I haven't been for several years, but I wouldn't foresee a problem. If a pontoon isn't available in Douglas, rafting on the wall will be available, or even rafting on the visitors' pontoon in the outer harbour. ( Not in a NE'ly though ). Ramsey also should have plenty of space on the walls, but you might have to raft out. Last time I was at Ramsey they didn't seem go out of their way to make yachts welcome, but I'm told its better now. You might have fishing boats as close companions though.
2) Port St Mary alongside was empty for last year's TT ie only 6 boats max on 4 ladders at any time during the whole period. Peel was full. Douglas had spare places apart from Thursday night.
Hi A_7, no sorry, don't have a Caterham. Used to have bikes and used to go to the IoM for TT and really enjoyed the atmosphere. Mad Sunday was really MAD and the actual races were/are awesome. If I sail over, the trouble is I could only fit a push bike in the boat! Not sure how I will feel about that!
We have been a number of times in the past To both the TT and the MGP. went alongside the harbour wall in Douglas on the last day and had a grand time with the peeps waiting for the ferry's Make sure you have plenty of Tea and Coffee O and some booze and you will have a good time and if you stay on board it will let some have a little brake and go off in the town for some grub with out loosing their place it Que all were thankful and appreciated that after queueing for over 12 hrs or all night Go and Have Fun.