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It’s a big step for a guy to take a vacation with that special lady in his life. Depending on how the trip goes, the overall outcome can bring them closer—or push them apart. So how can he make sure that their time away together stays fun and avoids frustration? We’ve asked leading male travelers for their advice on how to plan a trip that eliminates any chance of headaches or heartbreak. Here’s what they told us:

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couple on vacation in beach

Look at how much time you’ve already spent together

Before getting excited about going out of town, consider how many moments you’ve shared as a couple close to home first. “You need to consider how much time you’ve spent with her already,” says Lee Abbamonte, the youngest American to visit every country in the world. “There’s a big difference between going on a few dates and spending 24/7 with someone.” Matt Meltzer, a travel staff writer for Thrillist, also points out that it’s one thing to spend the night together, “but how people are on mornings, when they don’t have to go to work, says a lot about how compatible you’ll be on vacation.” Not sure? Perhaps plan a staycation first.

See how your personalities blend

Keep in mind that how you get along locally could turn out to be much different on the road. Michael Hudson, founder of Go, See, Write, recommends comparing your Sig O’s personality traits to yours and seeing what gels. “I’d look into whether or not she’s a planner or a more ‘go with the flow’ person,” he says. “Take her sleeping habits into consideration, and see if [you] have the same nightlife expectations,” he adds. Plus weigh other factors such as “any dietary restrictions and … any fears like heights before planning activities,” suggests travel expert Johnny Jet.

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Go short on time and distance

A shorter vacation, as in a weekend, can have a long-lasting impact on romance. Consider a getaway that’s not too far from your home base, with a number of indoor and/or outdoor attractions. Also, go for lodging that gives you both a fair amount of space like a suite arrangement. “Depending on each other’s personality, I would recommend a cool, quaint place in a city or a busy inn with a lot of room in the country,” says travel expert Charles McCool. For ideas, Will Tang of Go Awesome Places suggests an all-inclusive vacation “because it’s relaxing, stress-free, and easy to plan. Alternatively, a long weekend city trip would also be a great option.”

couples sightseing

Get an itinerary started

Discuss what ideas you have in mind about what you’re both itching to do ahead of time. “Talk before you go about what she wants to do while you’re there, and see if it aligns with your interests,” says Meltzer. And don’t forget to factor in meal times. “Not every meal has to be at a restaurant, but I can’t tell you how much time I’ve wasted on vacation figuring out where to eat,” adds Meltzer. Leave yourselves some flex time, too. “Whether you or she wants to watch Games of Thrones, needs to check in with the office or wants to do a solo run or Soul Cycle, allow it to happen,” says McCool.

Be frank about your finances

Yes, money can be an argumentative subject, but it’s one to be discussed. “This all depends on the people involved,of course, but for me personally, I like to pay for things but you also don’t want to be pushy,” says Abbamonte. “Maybe agree that she will pay for her ticket and you get the rest.” Or perhaps divvy up costs, where maybe “one person could pay for lodging and the other takes care of meals and gas,” says McCool. For tracking larger cost items like hotels, gas, and rental cars, Tang suggests using personal finance programs (Venmo or SplitWise are good examples).

Remain open to a compromise

She wants to go exploring, while you prefer lounging. You’re interested in doing certain things, but she isn’t, and vice versa. In the beginning of your union, and during your trip, it’s best to be willing to find common ground. “You cannot be demanding, and neither can she, especially this early in a relationship,” says Abbamonte. “Be clear on what’s important to you and be accommodating to what’s important to her!” Or, plainly as Hudson explains, do these activities together anyway.

couple on the road 

Fight fair

Unfortunately a va-cay fight could be possible, yet how you both handle it counts more. If it’s over a small matter like lateness, “make sure it doesn’t spiral into something personal or large scale,” advises Meltzer. If it’s major, Meltzer recommends trying to put differences aside for the remainder of the trip and discuss your relationship status when you’re back home. If your debates continue to escalate, Hodson advises to “take a break from each other, try to have a calm conversation and see what you can work out together.” 

Learn from each other

One takeaway fromyour trip is not just discovering more about your partner, but also teaching each other a thing or two. When Jet first traveled with his now-wife, Natalie DiScala, he remembers her looking “like a 1920s transatlantic passenger with the size of her trunk. I had to put on the brakes and show her the light. Now, Natalie packs lighter than I do, and when I suggest she should check a bag for one of our round-the-world trips, she looks at me like I’m crazy.”

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Michele Herrmann

Michele Herrmann

Michele writes about women's travel, destinations, culinary, and cultural topics for various outlets and has ventured as far as Fiji, to date. She also muses her tales on She Is Going Places.
Michele Herrmann

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One thought on “8 tips for guys on how to plan a first vacation with her”

  1. Ha, that Natalie story reminds me of the scene with George Clooney going on a business trip and showing the woman what to bring. Thank you for letting me be a part of this collaboration.

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