The easiest way to reach Kuressaare from Tallinn is by plane. Please look up the Flynyx website and book your tickets well in advance. Tallinn Airport is located 4 km from the Old Town and Kuressaare Airport is less than 3 km from Kuressaare Castle Park. Kuressaare is easily accessible by bus if you are traveling from Tallinn, Tartu, and via Pärnu from Riga (https://www.tpilet.ee/en/).
Kayak rentals:
For kayak rentals in Kuressaare, see here or here.
Accommodation:
Kuressaare has a large number of options when it comes to accommodation. Hotels and spas are plentiful, while Airbnb is also a good option.
For more information on accommodation and sightseeing on Saaremaa Island, please see https://visitsaaremaa.ee/en/.