Tallinn or Riga? Which is more interesting and why?
 

I read they are similar. I prefer to concentrate on one instead of moving too much. Riga is bigger and less touristy so I heard, for that reason I am leaning towards Riga. Will be taking overnight ferry from Stockholm. I believe ferry goes to both, please correct me if I am wrong.

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There is a ferry from Stockholm to both, Tallinn and Riga respectively.
http://www.tallinksilja.com/en/

Riga is the bigger city of the 2 (more than twice as much inhabitants as Tallinn) - and would keep me entertained for longer than Tallinn.

The main reason is that while both have attractively well preserved medieval Old Towns, Riga in addition offers a belt of magnificent Art Nouveau buildings surrounding its Old Town, whereas Tallinn outside its also attractive Old Town is predominantly modern, but bland.

Find good info on both here:
http://www.inyourpocket.com/estonia/...l_features=500
http://www.inyourpocket.com/latvia/riga

Tallinn by a mile! There's a reason why Riga is "less touristy" - I felt that there was a lot less to it than Tallinn. Tallinn is really stunningly beautiful and while Riga is nice in parts, the level of preservation of the medieval walls and buildings in the old town would swing it for me.

In addition, I found Tallinn a lot friendlier than Riga - Riga got quite threatening at night with stag parties (although Tallinn has this too) and aggressive locals. Just IMO.

Thankyou both. I need to do more research but I read that I need to buy the ferry tix asap. Is that true? I plan to be in Stockholm middle of May and Tallinn and/or Riga the following week. I don't like crowds, I plan to take the ferry on week days and buy the tix in Stockhom few days before, is that ok? I check the ferry website and I don't see any promotions or deal for buying the tix early. Is there a third party I should buy the tix from? How was the ferry ride? I am the quiet type and don't care to party, I wonder how much scenery I get to enjoy since it's dark most of the way. I am prone to motion sickness, the water should be really calm, right? Too many questions. Thanks in advance.

Indeed there is a reason why Tallinn is more touristy: Booze.

Tallinn is just a short hop across the Baltic Sea from Helsinki - and it's cheap booze paradise for the poor Fins who'd get broke by getting drunk at home, whereas in Tallinn, that's not an issue. That's why they flock there.

Tallinn's Old Town indeed is pretty. Takes a max. of 1.5 days and you have seen it all and again. A bit like Disneyland.
Go to Riga and explore Old Town in 0.5 days, add the Market Halls and the Art Nouveau district another day, then head out to Meza Parks for another half day and you are only scratching the surface.

If anybody tells you the sea will be calm all the time for your trip, they should better keep their big mouth shut. It's a sea - and it can get rough.
That said, the ships are large and comfortable and are equipped with stabilisers, so they will be reasonably comfortable.
Passing through the Stockholm archipelago is very scenic - and it should not be too rough in there.
If you don't want to party, the ferry company will not force you to. Retreat to your cabin. Simple.
Why would you want to buy the tickets through a 3rd party?

Riga/Tallinn, I think it's a toss-up, except that Riga has the most beautiful women in Europe. If you choose Riga have dinner at the Lido in old town, not the other one. The Lido has a buffet which you pay for by weight. Great seafood. Excellent steak and cheap at the bar in the Dicken's Pub. In Tallinn the Stockmann department store has a great buffet for breakfast and lunch.

Thanks again. I just want to do sight-seeing. I am very quiet, I like to meditate and do yoga on the ferry if I can. I still can't decide if the ferry ride is worth $500+ It seems that cheap booze is the reason people take the ferry and go to Tallinn. Can't imagine people are paying that kind of price to drink cheap.
RE:third party. In some cases, booking with a consolidator can be less expensive.

Have you considered a EurailPass? With that the ferry ride is free. The buffet dinner from Stockholm to Helsinki is about $50 and is world class. You can take another ferry over to Tallinn.