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Congratulations!! Wow, this is tough.... I was going to choose option 1, but if you are going to pop the question that might change things. It's so dark in the San Angel Inn and you want her to be able to see the ring. lol Kidding aside, I would choose between 2 or 3!
 
Oh, I am no help because I'm essentially about to be on my first trip, but they all sound absolutely wonderful and magical! I wish the best for you both and your family! :) I hope others chime in with more advice!
 
Wife and I will be doing option 1 on our trip in June, except dinner at Le Cellier instead of San Angel.
 

I'd say option 1 but add checking out boardwalk to see if any entertainers out. Wife and I are coming down for two weeks may/June and we have two "date nights" planned. 1st we are going to dinner at Moroto Asia and then just walk around Disney springs. 2nd, close to your #1, and probably be what we like best, dinner ar rose and crown (we just aren't v&a type) and then walk around Epcot world sections, maybe check out entertainment at Boardwalk, see illuminations and then back to resort.
 
We are doing a very similar night! Will likely be getting engaged this day as well!! :lovestruc

AM: Pool/resort time (AKL Kidani Village)
1:00: couples massage and pedicures @ Saratoga Springs (my parents watching the kid- taking her to MK)
4:30: drop off kid at Lilo's Playhouse
Evening at EPCOT; dinner at Teppan Edo or Le Cellier (have both booked- can't decide which yet)
Illuminations (fastpass+ so great viewing)
Boardwalk after park close, then pick up kid at midnight and grab a cab back to resort!! (or maybe I can sucker my parents into picking her up too? :stir:)

Originally had us hanging out at Trader Sam's after EPCOT closed, like you, but we will be at the Poly with the whole family later in the trip for 'Ohana and we will enjoy it then :drinking1
 
I like the sound of 1. The best, because Epcot is my favorite park. However, I might choose Hacienda instead of San Angel (I love San Angel, but it is crowded and what I think of as kid friendly.) hacienda seems more adult. I also am worried about your timing. That is a lot to squeeze in with transportation to and from Poly. I would possibly do Trader Sam's first, or be prepared to skip it. The age of your kids might change my mind.... Are they old enough for big rides? (Might go with MK if not.) have you considered Cali grill? Saw a proposal there that was stunning! Best of luck with whatever wonderful plan you choose!
 
Personally, I'd pick option 3 BUT if walking World Showcase is your favorite thing, I'd do that. Have a wonderful time! :lovestruc
 
We did option 1 on our last trip and it was fantastic. Our dinner was at the table service in Morroco, which is a really nice place to sit and watch illuminations if you can time your reservation right. I agree that the proposal would be more romantic during fireworks.

OR! If you're thinking of going to Trader Sam's, they play the wishes music outside. You could propose at just the right sappy moment during the fireworks there, sitting out on the patio! Follow that up with a moonlit walk along the lagoon.
 
I like 1 or 3 but with the caveat that any questions get popped during fireworks and not dinner. I'm sure dinner would be fine...but during fireworks would be incredibly romantic.

I would choose Option 1 as well. I like SAI though and find the atmosphere to be romantic. Dark and a lovely sky! Tell the server when you chack in the occasion, and even though you may want to wait until Illuminations to propose, I bet the server will help in you seating arrangements.
 
If you decide to do Option 1, switching from Lilo's to Sandcastle Club will save some running around. I also prefer a place for the kids that is closer to where we're going to be in case of an emergency.
 
One other thing, if your planning on being out late, look into having fairy godmothers (yes that is their name) as they will come to your room and baby sit. That way when you do get back, kids are asleep and you don't have to wake them, etc. they are not Disney affiliated but I've heard good things about them.
 


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