Portugal & The Azores: A Journey Through Cobblestone Charm and Ocean-Kissed Wonders
Some places capture your heart slowly – Portugal grabs it from the moment your feet hit the cobblestone.
From the historic charm of Lisbon’s tiled streets to the jaw-dropping natural beauty of the Azores, this trip was nothing short of magic. The kind of magic that lingers in your soul long after the last bite of a custard tart and the final sunset over volcanic lakes.
Let me take you there.
Lisbon: Where Old-World Charm Meets Buzzing Energy
We started in Lisbon, a city that feels like it’s been dusted in golden light and sprinkled with music. Winding alleys, pastel buildings, historic tram cars – every corner told a story. We checked in, freshened up, and dove straight into Lisbon’s food scene with Ramen House Aska for dinner and dessert at the iconic Chocolateria San Ginés (because every great adventure starts with chocolate, right?).
But Day 2? That was the real Lisbon deep dive.
A half-day tuk-tuk tour whisked us through the city’s most breathtaking views and landmarks – from the mighty Lisbon Cathedral to the sweeping lookouts at Miradouro da Senhora do Monte and Portas do Sol. We strolled through Alfama, explored the National Pantheon, and stood in awe before the Jerónimos Monastery and Belem Tower. We may have eaten our weight in custard tarts at Pastéis de Belém (completely worth it).
The day wrapped up with Lisbon’s trendy vibes on Pink Street, refreshing eats at Honest Greens, and a tram ride adventure using our trusty 7 Colinas card. Pro tip: get the card, trust me—it’s a game-changer.
Lisbon continued to steal our hearts on Day 3 with a walking tour through the castle district, cozy cafes like Cafe de Forte, and spontaneous pastry stops because… when in Portugal, eat like the locals (which means often and deliciously).
Underwater Wonder & Rooftop Views
From the mesmerizing Oceanário de Lisboa—one of the most stunning aquariums I’ve ever seen – to panoramic cityscapes from Santa Justa Lift and Miradouro da Senhora do Monte, every moment felt like a postcard come to life. We capped it off with massages at Thai Sensation and ramen dreams at KOPPU. Pure bliss.
A Day in Sintra – Fairytale Vibes & Coastal Charm
No trip to Lisbon is complete without a full-day escape to the enchanting town of Sintra—and wow, this place feels like it leapt straight out of a storybook.
We kicked off the day wandering the vibrant town of Sintra, surrounded by lush greenery, whimsical architecture, and a sprinkle of magic at every turn. Our first stop? The majestic Pena Palace, perched high on a hilltop like a crown. Its bold colors and romantic architecture are straight-up dreamy, and the panoramic views of the entire region were jaw-dropping.
Next up: Quinta da Regaleira—this mystical estate is full of hidden tunnels, gothic turrets, and the famous Initiation Well (yes, it’s as wild and otherworldly as it sounds). It’s a must-see for anyone with a love for legends, symbolism, and lush gardens.
After soaking in Sintra’s spellbinding beauty, we made our way to Casa Piriquita, where we devoured traditional Portuguese pastries that were flaky, sweet, and unforgettable.
From the fairytale forests, we headed seaside to the charming coastal town of Cascais. For lunch, we found ourselves in Italian heaven at Aqafarina, with pasta and pizza that hit the spot perfectly. We then wandered through the pretty streets, grabbed artisan coffee in Cascais, and topped it all off with a refreshing bubble tea from Two Too. A little unexpected? Maybe. Delicious and fun? Absolutely.
The whole day was the perfect blend of regal palaces, magical gardens, indulgent eats, and coastal beauty. Sintra and Cascais gave us memories we’ll never forget—and totally deserve a spot on any Portugal itinerary.
Azores: The Wild, Untamed Beauty of São Miguel
Then we flew to the Azores, and honestly… I didn’t know a place could be this breathtaking.
Tucked away in the Atlantic, São Miguel felt like we stepped into another world – a place where nature reigns supreme. Rolling green cliffs, deep crater lakes, dramatic coastlines, and air that smells like rain and possibility.
Our base was the incredible Octant Hotel, where every window framed a view worthy of a canvas. Dinners at A Terraand late-night drinks at the hotel bar set the tone: relaxed luxury in the middle of wild beauty.
We wandered through downtown São Miguel, sipped velvety coffee at Intz48, and then hit the road to explore the island’s west side: the stillness of Lagoa de Santiago, the otherworldly views from Miradouro da Vista do Rei, the dramatic cliffs of Varzea, and a soak in the Termas da Ferraria hot springs as the ocean crashed nearby. It was epic.
Nature’s Playground
One of my favorite moments? Visiting a pineapple plantation (yes, in the Azores!) followed by a peaceful walk through the lush Jardim Botânico António Borges. Lunch at Jardim Natural Food & Coffee was so good it deserves its own standing ovation.
We cruised through the north side of the island, from the charming town of Ribeira Grande to the hidden Salto do Cabrito waterfall, and finally stood at the top of the Fogo Volcano in total awe. The views? Unreal. It felt like we were standing on the edge of the Earth.
