A long weekend for Lisbon and the surrounding gems of Sintra and Cascais

The wow factor for nature - does it show nature at its best? Doesn't need to be the wilder-beast migration or diving with hundreds of hammerheads. Rather make you pause as you realise just how awesome the natural world can be
How much does this experience showcase some of the better and finer things that us humans can offer? Sure, it can be ancient ruins and renaissance churches, but it can also be festivals or soaking up some of the great modern cities of the world
Fun factor/activity
Very simple - was it fun? This is usually linked in with doing some kind of activity - i mean, walking along some cliffs is nice, but paragliding from them, now that is fun. Its a vastly underrated factor in a truly great experience
Avoid the crowds
Big tour groups and being surrounded by loud fellow tourists can sap the life out of even the greatest of travel experiences. This score is to reflect just how much you can avoid this. But. . . The score also takes into account if the crowds actually add to the experience, such as with a party town or a bustling food market
World famous
How world famous is the experience?
How hard is it to have a similar experience in other places round the world?
Overall Score
The highest score of nature or culture, + fun factor, + avoid the crowds, + the highest score of world famous or unique. Then turned into a score out of 100. More details at the bottom of the page
57 *What the scores mean and where do they come from
Length of time
3-4 days
Rough cost
Obviously people have different tastes, so this will depend on those tastes, but this is a rough idea of price of the whole experience based on 2 people able to split the accommodation costs and excluding travel there and back
$ 425
Time of year visited
Primary Tags
Click on any of the tags to see all travel experiences with the same tag
How this travel experience ranks compared to all the other experiences on this site
244th/372 This travel experience's ranking compared to all the other experiences on this site
Top 70% SUMMARY RATING: Worth doing


Lisbon is a supremely elegant city stepped in history and with atmospheric neighbourhoods to head off and explore, but I actually found the two surrounding places of Sintra and Cascais to be the real gems of the visit

I would suggest staying in Sintra or Cascais rather than Lisbon. Staying in Lisbon you are always going to be surrounded by fellow tourists, day or night.  Whereas places like Sintra and Cascais offer a very different experience when the crowds have left for the day (or before they arrive if you’re an early bird). And the trains / Ubers make it so simple to pop between the 3 of them. I had some magical times in the likes of Sintra wandering around in the early morning having the place to myself, and enjoying the quieter evenings in Cascais.  Be bold and stay outside of Lisbon for the better experience


#1 Wandering around the otherworldly and magical gardens in the forested hills of Sintra

#2 Looking over Lisbon with great views from the grounds of the Castelo de Sao Jorge

#3 Getting lost in the gorgeous cobbled street and seafront spots of Cascais

#4 Descending the rather mysterious steps of the inverted Tower Poco Iniciatico in the Quinta de Regaleira in Sintra

#5 Exploring the narrow alleyways and hidden restaurants of the Alfama area of Lisbon

#6 Walking along the walls of the Moor Castle that provides 360 views of Sintra and Lisbon below

#7 Seeing some of the grander architecture in the Baixa and Rossio areas of Lisbon

#8 Heading deeper into the caves in the grounds of Quinta de Regaleira in Sintra

#9 Having a sundowner overlooking the beaches from the elegant Albatroz Hotel in Cascais

Rough itinerary

Basically try to spend a day in each of Lisbon, Sintra and Cascais, but base yourself in Sintra or Cascais rather than Lisbon

Travel Tips

  • Sintra:
    • Sintra does at times really feel like something out of a fairy tale and, when you get off the train, you’ll notice an immediate different feel to Lisbon. For one – it’s a lot cooler as its up in the hills! Which is a nice change in the summer
    • The two highlights – there are plenty of places to go off and explore, but the two highlights for me were the Quinta de Regaleira with its inverted tower (Poco Iniciatico) and stunning grounds, and the Moor Castle which gives wonderful views of all around.  For Quinta de Regaleira make sure to get there early and head straight for the inverted tower to avoid the later queues – we got there right at the opening and had a few wonderful few minutes of it totally to ourselves – although watch out for the wet floor as it’s very easy to fall arse over tit! Also make sure to investigate a lot of the small entrances to the hidden caves – you’ll be surprised how far they go and what you’ll find
    • Try if you can to walk around the town early in the morning (730ish). I did and had it all to myself – couldn’t believe how few people were up
    • Where to stay – we stayed in the Chalet Saudade which felt like being in a fairy tale and I would highly recommend (especially if you can get the room on the 1st floor with the balcony)


