We are arriving in Lisbon from the US the morning of October 31, and neither my wife nor I can sleep on a plane. So we will be quite jet-lagged. I think the most we might be able to manage that day would be one of the three self-guided strolls the Steves guide details (Bairro Alto & Chiado Stroll, Alfama Stroll, and Baixa Stroll). Which of those is the easiest, in terms of both distance and elevation change?
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Northern California
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Baixa Stroll is the easiest in terms of elevation gain and walking. The Bairro Alto is easy if you have a transportation pass and are taking the funicular and elevator. All three are pretty tiring. If you are jet lagged and still want to get some sightseeing in I would suggest his trolly tour. I don't have the book in front of me right now but I think there is a number 28 trolly tour. Get on and sit and enjoy the sights. You can get off at the castle stop and have a drink and enjoy the view. Then get back on. Just don't attempt to walk up the hill to the castle as it is a large hill and can be saved for your Alfama Stroll.