Flatwoods Park http://outdoortravels.com/biking_fl_overview_flatwoods.html
There are two entrances to the park - one off of Fletcher Avenue and one off of Bruce B Downs (both on 75 north of downtown). The Bruce B Downs entrance is a lot easier to get to. Once you park in the lot you have a two mile skate on the extension out to the 7 mile loop. Smooooooth! Also the home of Squiggy Classic Inline http://www.squiggyclassicinline.com/
Upper Tampa Bay Trail http://outdoortravels.com/biking_fl_overview_uppertampabaytrail.html
This one can be a little tricky to get to, but it's closer to the airport. It has a few stops, but it's got a lot of character! Lots of twists and turns and even a few tiny hills! To get there take the Veteran's Expressway north to Linebaugh Avenue, go right. Then turn right on Wilsky. The trailhead is on the left before the bridge (very easy to miss!)
Suncoast Trail http://www.dep.state.fl.us/gwt/guide/regions/westcentral/trails/suncoast.htm It's actually hard to put this one on the bottom of the list because we love it too :) It's 40 miles long, but weI have to warn you that the South section is pretty darn boring. It's very flat with not much in the way of scenery. We do a lot of our hill training here now, starting at SR50 and going north (about an hour's drive from Tampa). Believe it or not, it's incredibly hilly up there. If you start closer to Tampa, there's another park you can skate into called Starkey Park. It's pretty but the pavement's fairly rough.
Bayshore Boulevard http://goflorida.about.com/od/tampa/ss/tampa_downtown_2.htm
The longest uninterrupted sidewalk in the country! It's definitely nice to run/walk on, but we wouldn't recommend skating on it. There are waaaayyy too many people with kids/dogs etc. trying to occupy a very small space. On top of it the cracks are very irritating on skates. We are bitching about it, but we would bet a lot of people would kill to have a trail like it. The good thing about it is it's right next to the downtown area so it's very convenient if you're staying there.
These are actually just a few of the local trails. There are quite a few places to skate on the Pinellas side (including some we have never been to). The biggest one over that way is the Pinellas Trail http://www.pinellascounty.org/trailgd/ which is very long but also sadly unmaintained. The pavement is very rough and dangerously cracked in some places. It would be awesome if they repaved it.
Further north is the Withlacoochee Trail (you can laugh, it's ok) It's a bit out of the way though. http://www.dep.state.fl.us/gwt/guide/regions/crossflorida/trails/with_state.htm It's a very nice trail with so-so pavement.
If you have another trail close to your home that you would recommend other skaters to try - please send us an email at firstname.lastname@example.org and we will update this page with your favorite trail.