An 8-Day Portugal Adventure: Lisbon, Cascais, Sintra, and the Azores
Portugal is a captivating country, offering stunning coastlines, historic cities, and delicious food. My recent journey took me through Lisbon, Cascais, Sintra, and the Azores, full of scenic walks, cultural experiences, and culinary delights. Here’s a detailed day-by-day guide to my itinerary to inspire your next adventure. I am so lucky to have a travel agent for a mom, she has taken me on so many amazing adventures! Check out her website here!
This trip was so needed! I have only left my boys for a few days for little work trips. As I was planning the trip, I was worried that I would just want to sleep the entire trip or not know what to do because I wouldn’t be chasing a little one! My boys are not good sleepers! But the travel adventure returned to my soul and I coudn’t fit enough in! I love traveling and experiencing the world!
Here are a few other adventures that I have taken: Nepal, Costa Rica, Faroe Islands…. Where should I go next?
Day 1: Arrival in Lisbon
After a long travel day, we arrived in Lisbon and headed to the Marriott Lisbon to drop off our bags and refresh before venturing into the city. We had to keep going or we would have crashed in our hotel room! While preparing for this trip, I told myself that it would be okay to rest and relax, but once the plane landed, I knew I couldn’t relax, there are way too many things to see and experience!
For dinner, we visited the famous Time Out Market. I dined at Maslene Vieira, where I enjoyed a delicious cod risotto, a signature Portuguese dish. When I am near the ocean, I eat fish as much as possible! I love seafood! The evening wouldn’t have been complete without a classic dessert: pastéis de nata (Portuguese custard tarts). We may have eaten one or two after every meal!
After dinner we strolled along Lisbon’s stunning coastline, enjoying the crisp air, scenic views, and nightlife before returning to the hotel for a good night’s rest.
Day 2: Exploring Lisbon and Belém
Lisbon’s charm is in its diverse neighborhoods, we loved exploring all of the different districts.
We took a tour of the historic Belém district in the morning, home to iconic monuments like the Jerónimos Monastery and Belém Tower. The area is rich with history, and the views of the Tagus River are simply breathtaking. The sites that we visited were so beautiful, but later in the day we found out that Tuk Tuks are the way to go with touring and exploring Lisbon.
Pastéis de Nata at Antiga Confeitaria de Belém is a must-do while in Belém is to stop by the renowned Antiga Confeitaria de Belém, where we indulged in freshly made pastéis de nata. These tarts are world-famous, and for good reason.
When preparing for my trip I asked one of my clients for recommendations before we arrived, and she said a Tuk Tuk tour was a must, if she wouldn’t have given this recommendation, I wouldn’t have looked into it! We had the most fabulous driver! It was so fun, anytime that I tried to take a photos while driving, he noticed and stopped immediatley, it was perfect! If we would have had more days in Lisbon, I would have done this again in another area!
For dinner, we enjoyed authentic Italian cuisine in one of Lisbon’s charming neighborhoods, ending the night with a search for the perfect piña colada. When we were walking around earlier in the day, there were piña colada carts everywhere, it seemed like the perfect way to end the day. But the carts were not so appealing by the end of the day!
Day 3: Cooking Class, Cascais, and Coastal Views
Every time I travel, one of the first things that I look into is a local cooking class. It is one of my favorite ways to get to know a country. They usually end up being one of the highlights of my trips.
We spent the morning in a pastéis de nata cooking class at Cooking Lisbon. Learning to make these iconic treats from scratch was so fun, and the class gave me a deeper appreciation for Portugal’s rich baking traditions. Many of the famous bakeries, make 15,000-20,000 daily!
Afterward, we caught an Uber to Cascais, a picturesque coastal town. We checked in at the Sheraton Cascais Resort and spent the afternoon exploring its charming streets and beautiful beaches. I was lucky enough to photograph one of my past clients who are currently living in Cascais, I will share their session soon!
We had lunch at Taberna Clandestina, a cozy spot known for its modern take on traditional Portuguese dishes.
After lunch, we walked along the coast, soaking in the stunning views, and scouting out locations for my photo session. Praia da Conceição was the perfect location for a photo session—capturing the beauty of Cascais’ beaches and coastline.
We ended the day with a delightful dinner at Malacopa, where we sampled some of the region’s fresh seafood and their take on tacos, you can’t go wrong with tacos!
Day 4: A Rainy Day in Sintra
Sintra, a UNESCO World Heritage Site, is famous for its fairy-tale palaces and lush landscapes, and we were excited to explore it, despite the rainy weather.
