A lot of jurisdictions are requiring foreign travellers to quarantine themselves for two weeks on arrival in a country, so that would make a round the world trip using only surface transportation problematic these days. If you allow for air travel, it would be easy.
On #2, Francis Drake did it in a little over 1000 days, in the 16th century. Allowing for better 17th century maps allowing for a more direct route, and taking less time off for plundering Spanish shipping and towns along the way, I think 800 days would be quite doable.
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