12.) Do your research before you get to your destination. A last-minute Google of Chicago isn't enough for you to get a good idea of what you'll need to cram into a three-day visit. Spend some time with the internet getting to know a place before you blow a vacation sitting in your hotel or a mall. What is the city famous for? What puts it on the map? Find out and do those things.
11.) And speaking of malls, unless it's got a roller coaster inside, skip the mall. You can have that experience in any town in America. Go look for some local color.
10.) Don't be afraid to try local food. I really like to look up favorite or trending restaurants on Yelp or UrbanSpoon to get the skinny on authentic cuisine I can't get anywhere else. I look for holes-in-the-wall or other notable restaurants in the area. Avoid chains like the plague.
9.) If you want to get to know a city, spend some time in its coffee shops.
8.) Some experiences are worth paying for, like the Monterey Bay Aquarium. That doesn't mean that the only things you need to pursue cost money. Sometimes, just walking around a new city is enough. And I prefer walking around on my own to taking a packaged tour, which I see as a canned experience. You want unique memories. Go and make some.
7.) Make an effort to think like a local. Where would they spend their Saturday afternoons?
6.) Spontaneous vacations are awesome, but if you're planning on visiting a tourist hotspot, make sure it will be able to accommodate last-minute visitors. Like that time my dad and I made a spontaneous trip to Alcatraz... Oh, wait, we didn't get to go because it was booked months in advance. Check on these things before you expect tickets.
5.) Small towns can be just as entertaining as big cities. Keep an open mind when you're booking your travel.
4.) Take lots of pictures. Memory fades, but a well backed-up hard drive is forever. But also remember not to overdo it. Don't be so focused on capturing the experience you forget to live it.
3.) Linger over dinner.
2.) Learn a different language. You'd be surprised at how genuinely helpful this is — for one thing, you'll receive cultural insight you'd miss as an English-speaker only, and for another, the cultural immersion will make your trip richer. Use your new skills when you travel.
1.) Don't overplan. You're not vacationing to increase your stress level. Offer yourself a little wiggle room in case you want to be spontaneous, in case you discover something new you want to check out after you arrive.
I hope these help. Remember ... stay adventurous!
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