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Some of the best trips I've taken are the ones I didn't plan for. Go with the flow, let the city open up to you and take each turn as it comes.
Set a Budget
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If you want to avoid overspending, which is easy to do while you're in "vacation mode", set a budget and stick to it by either using cash or tracking your expenses at the end of each day using Mint.com.
Use a Map
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Don't be afraid of looking like a tourist; it's a sacrifice I'd rather make then spending my time getting lost. I always use Streetwise maps because of their clean design and the way they fit nicely into my bag without getting all crumpled.
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Remember to take photos! I bought a Nikon SLR digital camera about a year ago and it was hands down one of the best purchases I've made. Save up for one; it's worth all the special memories you'll capture.
Be a Good Tourist
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Read about your city. Be a good tourist and pick up a book on the city you are planning to visit. Not only will you learn a thing or two about the history and culture, you might get a few ideas of things to do while you are in town.