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

Nature
The wow factor for nature - does it show nature at its best? Doesn't need to be the wildebeest migration or diving with hundreds of hammerheads. Rather make you pause as you realise just how awesome the natural world can be
7
Culture
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
8
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
5
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 local market
3
World famous
How world famous is the experience?
7
unique
How hard is it to have a similar experience in other places round the world?
6
Overall TE Score
The overall travel experiences score:  fun factor + avoid the crowds + (best of nature or culture) + (best of world famous or unique). Then convert into a score out of 100
57 *What the scores mean and where do they come from
RANKING
How this travel experience ranks compared to all the other experiences on this site, based on the travel experience (te) score
314th/457
Top 70%
continent
Europe
country
Portugal
Length of time
3-4 days
Typical daily price
This gives you a rough idea of the daily price based on 2 people travelling where they can split costs like accommodation. It excludes travel there and back, and factors in inflation the numbers in brackets show the price range for the full time of the experience (so not necessarily daily). It is a range to reflect different budget vs higher end
$150 (typically $80 - $220)
Time of year visited
August
Primary Tags
Click on any of the tags to see all travel experiences with the same tag
Beach promenade Castles / Fortresses Old town
All Tags
Beaches Big city Caves Christian site City Walls Cool neighbourhoods Forests Gardens Hilltop towns Local villages Restaurant recommendations Rooftop Bars Sunsets UNESCO world heritage site Unusual hotel
Wow Factor
Two scores: first is the wow factor which ranges from ⭐️ ⭐️ ⭐️ ⭐️ ⭐️ to ⭐️, and a separate category for the truly "gash". The second is the more analytical travel experience score, which considers 6 varied criteria to give an overall score out of 100.
⭐⭐⭐

Summary

Lisbon is a supremely elegant city steeped in history and with atmospheric neighbourhoods to head off to and explore.  But, I actually found the two surrounding places of Sintra and Cascais (30 mins and 1 hour by train) to be the real gems of the visit.

 

I’ve written a bunch of travel tips for Lisbon and the surrounding areas below, but my #1 tip is to stay 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).  My favourite, most magical times of the trip were early morning in Sintra having the fairy tale-like streets all to myself and early evening beach sunsets in Cascais once the day trippers had left back to Lisbon.  Plus, the trains / Ubers make it so simple to pop between the 3 of them.  Be bold and stay outside of Lisbon for the better experience.

 

Lisbon - the Moor Castle views from a Sintra Visit

The fairy-tale style Moor Castle sitting on the hills surrounding Sintra, 30mins from Lisbon

 

My Top 9 Experiences from a visit to Lisbon

#1 Wandering around the otherworldly and magical gardens in the forested hills of Sintra, in this case the Quinta de Regaleira

#1 Wandering around the otherworldly and magical gardens in the forested hills of Sintra, in this case the Quinta de Regaleira

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

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

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

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

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

#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 atmospheric Alfama area of Lisbon

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

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

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

#7 Soaking up some of the numerous grand architecture spots in the central Baixa and Rossio areas of Lisbon

#7 Soaking up some of the numerous grand architecture spots in the central Baixa and Rossio areas of Lisbon

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

#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

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

Tips for 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.

 

The blue and white tiles that appear just about everywhere throughout Lisbon

The blue and white tiles that appear just about everywhere throughout Lisbon

 

Be sure to make the walk up to the Castelo de Sao Jorge

The grounds are fab, nice coffee / drinks areas and I thought had the best views in Lisbon.

 

Tips for Sintra

 

Sintra does at times really feel like something out of a fairy tale

When you get off the 30min 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, but bring extra layers for the winter.

 

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.

 

Lisbon - Quinta de Regaleira's unique inverted tower (Poco Iniciatico) by Sintra

Quinta de Regaleira’s unique inverted tower (Poco Iniciatico)

 

Early is magical

Try if you can to walk around the town early in the morning (730ish, especially if you’re staying in Sintra).  I did and had it all to myself – couldn’t believe how few people were there.  One of my highlights of the whole trip.

 

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).

 

Lisbon - I'd recommend staying at the magical Chalet Saudade in Sintra

I’d recommend staying at the magical Chalet Saudade in Sintra

Tips for Cascais

 

Where to focus

It’s nice walking around the narrow lanes around around the centre and just between Ribeira and Rainha beaches.

 

Hotel Albatroz

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 sun-downer.

 

Sundowners a little further east from the main Cascais Beach area, just outside of Lisbon

Sundowners a little further east from the main Cascais Beach area

 

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.

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.

 

The magical beach that is in the inlet round the back of the Museu Condes de Castro Guimaraes, Cascais near Lisbon

The magical beach inlet behind the Museu Condes de Castro Guimaraes in Cascais

 

Further Portugal Tips

 

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, including the fantastic trip to Wine tasting around Pinhao in the Duoro Valley.

 

Experiences Nearby

Wow Factor Score Two scores: first is the wow factor which ranges from ⭐️ ⭐️ ⭐️ ⭐️ ⭐️ to ⭐️, and a separate category for the truly "gash". The second is the more analytical travel experience score, which considers 6 varied criteria to give an overall score out of 100. LowHigh
  • Elite, unmissable
  • World-class, downsides
  • Meets the Wow Factor
  • Worth it
  • Meh
  • Gash

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Score Detail

The scores above are the real point of this site.

Over 20+ years and 100+ countries, I’ve tried to rank the world’s best travel experiences - from genuinely mind-blowing ⭐⭐⭐⭐⭐ to the properly gash.

Every one of the 500+ places on this site has both a Wow Factor rating and a more analytical Travel Experience (TE) score based on the things that actually make travel memorable.

If you're curious about the thinking behind it, head to the About page.

Otherwise, explore the map above or on the Home page and see which places truly deliver maximum wow.

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