Visit Tallinn or Riga (or both) prior to arrival in Helsinki?

1. In 2018, I spent 4 nights in Tallinn and 3 nights in Riga and did day trips from both. If you have 5 nights, you could probably do both. Tallinn, of course, is medieval charm. Riga is Jugendstil/Art Nouveau heaven. Both have nice histories.
2. I have not been to Vilnius, so I would have to defer to someone else to answer.
3. Five days to cover both seems rushed to me, especially if you are recovering from a transatlantic flight on arrival, but it depends on your travel style. I personally would pick one or the other because (1) it takes a day or two for me to get in the flow of living on Europe time and (2) I like to explore places in a little more depth.
   
4. I don't think it really makes a difference on RIX or TLL. You will have to connect somewhere in Europe to get to either. Of note, if you connect on Air Baltic, their employees were very strict on carry on size meeting the airline's size policy in 2018 (unless traveling in business class)

My trip report from 2018: https://community.ricksteves.com/travel-forum/trip-reports/one-of-my-best-travel-days-ever-a-trip-report-for-latvia-and-estonia

I have been to all three capitals. (Riga twice).

With five days you really need to choose two at most. The problem being....which ones. Each has a different vibe.

My suggestion would be to do a little research on all three and choose the two that speak out to you the most. They are different.

Tallinn is easy because it's only two hours by ferry from Helsinki. But getting between the cities isn't difficult. You can fly, take the train (once a day) or one of the numerous coaches. (Very nice. Don't compare to US coaches.)

As for flying in, there are no direct flights from the USA to any of the Baltic countries.

I have been to all three airports. Riga and Tallin are modern and practical. Vilnius still has the old, communist feel to it. It's not necessarily bad, just different.

There are also short flights to all three capiltals from Helsinki.

The other option is to visit Tallinn for a couple of days and save Latvia and Lithuania for a later visit. Use the extra time to visit other areas of Finland or perhaps the Aland Island between Finland and Sweden.

I'm heading back to the Baltics this fall.

Oh, and....Go Gators.

Thank you both for excellent points and suggestions! We've decided to fly into Tallinn and spend 5 nights there; we may make a day trip to Riga but probably not as we'll be recovering from some jet lag upon arrival from Florida plus with the numerous activities in Tallinn the time will go quickly. Happy Travels!

Which day trips would you especially recommend from either city?
Also, could anyone comment on how safe a single woman would be / feel, traveling alone in Estonia and Latvia?

I’m going to the Baltic States in September, so don’t have first hand knowledge yet, but from what I’ve researched, five days in Tallinn, although much better than a daytrip from Helsinki, is a long time there, but a daytrip to Riga is too much travel time. So with five days I’d do both, with at least one night in Riga. My trip will be 4 nights Vilnius, 2 Riga, 3 Tallinn.

If Tallin is the choice, I strongly remind a side trip to Tartu. Easy train ride from Tallin. The Estonian Museum there is very new, big and just sparkles. Tartu is a university town and a modern European city. Bonus is there is lots to see, not many tourists and you can say you were 35 miles from the Russian border.

Good choice on choosing just Tallinn, arriving with jet lag. There is plenty to see and do there and in the area. Riga is my favorite (of course, I didn’t know that before visiting) and I can’t imagine only having 1 full day there.

Laura, you will want to start your own thread so you receive all the replies instead of this OP.