First timers, what would you do?

Always recommend Disney resort first. But if you use offsite hotel try using the Priceline (hidden hotel) forgot the name search. If you search for Disney Bonnett Creek area sometimes you can snag a Disney hotel for super cheap. Someone will think of it, too early for me this morning brain not working. lol
 
So, "you will need a car" sounds like rental almost - a rental is definitely not needed. I've stayed at the Swan a few times, and though I don't have interest in Legoland, I doubt I'd rent a car even if I did.
You are right. You don’t necessarily need a car and Uber or Lyft are good options. Legoland is about 40 minutes from Disney. So it’s going to be a more expensive ride. We did it a couple years back and rented a car for the day. It was less expensive than Uber. This was prior to the Disney hotels charging for parking though. So they would need to do the math to determine their best options, especially if the OP chooses to do the other side trips that they described.
 
Another vote for the Swan.

Yes, Disney will move your bags from one resort another. When you get up and are ready to leave give your bags to Bell Services and tell them where you want the bags transferred, then go about your day. make sure that you have everything you will need until some time that evening. Then go to the theme park that you have for that day. When you are ready go to your second resort to check in. When you are in the room call bell services to deliver your bAgs to your room. be aware that it might be evening before the bags are at the second resort. If you will want your bags earlier then take Lyft or uber and bring your bags over yourself in the am, check in and go about your day.

It is really easy to do a split stay. We do it all the time.
 
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I agree with others on splitting it up. You can stay at Swan for 2 days and Disney will transfer your luggage to a Disney property hotel. We did that before, and that allows you to take advantage of the strengths of different properties. Taking the boat from the Swan to two parks is awesome, but it is only helping you at two parks
 


Ok, new round of questions. Way back when we did our DCL cruise, I bought gift cards at Target and paid for them with my Red Card and got 5% off. It was relatively easy to load the gift cards into my Disney Vacation Account, but I know they’ve stopped that program. Is it still easy to pay for a trip with a gift card, or is it not worth the hassle?

Next question is Swan to Magic Kingdom for Early Morning Magic. What’s my best bet, transportation-wise? How long does the bus take from Swan to MK? Are we better off driving?

Thanks for all your help!
 
Ok, new round of questions. Way back when we did our DCL cruise, I bought gift cards at Target and paid for them with my Red Card and got 5% off. It was relatively easy to load the gift cards into my Disney Vacation Account, but I know they’ve stopped that program. Is it still easy to pay for a trip with a gift card, or is it not worth the hassle?


Very easy. We pay for every trip with Gift Cards we get at a discount. Great way to save $$.

Next question is Swan to Magic Kingdom for Early Morning Magic. What’s my best bet, transportation-wise?

Bus.

How long does the bus take from Swan to MK?

About 10-12 minutes drive time.

Are we better off driving?

In our opinion, no.
 
I'd forgo Legoland ... your 7 year old is at the top end for it age-wise, in my opinion and then have 5 days for your in and around Disney. Of your hotel options, I haven't stayed there, but I think the Swan would be a good choice with the ability to walk to HS and Epcot, plus the boat and buses. Although I am a huge fan on staying at Disney owned hotels (but not a huge fan of All Star, lol).

I totally agree. Legoland would be nice for toddlers, but I wouldn't bring a 7 year old there.

I love the Swan, but if you're flying in, staying at a true Disney Resort gives you the whole Disney bubble feel (magic bands and Magical Express to and from the airport). A family suite at the All Star Music would be nice, but honestly with just one child, a room is fine too.

Don't underestimate the size of Disneyworld. I've been well over 30 times, and never seen everything!

Also, my kids' favorite park was always Epcot. They do love Magic Kingdom too, and Animal Kingdom is amazing as well.
 



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