Making Vacations Fun Again

Posted by Jacques - April 23, 2009

Okay, so I’ve been on a vacation… sort of. But I’m going on another one shortly. One of the things I’ve noticed is that planning a vacation can sometimes be a logistical nightmare and really feel like more work. So the trick for me was to imagine that our vacation was a business trip, and plan it accordingly. I realized, on business trips, I don’t stress about the hotel I’m going to be staying at, or what time my flight will get in. Immediately, the burden of having to create the perfect itinerary and activity schedule melted away. The point of a vacation is to have fun, getaway, and relax. If you don’t do those things, you might as well stay home.

frustrated-planning-vacation Follow my simple rules for planning a vacation.

1. Stick to the big cities for consistency.
It is possible, but much more difficult to plan a vacation in a smaller city. Big cities tend to have cheaper flights, more options for stay, a larger variety of activities, and some have really functional and cheap mass transit.

2. Always have a vacation bag pre-packed with everything but clothes.
This would be things like bathing suit, travel charger, passport, or other things that you know you’ll take. The clothes you pack will change depending on the weather, but at least this way everything else will be done.

3. Don’t bring more than 2 of each type of clothing.
2 t-shirts, 2 shoes, 2 shorts, 2 pants, etc, I would never pack more than two of any kind of clothing. Exceptions are of course, vacations longer than a week and clothing such as underwear and socks.

4. Use only carry-on bags.
One of the most unpleasant things about vacation are dragging around huge luggage or getting it lost. Pack light and it will make all the difference.

5. Plan one big event per day.
People often stress about filling their itinerary with constant action. This is more likely to make you unhappy if you fall behind or unable to do all of the activities. If you stick with one major thing you want to do that day, then any additional activities that are recommended by the locals will feel like a bonus.

6. Comfort, comfort, comfort.
Always focus on comfort. There’s nothing worse than being unable to enjoy your time because you have blisters from wearing those designer shoes you almost forgot about. Bring the tennis shoes, sandals, or other comfortable shoes that you wear everyday.

7. Use a checklist.
I know it sounds stupid, but use this checklist. You’ll never know if it helped you until you don’t use it, but I will.

- Toothpaste
- Toothbrush
- Sneakers/Sandals
- Laptop and Charger
- Cellphone and Charger
- Driver’s License and Passport
- Cash or Credit Cards
- Flight Tickets or Confirmation Number
- Hotel Reservation Number/Address/Phone #
- Socks
- Underwear
- Bathing Suit
- Glasses/Sunglasses
- Travel Shampoo (buy sample and fill it with your own)
- Large Tote

Anything you like? Please share!

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