We sold up and moved to Malta. Its just south of Sicily and culture is a cross between the UK and Italy. It has two official languages, one of which is English.
As few things to consider:
- You cant get out of US taxes so count on paying the same taxes as you would at home. Moving to another state before you move can save you some money, but that wont work if you keep your primary home and rent it out. California in particular will not recognize your move if you do this. However most countries in Europe will also declare you resident after a few months and then tax your worldwide income including social security etc, even if you leave that money in the US. You may find this makes living in Europe more expensive tax wise than staying at home. The only countries I have seen that dont do this are the former British colonies: Gibralter, Cyprus and Malta.
Even though you are an EU citizen living in another EU country, you dont get free healthcare unless you are working and paying into their system. Infact nearly all EU countries will only allow citizens from other EU countries live there if they carry private insurance. That said, insurance is much cheaper than the US.
The language barrier is real. Even in places like portugal you will find that the locals all speak portuguese to each other and if you are away from the gringo areas many will not have english. The netherlands is probably the best country for multilingual english speakers and even there its common to find yourself stuck if you dont speak dutch. Malta and Ireland are the only two remaining English speaking countries in the EU and Spanish is really only useful in Spain. Be careful with crime. The chances of being attacked are in general lower than in the US, but in many places, property crimes are much higher. Having your home robbed is still an unpleasant experience. I always look for bars in ground floor windows on houses to determine if the crime is too high for me to want to live there