A hostel roommate in Lisbon said one sentence about day tours that saved me $180
She said the free walking tour guides get paid by the restaurants they dump you at, so I skipped the $60 Sintra day trip and took the 4 euro train myself. Did the same route, saw the same castle, ate a 3 euro sandwich instead of a 15 euro group lunch. Anyone else find that just buying the train ticket beats the packaged tour every time?
A buddy of mine paid for one of those Tuscany wine tours and the van stopped at a place where the "family winery" was just a room with folding chairs and a guy pouring boxed wine. He looked up the same spot later and the train ticket plus tasting was half what he paid. Packaged tours mostly sell you the feeling of not having to plan anything, and that feeling costs a lot.