Day One: Thursday
Lunch is a good place to start. Hit Tijuana Flats for fresh, zingy Tex-Mex. There are a variety of locations, but the one on SR 436 in Casselberry is nice and roomy. Enjoy the funky décor, watch some sports on the screens. Be sure to sample the Hot Sauce Bar! It ranges from mild and tasty to melt-your-face. Good prices on cervesa. The Ultimate Nachos will feed two as a meal, the burritos are awesome any way you like "em.
After lunch, head over to Harry P. Leu Gardens. This place is packed on nice weekends, so hitting it during the week is a must. It costs a couple of bucks but is worth it for a nice stroll. What sort of plants do you fancy? Roses? Got "em. Bamboo garden? Wetlands? Butterfly garden? They even have a vegetable garden and notes on Florida history. You may be able to catch an event on orchids or potted herbs. This place can take an hour or four, depending on your level of interest.
You are close to downtown, so you might as well head there next. Wander around the ViMi, that is, the Vietnamese District. Have a Bubble Tea. Check out the import stores. You will find the streets downtown a little confusing, once you turn down Orange Avenue. Fortunately, this is the only area in the city navigable by foot (aside from International Drive). So after ViMi, drive over a few blocks to Church Street Station.
Shell out for a decent parking garage, I'm keeping you here for a while. First, check out what is going on at the comedy club, Orlando Improv-see when the show is. But don't plan on eating there! If you want to check out the Church Street Station itself, excellent. Otherwise, there are loads of shops and restaurants off the side streets of downtown and you don't have to pay to access them. You have your options for dinner, Manuel's, White Wolf Café-it all depends on your price range! But avoid the chains in this part of town. No reason to go with familiar when there is all this local fare to choose from!
After a late dinner (or a normal dinner and a comedy show), you'll notice the atmosphere changing. Around 9 and 10, the clubs start to open up. And there are a lot of them! All the way up and down Orange Ave and near Church Street. But it's a Thursday, you say? Yes! The locals love a Thursday downtown, especially the young and the hip! Stay away from Paris Hilton's monstrosity. The kids love Bar-B-Q Bar, Independent Bar, and hanging around wherever has the best drink specials. The little dance floor at Independent Bar (formerly Barbarella's) heats up after midnight with the latest hipster music-poppy, fun stuff. Watch them shake and jerk, admire the hairstyles, or enjoy cheap drinks and awesome bartenders! An alternative to any of the clubs I mention throughout is Parliament House, if you are gay or very, very gay friendly. Additionally, Southern Nights is slightly lower key-both near the downtown area.
Day Two: Friday
After last night, might you be wanting a hangover breakfast? First Watch on 17/92 a.k.a Mills Ave, has great options but can involve a wait any day of the week. Back in Casselberry is a hole in the wall place called Bagel King. Eggs, bagels, pastries, and home-style potatoes for cheap. You'll notice the chatty wait-staff really knows their regulars and they'll treat you just the same!
After getting fueled up, take your coffee over to Park Avenue. On one end is Rollins College, the home of education for the rich and spoiled here, and on the other end the street fades into elegant residential areas once past the Morse Museum which is home of the world's largest Tiffany Glass collection. Park Avenue is shopping heaven! Cute locals stores, art, fashion, a few chains and a collection of eclectic restaurants and wine bars all set in a gorgeous landscape of roses and oak trees dripping with Spanish moss. You've got your work cut out for you. Someone wants to shop and the other doesn't? Plop yourself down somewhere and sample wine. Don't miss out on the specialty chocolate shops, and try something new like chocolate dipped potato chips or lavender truffles. No doubt you'll have to fight it out about where to eat lunch!
*All right, now, I know I said you wouldn't go near a Theme Park. And you're not, really. It just happens to be on the same I-4 exit. You are going, after you finish shopping, to Downtown Disney. From Park Ave, the drive can take a while. This place is a good way to spend the entire rest of your day. Wander the shops, get sucked in to the Virgin Megastore, enjoy the screaming children in the Disney Stores and then eat dinner. After dinner, you are going to make it ON TIME to a show at the Cirque Du Soleil. This is the most expensive thing you'll do all weekend (on this itinerary) and you must get tickets in advance. But it is worth every penny.