I have personally gone on Friday and Saturday. The boats (Tango and Lambada with the preference being Tango) do a good job of finding the action. On Friday the action usually starts in Simpson Bay and goes around the island. You will be close to the start and probably not go too far so there should be a lot of action. On Saturday (if I recall correctly from last year) we had to motor for quite some time to find the boats. I don't think you could go wrong with either Friday or Saturday.

Even though this year will be less crowded, the Tango often books up quickly so I would not hesitate too long to make your booking. Do make sure you specify the boat you desire. You have two times slots available on Friday and just a morning slot available on Saturday. If you are really into sailing or just watching, I would book both Friday and Saturday morning. If you just want to go out one day, I would probably lean towards Friday due to knowing how the race usually gets going. I have never been on the Sunday trip.

Another nice option to watch the boats on Friday is get to Simpson Bay Beach or my preference is Mullet Bay early and watch from there as the boats come by. Karakter Beach Bar is an option for Simpson Bay (get there early) and they have food and facilities. Mullet Bay may or may not have food and facilities but is a really nice spot to watch the boats sail by in the distance.

Feel free to send me a private message if you have more specific questions.

Have fun!