Lisbon: Three Days in the City of Art and Views

I've been to Lisbon twice now, and still, every time I start thinking about taking another trip, I think, Lisbon, again? There's always that internal battle between returning to a place you know you love and the adventurer's pull to go someplace new.

I'll take a third trip to Lisbon soon. I know I will. There are still too many bougainvillea-filled views left unseen and too many laid-back, peaceful days under the warm Portuguese sun still waiting for me.

I once described Lisbon to a friend as a city full of art and views. It really is that simple.

The artistic personality of Lisbon is everywhere. Building facades are bright, colorful, and covered in elaborate tilework - azulejos in Portuguese. You can buy these tiles all over the city, some hand-painted and others mass-produced for tourists, but the azulejos that cover Lisbon's buildings are something special. Street art abounds, and you're likely to hear music being played on the streets at nearly all hours and in all corners.

And then there are the views.

On my first trip, I remember feeling like every direction I turned revealed another, each more stunning than the last. It probably helps that Lisbon is built on seven hills. There are so many hills - and so many views - that some of the city's most iconic landmarks are its miradouros, or viewpoints.

But the miradouros are more than places to take a picture. They're gathering spots where friends meet and mingle, vendors sell their wares, and musicians play for passersby. Some have full cafes and bars, while others are quieter and more peaceful. But every one has what you came for: a jaw-dropping view over Lisbon's terracotta rooftops and colorful facades, stretching all the way to the sun-drenched waters of the Tagus River.

Arrival Day - Baixa, Chiado & Your First Miradouro

For a first trip to Lisbon, I recommend staying in either Baixa or Chiado if you want to be right in the thick of things. If you prefer something a little quieter - and enjoy high-end shopping - Avenida da Liberdade is another great option. All three put you within easy reach of Lisbon's main attractions while still giving you plenty of atmosphere.

I've stayed twice at Hotel da Baixa, a luxury boutique hotel in Baixa, Lisbon's historic center, and I highly recommend both the hotel and the neighborhood.

Like I always suggest, one of the best things to do on arrival day is simply walk. Drop your bags, get your bearings, and start experiencing the rhythm of the city. Lisbon is especially good for this, and Baixa gives you an easy route past several iconic sights without committing you to much of anything.

Start with the Santa Justa Lift, an elaborate neo-Gothic iron elevator that has been carrying people between Baixa and Chiado since the turn of the 20th century. Remember those seven hills I mentioned? Over the years, Lisbon has come up with all sorts of ways to navigate them - elevators, funiculars, and, of course, those famous yellow trams.

From there, wander toward the waterfront. Many of the streets through Baixa are pedestrian-friendly, and eventually spill out into Praca do Comercio, Lisbon's grand riverfront square.

There always seems to be something happening here. Festivals and events regularly take over the square, but even on an ordinary day you'll find street performers, artists, vendors, and plenty of people milling around. Grab a seat at one of the surrounding cafes, do a little people-watching, and take in the Tagus. Or, if you're already ready for another view, head to the top of the Rua Augusta Arch for a sweeping look over Baixa and the river.

Before calling it a day, I recommend visiting at least one miradouro. For this route, make it Miradouro de Sao Pedro de Alcantara.

On the way, pass through the ruins of Carmo Convent, a Gothic church destroyed in Lisbon's devastating 1755 earthquake. Much of it was never rebuilt, and its roofless stone arches still stand open to the sky today.

Then continue to the miradouro. Sao Pedro de Alcantara has an incredible view across Lisbon toward Castelo de Sao Jorge, but this is one of the livelier viewpoints, too. Grab a drink and a snack from one of the kiosks and find a place to sit.

Watching Lisbon go by over a glass of wine, with the city spread out below you, absolutely must become one of your go-to activities while you're here.

Day Two - From Alfama to Belem

A Slow Morning in Alfama

On day two, head to Alfama, Lisbon's oldest and most traditional neighborhood, with Castelo de Sao Jorge as your first destination.

I recommend going to the castle early to beat the crowds - but don't make the mistake of treating everything between you and the castle as something to rush past. Alfama deserves to be enjoyed slowly.

The walk up can easily take an hour, especially if you stop at Miradouro de Santa Luzia along the way - and I think you should. It's my favorite miradouro in Lisbon, with all the tiled walls, bougainvillea, and sweeping views that make this part of the city feel impossibly picturesque.

