Time of Year to Visit

Thanks for all the feedback everyone! I have a while to decide what to do. I'm gong to look into visiting multiple islands. Not sure where we would stay on the other islands. For those who have done this how do you get to the other islands? I'm not a huge fan of flying and having to take a puddle jumper freaks me out. Will this be an issue? Can you travel by boat? I've sailed on several Disney ships, but I imagine if there are boats they aren't that big. I guess I'm clueless about all of it. :)

I think I'm leaning more towards going on my birthday as I just want to celebrate over my 40th. My b-day is on July 19th and my son's is on the 16th so we really could both celebrate. My daughter, however, hates this idea s she NEVER (her over dramatic words) gets to do stuff on her birthday. She's the youngest and always looking for fairness so I worry about that a bit. We spent my husbands birthday last year on Castaway Cay. And if we spend mine and my son's in Hawaii my daughter will have an issue. Even though she spent her last birthday at Great Wolf Lodge - must not count because there is no Mickey Mouse.
The planes are not puddle jumpers - they are full size jets. We flew Hawaiian airlines from Kona to Oahu quite easily
 
Thanks for all the feedback everyone! I have a while to decide what to do. I'm gong to look into visiting multiple islands. Not sure where we would stay on the other islands. For those who have done this how do you get to the other islands? I'm not a huge fan of flying and having to take a puddle jumper freaks me out. Will this be an issue? Can you travel by boat? I've sailed on several Disney ships, but I imagine if there are boats they aren't that big. I guess I'm clueless about all of it. :)

I think I'm leaning more towards going on my birthday as I just want to celebrate over my 40th. My b-day is on July 19th and my son's is on the 16th so we really could both celebrate. My daughter, however, hates this idea s she NEVER (her over dramatic words) gets to do stuff on her birthday. She's the youngest and always looking for fairness so I worry about that a bit. We spent my husbands birthday last year on Castaway Cay. And if we spend mine and my son's in Hawaii my daughter will have an issue. Even though she spent her last birthday at Great Wolf Lodge - must not count because there is no Mickey Mouse.

Hawaiian Airlines is a great way to see multiple islands during your visit. We used them last time we were there to get from Oahu -> Kauai (and back) and had zero issues. Definitely not a “puddle jumper.”
 

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