Nothing tests a blossoming relationship more than taking that first trip together, so save the hike across the Chilean desert for another time and keep your plans simple both in terms of planning and activities. Avoid either of your old stomping grounds as well, and instead pick a neutral destination. Your first trip away with your new love should be about getting to know each other, not meeting all of yours (or his) out of town family and friends.
Whether to a foreign country or the next town over, going away forces you to get to know the other person at light-warp speed. However, it's possible to avoid a large amount of surprises and disappointment if you discuss your vacation objectives ahead of time. From choosing the destination to planning the itinerary, accept that your new boyfriend's idea of the perfect vacation may differ from yours. For example, if his includes spending ample time golfing, whereas you'd prefer partaking in a massage, be prepared to compromise or at the least take turns with the decision making instead of arguing and trying to change each other's minds. Any successful merger is the result of a series of negotiations, so why should your relationship be any different?
Some questions to bring up in advance: How much time do you want to spend together? How much money? How much socializing do you want to do?
Although the first trip you take as a couple is definitely a milestone, try not to think of it as a litmus test for your compatibility. If you're keeping it simple (see tip #1 above), then there shouldn't be any need for a rigid itinerary and you should be free to be spontaneous and try something new. By keeping your options open, you can focus on spending time with each other and not just checking off boxes on your itinerary to-do list.Taking a vacation together may mean you are becoming serious as a couple, but it doesn't mean you have to act it! Most importantly, try to relax and have a good time together; remember it is only the first of many adventures you and your love will share.
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