Lisbon - October 5 days

Only specific advice I can offer is to not completely ignore some things that are popular with tourists. Around Lisbon, although now very popular with tourists, I still think Sintra is delightful and worthwhile. You can emphasize the active/outdoor parts, walk up to the Moorish Castle, walk the ramparts (very extensive, and a great hike of its own) and surrounding grounds -- you'll get plenty of "vertical gain" and will enjoy some of the best views in all of Europe. It's an amazing place, don't miss it. Bonus: being there in October, you won't have to fight the high-season (summer) crowds.

Lisbon is a great city for walking, with plenty of serious hills right in/around the center. Walk up to the castle (great views), walk down through the historic Alfama (oldest and most unique neighborhood), walk up (or take the unique Santa Justa elevador up and walk down from) the Barrio Alto ("high town" neighborhood). Lots to see and do, much of it outdoors

Lisbon is a great place to stretch your legs - literally. You will get your steps in!

Thank you, this sounds great, can you make any suggestions about areas for bike rides, Wine tours?

You might consider Cascais as a home base for at least part of your visit to Lisbon. There is a good, fairly short bike trail from Cascais to Guincho beach, and From Cascais along the shore to the east. It is easy to rental bikes in Cascais. There are many hiking trails in the Parque Natural de Sintra-Cascais. Transportation between Cascais and Sintra by municipal bus or Uber.

This sounds great, what is the best way to do this, is it best to stay in Lisbon and do this for a day? Could we go to Cascais for a day and rent bikes, are bike trails obvious
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Hello from Wisconsin,
I used to be a bike rider. I would not try cycling in the old district of Lisbon. Way too dangerous in my mind. And as long as I am on that topic. I would discourage driving in the same.

I envy you being in Lisbon in October. As someone else suggested, the crowds should be much diminished. Before we landed I had read a lot of Portuguese history, some serious histories, some murder mysteries, a biography of Salazar. I loved the old district. It felt as those I could feel ghosts of WWII.

I would suggest a good paper map and to just start out walking and see where yo end up. There certainly are hills. But from those hills are fantastic vistas.

You could buy the two books, Walk and Eat: Lisbon, and the companion book, Walk and Eat Around Lisbon. You can get both from eBay for a total under $20. Might be a cheap way to find something right up your alley.

wayne inWI

Thank you for such thoughtful reply!

Learn in advance how public transit works, for when the hills get too serious. Some of the city's street signs are inscrutable, especially side streets, either too dim to read or missing altogether. That's when to seek out a taxi, moderately priced transport.

We have five full days in Portugal, flying in and out of Lisbon. We are now thinking of driving or taking a train to Prado form Lisbon. What are thoughts on how best to do this? Drive or train? Where is a good place to stay in Prado?

More questions, we are now wanting to include Porto. If we do this, can we stay in Porto and do a day wine tour to vineyards in the Douro or should we plan to stay for a night or two in the Douro? I know this is fast travel. I read that there is a company that can do this?
Thank you,

We just finished our Portugal trip: 7 nights Porto with a day trip to Guimaraes, 2 nights Douro Valley, 7 nights Lisbon, one night Sintra. Being retired,, we like slow and enjoyable traveling.

I think you need 3 full days (not nights) in Porto, and 4 full days in Lisbon so you wouldn’t feel rushed between the sites.

For Douro Valley, We rented a car in Porto and drove to Paiva Walkways (warning: GPS may not know the trail end, use google map on your cell) and did the beautiful 8km hike and stayed in Lamgo the 1st night, drove to Pinhao via N222 next morning and took the train from Pinhao to Pocinho (and return), highly recommended the ride: beautiful scenery along the Douro River, very few people on the train (Sept 28th), likely better than on the boat (and cost much less).

We took the fast train from Porto to Lisbon, very comfortable and not many people (1st class seats). The trick is to buy ticket early (at least 7 days before) and choose the promotion rate on CP website. Or choose senior rate if you are over 65 (half price).

We have decided to not go to Porto. I know it was what we wanted but we have decided to wait for another time. We fly in and out of Lisbon and have 6 nights and 5 days. We are wanting to not deal with the longer trains to and from Porto. Should we split up Lisbon with a smaller close by town? We will be there in a week. I feel that cities are not doing it for me the way they use to. Is there something slower? We do like the idea of an area where we can bike ride? Thank you!

Sad. I think the Porto + Douro is better than Lisbon

We really wanted that too, Not sure if the many hotel moves would be wiorth it? How can I make this work, we have 6 nights and 5 days.
We arrive in Lisbon late and fly from Lisbon early, should have waited to book air before planning our 6 nights.

Thank you so much!

We are currently in Sweden, flying to Lisbon next week, we do not want to stay in a city for the 6 nights we have in Lisbon. How would it be if we stayed in Cascais the entire time and trained to Lisbon for sight seeing. We are wanting a calmer environment. We are thinking of staying at the Pergola or Casa Vela guest house. Would this be a mistake?