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I currently have a valid B1/B2 visa until 2029.

I originally arrived in the USA in December 2019 for a non-employed ski season. After the lifts closed I looked out the window at the national park and decided I was going to stick around. I applied for an extension, but left (end of July 2020) before I received a decision (I was assured by CIS over the phone that this wouldn't be an issue on my next entry provided I arrived at the border with proof of my application). I'm hoping to try the ski season again and arrive in late November. I'll have been out for ~115 days, but whether or not this is a meaningful departure etc. I think is outside the scope of this question, I'm just providing context in case it suddenly becomes relevant. I'm currently resident in Austria.

Based on the various proclamations (https://travel.state.gov/content/travel/en/News/visas-news/presidential-proclamation-coronavirus.html), it's my understanding that if I spend 14 days outside of one of the name countries prior to my arrival (e.g. the Caribbean, Colombia) there's no Covid-19-related reason why I wouldn't be granted entry to the USA.

The FCO (UK foreign office), had this to stay (https://www.gov.uk/foreign-travel-advice/usa/entry-requirements):

Our understanding is that British nationals currently in the USA on one of these visas can depart and enter as long as their visa is valid – subject to other rules.

I was in the USA at the time of the proclamations and my visa is still valid. Are there any "other rules" that I have missed?

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    FYI My local ski mountain in the US recently announced its COVID plans for the 2020 season. They are severely limiting passes and require all passes to be pre-booked. I'd expect other places to do similar things. This season is going to be unlike anything in the past, so I'd be looking into the situation at what ever resort you are thinking about, and how it will change affect you plans.
    – Peter M
    Commented Oct 16, 2020 at 13:44
  • Yep - that is a big concern. Fortunately, my resort of choice (Jackson Hole) has assured no reservations for season pass holders, and I bought mine back in June when they offered the renewal deal for the curtailed season. Part of why I want to do this now is that this season will be like no other - to stay in Europe is to do more skinning than I find fun. Thanks for thinking of that part though!
    – jimbofreedman
    Commented Oct 16, 2020 at 14:01
  • Another entry restriction is that entry to the US through the land borders (US-Canada and US-Mexico) is currently restricted to essential travel, so (assuming the restrictions continue) you will need to enter the US by air.
    – user102008
    Commented Oct 16, 2020 at 17:57
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    Your quote is about H/J/L visas and is not relevant to you.
    – user102008
    Commented Oct 16, 2020 at 17:58
  • @user102008 Absolutely correct, well spotted, thank you!
    – jimbofreedman
    Commented Oct 17, 2020 at 11:15

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I believe that the FAQ here: https://uk.usembassy.gov/information-for-nonimmigrant-visa-applicants-following-the-coronavirus-covid-19-outbreak/ answers my question.

Can I travel to the United States through a country that is not covered by Presidential Proclamation 9996?

Travel to the United States from a country that is not covered by the Presidential Proclamation may be possible, but we advise you to verify whether the country to which you intend to travel has implemented travel or other restrictions before you make travel arrangements.  One possible source of such information is travel.state.gov which contains links to the websites of other countries’ immigration authorities.

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