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For what it's worth Princess and Holland America have been cruising to Alaska the longest.


Look for an itinerary that visits Glacier Bay...it's a highlight when cruising Alaska.


Prices are usually the best (read cheaper) at the beginning or the end of the season.  I have cruised to Alaska in September.  It rained every single day.  That being said you risk rain in Alaska at any time of the year.  The autumn colours were spectacular.  I have also cruised to Alaska at the beginning of June (as I recall the ship left Seattle on June 4th).  The weather was superb.  In fact we got sunburned on our deck and we were able to sit out on the deck every day and enjoy it!  I did miss the fall colours though.


If the budget will run to it do book yourself a balcony cabin.  You will be able to step out and watch for wildlife whenever you wish....even though you may have to put on a sweater or jacket!


Pack so that you can dress in layers no matter which month you book your cruise in!  When the ship is at sea it will be chilly whenever you are out on deck.  Pack somekind of windbreaker/waterproof jacket "just in case"!


If you have a good set of binoculars...pack them!


Have fun planning your cruise.


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