What you’re describing isn’t working on holiday but being a digital nomad, what your boss suggested. Friends of mine do it too. Go somewhere for 3 months, work from there. Usually in the same timezone or close to it and a cheap country so renting an airbnb isn’t too expensive. From The Netherlands there are many options. Friends of mine go to Portugal(-1), Brazil(-4), South Africa(+1), Turkey(+1), Egypt(+1), Montenegro(+0), or sailing on the Mediterranean.
What you’re describing isn’t working on holiday but being a digital nomad, what your boss suggested. Friends of mine do it too. Go somewhere for 3 months, work from there. Usually in the same timezone or close to it and a cheap country so renting an airbnb isn’t too expensive. From The Netherlands there are many options. Friends of mine go to Portugal(-1), Brazil(-4), South Africa(+1), Turkey(+1), Egypt(+1), Montenegro(+0), or sailing on the Mediterranean.