Notice removed Authoritative reference needed by Flo
    Bounty Ended with Stephen Ostermiller's answer chosen by Flo
3 added update 1
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I'm totally revamping my site's URL structure and have now defined the following structure of URLs to prevent duplicate content (in which the /c/ part in the URL determines that a country filter is applied) and each URL has the corresponding canonical URL (some I'm still not sure of and are marked with OR):

  1. URL: /vendors/venues/c/usa/massachusetts
    Canonical URL: /vendors/venues/c/usa/massachusetts

  2. URL: /vendors/venues/c/usa/massachusetts/boston
    Canonical URL: /vendors/venues/c/usa/massachusetts/boston

  3. URL: /vendors/venues/c/usa/massachusetts/region-boston
    Canonical URL: /vendors/venues/c/usa/massachusetts/boston

  4. URL: /vendors/venues/beach/restaurants
    Canonical URL: /vendors/venues/beach/restaurants OR /vendors/venues?

  5. URL: /vendors/venues/beach/restaurants/c/usa/massachusetts/boston
    Canonical URL: /vendors/venues/c/usa/massachusetts/boston OR /vendors/venues/beach/restaurants/c/usa/massachusetts/boston?

As you can see users are allowed to add multiple venue categories, in this case just beach and restaurant, but users can filter down using more than 20 venues categories. Venue category filters are added in front of the /c/ part in the URL.

Now my question is: is this the recommended and most logical URL structure and canonical URL approach? And for items 4 and 5 specifically, which canonical URL is recommended?

update 1

Regarding "venues for Boston vs Boston-region" (example 2 vs 3). When loading these URLs, the results on the first 10 pages are exactly the same, as I'm sorting by georadius from city center outwards. The first URL shows only venues in the city of Boston whereas the second has a greater radius to include more venues. I do not know on which page the results really start to differ, it might be page 11, or page 14 etc. Should I perhaps remove 1 of these URLs? Or what would be the canonical URL? I'm now thinking I should set the canonical URL of URL 3 to URL 2 (and omitting all pagenumbers in this canonical URL)

I'm totally revamping my site's URL structure and have now defined the following structure of URLs to prevent duplicate content (in which the /c/ part in the URL determines that a country filter is applied) and each URL has the corresponding canonical URL (some I'm still not sure of and are marked with OR):

  1. URL: /vendors/venues/c/usa/massachusetts
    Canonical URL: /vendors/venues/c/usa/massachusetts

  2. URL: /vendors/venues/c/usa/massachusetts/boston
    Canonical URL: /vendors/venues/c/usa/massachusetts/boston

  3. URL: /vendors/venues/c/usa/massachusetts/region-boston
    Canonical URL: /vendors/venues/c/usa/massachusetts/boston

  4. URL: /vendors/venues/beach/restaurants
    Canonical URL: /vendors/venues/beach/restaurants OR /vendors/venues?

  5. URL: /vendors/venues/beach/restaurants/c/usa/massachusetts/boston
    Canonical URL: /vendors/venues/c/usa/massachusetts/boston OR /vendors/venues/beach/restaurants/c/usa/massachusetts/boston?

As you can see users are allowed to add multiple venue categories, in this case just beach and restaurant, but users can filter down using more than 20 venues categories. Venue category filters are added in front of the /c/ part in the URL.

Now my question is: is this the recommended and most logical URL structure and canonical URL approach? And for items 4 and 5 specifically, which canonical URL is recommended?

I'm totally revamping my site's URL structure and have now defined the following structure of URLs to prevent duplicate content (in which the /c/ part in the URL determines that a country filter is applied) and each URL has the corresponding canonical URL (some I'm still not sure of and are marked with OR):

  1. URL: /vendors/venues/c/usa/massachusetts
    Canonical URL: /vendors/venues/c/usa/massachusetts

  2. URL: /vendors/venues/c/usa/massachusetts/boston
    Canonical URL: /vendors/venues/c/usa/massachusetts/boston

  3. URL: /vendors/venues/c/usa/massachusetts/region-boston
    Canonical URL: /vendors/venues/c/usa/massachusetts/boston

  4. URL: /vendors/venues/beach/restaurants
    Canonical URL: /vendors/venues/beach/restaurants OR /vendors/venues?

  5. URL: /vendors/venues/beach/restaurants/c/usa/massachusetts/boston
    Canonical URL: /vendors/venues/c/usa/massachusetts/boston OR /vendors/venues/beach/restaurants/c/usa/massachusetts/boston?

As you can see users are allowed to add multiple venue categories, in this case just beach and restaurant, but users can filter down using more than 20 venues categories. Venue category filters are added in front of the /c/ part in the URL.

Now my question is: is this the recommended and most logical URL structure and canonical URL approach? And for items 4 and 5 specifically, which canonical URL is recommended?

update 1

Regarding "venues for Boston vs Boston-region" (example 2 vs 3). When loading these URLs, the results on the first 10 pages are exactly the same, as I'm sorting by georadius from city center outwards. The first URL shows only venues in the city of Boston whereas the second has a greater radius to include more venues. I do not know on which page the results really start to differ, it might be page 11, or page 14 etc. Should I perhaps remove 1 of these URLs? Or what would be the canonical URL? I'm now thinking I should set the canonical URL of URL 3 to URL 2 (and omitting all pagenumbers in this canonical URL)

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    Notice added Authoritative reference needed by Flo
    Bounty Started worth 50 reputation by Flo
2 more descriptive title
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Validation on URL path format and What should the canonical URLsURL be when users can filter on multiple categories at once?

1
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Validation on URL path format and canonical URLs

I'm totally revamping my site's URL structure and have now defined the following structure of URLs to prevent duplicate content (in which the /c/ part in the URL determines that a country filter is applied) and each URL has the corresponding canonical URL (some I'm still not sure of and are marked with OR):

  1. URL: /vendors/venues/c/usa/massachusetts
    Canonical URL: /vendors/venues/c/usa/massachusetts

  2. URL: /vendors/venues/c/usa/massachusetts/boston
    Canonical URL: /vendors/venues/c/usa/massachusetts/boston

  3. URL: /vendors/venues/c/usa/massachusetts/region-boston
    Canonical URL: /vendors/venues/c/usa/massachusetts/boston

  4. URL: /vendors/venues/beach/restaurants
    Canonical URL: /vendors/venues/beach/restaurants OR /vendors/venues?

  5. URL: /vendors/venues/beach/restaurants/c/usa/massachusetts/boston
    Canonical URL: /vendors/venues/c/usa/massachusetts/boston OR /vendors/venues/beach/restaurants/c/usa/massachusetts/boston?

As you can see users are allowed to add multiple venue categories, in this case just beach and restaurant, but users can filter down using more than 20 venues categories. Venue category filters are added in front of the /c/ part in the URL.

Now my question is: is this the recommended and most logical URL structure and canonical URL approach? And for items 4 and 5 specifically, which canonical URL is recommended?