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. In respect of Saaremaa Kayaks, the rental fee for a double-seated plastic kayak for a day (transportation and equipment included) stands at 70€. The rental fee for a single-seated kayak is somewhat lower. Faster A-Core rental kayaks are a bit more expensive.
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/.