Over the last few years, I have taken a number of vacations with my wife and kids, or just my boys. I normally carry a gun every day, and that's something I have to take into consideration when getting ready to travel.
People carry guns "just in case," but bad things don't always happen at home. I and a lot of people I know carry guns while on trips, but before you decide if and/or what to bring/carry while on vacation, there are a lot of things to think about. All of those things, however, can be covered by looking at two simple questions:
1. Where are you going?
2. What are you doing?
If you plan to travel to a state or country where transportation or carrying of firearms isn't allowed, there's not a whole lot to think about. However, what if you're traveling through a restrictive area (i.e. Chicago) en route to your final destination? Knowing what the laws are of the states/big cities you pass through is something you need to do.
Also, if you are legally carrying a gun and get pulled over for a traffic violation in a different state, do you know what the state regulations are for declaring that gun to the officer? You should. You should also know local regulations regarding carrying guns in establishments serving alcohol, or in large venues seating in excess of any given number of people.
Carrying a gun on vacation may require you to make some hard decisions. For example, as far as I'm concerned, Disney World would make a very attractive target for an active shooter or a terrorist. As near as I can determine, there is no prohibition in Florida law for someone with a CCW to carry in Disney World. However, Disney is very anti-gun and does not allow concealed carry in their parks, and they do search the bags of people entering the parks, so carrying a gun into Disney World to protect yourself or your family is not against the law, but if spotted, you may be ejected (and those park passes cost a lot of money). Life is full of decisions, some of which are easier than others.
What you plan on doing on your vacation can also affect not just if you can carry, but what. I know someone who was recently at a Six Flags-type amusement part with their kids, and they had to trade in their full-size gun for a small pocket gun because they decided big belt guns and high-speed roller coasters that turn upside down are a bad combination.
Are you going to be spending the majority of your time around a pool or on a beach? If you want to have a gun with you, where are you going to put it when you're in the water? These are questions you need to think about before you leave the house.
Taking a cruise? Check the regulations of the cruise line. Even if your boat doesn't travel to a foreign country, chances are they won't allow you to bring along a gun. In this post-9/11 world, there's a good chance both you and your luggage will go through TSA-type screening before you're allowed on board.
Most vacations involve some sort of hotel stay. If you have your car or a rental car, I would highly recommend not leaving anything of value, including a gun, in that car or in your hotel room when you are not in it. Guns, computers and other valuables are always with me when I travel, not left in the hotel room during the day or in the car at night. I know too many people whose cars have been broken into while on vacation, and I know someone who had their Kindle stolen from their hotel room by the maid not two weeks ago. Luckily, the Kindle was recovered, but what if he'd left a gun in the room?
Deciding to carry a gun is never a decision to take lightly, and you should always try to plan for the situations you'll find yourself in, even if that situation is a family vacation.