Private driver/guide in Estonia?

I used Mati Rumessen. He is a driver and guide. He has lived the history of Estonia. I wouldn't call him dynamic, but he knows his stuff. He's kind of grandfatherly -- depending on your grandson's nature, that may be a plus or a minus.

http://www.tourservice.ee/index.html

You can also use the Bolt service for an on demand private driver. Bolt is much like Uber at home, but founded in Estonia. Of course the drivers are just that, they're not guides.

I would recommend downloading the app and setting up your account ahead of time. Then just call up a driver as needed.

Super helpful. Thank you so much for reaching out. I will look into these options. Much appreciated!

There are lots of places he would like to see, including islands...

You might want to check to find out which specific "islands" he has in mind (there are two big ones, countless smaller ones), that probably makes a difference. Although Estonia is not huge, it's also not tiny (it's about 1/3 the size of Illinois...consider what it might cost to get a tour around a large portion of your home state by Uber). Getting to and around some of the islands might be quite expensive if you hire a guide and car that way. The islands are beautiful and interesting, but maybe not cheap to get to that way.

I'll add that driving in Estonia is super easy, roads are great (as easy and as good as anyplace I've ever driven). We spent a couple days island hopping in our rented car and loved it.

Great info. Thank you to all for your thoughtful responses.