With Corona wrecking everyone's travel plans, traveling alone on your motorcycle to nearby well doing countries seemed like a great option for a change of scenery. It's also something I was dreaming about for years (since I got my motorcycle license). It seems like it's a best time to find if it's something I would like, or it just sounded nice in my head.
You can't plan for everything, and you will learn things on the road (things will fail) which will make you rethink your strategy, but you can at least make some preparations so it would be possible to continue your trip even when it's not going great.
Before leaving I did some basic maintenance on my motorbike, you just don't want it breaking in the middle of no where. I also got a new back tire, and really glad I got partly enduro tire (with all the dirt roads, road constructions, partly flooded roads, gravel patches on road) which I'm sure saved my ass countless times.
One of the most important things to take was my laptop, because it's used for work and if you earn money you can buy whatever else you might need on the road. Would like to have some nice sturdy case for it, but can't find anything good so it's mostly traveling as is. I also got a waterproof bag for putting everything on the back of motorcycle. Waterproof bag is put in the Pacsafe Anti-Theft bag protector, if someone really wanted to steal it they would be able to get through it, but at least it gives some peace of mind leaving your things un-attended for a few minutes.
Also take basics like cash, another card, backup phone, extra motorcycle keys, etc with you and split them up, so you always have one set with you and another set with your bag, in case something happens to one of them.
My main phone provider does not support roaming data, so I got myself a top up SIM card from different provider (Labas in this case) and purchase a roaming data plan as needed. It's expensive so it's still better to get local SIM card on arrival, but it's also good to have some back-up until you are able to do it (because for example no one is working so it takes a while until you find where to buy one).
In Latvia you can get ZZ card for about 3 € and then a top up code. By sending SMS "BI" to 1616 number you can get fast unlimited internet for 2.49 €
In Estonia you can get Super card. It doesn't have unlimited internet and price would depend on the available plans at that time, but for 3-8 € it should be enough to last.
You could keep your expenses much lower by camping, but because I still need to work I want/need at least OK places where I could do it comfortably. It would also increase the amount of gear you will have to take with you and I was already not happy when having to buy a bunch of stuff since the rainy days started. I'm sure the rain would also make camping suck, because after riding for hours in strong wind and cold rains the only things you want/need is first a hot long shower and later to snuggle up to some heater (once you start feeling like human again you have to deal with starting to get your gear dry for next day's riding).
Logistics are a bit complicated, but usually I tried finding places where check-out is 12 PM, then you ride for a couple of hours, and do a check-in around 2-3 PM (sometimes asking hosts if it would be possible to check-in early if you don't have a lot of riding).
My bike is not the newest or expensive, but still you feel much better then it's inside some private parking place. A lot of places don't bother mentioning if it's a street parking or if they have some private parking space. Sometimes you will book some place just because you can see it has a private parking spot (in a photo or well defined text). With a small bike you also sometimes get an option to drive it past narrow walk-in gate and park it in the inner yard.
First option for booking a place is Airbnb (I just prefer using it). If I could not find anything good then would look at Booking. If I still could not find anything I would like, then I would drive for more/less than planned or choose a different route. Most of the places was booked by looking for them in the evening the day before or in the morning before check-out.
Below will be a list of some of the places I visited and liked along the way.
Liepāja - small beach town, nice to walk around and look for sculptures/art. Nude beach too far away to walk to it (weather was too bad for beach in any case).
Ziemeļu forti - fort which is being taken by the sea
Ventspils - small beach town. Nude beach is very stony but it's close to city center. Fun activity is walking around the town trying to find cow sculptures or some oter interesting sculptures. For example traveling cow
Cape Kolka - something like a shallow beach so probably more interesting for people with small kids so they could play in it.
white dune - slowly disappearing dune which looked really cool to me.
Kaltenes akmeņainā piekraste - stony beach which is a good place to relax for a bit before continuing your trip.
Bastejkalna park - nice big park in the middle of Riga.
Saule Perkons Daugava graffiti - large graffiti, if you explore the area you can find other nice art.
Riga Motor Museum - museum of old cars and motorbikes, was really interesting to see some of them.
Vecāķu nūdistu pludmale - nudist beach if you need to get some sun, nice walk in the forest until it, but the parking situation is terrible.
AERODIUM, Sigulda - very fun way to enjoy some flying above a giant fan (because free fall with parachute ends up before you understand that is going on). Take 4 minutes option, because 2 minutes would not feel like enough, and 4 minutes is just enough (because it's tiring).
Pärnu muul - stony pier, was very nice walking it barefoot (takes about 15 minutes one way if I remember correctly). Nearby beach has warm water (on cold rainy day) and is shallow to walk it all.
Saaremaa - I heard this island recommended multiple times, even had housing booked for it, but after waking at 5 AM and hearing hard rain decided to skip it as it would have been miserable many hours in rain (which I didn't know at that point how miserable they would be).
Ruumu - flooded prison, tried diving for the first time here. You can also enjoy other water activities here or just walk around.
Tallinn - very nice downtown (even if not much to do in it because it's mostly overpriced restaurants).
Valaste Waterfall - waterfall near beach with hiking paths.
Estonian Aviation Museum - open air museum which makes you better understand the size of some of those rockets/fighters.
Rõuge Ööbikuoru vaatetorn Pesapuu - watch tower, it was right by the place I was staying for the night, some nearby hiking trails.
Lake Zarasai Observation Circle - observation place near the lake, nice views. Can see some graffiti on nearby building and can take a walk by the lake.
DriftLand Vilnius by SideToSide Drift Team - drifting lessons which can be very fun.
Epower Arena - indoor place to ride electric motorcycles and kartings.
Stone Sculpture Park Vilnoja - park full of stone sculptures. Can enjoy water entertainment nearby.
Pilaitės windmill - a windmill, nice walk around the place with some old technology which reminds of childhood visiting your grandparents.
Puvočiai Lookout Tower - observation tower, nice views, can see the tops of the trees.
Meteliai observation tower - observation tower with nice view of the lake.
Arkadia - nice lake in the city.
Šaudykla ShootingClub.lt - good place for shooting at clay pigeons.
Lokės pėda - adventure park, enjoyed being shot by "catapult" and prefer it to bungee (quicker and cheaper).
Belvedere Manor - "abandoned" house, entrance ticket is 3 €, you get a flashlight and you can walk around the basement.
The Museum of Ancient Equipment - open air museum to look at some old things.
Raganų eglė - some old tree which is so-so, but nice walk in the forest, terrible dirt road to reach it.