Disaster-proof Your Vacation Together

Things have been getting hot and heavy in the new relationship. You’ve explored your new city’s art scene and conquered all the clubs in town. What is left for two intrepid explorers when local pursuits start to falter? Plan a vacation together, of course.

Vacations are fun. Being with your new girlfriend is fun. It only makes sense to combine the two for what will undoubtedly be the Weekend of the Year. After all, what could could possibly go wrong?

The first trip together as a couple will shine a lot of insight on your relationship and determine if you are compatible for a more serious affair. Ideally, you work in tandem as a well oiled machine, each of your strengths coming to the forefront to cover the other’s weaknesses. She might be the organizational mastermind while you counter setbacks with light-hearted joking.

Or things could be a total catastrophe and the stresses and unpredictable nature of travel could obliterate the little house of cards that is your relationship. You don’t want that to happen, but if you survive more than 48 consecutive hours together and still want to see her soon after, that’s a good sign for the future. Here are a few tips for surviving your first vacation together.

1. Short and Sweet

You rub your tired eyes and wake up on the sixth consecutive rainy day. The beach is absolutely out of the question, and even trekking through the mud to town seems like a chore, but the thought of ordering another round of bland overpriced room service food sends you into a fit of despair.

Faced with a host of unsatisfying options, you mindlessly turn on the fuzzy hotel room TV while she opens her novel. The weatherman announces that showers are expected to continue throughout the day and show no signs of abating over the weekend. You both wince in tense silence, nothing left to say to one another. Thunder claps outside and a sudden terror grips you as you realize that there are still three days left on your “vacation.”

In the untested waters of a new relationship, it is best to play it short and sweet on the first trip. This is doubly true if you have only been together a couple months. The weekend bed and breakfast or resort is always a safe bet, and the two week long cruise should be avoided. Cities can be stretched a few more days, because they have more distractions in the case of inclement weather. But you want to return home from your first trip feeling like it was over too soon, rather than like it dragged on too long.

2. Cut Down on Time In Transit

One of the cruel ironies of vacations is that they can be totally stressful. Especially if you are constantly moving around, switching hotels and taking overnight trains to a new place every other night. Packing, unpacking, managing reservations, finding hotels, dealing with transportation, eating rushed meals while negotiating with a taxi driver; that shit is for the birds. Leave the grand tour of Europe for later down the road when you have more experience weathering stressful situations. On your first trip together, pick one destination and stick to it. That way once you’re settled in you have nothing to worry about but relaxing and getting to know the area you’re visiting, be it a city, beach resort, mountain lodge, whatever.

3.  Do Plenty of Research Beforehand

I embrace a principle of “educated spontaneity” when traveling. I don’t obsessively plan a travel itinerary down to the minute or come up with a checklist of things that need to be done when traveling. That being said, I will put in some research to make sure I know the basics, like what neighborhoods have a happening scene, or which beach is most scenic. That way we have contingency plans and the confidence to make off-the-cuff calls when we get where we’re going.

Also, make sure you have the logistics down pat. Don’t be the asshole who forgets the flight times or has no idea how public transportation works in the city.

4. Plan Your Trip Together

This is all about bonding, right? Well the actual week of the vacation should be the culmination of–not the extent of–the bonding experience. Planning is a harmonious process and can be one of the first major projects you work on together, so don’t leave all the legwork to her or shoulder the entire burden yourself. Plus, if there’s a lot of friction and frustration in the planning stage, expect difficulties later on down the road.