Of course anything is possible but so many people in front of you in line to book the cabana and just not many cabanas. It also depends on the ship. Wish has 2x the concierge cabins that Dream has, for instance. We have only sailed concierge with a group of friends and family during Tgiving over the years. None of us ever had a problem getting a cabana when we were on the Dream. This past Tgiving on Wish 2 of the cabins (concierge) could not get a cabana (emailing literally at midnight when concierge window opens). One of those is doing a cruise with some other friends in February on Wish and both cabins put in requests for cabanas again the second the window opened and both got shut out. In your situation, you also have Platinum, Gold & Silver that can book a cabana before your window opens. Even during off-peak dates it is still difficult due to the low amount cabanas on CC. Of course, there is always a chance someone can cancel. My guess is that is your best bet.