe. We had dinner with our guide before being dropped back at the villa.

Day 10: Return home

An airplane on the tarmac in the Azores.

Day 10 brought us to our final stretch. After breakfast at our villa we headed to the ferry port. We embarked on a short scenic 25-minute ferry ride to Horta. From there we took a cab to the airport ready to make our way back to Ponta Delgada and then back to the US.

Need to Know

Looking for more travel inspiration? Check out my guide, Wander Your Way Through Barcelona.

Advisor - Wendy Ritter

Travel Advisor

Wendy Ritter

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This guide is part of our ongoing series on travel to Lisbon.