  • For Cascais:
    • It’s nice walking around the narrow lanes around around the centre and just between Ribeira and Rainha beaches
    • Be sure to have a drink or afternoon tea in the wonderfully located Hotel Albatroz. It has great views over the nearby main beaches and is in the heart of the beautiful narrow lanes that make Cascais so lovely
    • If Hotel Albatroz is full, or if you just fancy more drinking locations, the Villa Cascais has a great balcony overlooking the other main part of town and is a good spot for a sundowner
    • For a less traditional, but far cuter, beach – make sure you head to the beach that is in the inlet round the back of the Museu Condes de Castro Guimaraes. Easy to find when you get there, it has an almost picture perfect setting behind the bridge and the mini castle with plenty of people jumping off the bridge into the cool clear water
    • Great walk – there is a boardwalk that follows the coastline around 5kms to the east of town. Worth a wander as there are some nice restaurants along the way


  • Lisbon:
    • Don’t take the tram – you’ll read most of the guidebooks talking about taking the Tram 28E for an authentic tour around the key sites and neighbourhoods of Lisbon.  Yes the route is great, but on a busy day the queues to get on it are long and you’re then crammed in for a not particularly fun experience.  Instead, just get one of the electric tuk tuks.  It’s a little more expensive (€40-50) for the hour, but you get to choose your route (they’ll take you to better viewing points and drop you off where is most convenient), you get a guide, no time waiting at tram stops and you can have a better view as you go round.  If in a group it’s a no brainier
    • Alfama, Graca and the Castle – the Baixa and Rossio areas have the grand buildings (make sure to check out the train station which I thought was beautiful), but the highlight is the white cobbled narrow streets around Alfama, Graca and the castle.  They really are super pretty
    • Be sure to make the walk up to the Castelo de Sao Jorge.  The grounds are really nice and the views I thought were the best in Lisbon


  • The trains between Sintra, Cascais and Lisbon run regularly and take around only 30mins Lisbon to Cascais / Sintra and an hour between Sintra and Cascais
  • For further tips on Portugal’s other top experiences, and for a 2 week itinerary, see the travel entry for 2 weeks for the best of Portugal

Experiences nearby

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Score Detail

Background - how many times have you asked someone what a travel experience was like and the response was "amazing" or "awesome"?  That response is nice to know, but it makes it hard to differentiate that experience compared to others.  That is exactly what these scores are trying to do - differentiate the experience by giving a score out of 10 based on 6 categories and then giving an overall experience score

This overall experience score is calculated by:  take the highest of the "Culture" or "Nature" score (1-10) + "Fun factor" (1-10) + "Avoiding the crowds" (1-10) + highest of the "Unique" or "World Famous score" (1-10).  Then convert into a score out of 100

Extra detail - the logic being that I find all of the 6 individual scores important, but I don't want to mark an experience down just because it doesn't cover both "Culture" and "Nature", or because it isn't both "World Famous" and "Unique".  Take the examples of Safari in The Serengeti and walking through Rome - they both appeal at opposite ends of the nature / culture spectrum, and you can have a fantastic time without needing to appeal to both sides.  So, their overall scores aren't penalized for their lack of one or the other, and I've done the same for "World Famous" vs "Unique".  But . . . I do think that the "Fun factor" of an experience is important, irrelevant of other factors, and so is "Avoiding the Crowds" (or where there are crowds that add to the experience).  So, both of these scores are standalone