lisbonrooftops

From the heavenly floral bouquet of blooming Jacaranda trees to fresh salty sea breeze, there’s nothing like actually getting to Lisbon in person and finally experiencing the beauty of this ancient capital city in person with all your senses. Instagram might have pointed out its loveliness, but being there in person, eating the food, seeing the bright colors, and talking to the friendly locals will all wish you stayed longer.

This June, my family of five finally made it to Portugal. We’ve talked about going for years, as my husband’s great grandmother and her whole family trace back generations there. We wanted to experience everything, though we only had eight days to spend, including our flight out. That meant I had to do a ton of research ahead of time to make the most of our first trip there. We knew we’d be back, but we wanted to get a good overview and first taste, if you will. What follows is my advice for a great week or so in the Lisbon area, plus what I really wish we did. (Yes, I do wish the trip was longer. Even just one more day.) A fellow Portugal Redditor asked me for this advice, so hope it helps him and you too!

Day 1: Lisbon’s Chiado/City Center

I have a very detailed first day itinerary already outlined here, from the minute you land, what to expect in customs, how to get into the city center to your hotel plus what to do on your walking trip once you drop your bags off at your hotel.

What to do in Lisbon After You Land Before Hotel Check-in

I think this might possibly the most asked question in the Portugal Reddit boards. I’ve answered it countless times for my fellow travelers excited for their upcoming journeys. So I thought I’d share my hot tips here too. You can apply the gist of this advice to any travel, anywhere if you’re staying at a…

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Day 2: Sintra

Day two, you know you’ll be up early as a result of time zone adjustment, so maximize that by heading to Sintra. If you arrive on a Sunday, then move Sintra to another day of your trip, as you don’t want to be here Monday when a lot of people “think” they’re being smart heading here when lots of other things are closed in Lisbon. But that’s exactly why you don’t want to go to Sintra then, unless it is your only option. Also, avoid the weekends. That means premium days to plan for Sintra are Tuesdays, Wednesdays and Thursdays. We did Pena Palace and gardens first thing, hike down to town, followed by lunch in the historic center, then a full afternoon at Quinta da Regaleira. It was a great plan and I’d repeat what we did exactly because it turned out well. Read more in this post with everything you need to know about planning your Sintra day trip:

Day 3: Cascais

We did a full day in Cascais. If we had two more days in Portugal, one of those would go to spending the night here. What we did on our daytrip this summer was good and so relaxing. After taking the train over (it’s cheap and easy!). Once in town, we did a 2-hour bike ride, visit to Boca do Inferno, walk around the city center, relax/explore at two beaches and the sea, plus lunch and dinner. What I would add with another day would be more beach time, more shopping time, a longer bike ride adding on Estoril, visits to both the lighthouse and the Museu Condes de Castro Guimarães. So yeah, you could do much longer than two nights here too. Cascais can be done any day, really. So you can move it around to fix the other things in your schedule accordingly. We hit it on a Friday, which I’d definitely do again. Read my detailed guide to one day in Cascais here.

Daytripping Guide to Cascais, Portugal

I’m smitten. The azure sea, golden sands, views equal in loveliness with the the people, and incredibly easy commute to and from Lisbon all make Cascais a “must visit” in Portugal. First, let me just say, if you can spend even one night in Cascais, do it! We didn’t and I really wish we would…

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Day 4: Lisbon’s Alfama

Alfama is classic Lisbon. It survived the famed earthquake that you can’t help but learn about on your visit. In that way, you feel the history here in ways you don’t necessarily get in other areas. It’s also your gateway to Castelo de São Jorge. To me Alfama is all about the beauty of the views. There are murals, street art, azulejos and mirodouros a plenty. Read more detailed suggestions for a self-guided walking tour of how to spend this day here.

DIY Walking Guide in Lisbon’s Famed Alfama

Crimson tile roofs juxtaposed with bright blue of the river Tagus, framed by the purple paradise of jacarandas and magenta bougainvilleas, all accented with blue and white azulejos. It’s hard to believe the views from Lisbon’s miradouras are real when you see them with your own eyes, no Instagram filters, no editing. They’re really just…

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Day 5 & 6: Sesimbra

Sesimbra will likely be the least crowded place you visit. This is due to not being on a train route. You can get here on a bus. But it’s faster and pretty cheap to get here by Bolt (or Uber). It’s about 40 minutes from Lisbon’s downtown to Sesimbra. This is a place we stayed one night (at the 4 Points) but I’d plan two nights the next time. If I only had one extra day to add to our Lisbon trip, I would have added it here in retrospect! We picked this spot specifically to snorkel and take a small local-led boat ride. But it turned out to be SO much more than that. You’ve got a long beautiful beach connected to more beach. You’ve got historical boat rides, a free castle, and great food. I detail it all here.

5 Reasons Sesimbra is a MUST-VISIT in Portugal

In the foothills of the Serra da Arrábida along the azure Atlantic Ocean in what’s known as the Setúbal district, you’ll find what amounts to a hidden treasure of Portugal: Sesimbra. It is so very worth your while to bother going to this quaint fishing village meets relaxing beach town. Yes, it’s not on the…

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Day 7 & 8: Back to Lisbon

Now what else you want to do in Lisbon on these last days comes down to your tastes, hobbies and interests. We did the day in Belém, visiting the maritime museum, which turned out to be all three of my teenagers’ favorite museum of the trip (and one they’re still talking about). It was so cool – with not only history of the spice trade and how Portugal basically changed the whole world (for good and bad). But there are also real GIANT boats. Lots of them! There’s a whole hangar to explore after you go thru some cool models and history lessons.

Of course, you’ve also got the Monument to the Discoveries (only need to view from the outside, but there is a museum inside), Belém Tower (when it reopens), the Jeronimos Monastery and the crown jewel: the birthplace of pastel de natas: Pasteis de Belém. We did lunch at Pasteis and would do it again. It’s bustling but good. Try more than the pastel de natas here. And that’s just the tip of the iceberg. There’s so much other stuff in Belém, including gardens and a really cool art museum (which I plan to go to next time).

I immediately started planning for my next visit on the flight back. I’m lucky to know that would be happening for sure, as I’m going to lead a study abroad in Lisbon in May that will put me back in this beautiful city for a month. I can’t wait. Have tips for what me or others should add to this list (there’s so much, I know), leave a comment here or Insta or send us a DM on Instagram.

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