If you are willing to stay flexible (which is easier said than done), then I believe now is a good time to travel to Europe. Pick a country that will allow you entry and start from there, with a rough plan mapped out that you can finalise during your travels depending on the latest changes.

I've spent time last Autumn in Italy, Greece, Austria and Portugal, and am now 2 weeks in to a month long trip round Italy (including a cruise round Italy at the end of April). Instead of working from home I'm working from some really wonderful places with many different opportunities at the weekends. If restaurants are closed then you might need to get up early and buy fish from the local fishermen to cook yourself (or just order take-away). There are other tourists, but mostly local or European and very few Americans. Beaches and outdoor activities are busier than I expected, but not overcrowded. Capacity limitations make many potentially unpleasant experiences enjoyable - such as we spent 11 hours on a bus through Germany, Austria, Switzerland and Italy that was limited to 50% capacity so everyone had a free seat next to them. The cruise was also limited to 50% capacity, so the service was excellent.

Use https://reopen.europa.eu/en as a guide to what need to move between countries (unless flying, then use timatic) and what is open or closed, or what you need to do in each country.

If you were travelling tomorrow, my plan would be to fly to Greece (as you would should be able to enter Greece), and move on from there based on local restrictions. For example, if you have to spent 14 days in Greece you should be able to freely enter Italy from 15th May (but don't confirm your plans until it actually happens). Croatia also seems an option for the starting point.

My opinion, it all goes back to being flexible. Early mistakes I made was making lots and lots of plans, updating them regularly, rechecking prices, and wasting far too much time on planning iterations as opposed to just planning one week at a time. Keeping the itinerary simple will make things a lot simpler - each country will have their own rules and regulations so the more countries you visit the more complicated it will get.