Travel Advice from Lisbon to Madrid

Bom Dia! My friend and I (2 females, single, in our late 20's) are flying into Lisbon in late June and out of Madrid 10 days later. We are most interested in spending our time in the citiies of Lisbon & Madrid, taking day trips outside of Lisbon before moving south to the Algarve and then to Southern Spain & finally up to Madrid. If you can recommend any locations/experiences/restaurants/hostels that we should know about while planning our trip - please advise!! Of course our starting point has been the Lonely Planet guides.

1. Lisbon Housing: We are interested in upscale hostels/guesthouses, etc for the interaction with fellow, like minded travellers but we would prefer to have our own private room with a bathroom attached. We'd also like a central location for exploring Lisbon - any suggestions? We hope to be able to change our plans so if we book online (LP website) are we locked in for the number of days or can we be refunded if we decide to leave early?

2. Transportation: In my reserach it sounds like buses are a convenient way to travel this route. But renting a car would probably give us more freedom. What do you suggest? Is it difficult/expensive finding overnight parking in Lisbon and Madrid? Is it easy to pick up a car in Lisbon & return it to Madrid? Any suggested Car Rental Agencies?

3. Excursions from Lisbon: I am interested in taking a day trip to the wine country outside of Lisbon - which is the best destination for this if we are travelling via bus? I'm also interested in spending a day in a surf camp or taking surf lessons outside Lisbon (or later when we are in the Algarve). Which beach/surf company is best to do a surf day with?

Obrigada for any advice you can provide!!

Edited by: siotravel

If you go to Algarve Alvor is a lovely small town with a great sandy beach.
You can look for a hotel or self catering apartments. Also you can
rent a room in private villas.

As for Lisboa (but not only this town of course):
Beware of pickpockets and esp in tramline 28.
I accompanied a victim being robbed, as a translator (thought the police were speaking English very well, appeared) and they were overcrowded by naive (..) people, robbed from their purses. A ten-people-staff worked on this form of pickpocketing...
Sorry, there's much more about Lisboa but this is was first occurred to me.

As for the Algarve, Tavira would be my bet. A small authentic town, nice beach.

Lisbon Housing: We are interested in upscale hostels/guesthouses, etc for the interaction with fellow, like minded travellers but we would prefer to have our own private room with a bathroom attached.
I'm sorry but could you translate that into English, please?

You plan to travel from Lisbon to Madrid in 10 days.

Day 1 you arrive in Lisbon, and I would suggest that you leave on day 4, giving 2 full days in Lisbon (not enough, but you are time poor). If you do the same thing in Madrid, that is arrive day 7, stay days 8 and 9 and leave day 10, then you only have days 5 & 6 in between. That does not give you time to travel to the Algrave, across to Southern Spain and then up to Mardid.

{quote:title=siotravel wrote:}{quote}
We are interested in upscale hostels/guesthouses, etc for the interaction with fellow, like minded travellers but we would prefer to have our own private room with a bathroom attached.

"Upscale hostels" is an oxymoron since, by definition, hostels have dorms (even if they also have private rooms).

I think you're probably looking for something like this though:
http://web.mac.com/travellershouse/iWeb/Site/main.html

I think you're probably looking for something like this though
We may never know what the OP was looking for since it has been almost 3 weeks since the original post.