Tallinn is a city of interesting mixes. Culturally and linguistically, it has very close ties to Finland, though politically and for a significant part of its history, has ties to Russia. It was part of the Hanseatic League, and ruled for a while by the Danish. Despite this mix, overall, Tallinn is a city of its own. It is this combination that makes Tallinn the gem of the Baltics for me. Reminiscent of Prague, Tallinn is somewhat of a stepping stone between what can be called Eastern and Western Europe. It is like no other city that I have ever traveled to.
The Estonian people are some of the friendliest that I have met, and are very willing to help you in any way possible. Most people in the city are fluent in Estonian, Russian, Finnish, and English (often German as well), so there is little chance that you will not be understood. As you venture outside the centre of the city however, less people are likely to speak English, and you may have to get by on Russian or Estonian. Even if you only plan on staying within the city, I recommend picking up some of the Estonian pleasantries, as the locals will be impressed and very appreciative of your attempts to learn a little of their language. The locals will even help you with your Estonian if you ask.
Although most visitors are only day-trippers from Helsinki, there is a lot more to do than just what can fit between the first ferry arrival and last ferry departure of the day. Within the city, there are many different areas that each would afford a portion of the day on your itinerary. Toompea Hill, the Old Town, and Town Hall Square should not be missed in the town centre, and if you have time, a trip to Kadriorg, just 2 kilometres east of the centre has many historical buildings and palaces. Medieval churches abound and are difficult to miss in this city that has so many of them. ${QuickSuggestions} The best suggestion that I can make, regardless of the city, is to stay in or near the centre of town. This cuts down on the transportation costs to get to the attractions, as well as cuts down on the time it takes to get there. Even if it costs a little more to stay central, it's probably worth the travel time and hassle saved. Although there are some very good restaurants in the Old Town, they are generally a bit more expensive than you can find in other parts of the city. The prices there are comparable to what you would expect from a Western European city such as Munich or Rome. For cheap eats venture outside of the Old Town, and to a lesser extent Toompea Hill, and not only will you find cheaper food, but also local Estonian cuisine, and be able to experience the beautiful Estonian culture.
If you are planning on doing a bit of travel by bus and exploring the many museums and other sights of Tallinn, investing in a "Tallinn Card" may be the most economical solution. With this card, you can gain free bus travel, free access to most museums, free sightseeing tours (including a bicycle tour), nightclub entry, and even free bowling. The card is available in time allocations, 6h, 24h, 48h, or 72h, with prices of EEK130, EEK350, EEK400, EEK450, respectively. Children prices are half of the adult price, though note that some attractions are not available with the 6h card.
It all depends on the season as to what clothes to bring, and what good sightseeing tours there are to do. If you are venturing to Tallinn during the late fall to early spring, be sure to bring warm clothing as the average temperatures are below freezing. Though, visiting in the winter will allow you to visit the Christmas markets in the Town Hall Square and other seasonal festivities. The autumn months generally have more precipitation than spring. Summer is the ideal time to visit with temperatures reaching anywhere up to the low 30s Celsius (80s Fahrenheit), so a short sleeve shirt and shorts is the best way to go. Though, due to its location on the Baltic Sea, weather changes any time of year are possible, so be sure to bring a jacket during the summer just to be safe.${BestWay} Most people visit Tallinn only as a day-trip from Helsinki, but I believe that to fully experience Tallinn, you need a few days to explore this beautiful medieval city. Getting to (or from) Finland is relatively easy, quick, and cheap. From the seaport located in the middle of the city, numerous different ferry lines offer services on the heavily trafficked route between Tallinn and Helsinki. From my experience, I recommend Silja Lines, as they have most often the cheapest fares (though all the companies are relatively priced the same), and their staff is exceptional, both extremely friendly and extremely helpful, going out of their way to assist you. I would choose Silja Lines again simply because of their marvellous staff.
Once in Tallinn, travel to get anywhere is quite easy. The city has a vast network of public transportation available, from buses to trams to trolleys. Though, make sure that the service you want is running, as twice in Tallinn we experienced that that tram we wanted was inoperational due to mechanical problems. Bus fares are extremely affordable, and have services to anywhere in the city you could ever desire to go. It is most economical to pre-purchase a ticket from the kiosk at any bus stations, and then validate it once entering the bus (read my article about validating your ticket so you don't get a ride in the "red van"). A pre-purchased ticket can save you up to half price of the fare. The tickets are a flat-fee, meaning that it costs EEK5 (about $0.35) for students and EKK10 ($0.70) for the adult fare, regardless whether you ride one stop, or ride until the end of the line.
Though, my favourite way to get around any city is by using my two feet. It costs nothing, gives me a little exercise, is environmentally friendly, and is the only way to experience those off-the-beaten-track things that you stumble upon whilst exploring a new city. Since Tallin is not too spread out, everything that one would want to see of this medieval city is within a short walking distance. Even the seaport is only a short walk from the centre of town.
Taxis are plentiful, and depending on where you are looking to go, offer very inexpensive fares, especially if you are travelling in a group.
From journal Traversing Tallinn