1

It is not a bit difficult. Chill.

I spent 4 nights in Sintra. Its an hour west of Libon by train. I shoulda stayed longer. These places unfold for us.

After Sintra, I took the bus to Cascais. Great ride.Pardon the expression, "Awsome!" You'll be glad you ain't drivin!
Drivers miss seeing much. Glances just don't cut it.

In Sintra, take the city bus to the Royal Castle. The foot path, in the park *not the road, to the high point is other worldly!

2

For four daysI would recommend Porto or Coimbra and Porto!

There are good express bus services and trains (when not one strike) to both from Lisbon.

You will need max 2 days in Coimbra.

Porto has it all! Culture, History, Port Wine, Boat Trips up the River Douro etc.

3

Coimbra is very pretty but not on the coast, so combine with Nazare. Obidos is small and can be easily seen in an afternoon. I get tired of reading the same information about Sintra – been there many times, it’s pretty and charming but is only a day trip from Lisbon the same for Cascais. You don’t indicate when you planning to go but if it’s before xmass I would agree Porto or Coimbra over the Algarve as the weather can be unpredictable.

4

I am going to be Lisbon in middle of November. Isn't it a rainy season in Porto in Nov/Dec? This is the reason why I want plan to head to Algarve after Lisbon.

gawkabout, How long is the bus ride between Sintra and Cascais? What is there to see on that route? I am currently planning to visit both places as day trip from Lisbon. Not sure if I should do it in one day or two.

5

Hi) this will really depend on your cultural -social life- gastronomic preferences.. But Porto + Douro Valley tour and wine tasting while staying in a palace / mansion (pousada) is incredible..
Lisbon in the best example of 'Old Europe' charm of course. You could stay in old city or in Cascais (Oitavos, Pousada de Cacais, Farol Design hotels) on a ocean side.. to be able to travel around to see amazing monuments
Surely city of Coimbra is extremely interesting too..Braga, Evora, Viseu, Portumao..
Ahh, so many!
Take a car and go along he coast line Lisbon - Algarve. Hidden gems. Amazing landscapes, food, historical sites.
good luck )

6

It's a 3 hour express train ride up to Porto and you could base yourself in the historic centre. There is a tram which takes you to the beach at Foz. From the train stations of Sao Bento and Campanha, you can head up to the Douro wine region. A good area is around the village of Pinhao on the Douro river (change trains at Regua). Best to go for a couple of nights. October is a beautiful time, with autumn colours and end of harvest. There are some nice B&Bs near Pinhao, catch a taxi- reasonable. Good walking country, authentic. For more info, this may help. http://www.hideawayportugal.com/modules/home/home.php

7

For four days, Porto would give you everything you're looking for without the need to change hotels. I love Porto and if you decide to go there, can give you a few more tips on where to go, depending on your interests and tastes.

However...the reason everyone goes on about Sintra is because it's stunning. I spent two days there and would go back in a heartbeat as there's still plenty I haven't seen, like Monserrate Palace and the recently opened Chalet da Candessa d'Edla. If you go, make sure to visit the Convento dos Capuchos - I walked and it's quite a hike from Sintra but you could take a taxi.

Coimbra is very pretty and although you won't need four days there, you can do day trips to the Roman ruins at Conimbriga or Bussaco National Forest, or catch the train to Figueira da Foz (and get the best ice cream sundae ever).

I live in Portugal and have blogged about many of the places I've mentioned, and others besides, here: http://juliedawnfox.com/blog-julie-dawn-fox-in-portugal/

Have fun!