I always hint around and ask my kids what they'd like. I even have a neighbor or friend ask them. You have so many ideas and options so far, I'm sure he will be excited with any of the choices you've come up with. Sorry I couldn't help more. My son is older. I always surprised what makes it past the 6 month mark at our house, you know...6 months after they get things what do they still play will routinely, and what gets played with once in a while. As far as coming up with the other 6 gifts, my kids love books, so a book from their favorite series is always a hit. Gift card for lunch/dessert at a favorite place is a fun day just for them, especially if they don't always have the chance to have you all to themselves. I'm sure others will come up with better ideas :)

Diane- books are always given 1 or 2 of the 8 days of Hanukkah.  We have a very extensive library at my house b/c I love books, now the children love books too.  My 6 year old is getting my old Flip and he is so excited, so I want to give something to my 5 year old that would be equally as exciting KWIM?

Aracely- thank you so much for the MobiGo review.  Do you think a 5 year old would be engaged?

It's not even Thanksgiving yet and you are already in a panic? Calm down! I'll reserve my panic until the Thanksgiving  leftovers are gone. 

In the mean time, I am handing over the target and toys R us catalog to the kids along with a highlighter for each of them. 

Don't panic....does he "wish"??  I wrote a blog on this...let him peek through a toy magazine and circle what he wants?? 

For my son't 5th we got him the nintendo DS.  They have so many games (educational and fun) and I knew it would last years.  He loves it.  Of course I didn't get a DS for my oldest until he was 7, but with my younger son seeing my older son he got one younger. 

Good luck!!!  You'll find the perfect gifts!!

Megan- Hanukkah starts 12/1 so I kinda' have to decide now since that's 3 weeks away.  Since it essentially starts 5 days after Thanksgiving I have to at least be mostly done.

Jodie- I did give him the toy magazine and that's when I decided on his b-day present from what he wished for.  I want to get him a DS, but our budget is very tight due to DH's job loss, so I can't afford it.  PLUS I got one for DS1 last year and DS2 "borrowed" it and lost it.  I feel like if I get 1 I have to get 2 b/c DS1 deserves to have one back right?  That is definitely not in the budget.  :(

I think the best gift you could get him which a gift that will keep on giving is an xbox. You probably laughed just then or think im an idiot. But think about it. It will entertain your whole family and it gives you easy gift ideas in the future. There are some awesome games for little kids like lego star wars and up the video game. When you think of an xbox dont always think of the shooter or car games because these are not good for young children. Well if this did not help im sorry but i bought one and I could not be happier, happy hanukkah! 

This is so ironic, I read this post, and having two girls myself, had zero suggestions! But then I saw this link on Twitter yesterday!  Good timing...

http://www.lilsugar.com/Best-Gifts-5-Year-Old-Boy-12009067

Good luck!