At the top, Castelo de Sao Jorge rewards you with what I think are some of the best views in Lisbon. Take your time. Take your photos. And keep an eye out for the peacocks wandering around the grounds - and up in the trees. On one of my visits, there were even babies.

There's a small cafe and gift shop inside the castle, fine for a drink and a quick browse, but save lunch and the real shopping for outside the castle walls.

Then start making your way back down through Alfama.

There are plenty of sights worth stopping for along the way, including Se de Lisboa, Lisbon's oldest cathedral, and the ruins of the ancient Roman Theatre. But more than the castle, the cathedral, the ruins, or even the miradouros, Alfama itself is the attraction.

Slow down.

Look up at the colorful, azulejo-covered facades. Wander down a street simply because it looks interesting. Pop into the little local shops and cafes. Wait for one of those famous yellow trams to rumble past.

On both of my trips to Lisbon, I stopped at a small ceramics shop called By Nunes for handmade, painted pottery. I bought myself a hand-painted tile and little jewelry dishes for my daughters. We stopped for gelato. We waited until just the right moment for a yellow tram to pass behind us so we could snap a picture.

We soaked in the views, the color, and the atmosphere that only Alfama can give you.

If there's one piece of advice I can give you for a morning in Alfama, it's this: slow down.

An Afternoon in Belem

In the afternoon, head to Belem, a historic riverfront neighborhood just outside Lisbon's center with plenty to see - and home to the most delicious and iconic treat of your trip: Pasteis de Belem.

There are several ways to get there. I've taken the train once and Ubered once, but you could also walk along the riverfront or even rent scooters. It's about three miles from Cais do Sodre to Belem, and you'll do plenty more walking once you arrive, so I'd only walk if you're really up for it and have the time.

The point is, Belem isn't far away, but it feels entirely separate from the energy of central Lisbon.

First things first: go immediately to Pasteis de Belem, the famous bakery that has been turning out warm, eggy, flaky pasteis de nata for nearly two centuries.

As you approach, you'll probably smell them before you see them. Then you'll know for sure you've arrived when you spot the line of hungry visitors snaking out of the building and onto the street.

I have an important tip for you:

Do not wait in that line.

Instead, head to the carryout entrance next door. Standing in front of the bakery and looking directly at it, you'll see the huge line to the right. Go to the entrance on the left. There may be almost no line at all, and you'll think, This cannot possibly be right.

It is.

Go inside, order at the counter, and within a few minutes you'll be walking away with a box of warm pastries in hand. Find somewhere nearby to sit, sprinkle on a little cinnamon and powdered sugar, and enjoy. Everyone else will still be waiting in line.

Once you've had your pastel de nata - and yes, you need to have one - start exploring Belem.

The Jeronimos Monastery and Monument to the Discoveries are two of the neighborhood's major landmarks. So far, both have only been outside stops for me, but you can absolutely buy tickets and explore further if you have the time and interest.

There are a number of museums here, too. I've visited the National Coach Museum, which houses a magnificent collection of ornate royal carriages dating from the 16th through 19th centuries. It's smaller and perhaps less obvious than some of Belem's better-known attractions, but I really enjoyed it.

Then make your way toward my favorite spot in Belem.

Walk along the river, past boats sailing on the Tagus and others bobbing in the marinas, until eventually you reach Belem Tower.

The first time I saw it, I was genuinely struck by how strange yet beautiful it looked sitting there in the water. Completed in the early 16th century, the limestone tower rises out of the Tagus like something from another time - which, of course, it is.

Maybe this is my American perspective showing, but I'm just not used to standing in front of things that old and enduring.

One of my slightly sarcastic lines whenever I'm in Europe is, "We just don't build things like this anymore!"

But what I really mean is that we don't often value that level of detail and ornament in modern architecture. We're much more function over form these days, and while I understand the utility, there is something marvelous about standing in front of a building created centuries ago with that much beauty simply built into it.

Belem Tower began as part of Portugal's coastal defenses and was later used as a prison. Today, you can buy a ticket to go inside and climb the tower, or simply admire it from the outside. Either way, expect crowds - and go anyway.

Then head back toward central Lisbon for the evening. Have seafood by the water or catch a Fado show. Wander through the shops of Baixa. Buy your souvenirs. Get some gelato - or, honestly, another pastel de nata.

And enjoy Lisbon as the sun sets on a long but very satisfying day.

