Lisbon is one of our favorite places, a romantic city full of charm and color. We love getting lost in its cobblestone streets, discovering hidden viewpoints, and exploring neighborhoods like Príncipe Real, Alfama, and Bairro Alto. A few foodie musts: grab a pastel de nata at Manteigaria or Pastéis de Belém, fresh seafood at Ramiro, a traditional Portuguese meal at Pica Pau, and don’t miss As Bifanas do Afonso. For a more contemporary take on Portuguese food with small plates, try Tricky's or Bar Alimentar. James also loves the original Time Out Market where you can find Lisbon's greatest hits. Getting around is easy with Bolt or Uber, but a friendly warning, Lisbon is very hilly, so be ready to climb as every hill leads to an incredible view, like at the city’s famous miradouros. For a classic experience, hop on the historic 28 tram and see the city from a unique perspective. Lisbon is magical, vibrant, and a place we always love to return to.
Sesimbra is a picturesque seaside town with golden beaches and stunning views at the edge of Arrábida Natural Park, a protected area with dramatic cliffs, lush vegetation, and crystal clear waters. For outdoor adventure, the Ribeira do Cavalo Beach Trail is a must, leading to the wild and beautiful Ribeira do Cavalo beach. A short drive from town is Cabo Espichel, where you can see over 600 fossilized dinosaur footprints from herbivorous and carnivorous species dating back 129 million years, set against breathtaking coastal cliffs. Nearby, the Sesimbra Castle, perched above the town, offers panoramic views of the ocean and surrounding hills and is a perfect spot to explore history while taking in the scenery.
Katie's sister’s home and one of her favorite places. Just under an hour from Lisbon, this coastal town is a World Surfing Reserve with amazing waves, beautiful beaches, and a relaxed vibe. Our favorite places to stay are Aethos or Immerso. For food and drinks, we love Mar das Latas, Costa Fria, La Popular, Terço do Meio for sourdough and pastries, Ippolito and Maciste for drinks, and Magic Quiver for matcha or iced coffee. For beaches, check out Praia de Ribeira d’Ilhas, Praia da Foz do Lizandro, and Praia de São Julião.
One of James’ favorite places in Portugal. The Douro Valley is known for its dramatic terraced vineyards that stretch along the Douro River, creating some of the most breathtaking scenery in the country. It’s the heart of Portugal’s port wine production and the perfect spot to spend a day wine tasting, taking a scenic river cruise, or enjoying a long lunch with vineyard views. Peaceful, picturesque, and unforgettable, it’s a must-see.
Another one of James’ favorite places in Portugal. Nestled in the hills just outside Lisbon, Sintra feels like a fairytale with its colorful palaces, misty forests, and historic castles. Wandering its charming streets, exploring the ornate Pena Palace, or strolling through the lush gardens of Quinta da Regaleira makes you feel like you’ve stepped into another world. It’s magical, romantic, and impossible not to fall in love with.
One of Katie’s favorite places in Portugal. It truly feels like stepping onto a movie set. The property is stunning, surrounded by incredible vineyards, olive groves, and sweeping Alentejo landscapes. Just nearby is the charming medieval hilltop town of Monsaraz, with cobblestone streets and beautiful views over the countryside. The Alentejo region is incredibly special and known for its wine, food, and slower pace of life, making it well worth the trip. Don’t miss a visit to Herdade do Esporão Restaurant for a memorable meal and local wine tasting.