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In North America? I'd have to say of all the places I have been it is hands down Guanajuato, Mexico (and this coming from someone who grew up in Savannah, been to Charleston many times and has been to Montreal, SF, Asheville, NYC, and New Orleans): https://travelmexicosolo.com/things-...ajuato-mexico/
Funny enough I went with my best friend and it was funny feeling like the only two that weren't a couple there and we happened to stay in one of the most romantic lodgings in the city for couples too without realizing it until we got there haha. Seriously though, it is one of my most favorite cities and well worth a visit (a place I am also considering retiring too).
I spent a day in Guanajuato one time and there happen to be a large street festival going on that night. Literally one of the most memorable cultural things I have ever done. Couldn't agree more. The little intimate stairways and walkways there are awesome. Very colorful city.
I have never been to Quebec city before, but I would like to go there one day.
Urban Renewal screwed up US cities so badly, I don't really find any of them to be overly 'romantic'.
Santa Barbara
Jim Thorpe, PA and other towns in the Poconos region
Newport, RI
St. Augustine
Washington, DC in its nicest sections like Georgetown and upper NW
Nashville (Bachelorette parties)
New Orleans (French Quarter)
Kansas City, MO. I just saw their Union Station last weekend and that it was more beautiful than Chicago Union Station. To get off the train, eat a fancy meal in the station, then walk across Washington Square Park and up Main St or McGee St, that would be romantic. The way those streets cross the railroad tracks with views of the hills to the West and downtown up the hill to the North by the curved Western Auto Building is very striking
1. Havana
2. Montreal
3. New Orleans
4. Mexico City
5. New York
6. Santa Fe
7. Charleston
8. Miami Beach
9. San Juan
10. Los Angeles
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