| Description | City | Hint |
| The Greatest City on Earth | |
| The Also Greatest City on Earth | |
| One of two places in Canada | |
| The other one in Canada | |
| The Farthest South I'll Consider | |
| The Greatest City not on an Ocean (except Vegas) | |
| The Most Remote Place on this list | |
| Rain and Hipsters | |
| | Description | City | Hint |
| On second thought, might be too cold | |
| I like Georgetown, what can I say? | |
| The Smallest Place I've Considered | |
| My Birthplace | |
| Never Been Here but It Seems awesome | |
| Same for this one | |
| The One I'm in Now | |
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