Tampa Bay/St. Pete vs. Clearwater/Gulf side in CP23

[HJ51]

Hello fellow CP owners.   The last several years I have been trailering my 23 to Pensacola at the beginning of the winter season and leaving it there so I can pop down for extended weekend sails in warm weather (I'm in Tennessee).   Have really enjoyed sailing around Pensacola Bay and parts of the ICW.   This year I'm considering doing the same thing in the Tampa Bay area but was hoping to get some opinions on what part of the Tampa/St.Pete/Clearwater area to target.  I need to choose carefully because in a typical three-day weekend I won't have the range to cover all of it.  Also need to be within a reasonable cab/Uber ride from the Tampa airport.  Basically I am trying to figure out which side of the peninsula to be on. 

Factors are:

-  Reasonable distance from Tampa airport
-  Overnight opportunities both anchoring out and at transient slips with fun restaurants
-  Opportunities to explore by boat, gunkholing, etc.
-  Open water for sailing, but not deep blue water (fine with sailing around barrier islands, but won't be heading out into the Gulf much)
-  A home base marina where I can leave the boat on its trailer

Anybody familiar enough with the area to help me make an informed decision?   Pensacola was just right for all of the above, but want to try something different for a season or two!

[cdflan]

You might take a look at Gulfport on Boca Ciega Bay.  On ICW with access to Tampa Bay, the Gulf and northward via Gulf or ICW to Clearwater.  City runs a marina with slips and has a mooring field in the bay.  Gulfport is a funky little city with lots of restaurants and is about half hour from Tampa airport.  Don't know about leaving boat on trailer overnight or for week - might call the harbormaster - Denis Frain, CMM Harbormaster. Phone: 727-893-1071

[Gerry]

Two areas I have enjoyed.  Gulfport and Ciega Bay.  It is everything described by cdflan.  Secondly, consider north of Treasure Island Causeway, including John's Pass.  The whole area is a boater's paradise.  If you have a motor it is fun to go all the way from Passe-de-Grill north thru John's Pass.  Great motoring and sailing and along the ICW. Google Earth and lots of information is available on-line.

[relamb]

Boca Ciega sailing club has a ramp and dry slips, and if the Gulfport city marina doesn't have a place to keep it on the trailer I think there are a couple of other boatyard/storage places in the vicinity.   I didn't like that area as much as St Pete and Tampa Bay. I've been at Maximo Marina and St Pete.
My CP27 has been in St Pete for several winters now, and although I have a trailer I keep it in a slip.  My CP23 and other small boats I just kept in a self storage lot away from the water, and trailered to wherever I wanted to launch.  Often I'd get a campsite at Ft DeSoto Park and then daysail from there, but I also kept a boat on the east side in storage near Riverview.