We took an Uber to the National Palace of Pena, a striking 19th-century castle that looks like it came straight out of a storybook. Unfortunately, traffic delays and rain made the visit more challenging, but it was still worth seeing. By the end, we were trying to walk up rocks stairways that had become waterfalls, it was an amazing rain storm.
We stopped by Casa Piriquita for a little lunch and to escape the downpour. Casa Piriquita is an iconic pastry shop in Sintra, perfect for a little treat!
After returning to the hotel wetter than I have ever been. We had a cozy dinner at Glass House, a restaurant offering a warm and inviting atmosphere with a menu that highlighted local ingredients.
Day 5: Journey to the Azores (Terceira Island)
After a brief stay in Lisbon and Cascais, we flew to the Terceira, a stunning island off the coast of Portugal in the Azores Islands. My mom had a conference the entire time while we were on the island, so I was on my own to explore. I rented a car, downloaded several audio books, and had a bag full of film and my Rolleiflex from my Great Grandpa. I loved exploring with no agenda, except looking for my next photo.
Getting around the island was very easy, we made it to our hotel with no trouble. Our hotel was in the Angra do Heroísmo, a UNESCO World Heritage town. Our hotel had just opened a few weeks before, Azores Book Hotel was the perfect place to stay.
I spent the afternoon walking around Angra do Heroísmo, exploring the cobblestone streets, historic buildings, and beautiful coastline.
We had dinner at Chefes Do Pátio known for its fresh seafood and Portuguese specialties. I tried Octopus, and really enjoyed it!
Day 6: Hiking and Coastal Adventures in Terceira
Terceira Island is known for its volcanic landscapes, and I was eager to explore the island’s natural beauty.
In the morning I embarked on the Misterios Negros PRC01TER trail, a 4.9 km hike through lush forests and volcanic terrain, offering amazing views of the island’s rugged coastline. I was a little worried about hiking alone, but as soon as I hit the trail, my worries disappeared. The trail systems in The Azores are amazing, every turn was so well marked. I think I had a smile on my face the entire time.
I had lunch Queijo Vaquin a local cheese factory, featuring the island’s famous cheeses.
After lunch I explored Piscinas Naturais dos Biscoitos, natural volcanic swimming pools I wish I would have had my suit, it was so cool.
I ended the day with a cozy dinner at Restaurante Típico in Biscoitos, a traditional Portuguese restaurant.
Day 7: Cooking Class, Lava Caves and Praia da Vitória
I attended a cooking class where I learned to prepare Alcatra, a slow-cooked beef dish, and homemade bread—a real treat for anyone interested in traditional Azorean cuisine. I loved the class by Pro Tours, they have built a beautiful kitchen overlooking the ocean, it was perfect. Cooking classes are one of my favorite ways to travel. I love to learn to cook new cousines!
After the class I set out to explore more of the island, Algar do Carvao is a must see, and there is nothing else like this in the world. I was able to walk down in to a Lava tube, most get destroyed after the volcano is done erupting, this one is in tact still and covered in lush greens and ferns. Such a neat experience.
I drove around to different areas of the island to see the views. I loved the patchwork views of all of the fields.
Later I explored Praia da Vitória before making my way back to my hotel.
Day 8: Hiking and Exploring the Island
There were so many trails on my list, I wish I could have done all of them. Terceira is the perfect island for you if you like to hike!
In the morning I hiked Baias da Agualva, a scenic trail that offers stunning coastal views and a glimpse of the island’s unique volcanic landscape.
Later, we hiked from our hotel to Monte Brasil, which offers panoramic views of Angra do Heroísmo and the surrounding areas.
I wrapped up the day with a delicious dinner at Birou, a local restaurant in Angra do Heroísmo offering a mix of contemporary and traditional Portuguese cuisine.
Day 9: Farewell to Portugal
My last day in Portugal was bittersweet, excited to see my boys, but there were a lot of things I didn’t get to see. I felt bad that my mom didn’t get to experience the island like I did. As we were on the way to the airport we kept getting notifications of delays, and so we kept exploring until the very last moment. I showed my mom a few of my favorite things from the island!
In Conclusion
From Lisbon’s charming streets to the Azores’ volcanic landscapes, this trip to Portugal was unforgettable. I loved traveling with my Great Grandpas camera, all of these images were taken with his Rolleiflex Model T, and I can’t wait to create a special print release of these images.
The combination of history, culture, and natural beauty offered the perfect escape. Whether you’re seeking culinary adventures, outdoor exploration, or a dose of history, Portugal has something for everyone.
I have been talking with another photographer, and we are in the process of planning a little workshop in this beautiful place! Stay tuned, and come travel with me!
