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:
PaddlingCoach offers many quality kayaks (one-person or tandem) for rent, see here: Kajaki, kanuu ja varustuse rent - Kvaliteetne varustus. For example, the popular tandem kayak WK640, which comes with Braca carbon racing paddles, life vests, and sprayskirts, is available for rent for 100€ (transportation to the start and from the finish included). Also included is the free test run in the previous evening, for example, by participating in the safety training or the fairway race (3km).
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€ ( transportation to the start and from the finish is included). 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/.