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It sure is! We rented a place for our vacation on Kauai, that is more than half that a day, and it doesn't have a pool! But it has an ocean right out the back door!
I think it would be worth it if you are staying a week or more, even more so if you could plan a stop at a nice lake for a couple days on the way down and back.
Like @Big Shasta said, I can only think of one or two times that I've had the boat out down here in the Panama City area that I didn't see Dolphins.
The very first time we took the boat out after buying it, 4-5 dolphins breached the water right beside the boat where my 7 year old was sitting, the look on his face justified the purchase at that moment.
Being able to go to any part of the beach you want is a big plus as well, it's easy to walk out from your resort and be on the beach with hundreds of other people and nothing but hotels lining the shore, but it is a whole different experience to take your boat to an unpopulated area and have it all to yourself. In this area, PCB is lined with resorts, but East of the pass is 20 miles of seemingly untouched beach. If you are in the mood to anchor with a bunch of other boaters there is plenty of that as well on the bay side of Shell Island.
If you are looking to have a water sports vacation I would not go to Ft. Myers. Ft. Myers has narrow channels that are busy and rather shallow if you go outside of them. Water in Ft Myers is nice until full rainy season (late July/August). During rainy season the fresh water releases from Lake O turn the water brown/red.
Clearwater would be my suggestion. We boat all over the state and we love the Clearwater area. We usually stay at Sheppards Beach Resort. They do not have a marina but there is a public marina about 3 miles away that we park our boat for $1.00/ft overnight. We leave our trailer there and use our vehicle to get back to the resort. Live music everyday. Starts around 10:00 am. Here's a pic on one of the holidays. Not usually this crowded but on holidays it is. It doesn't get any better.
I've boated in Destin and Panama City Beach FL before. I've enjoyed both of those places. I've spend alot of time in the Clearwater area for work. I've never boated there but I really enjoy that area and have always wanted to bring boat there.
I boat on a lake normally. I did purchase all the flares, handheld GPS, handheld VHF radio. Basically everything to pass a Coast Guard inspection.
We were worried about doing the same exact thing, but I said to heck with it and just did it. Towed it from Atlanta to Panama City Beach. Had covered parking at the Condo on Front Beach Rd and Management allowed us to park the boat there as well. I just googled boat ramps for PCB and I ended up using the state park Which was really easy and close to the bay. I have a 192, and the wife was real nervous about going into the gulf. We paralleled the beach for a mile or so and went back to the bay and played at Shell Island. And we saw dolphins on every outing. It really wasn't that big of a PITA other than just flushing and washing the heck out of it....I only have a painted trailer and I sprayed a hole can of WD 40 or something similar all over it and haven't had any issues. Overall it was a blast, and we plan to do it again this year.
We rented a house with a boat in Cape Coral (Fort Myers) last February. It was great fun, but the boating is very different than we were used to. We mainly boat on deep lakes and rivers in the Pacific Northwest. Around Fort Myers, the water is very shallow mostly <10'. You really have to keep to the navigation channels. It was very limiting for us as we enjoy tubing and wakeboarding with lots of open water. We did not have a chance to get out on the Gulf though. Another good thing is there a lots of boat-in restaurants and public docks. And great fishing.
I have trailered my boat from Ohio to south Florida twice. 1st time we went to Marco Island and last year we did Punta Gorda. I rented a house in Marco and would trailer the boat daily to the public launch, I believe it was $8.00 per day. We would boat north to Naples via the inter-coastal. Loved it! I flushed and rinsed the boat daily back at the house. Last year, I rented a condo at a marina and left the boat in a slip for the 9 days. I took the boat out midweek to flush. It was a great time and I would definitely do it again. Let me know if you any questions about the trip etc..