Cruising to a new country for the very first time can be challenging. In Estonia, the officials are generally English-speaking, the currency is the euro, and regulations are fairly loose, so no worries.
Estonia is a proud member of the European Union and part of the Schengen Area, therefore there is no problem when arriving from other EU countries. Just contact the harbour master via mobile or VHF prior arrival and enjoy your trip. To help you – State Port Register will provide an overview and contacts of all the ports registered in Estonia.
When arriving from Third Countries (non-EU countries, like the Russian Federation) the first stop should be preferably in ports listed as border checkpoints to contact officials and pass customs procedures shortly after mooring. For example, suitable destinations are Dirhami (north-west Estonia), Sillamäe (north-east), Praaga (Lake Peipsi), Roomassaare (Saaremaa Island, open 24 h). You must also report in to the officials at least one hour before leaving Estonia.
To clear customs, the list of crew members must be presented. Also keep in mind that it is not allowed to bring any meat or dairy products from Third Countries, and a limited amount of tobacco products, alcohol, and motor fuel are allowed. See more from Tax and Customs Board webpage.
These are the most convenient routes when arriving to Estonia with a sailboat: