How to Travel With a Woman For the First Time, Part 1: Before the Trip

Taking a trip with a romantic partner is a huge milestone in a relationship. Vacationing together is an opportunity for you to learn way more about each other than you even thought possible: you’ll learn more about each other’s idiosyncrasies, how you both handle stress, and how well you compromise with each other. It’s also an awesome way to make your relationship stronger. So, traveling with your girlfriend is a pretty big deal. And if you’ve never traveled with a woman before, or your woman before, there are a number of things to keep in mind, both before the trip and during the trip.

In our two-part series, we will walk you through everything you need to know in order to have the best vacation ever with your significant other. Bon voyage!

Prepare for Things to Get Intense

How much do you like spending time with this woman? No, really. Because if you’re the type of dude who needs his space, or thinks that weekly sleepovers and regular Sunday brunches are “too fast, too soon,” then taking a trip with your lady love isn’t for you. That’s because, on vacation, you will be spending basically 24 hours a day with her. She’s the first thing you will see in the morning, and the last thing you’ll see at night. That, and you will be spending all freakin’ day with her (as you should because, well, why else are you traveling together?). Even if you decide to have some downtime separately (which I highly recommend), the sheer intensity of being together all the time is bound to test even the strongest of relationships. Don’t say we didn’t warn you.

Go Where You Both Want to Go

You probably have your own bucket list of countries and cities where you would like to visit. Maybe Graceland sounds like a barrel of monkeys to you, but if your gf doesn’t even know who’s Elvis, then that’s no bueno for her. A good exercise would be to each write down your top 10 destinations separately, and then cross match them with one another. Hopefully you’re compatible enough that you have at least one destination in common. If not, break up! Just kidding. Go back to the drawing board, and determine on a compromise (get used to that word because it’s going to come up again and again).  If you want adventure, and she wants the beach, maybe you’d both agree to travel to Mallorca, Spain or anywhere in Hawaii. Again: compromise.

The M Word

Money. It’s probably the number one topic that many couples fight over (that, and skipping ahead in the Netflix queue). It’s a wise move to discuss the subject of money before the trip, like setting a budget, which ideally will be guided by partner with the lower income. For example, a fight might break out when the breadwinner wants to stay at a luxe, four-star hotel, while the lower income earner would prefer to stay at a Ramada Inn. So nip the subject of money, however awkward, in the bud to avoid any conflicts. Note: if you’re thinking of pulling a Sugar Daddy and splurging on your woman, ensure that she’s comfortable with that, and also that you won’t regret the decision later. A couple of years ago, I was treated to a whirlwind European vacay from a bf. Not only was I unsure about how much say in what we did because it wasn’t on my dime—which made me feel uncomfortable at times—but he also tried to not-so-subtly hit me up for money near the end of it (“So are you going to pay for lunch this time, or…?”). Discuss $$.

Research, Research

Once you’ve decided upon a destination, now it’s time to research almost everything you possibly can to avoid future conflicts. Make it fun and invite her over to your place, and over a bottle of wine, work out a daily budget (yes, $$ continues to be important), as well as different sightseeing spots and various activities that appeal to both of you. It’s also a good idea to vet dining spots. If there’s a unique restaurant you want to try, you should consider making reservations well in advanced to ensure you get a table.

Know Your Wavelengths

If you’re a practical, “must plan every single little detail” person who lives and breathes by his Google Calendar, while your girlfriend is a spontaneous, flies-by-the-seat-of-her-jeggings person, then, Houston, you may have a problem. You’ll be like, “We have windsurfing at 9 a.m. and then sailing at noon,” and she’ll be all, “But I just want to lay by the pool right now. I don’t know if I feeeeellll like doing that.” There are all sorts of pressure when traveling together (the 24/7 factor being the main one), so if you suspect your lovefriend won’t be willing to stick to your itinerary, then expect to do either some activities separately or compromising (there’s that word again) so you might as well get used to it.

Join us next month when we discuss everything you need to know when you’re actually on the trip.

Brianne Hogan is a freelance writer based in Toronto, something of a humorist, and considers herself more Bridget Jones than Samantha Jones. Though she won’t reveal which parts, she will admit to liking emotionally unavailable men and drinking lots of wine.  You can follow her on Twitter  @briannehogan.

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