I'm writing this column from a balcony overlooking the ocean. The only reason I'm staring at sandy beaches - and not at a parking lot - is because of a few e-mails I sent a week ago.
After I'd booked us into the basic rooms at the three hotels we're staying at, I set out to try to get an upgrade in each hotel. About a week prior to arrival, I e-mailed each general manager directly and told them why I was travelling to their hotel, which room I was currently booked in, and the specific name of the suite I'd ideally like to be in. I then added a few things I could do in return for such a generous upgrade: post a positive review on tripadvisor.com, recommend the hotel to colleagues, friends and family, agree to return if possible in the future, etc.
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The key with most requests is to be gracious. Kindness goes a long way in getting more for less. Also, if you're part of the hotel's preferred guest program you should make that clear, but it's certainly not essential.
The lesson I learned: Don't wait until you check in to ask for upgrades. The first hotel wasn't able to upgrade us, but did give us a free brunch; the second bumped us up to an ocean-view room; and the third gave us an ocean-view suite and sent a bottle of bubbly to our room. If you're travelling soon and would like an outline of the letter I've been using, send me a message via Smartcookies.com.
Angela Self is one of the founders of the Smart Cookies money group. Read her weekly column on managing debt and saving money at the new globeinvestor.com.