I did a surprise 30th trip to Disney for my DH (I won't reveal exactly how long ago, but let's just say it was less than 8 years ago, but more than 6).
I recruited my MIL, FIL, SIL (and her boyfriend at the time) to come along with us, and exchanged my OCD planning skills for their complicity in the ruse. Of course, what they didn't know was that I had a surprise or two in store for them, as well. I think that I frightened myself with my capability for deceit... Here's what I remember went down:
Room:
MIL booked the room through Disney (we rented a Grand Villa at the Boardwalk for all of us to stay together). That way, no paper trail for my husband to "stumble" onto. I paid her our portion in small enough installments that DH wouldn't notice...
Finances:
I set up a fee-free savings account and would withdraw a little cash now and again from our joint account and deposit it into that account. I also was reimbursed for travel expenses from work on a monthly basis, and I had the reimbursement be split equally into two checks - one went into our joint account and one was deposited in the "secret" account. (Should I be concerned that DH never noticed that the reimbursements suddenly were smaller (by half!)??? And he's in charge of our finances!!??!!) I also started buying Disney Dollars in small amounts and tucking them away safely. I was surprised how quickly they added up, but then I had a year to plan (and buy)! I think that I also recall "demanding" my portion of our tax refund for "clothes shopping" - then I'd buy an item or two (on sale), and put the rest in the secret account.
His Work:
I called his boss, explained what was going on, swore/threatened him to secrecy and was able to secure the time off with no problem. I also enlisted the help of his assistant to make sure that there weren't any "emergencies" while he was away. Additionally, it gave us something to giggle about when I called his office the usual 200 times a day.
The Flights:
As DH's and my birthday are within a month of each other, my in-laws purchased our flights as our birthday presents. Again, no paper trail. DH was presented with his tickets at a family brunch 5 days before we left for Florida. I told him that because of the trip having been a secret, and my not being able to blow the budget without him knowing, we were staying at All Star Sports (which will be important later). I also told him that his sister had put the room on her credit card, and we had to pay her back (which will also be important later). He was so very stoked...
The Journey:
Our flights were at the crack o' dawn from LaGuardia (I remember it being dark going over the TriBoro Bridge - so that's got to be early). My SIL, who lived several blocks away from us, called the night before we were leaving and left a message asking me to drop off the "payment" for the room that she charged for me, as she needed to pay her credit card bill ASAP. So, I diligently made a fake envelope and told my husband that we would have to swing by her apartment building on our way to the airport and leave the envelope with her doorman. (Seriously, why does this man still trust me??) We pulled in front of her building, and out walks his sister with her suitcases. His jaw hit the floor. He had NO idea. I think he even got a little choked up - we all did, really.
The Hotel(s):
We rented a sweeeet electric blue Chrysler Sebring, put the top down (even though it was January and probably 50 degrees, but it was FLORIDA, dammit!) and headed off to our destination - All Star Sports. Bwaaahahahahaha. My SIL thought that we were just going there to continue the charade and kill time before we headed to the BW, but little did she know that when we parked the car, and headed into the lobby to "check in" (DH was SOOOO confused why we were leaving the suitcases in the car during check in... I just pulled the "I've been planning this trip for a year. My friends online told me that the best way to check in is to bring the luggage later!! Don't question me!" trick. Hee!) that I had arranged for her boyfriend to be waiting for us! He had flown in from business school in Chicago just for the occasion. Her jaw hit the floor. She had NO idea. I think she even got a little choked up - we all did, really. Hugs, kisses, laughter all around. THEN, SIL, her BF and I informed my DH that since there were ACTUALLY four of us, we had done the research, and it was cheaper to split a 1 bedroom DVC room and that we would switch off sleepling on the pull-out sofa. So back we pile into the Sebring and head over to the Boardwalk. We pulled into the driveway to drop our bags off, and there are MIL and FIL standing at the entrance. His jaw hit the floor. He had NO idea. I think he even got a ilttle choked up - we all did, really.
The Room:
We had a beautiful villa overlooking the Boardwalk. From the time that I started planning, I would buy little trinkets and things and began making 3 baskets (one for each couple). I had the baskets shipped down about a week before we left and they were waiting in the room for us, along with some chocolate covered strawberries and the chocolate carousel that I had ordered from the BW. The baskets had tons of little things - Shout Wipes, Breath Mints, sunscreen, disposable cameras, I had sent away for park maps (and had them sent to work) so they were in the baskets, I had also ordered Mickey ponchos for everyone, so I put two in each basket, and I put a little plastic figurine of Tigger (DH's favorite character) in each basket and asked everyone to try and incorporate tigger into as many photos as possible. We got some HILARIOUS shots, and after the trip, I made everyone an album with handwritten comments about every photo. Now that we were settled in, I was just happy that (almost) all of the surprises were done. After dinner on the first night, I told everyone to meet me at the boat dock. What none of them knew was that I had reserved an Illuminations birthday cruise. I think the quote from my MIL when we were in front of the bridge watching the show was, "I feel like I am in a movie." I think that's how Disney makes me feel too...
This turned out more as a trip report from 100 years ago than I had intended, but perhaps you can find something in it that is helpful! Have a wonderful time planning (I enjoy it almost as much as the actual vacation, I think!), have a great time plotting and most importantly, have a great time in The World!