How do you plan a vacation?

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What is the best way to plan a vacation?

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What kind? One you spend at home, go to another town or even another country? It makes a big difference.

My mother and I go on a road trip for a couple of days about once a year, and I normally pack the following things with me:

3 pairs of pants
3 T-shirts
4-5 pairs of underwear
4 pairs of socks
2-3 camisoles or undershirts
A coat or jacket.
My swimsuit for the pool at the hotel
Hygiene supplies such as my toothbrush and shampoo.
Paper and pens for doodling
Some light-reading material like comic books
My CD player and some music CDs to listen to during the long drive.
My 3DS and some games.
Money, since shopping is the main part of our trip.
A doll or stuffed animal.

Of course, that what I personally need for my trip, other people might not need that much stuff or they might need more depending on where they're going and for how long. But when I've packed my suitcase it looks more like I've packed for a couple of weeks instead of just a couple of days.

Another thing to consider is travel insurance which will cover any medical expenses, lost luggage or other issues that you may experience while travelling. You can get travel insurance for a single trip or a multi-trip policy that covers an unlimited number of trips within a certain timeframe.