Disney "Strategy" - Your advice please!

[misslissa]

Well, my quick "weekend" 3 night trip has been planned for May 20-23 for quite a while now... May 20th is a Sunday because I usually work Saturdays. Well, I just got my schedule for May and of course I have May 19th off. I checked the airfares and it looks like I could move my flight to (arriving) 7pm on the 19th without any charge instead of arriving at 10 am on the 20th.

It would cost $100 USD more per person to arrive in the morning of the 19th... which DH doesn't really want to do because we've spent so much already. But, it would add an extra day to our trip.

So, I'm looking at different ideas.

Should we book a late flight (no charge), stay near the airport and get to WDW early in the morning?
Should we book an early flight ($200 USD more), stay near Disney and add a day onto the trip?

And, if we do either... what do we do about transportation to and from WDW/hotel? We have NEVER ventured outside of Disney before and I'm considering picking up a rental for that day and maybe doing something outside of WDW...

What would you do???

 

[BitsnBearsMom]

Who are you flying with? I just booked air tran non stop leaving Rochester at 8am and going into Tampa for $84 on the 19th - we're coming home on the 22nd non stop again at 6:45pm for $59 per person from Tampa also. My dh was going to rent a car anyway so having a bit longer drive to Tampa was no big deal for us!

 

[MECH8T7]

Would this work?:

Fly out the evening of the 19th and book a night at one of the All-Stars or POP. Use Magical Express to get you to WDW (if you have ME handle your checked luggage make sure you pack a carry-on with all your PJs and change of clothes for the next day in case there is a delay getting the bags to your room). The next day, have the resort transfer your bags to SSR while you check-out and head off to the parks or you can take the bus to DTD and walk to SSR?

 

[misslissa]

Would this work?:

Fly out the evening of the 19th and book a night at one of the All-Stars or POP. Use Magical Express to get you to WDW (if you have ME handle your checked luggage make sure you pack a carry-on with all your PJs and change of clothes for the next day in case there is a delay getting the bags to your room). The next day, have the resort transfer your bags to SSR while you check-out and head off to the parks or you can take the bus to DTD and walk to SSR?

This is a great idea! I checked into it and it is going to be an awesome price!!! Yay! I'm going with this idea... we'll be able to spend some time that night at DTD.