Day 1: Kalamaja, Tallinn
Anytime is a good time to visit Tallinn, but if you're looking to listen to some awesome music in cozy, original venues (rap concert in a boutique bike store? folk concert in someone's living room? Jazz session on a tram?), then head on over during one of the many music festivals such as Tallinn Music Week, Jazzkaar etc.
For the best views of the industrial, medieval, and modern towers (not to mention the sea), make your way up the many stairs leading to the top deck of Linnahall. This large jewel of Soviet architecture is loved by Tallinners as a place to hang out, skateboard, and watch the sunset with your date.
For those curious about Estonia's 20th-century history, pop into Viru Hotel KGB museum and Patarei sea-fortress for dark tales of the bygone era. For architectural gems of Estonia's tsarist history, you should definitely pay a visit to Seaplane harbour, port Noblessner and Kultuurikatel.
Where to eat & drink
Estonia's most rewarding secret is perhaps its food. Indeed, here you can easily enjoy a delicious gourmet meal without having to break the budget. For an urban dweller, some of the best places to eat and be merry are F-hoone, Klaus, Sfäär and Von Krahl.
Where to sleep?
There's a range of guest houses and guest apartments to choose from, whether you want to cozy up in front of a warm fire or opt for no-frills accommodation. Tallinn also has several hotels known for their original designs, such as L'Ermitage and Telegraaf.
Day 2: Naissaar island