Mine is rather "pedestrian" but I would say going to Hawaii for a couple of weeks would be my dream vacation.
As for Akihabra and Japan in general, I would love to go there. Unfortunately I couldn't call it a vacation because I would be mentally & physically drained taking in the sights and exploring the shopping districts!
Nothing wrong with Hawaii. If you ever go to Oahu, Hanauma Bay is a spectacular sight and snorkeling there is amazing. You are in the ocean swimming in the crater of a dead volcano.
Also hike up to Manoa Falls. It's Jurassic park level rain forest (the restaurant at the bottom is terrible though.)
As far as restaurants go check out Franky Fresh it's an 80/90's style burger joint with an SNES and games you can play while you wait.
I did a video review here:
http://youtu.be/UW3BC9L0_14Also good on that island is Peal Harbor. You can take an individual audio tour narrated by Jaimie Lee Curtis and the aviation museum is nice.
There's horse rides on the beach at sunset.
The Polynesian Cultural Center is also a good way to spend a day. It's basically a Polynesian theme park. To get the full impact make sure to get tickets that include the fireshow "Ha Breath of Life". Also if you go on your birthday and attend the luau they dedicate a portion of it to you and bring you on stage.
If you want a good place to stay Turtle Bay Resort is on the opposite side of the island but is 5 star.
Wakiki will be temping with its cheap hotels and close proximity to stuff but it's like the West Philly of Hawaii.
This is all easily doable for 3 people in 6 days for under $5,000 including plane tickets from the US.
Guess you all know my dream vacation now. It was last year.