Whether you're going for the first time or you've been a dozen times, Gasparilla can still be a challenge, what with the parking and the uncertainty of the weather and the traffic and the crowds.
But we've been a few times, and we've come up with this laid-back way to enjoy the day. It's not for everyone, though, so feel free to make your own variations.
Our perfect Gasparilla day starts about 10:30 a.m. and envisions most of the time spent on Harbour Island near the Westin Hotel, witnessing the majestic flotilla of boats, then a nice lunch as we wait for the parade, followed by a jaunt into the crowds to experience the full-blown effect of beads + booze.
Park and party. Start by naming your designated driver, or just remember to know when to say when. We love the convenience of the Channelside district for parking, and use the main short-term parking terminal right across from the Florida Aquarium. You can reach it easily by going through Ybor City and turning left onto the Nick Nuccio Parkway. Follow the signs to the Aquarium/Seaport and hang in the right-hand lane. Watch for short-term parking (not the cruise parking) and turn right, then a quick left to get to the garage. Rates will likely be $10, according to a parking attendant we talked with on the weekend before the big day. But be prepared to pay more. There is also parking along Channelside Drive toward downtown near the St. Pete Times Forum if you want to take your chances on finding a spot. (Hint: Go before 10 a.m. and you should find plenty of spaces.)
Get ready to r-a-a-m-m-b-l-e! Now you'll have about a 10-minute walk over to Harbour Island. Pace yourself by going into the tourist info center at Channelside. Surely they will have pirate-related souvenirs. Then look for the Hut Bar and Grill (formerly Newk's), where you can enjoy a bloody Mary to start your day. Or check out the Tampa Bay History Center. If the Columbia Cafe is open, you should be bale to get a beverage there. Then cruise through the outdoor concourse at the Forum as you make your way toward the Marriott Waterside. Be sure to meander behind the hotel so you can marvel at the cabin cruisers docked there. Just before you get to the bridge that leads to the island, hang a right and traverse the "doggie walk" so you can access the bridge. From there, it's a quick hike to get to the Westin.
The Jackson's hive. You will be asking yourself, "Wow, why didn't I think of this before?" as you make your way through wenches and pirates and dogs and beer stands and the smell of burgers on the grill in the hub known as Jackson's Bistro. All of the normally chi-chi club's accoutrements have been stripped down so that maximum revelry can be attained without worrying about pricey cabana furniture. You'll want to soak it all in, so don't be too eager to launch into an alcohol binge just yet. Wander the waterfront and enjoy the show of people and obnoxiously large yachts -- serious vessels that require their visitors to slip their shoes off before boarding so as not to spoil the carpet. (Dream on if you think you can get on one, but feel free to make a fool of yourself trying.)
Your ships have come in. Whatever you do, don't leave the island until you've seen the Gasparilla invasion somewhere around 11 a.m. You'll see the small boats coming up the channel first, and the people on board will make ridiculous attempts to throw beads to the partiers on the water walk. Most will fall far short into the channel, so don't even bother yelling for them. Then the Jose Gasparilla will appear in all its pirate glory, with flags flying and guns booming and pirates packed to the top of its riggings. You will clap and hoot and yell and try to take a picture that will capture this spectacle. You will understand, at once, why this has been going on since 1904.
Food. Must. Have. Food. Why not stretch your legs again and head toward the Marriott? You'll meet lots of fun drunken people along the way. Head for the lobby bar, and order something expensive while casually asking for the bar food menu. Meet the exasperated look of the bartender with a steady gaze and tell her, "Hey, I know you're busy, but we'll make it worth your while." Tip well on the expensive drink to show you mean it. A nice bonus for you on this Gasparilla pitstop is an ATM in the lobby, and a really nice restroom to freshen up. (Be sure to tip the attendant well, ladies.)
Love a parade? Relax, it takes those pirates forever to get on buses after the invasion, board their floats and make their way downtown along Bayshore. So if it's 3ish, you can still safely take a hike west either on Brorein (probably less crowded) or Channelside Drive to try to catch some of the parade, which now ends near Curtis Hixon Park. It's the end of the route, but you can still score some beads. In fact, people and businesses are giving away beads all over the place, so no need to flash and dash the entire day. (Hint: Try to find a bicycle rickshaw driver who can ferry you where to want to go. Pay well. It's worth it.)
Wind it up. If you're still fresh and not ready to call it a day, head back to the Westin and mix with the well-lubed partiers there. But be aware that private events will be starting soon, and previously cover-free clubs will be charging. There are some stadium steps that look out on the channel, so plop there if the sun is hanging low, and watch as the marine patrol tags drunken boaters. If that doesn't sober you up, get yourself a Red Bull, sans vodka, please.
Decision time! Either you can continue indefinitely into the night, hitting the Pirate Fest downtown before wandering back to the partying in Channelside or Ybor ... or, you can take home some fond memories of your laid-back Gasparilla and be home in time for a nice dinner.