At least in Tallinn, most people speak some English. I met a surprising number of Estonians that were fluent too. There seemed to be a love affair with New York City, I saw New York pizza and clothes advertised everywhere in Tallinn.
Very far, you don't need to speak Estonian unless you plan to work as a local job position that requires doing customer support (such as shop-keeper). In such case (or policeman, lawyers, doctors, etc), it's mandatory to learn the language, and there is a special police that checks if you can speak and write in Estonian (Keele Inspektsioon).
This is done for a good reason, it's to make sure that everybody can get a good service and to protect Estonian heritage and culture (otherwise imagine older people, if their doctor can't speak with them).
You can fully live and work without speaking a single word in Estonian.
It's totally normal here to speak English.
Even at the cinema, movies are in English, subtitled in Estonian and Russian.
When you go to shop, many products actually have labels in English (or in German).
Estonian is a difficult language, Estonians know about it.
A bit generalising, but to get the idea:
Estonians don't want to speak Russian, Russians can't speak Estonian well.
So you have this society fragmented in half.
So overall, everybody settles for the easiest language that doesn't upset anyone: English (and German as a fallback).
It's easy to find schools in English too.
Even the tax board speaks to you in English, all the website for public services ( https://www.eesti.ee/ ) is all in English, even all the laws are officially translated in English ( https://www.riigiteataja.ee/ )
To IT foreigners, the country is very welcoming and very very easy-to-settle in my opinion.
To other foreigners, it's not true, because it's considered stealing jobs, bringing criminality, etc (basically same stuff that you have to prove when applying for an H1-B in the US)
To get a flat, real estate agents all speak English.
They won't get offended if you speak only English, it's normal for them.
Telecom companies speak English.
All apps (taxi, food delivery) are in English, because most startups and apps are not made for the local market as its too tiny.
From a political perspective, the country is now pushing more and more English; they'd prefer that you learn English than Russian.
So some shops are even removing Russian, and some administration now addresses you in 3 languages: [Estonian, then in English, and then Russian] (whereas before it was [Estonian, then Russian, and then English]).
The country is very well managed and organised, main issue with the country is:
- Darkness (coldness is fine, but half of the year you essentially live in the dark, almost like if it is always night). Summer is awesome though because you get day and sun almost all the time.
- A really unstable neighbour country on the East (it's not totally impossible that a war could break-out, though unlikely at the moment).
- Taxes may raise in order to fund the current war in Ukraine and balance the government budget.
but otherwise it's a really good place to live and raise a family.
I used to live in Tallinn as well (American expat) and echo basically everything rvnx says here. Some of the older people from the Russian community speak only Russian, but you're much more likely to encounter this in Narva (east) than in Tallinn. Estonians are also well aware that they are a tiny country with a difficult language so if you're not permanently settling, there is little expectation of learning more than a few words of Estonian. Super easy to navigate the bureaucracy (if you can even call it that), file taxes, etc.
One thing of note, with the caveat it's been a few years since I lived there (although I stay closely in touch with friends and visit often... actually I am typing this from my airbnb in Tallinn) -- you might get some looks if you're brown or black. From my experience this is mainly from older people and it's pretty benign, but it's not the most cosmopolitan place and most people of color you see are "students" for visa purposes who have been there for many years and work for gig startups delivering food or driving Bolt (Uber equivalent). I never felt unsafe or anything, but there were a few uncomfortable moments during my time there as a person of color.