Day Three - A Fairytale Day in Sintra

Save your final day for a trip to the storybook village of Sintra.

You can certainly get to Sintra on your own, but having done this twice, I recommend taking a guided tour. The lines can be long, the hills are steep, and the major sights are spread out. Having someone drive you between them and help navigate the entrances makes the day much easier. Plus, there's always so much to learn from a local guide.

I've taken two different tours, and both were great.

One went straight to Sintra, where we visited Quinta da Regaleira and Pena Palace, with time in between for lunch and exploring the town on our own. The other was a longer day that also included stops in the seaside town of Cascais and at Cabo da Roca, the dramatic cliffs at the westernmost point of continental Europe.

Both stops added even more incredible views to our Lisbon trip - but also about two hours to an already full day. Decide how much you're up for and choose your tour accordingly.

No matter how you get there, though, arriving in Sintra feels a little like stepping into a fairytale.

The town itself is charming, with narrow streets lined by local shops and brightly colored facades. But then you look up.

Perched among the lush mountaintops are castles and palaces that seem almost too fantastical to be real: the ancient Moorish Castle, Sintra National Palace, Monserrate Palace, Quinta da Regaleira, and, looming brightly above it all, the wildly colorful Pena Palace.

You cannot see them all in one day - and I wouldn't try.

Most tours will take you to two, possibly three. For me, Quinta da Regaleira is unmissable, so I'd choose that and then whichever other palace most appeals to you.

Quinta da Regaleira

You'll spend about two hours exploring Regaleira, and although it isn't one of the oldest places you'll visit around Lisbon, it might be one of the most unforgettable.

The estate belonged to an extremely wealthy - and apparently rather eccentric - man, and the Gothic mansion is only the beginning. Its sprawling gardens are filled with fountains, grottoes, lakes, towers, statues, hidden passages, and all sorts of unexpected details.

And then there's the Initiation Well.

I've tried to think of a good way to describe it, and I really can't do it justice. A spiraling stone staircase descends deep into the earth, surrounded by moss-covered walls, arches, and tunnels. It feels mysterious and slightly surreal and unlike anything I'd ever seen before.

Do yourself a favor and look it up.

Yeah, I have that picture on my iPhone. You should get it, too.

And remember all those views I keep talking about? You'll get more of them here, looking out over the lush Sintra hills all the way toward the Atlantic.

Pena Palace

Pena Palace is peculiar in an entirely different way.

I've certainly never seen a palace brighter or bolder than this one. With its vivid red and yellow exterior sitting high above Sintra, you can spot it from miles away.

The site has a history stretching back centuries, from a small medieval chapel to a monastery and, eventually, the extravagant palace you see today. By the 19th century, it had been transformed into the wonderfully ostentatious place it is now.

And it is a lot.

Color. Towers. Tilework. Arches. Views. Royal stories of love and betrayal. There is nothing restrained about Pena Palace, which is precisely what makes it so much fun to see.

Whichever palaces you choose, Sintra is a must on a trip to Lisbon.

You really do feel like you've stepped into a fairytale.

Leaving Lisbon

My first trip to Lisbon lasted three days, and it ended here.

Day one was spent getting acquainted with Baixa and Chiado. Day two took me from the hills of Alfama to the waterfront in Belem. And on day three, I escaped to the fairytale palaces of Sintra.

The next morning, I flew home.

But on my second trip to Lisbon, this time with my daughters, we had a fourth day before heading south to the beaches of the Algarve. And we spent it creating our own special kind of Portuguese art and views.

I hired a local photographer to spend a few hours with us, following us through the colorful streets of Alfama and eventually down to Praca do Comercio, taking photos along the way.

We walked the tiled streets. We stopped in front of colorful facades. We found those incredible Lisbon views. And somewhere in the middle of all of it, she captured us.

What came out of that afternoon were the most colorful, joyous photos of my daughters and me - our own little Portuguese works of art.

I have brought home plenty of souvenirs from my travels. Tiles. Ceramics. Jewelry. Things I've carefully wrapped and tucked into suitcases to remind me of where I've been.

But those photos are still my favorite souvenir I've ever brought home from a trip.

Maybe that's part of what keeps pulling me back to Lisbon. There will always be another tiled facade I haven't noticed, another miradouro I haven't climbed to, another view over those terracotta rooftops I haven't seen.

Another little piece of art waiting for me.

Go to Lisbon. Enjoy the art. Enjoy the views. Take some home.