Whew lots of questions--you have come to the right place. On my 1st cruise we were in a cat9 with the big porthole it was an awsome room. Cruise 2 we were spoiled by a handicap assessible room 6154 -last room on back of ship verandah was 1/2 the back of the ship. After that it has been hard to book a non verandah room, as I have done it twice but ended up before the sailing paying the difference to get verandah. Our 3rd sailing we were cat 6 mid ship don't remember the # it was a great location, 4th sailing we booked cat 7. I was a little concerned that it would not be as nice as the 6 but worried for nothing. I almost actually liked it better. I can't specifically say why, maybe it was just that it was a little cheaper than a 6 but still had an open area to outside. While midship locations are very convienant they also get much more traffic -noise in the hallways of others walking by, and the elevators are always busy / full / impossible to use so you end up taking the stairs more or walking forward or aft.
You won't be able to join CC club until you have sailed your 1st time then you would automatically be in it. Being a CC member means that you get invited to a private pre dinner cocktail party and get to meet the captain. You may also qualify for a small credit if you rebook and sail within a certain amount of time but it has been rumored on this board that
DCL may discontinue that. You also get a small gift in the room like a picture frame or tote bag (on your 2nd sailing)
On our 2nd cruise when we went with a group of 6 we booked 3 cat 6's ---if we had been smart we could have booked only 1 and 2 cat 11's or 12's across the hall. It would have saved bundles.... but everyone got to enjoy the verandah so looking back I am not sorry we did what we did ....if it ever comes up again for us we will do it the cheaper way (we will be the ones in the verandah!!
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As far as your months... I have only sailed Sept,June,Sept,Oct. June was good time but so were the others. Not much help am I
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Hopefully this will give you some help/ideas. I want to go again, we had 8/31/02 boked for the 7day Western but just had to cancel a few weeks ago due to some unexpected $$$$$$ car repairs. Dreaming of the day when it will be my turn again! Have fun on your cruise when you go.