5 Questions to Ask Before Taking Your First Trip Together

A couple looking into each other's eyes.

Planning your first trip together is exciting; you and your person are leaving the familiar to explore something new together. But, before packing bags and buying tickets, you should openly discuss your travel style, logistics, and timeline. A little extra effort in the beginning will save you stress, awkwardness, and potential misery once you arrive in paradise.

Discuss these five questions before taking your first trip together to guarantee smooth sailing—even if you plan on hiking, flying, or road tripping.

What’s your vacation style?

Until you get to know each other’s travel habits better, make your vacation plans together. Otherwise, that first getaway can seem more like a nightmare. You might think a secluded mountain retreat is the perfect vacation, but if your partner needs a strong WiFi connection to survive, you’ll end up with a crisis on your hands. Don’t plan any surprises for your first getaway, unless you know exactly how your partner travels. Playing it safe the first time around will ensure round two.

How long are you planning to travel?

Although that 14-day tropical island getaway is calling your name, it’s better to play it safe and work up to the big vacation. Start with a weekend trip first and gradually work up to longer more adventurous excursions.

How much are you willing to spend?

Be open about spending limits and spending styles. Unless you plan on picking up the tab, talk about costs before booking. Perhaps you plan to pay for hotels, while your date covers food expenses. Or, you may ask that your date book his or her own flight while you handle other expenses. Whatever your approach, discuss the logistics up front.

What activities appeal most?

Don’t feel compelled to fill every minute of your day with an activity. Figure out the things you want to do the most and schedule lower-priority items around them. Cramming as much as you can into one day will sabotage your vacation. Balance sight seeing with relaxation. Catch a late show but allow yourself to sleep in. Build free time into your schedule.

How will you make it memorable?

Unless you are traveling for a specific event, be open to different kinds of activities, food, and people. Instead of four days of beach lounging, add a day for visiting ruins or shopping in the city. Skip chain restaurants and opt for local cuisine instead. Talk to other hotel guests, get to know your concierge, and ask the locals about their recommendations. Research your surroundings. You’re more likely to build memories doing things outside of your comfort zone.

A couple that plans together enjoys better vacations. Happy traveling!

Joan Actually

Dating Expert

Joan is a writer and dating expert.

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