Taking a trip to surprise a friend or family member on a special occasion can be a great way to add some spice to any travel plans. The problem is keeping your scheme undercover until you show up at the door, much to the delight of your loved one.

I’ve been involved in the planning side of several secret trips recently and have honed my skills. Below are some of my best tactics to keep a surprise visit a secret.

  • Don’t Surprise Yourself – It’s important to do some reconnaissance before you book any solid plans. Begin asking months in advance to ensure your target is home and not traveling themselves.
  • Have Someone on the Inside – A trusted person can funnel you information so you don’t have to ask too many questions and get your loved one suspicious.
  • Send A “Fake Gift” – Find a medium-size box and fill it with some of your clothing, wrap it like a gift, and tell the person “do not open until your [birthday, Christmas, etc]. This will keep your loved one unsuspecting and help you to avoid airline luggage fees. (I’d think carefully about trying this with a boyfriend or girlfriend however.)
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  • Start Lying Well In Advance – There are only two crucial times to pulling off the surprise – several months before the occasion and a few days before. Outside of those times, don’t mention anything – have your informant send you information if anything changes.
  • Adjust Your “Out of Office” Reply – This gave away a friend recently, her work email sent an out of office reply to the person she was trying to surprise, tipping the person off. Make sure to set your out of office reply to not respond to specific incoming messages. Most email clients can be configured to not reply to the people you’re trying to surprise (here’s how for Outlook and Gmail).

The process of planning, taking, and assisting in surprise trips to friends and family is a new one to me,  though I’m learning fast. Taking part of surprise trips can enhance a  future trip or add some fun to your routine if you’re the insider helping someone out.

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[photo by: The Opus]