Going on a long vacation? Excellent idea. Booking that trip well in advance to save money? Even better. But doing those things with someone you've only known for a few months? Romantic, yes...tempting fates definitely. When you're both out of your comfort zone and spending 24 hours a day together, you'll find out quickly how compatible (or not) you really are, says Adam Seper, a BootsnAll.com travel writer
, who took a yearlong, round-the-world adventure with his wife. Certain personality traits or habits you or your boyfriend may have been able to keep under wraps at home can be revealed under stress. The length of your trip should be proportional to the length of your relationship. So if you've only been together a few months, test the waters with a weekend escape. Save the month-long trek through Walla Walla until you've dated a year or more, and always, no matter how short or long your relationship, buy the travel insurance. Although it can be tempting to put that extra money toward your trip, it will save you headaches (and money), if anything unexpected—say a breakup—interferes with your plans.