Technically, there are Gay Days events (such as a cruise and some Memorial Day-related parties starting on May 26th, but here's the Gay Days events I recommend:
Official Kick-Off: Tuesday May29th at Orlando Science Center-Ciocktails Under the Cosmos (Great drinks, great crowd, lame auction, great entertainment, speeches from both the Orlando Mayor and a City Commissioner, $25 ticket benefits Be Real, a local organization that addresses issues of concern to GLBT youth and their families)
Wednesday, May 30th: TBA (Most people go to Universal this day; for whatever reason, even though Universal has recruited the gay dollar, they have not been an official destination the past two years. I can't say why, but looking at the agenda, one can figure out what goes on behind the scenes.)
Thursday, May 31st: Gay Day at Disney's Animal Kingdom from 9am -6pm. Also, check out the official Gay Days Expo at the Hotel Royal Plaza on Hotel Plaza Boulevard in Downtown Disney. Participants last year included Macy's, 2xist, Virgin Megastores, Bloomingdale's, Metropolitan Community Church, and other gay-friendly businesses offering special deals, tons of freebies, and plenty of eye candy. Oh-and booze. Right next door, in the hotels' courtyard, is a car expo (this year's looks like it's just Satyrn but last year it was race cars, some antique cars, and so on.)
Thursday Night: Many options based on your own preference, from the Gay Days commitment ceremonies to Nelly Furtado to Junior vasquez and so on.
Friday, June 1st: Gay Day at Disney-MGM Studios 9am-midnight. (In addition to Gay Days, this is also a Star Wars weekend so gay sci-fi geeks have a total head rush this day.) Inaddition, the stages for One Mighty Party will be installed on this day so you can plan your best Donna viewing position ahead of time. (She'll likely be performing on the stage that wiull be placed in front of the Sorcer Hat icon.)
Saturday, June 2nd: Gay Day at Magic Kingdom (All Day) Be sure to stake out a spot on the parade route early somehwere from main Street to Cinderella's Castle fir the 3pm parade. Crowd seems thin first thing in the morning but if you're going for some quick lines, it's best to miss a little sleep and show up early. By afternoon, you'll be in very long lines--but with very good looking men.
Saturday Night: One Mighty Party w/Kathy Griffin & Donna Summer. Party starts at 8:30 with Kathy Griffin. Donna's time TBA but likely around 11pm or midnight. Last year, I think Gloria Gaynor hit the stage around 12. Tickets cost $85 for the Saturday night event--and get them early.
Sunday, June 3rd: Gay Day at Epcot
As for where to stay, the official Gay Day hotel for men is the Hotel Royal Plaza which is located right inside Downtown Disney on Hotel Plaza Boulevard but there are numerous hotels within walking distance, all within Downtown Disney area (The Hilton, The Grosvenor, Best Western, and so on). If not staying at any of these hotels, you might want to consider two things: staying on Disney property (as that ensures you can get around using the Disney Guest bus system) or renting a car. WDW is a huge place and aside from the Downtown Disney area, it's not a place you traverse on foot. Each portion of the property is relatively far from the other--particularly in the June Orlando heat. I recommend staying at either the Hotrel Royal Plaza or one of the other hotels in the immediate vicinity; stay too far away and you won't feel part of it all. (Some of the official Gay Day hotels are located off Disney property and while hotels such as Gaylord Palms are great hotels, the experience just isn;t the same. Stay there some other time.)
The Donna event is $85 in advance. Theme park tickets I don't know about; I get in free but I think they average about $60 per adult, per day, with the rate lowering slightly with multi-day tickets.
Shopping at Downtown Disney is a msut for Disney memorabilia, including the Disney-authorized rainbow Mickey Mouse head pin (found at World of Disney and Disney's Pin Traders). Non-Disney shopping is best at the Mall at Millenia and the best designer outlet shopping at Premium Outlets Mall.
And gifts for me may be dropped off at my house.