The Islet, the Stew, and the Steam of Furnas
The Islet of the Azores tour was one of those once-in-a-lifetime moments where words fall short. Crystal waters, dramatic rocky outcrops, and a sense of being truly remote. That feeling of “I’m so lucky to be here.”
In Furnas, we explored the volcanic landscape, tasted traditional volcanic stew cooked in geothermal steam, and even tried volcanic-boiled eggs (yes, really!). We hiked waterfalls and soaked in natural thermal baths at Octant Furnas—the perfect end to a day that felt like a fantasy.
Why You Should Go
Portugal and the Azores aren’t just destinations – they’re experiences that stir your soul. The people are warm, the food is unforgettable, the landscapes shift from romantic city streets to nature’s wildest wonders. You’ll fall in love with the rhythm, the richness, and the way this place makes you feel.
So if you’re looking for somewhere that combines history, food, natural beauty, and a little bit of magic… start planning. Portugal’s calling. And the Azores? They’re whispering secrets only the adventurous get to hear.
What We Loved About Portugal
- The Views: From the panoramic views at Pena Palace to the stunning coastline of Cascais, the scenery was breathtaking at every turn. Whether we were looking out over the Tagus River or wandering through lush gardens, Portugal has a way of making you feel like you’re surrounded by magic.
- The History & Culture: Portugal is a country with such rich history and culture, from its Moorish castles to Fado music, the unique art, and azulejos (tilework) everywhere you look.
Every corner felt like stepping back in time. - The People: The locals were so warm and friendly, eager to share their culture, history, and love for their beautiful country.
We were greeted with smiles wherever we went, and their hospitality made our trip even more special. - The Food: From Portuguese seafood to delicious vegetarian-friendly dishes, we were never short of incredible food to try. The sardines, bacalhau (salted codfish), and the array of fresh vegetables and cheeses were simply divine.
Until the next adventure… keep chasing the beauty. 
Mini Itinerary: Portugal + Azores in 9 Dreamy Days
Lisbon & Sintra (Days 1–5)
Day 1 – Arrival & First Bites
Arrive in Lisbon
Check in & freshen up
Dinner at Ramen House Aska
Dessert at Chocolateria San Ginés
Day 2 – Tuk-Tuk Tour & Lisbon Sights
Breakfast at hotel
Half-day Tuk Tuk tour through Lisbon:
- Lisbon Cathedral
- Alfama District
- Miradouros (viewpoints): Portas do Sol, Senhora do Monte, Sao Pedro de Alcantara
- National Pantheon & Flea Market
- Commerce Square
- Pasteis de Belém (iconic custard tarts)
- Jerónimos Monastery, Belem Tower & Monument to the Discoveries Estrela Gardens & Basilica
Lunch at Honest Greens, coffee at Honest Bean
Stroll through Pink Street & Green Street Dinner at Amaru (Peruvian)
Dessert: Manteigaria – Pastéis de Nata
Day 3 – Walking Tour & City Wanders
Breakfast at hotel
Guided walking tour of historic neighborhoods
Explore the castle & old town
Coffee break at Café de Forte
Lunch at Pastéis de Belém
Explore Belem & Commerce Square
Dinner at Lupita Pizzeria
Day 4 – Magical Sintra & Coastal Cascais
Full-day trip to Sintra & Cascais Pastries at Casa Piriquita Explore palaces & gardens
Lunch at Aqafarina (Cascais)
Bubble tea from Two Too
Day 5 – Ocean Wonders & City Vibes
Sleep in, enjoy brunch
Visit Oceanário de Lisboa – one of the world’s best aquariums Walking tour in the afternoon
Ride the Santa Justa Lift
Souvenir shopping at A Vida Portuguesa
Family massage at Thai Sensation Spa Dinner at Koppu Ramen Izakaya Chiado
Azores – São Miguel Island (Days 6–9)
Day 6 – Fly to São Miguel, Azores Lisbon → Ponta Delgada Check in to Octant Hotel Dinner at A Terra (on-site restaurant)
Day 7 – Explore Ponta Delgada Breakfast at hotel Walk downtown Coffee break at Intz48 Coffee Roasters
Dinner at Namaste India
Late-night drinks & dessert at hotel bar
Day 8 – West & North Side Road Trip Highlights:
- Ponte dos Regos
- Lagoa de Santiago & Lagoa do Canário
- Miradouro da Vista do Rei
- Varzea Cliffs & Mosteiros Village
- Termas da Ferraria (natural hot springs!)
Visit Pineapple Plantation Jardim Botânico António Borges Lunch at Jardim Natural Food & Coffee – SO good! North Coast: Ribeira Grande & cliffs
Hike to Salto do Cabrito waterfall
Drive to Fogo Volcano crater lake
Day 9 – Furnas & Farewell
Morning Islet of Azores Tour Explore Furnas area:
- Try volcanic-boiled eggs
- See traditional stew pits
- Waterfall hike
- Soak in hot springs at Octant Furnas
Lunch at Espinha.come (veggie burgers!) Dinner at hotel
Pack up for travel day