A Tale of Many Cities

I have crafted a puzzle for the holidays, intended as a gift for my lexically or geographically inclined relatives, and I have posted it here for digital posterity.

There are two kinds of answers for the clues of this crossword. For the first type, the name of a city is contained within the answer with all the letters in order. As an example (only with fruit instead of cities), the clue “potable yellow liquid” gives the answer “lemonade” with the fruit “lemon” within it. Another example, this one with disconnected letters, the clue “santimonious, holier-than-thou” gives the answer “preachy” with the fruit “peach” within it. To be clear, the single restriction is the letter ordering. The name of the city could even be split among an answer with several words, such as the answer “Lemon Tree Hall” for the city “Montreal.”

For the second type, the answer is an anagram of the name of a city. I am defining anagram loosely, to say you can both transpose and make duplicates of the letters. The clue “former talk-show host” gives the answer “David Letterman” with the anagram “Nerd amid late TV.” And as another fruit example, the clue “prohibition or embargo” gives the answer “ban” with the fruit “banana.”

You are supposed to fill in the crossword itself with the answers to the clues, not the names of the corresponding cities. I figured you could decide how to record the city names: alongside the clues, next to the markings on the map, or wherever.

I recognize that this puzzle is hard. That said, some of the clues themselves are duplicates, in the sense that they refer to the same city. And a few of the cities indicated on the map share the same name, akin to Portland, ME and Portland, OR. Maybe the most helpful, a couple of the anagram answers resisted rearrangement. Forgive the typos and such, such as with Virginia Woolfe.

Hopefully it is easy enough to print out the images pasted below. Best of luck, and happy holidays!