Lisbon
Portugal's capital is a city that has a little bit of everything for everyone. Built across seven hills, Lisbon is steeped in centuries of history, from Moorish castles and ornate architecture to the iconic blue-and-white azulejo tile facades that line nearly every street. We even enjoyed learning how the slave trade started in Lisbon. But it doesn't feel like a city frozen in time. There's an electric energy here, a buzzing blend of old-world charm and modern culture, and the city is remarkably walkable.
We came for the history and stayed for the food. The seafood in Lisbon is some of the freshest you'll find anywhere in the world, grilled, salted, simply prepared and absolutely spectacular. And the wine? Portugal's variety will surprise you. We found ourselves returning glass after glass to the crisp, slightly effervescent Vinho Verde — the perfect companion to warm afternoons at a sidewalk café.
Often called the Hawaii of Europe and after visiting, we completely understand why. Just a short flight from Lisbon, Madeira feels like an entirely different world. Dramatic mountain peaks, lush volcanic valleys, and the deep blue Atlantic all converge to create some of the most breathtaking scenery we've encountered anywhere on the globe.
The island has its own rhythm. Days here are best spent exploring walking trails, savoring the island's unique cuisine, and soaking in ocean views that seem almost too perfect to be real. And you absolutely cannot leave without doing the iconic wicker toboggan ride launched down the hillside from Monte with skilled carreiros guiding the way. Followed by a scenic cable car ride back up the mountain. It's part thrill, part tradition, and entirely unforgettable.
Porto is already on our list and everything we've heard tells us it needs to be on yours too. Portugal's second city sits at the mouth of the Douro River and has a character all its own: gritty and gorgeous, raw and refined. The Ribeira waterfront district, the stacked wine cellars of Vila Nova de Gaia just across the river, and the legendary São Bento railway station with its stunning azulejo murals are the kind of sights that make you want to linger.
Head inland from Porto and you'll find yourself in the Douro Valley, one of the world's oldest demarcated wine regions and a UNESCO World Heritage Site. The landscape is extraordinary: mile after mile of terraced vineyards carved into steep hillsides that cascade down to the river below. This is the birthplace of Port wine, and river cruises through the valley have become one of Portugal's most coveted travel experiences.
Getting to Portugal from the US is easier than you might think — and once you land, navigating between Lisbon, Madeira, and Porto is straightforward with a mix of flights and trains.
Lisbon's Humberto Delgado Airport is your primary gateway. Several major carriers offer nonstop transatlantic service, including TAP Air Portugal, United, and Delta. Nonstop flight times from the East Coast run roughly 7–8 hours, making it one of the shorter European hauls. Midwest travelers (hello, Chicago!) typically connect through New York, Philadelphia, or a European hub. Total travel time around 11–13 hours.
Also consider: Porto's Francisco Sá Carneiro Airport (OPO) for direct access to northern Portugal.
Madeira is easily reached by a quick flight from Lisbon, typically around 1.5 hours. TAP Air Portugal operates frequent daily service between the two, and the island's Cristiano Ronaldo International Airport (FNC) is well connected. We recommend building in at least 3–4 nights in Madeira; it earns the time.
Traveling between Lisbon and Porto by train is one of the great European rail experiences. Alfa Pendular high-speed trains connect the two cities in under 3 hours, offering comfortable seating and beautiful countryside views along the way. Trains depart frequently throughout the day from Lisbon's Santa Apolónia or Oriente stations.