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The automatic upgrade to the next status level does take some time (2 weeks or more) for RCI's system to happen, however you can ask the Loyalty Ambassador or the Diamond Concierge on your first leg of the B2B cruises to manually change your status and they may do so. The concierge did that for us during a B2B for diamond to diamond plus. Never hurts to ask nicely.

Was on Ovation in September and had a great time. You have got all the major sights. Walk through the Sitka National Historical Park and cross the road to the Raptor Center. Very easily walkable from the bus drop off point near downtown Sitka. There is/was a reindeer hot dog station near the bus stop too. White Pass Scenic railway definitely a great excursion. In Juneau, there is also the Mount Roberts Tramway - if it is a clear day, you will get great scenic views. You may have to allow a bit more time if you want to hike the easy trail to the falls, closest to the Mendenhall Glacier. Consider too Tracy's Crab Shack in Juneau, although they did not have any king crab in September (not sure if any still now).