I've been to the western or Gulf Coast of Florida enough times in the winter to be able to offer some advice and hints if you are thinking of heading that way. Here are my thoughts, in no particular order except for the Big Number One.
[1] Weather. It's rarely hot. Pleasantly warm is about as high as the temperatures in Florida go during December-February. Think of a late spring day in Ontario, with temperatures in the high teens to low twenties Celsius, and you'll be about right. Sometimes (as this month) it can get downright chilly. In fact, most of my winter trips to Florida have included a day or two where the temperatures went near freezing overnight and barely rose to 10C in the daytime. Rainy days are also not uncommon. Bring layers and be prepared to roll with it. If you require "hot," then you'll have to get much farther south, down into the Caribbean islands. (I don't do "hot" very well, so Florida suits me right down to the ground.)
[2] Sun or Clouds. Bad news for sleep-in specialists. In common with tropical areas the world over, Florida almost always gets at least a bit cloudy as the day goes on -- sometimes more than a bit. It's the combination of daytime heating with moisture from the oceans. The clouds are very likely to appear right above -- you guessed it -- the beaches. In my experience, there's usually good sunshine until about 2:00pm. After that, some days are luckier than others.
[2] Sun or Clouds. Bad news for sleep-in specialists. In common with tropical areas the world over, Florida almost always gets at least a bit cloudy as the day goes on -- sometimes more than a bit. It's the combination of daytime heating with moisture from the oceans. The clouds are very likely to appear right above -- you guessed it -- the beaches. In my experience, there's usually good sunshine until about 2:00pm. After that, some days are luckier than others.
[3] South is warmer. You can usually find temperatures several degrees warmer by heading right down to Fort Myers/Naples on the west coast or Miami/Fort Lauderdale on the east coast. I still haven't been all the way down to the Florida Keys -- that's for another trip.
[4] "Beach front" versus everything else. The prime hotels, motels, condos, etc., are almost always the ones which stand right on the edge of the beaches. These are "Beach Front" locations. All the others, though, are very good at marketing themselves to make it sound like they are on the beach front. Sure, they're "On the beach" (the whole island is called "What's-its-name Beach"), and enticing words like "Sands", "Ocean", "Beach", "Sea", etc., recur in property names with great frequency. "Steps to the beach" is another good marketing dodge. Do your homework and verify the location online or with GPS if you absolutely need a room or apartment facing the beach.
[5] Wheels. You must bring a car, or get a car in Florida. Urban and suburban sprawl is the name of the game here. That nice little map on the website of that great restaurant makes it look like the place is right over there, and then it turns out to be a 30-minute drive or more. Beach parking in many areas is very limited; you must arrive early in the day to get a space, especially on weekends. Also note that gas is usually cheaper off the beach islands, and in any case there are only a tiny handful of gas stations on the beach islands.
[6] Shopping. It's not true that everything is cheaper in Florida. If you want to shop for bargains, you need to do price homework ahead of time and learn to calculate the exchange rates quickly in your head! And no matter what some people think, the word "Outlet" does not magically guarantee the lowest prices. There are many small shopping plazas and individual stores scattered up and down the beach islands, but the major shopping malls and outlet malls are all inland, sometimes a very long way inland. Plan plenty of driving time if you are on the beach but heading for the malls. The good news? There's always a chain drugstore nearby (Walgreen's or CVS). They're much like a Shoppers Drug Mart in offering a little of just about everything, including some grocery items.
[6] Shopping. It's not true that everything is cheaper in Florida. If you want to shop for bargains, you need to do price homework ahead of time and learn to calculate the exchange rates quickly in your head! And no matter what some people think, the word "Outlet" does not magically guarantee the lowest prices. There are many small shopping plazas and individual stores scattered up and down the beach islands, but the major shopping malls and outlet malls are all inland, sometimes a very long way inland. Plan plenty of driving time if you are on the beach but heading for the malls. The good news? There's always a chain drugstore nearby (Walgreen's or CVS). They're much like a Shoppers Drug Mart in offering a little of just about everything, including some grocery items.
[7] Happy Hour. It's not always loudly advertised, but many restaurants offer Happy Hour drink specials. There may be Happy Hour food specials too -- a limited number of menu items, at lower prices, available before 5:00pm or 5:30pm or 6:00 pm. Be sure to ask. Several places I know offer well drinks, house wines, and basic draft beers at 2-4-1 on their already low prices from opening at 11:00am until 7:00pm, and one of them has a similar Happy Hour promotion going on at all times they are open! Over on the east coast, some places offer half-price on all their bottles of wine on the slack days like Monday and Tuesday.
[8] Chain Restaurants. These are nearly non-existent on beach islands. There are all kinds of terrific restaurants, at all price points, all up and down the beach islands but rarely a Mickey Dee's or KFC. If you absolutely must eat chain "food," I feel sorry for you -- in more ways than one -- but you usually have to find it by driving off the islands and heading inland.
[9] Chain Hotels. Mostly located around the same areas as the chain restaurants. There are only a few chain hotels on the Gulf Coast beach islands. You notice them right away because they are such rare birds (except at Clearwater Beach, where there are a half dozen or more of them).
[10] Beaches. There are lots of beaches, but the Gulf of Mexico is really too cold for swimming in winter unless you have a wetsuit. I haven't seen anyone get right into the water without one. The water is a bit warmer on the Atlantic side, thanks to the warm current of the Gulf Stream. All beaches and beach parking lots get a lot more crowded on weekends -- Floridians love their beaches, too. Pick your beach with care. They're all different. Here's my take on some of the west coast ones which I haven't already written about this year:
[a] Clearwater Beach. Heavily marketed, Clearwater is the beach for those who want to escape from high-rises, crowds, and heavy traffic by coming to more high-rises, crowds, and heavy traffic. The traffic has gotten notably worse the last few years with a new crop of giant high-rise hotels and condo towers crowding the south end of the beach front. Giant and expensive.
[b] Sand Key, Longboat Key. These two, one south of Clearwater, the other west of Sarasota, are the beach resorts with cachet, suitable for CEOs and lottery winners. Properties here, especially on Longboat Key, have the rarest of all Florida beach luxuries -- space and privacy. If you have to ask the prices, you can't afford Sand Key or Longboat. Nuff said.
[c] Fort Myers Beach. Popular and crowded. Lots of island character and plenty of traffic congestion, mostly around the terribly-planned intersection just at the entrance to the island from Fort Myers.
[d] Fort de Soto county park. South of the city of St. Petersburg, a beautiful undeveloped beach with acres and acres of sand, and plenty of parking.
[e] Pass a Grille beach. The far south end of St. Pete Beach. A fine beach, backed by a village which preserves a bit of quaint old Florida character. Great spot for walking around, and plenty of top-notch eateries and drinkeries as well.
[f] Bradenton Beach. Unusual, a sizable beach park lined with trees instead of condos. Nice rural feeling, gets crowded on weekends. Actually, all the beaches do.
[g] Sanibel Island. Beaches everywhere are littered with shell fragments. Sanibel's beaches are shells and shell fragments. Sanibel was famous among shell collectors long before the high-rise world discovered Florida. It's the easiest place in the world to get bitten by the shell-collecting bug!