Kelleher International Blog

The First Vacation Together

One sure way of getting to know a new love is on your first vacation together. As a couple, the learning curve in the early days of dating is steep. And every interaction can reveal something new.

And there’s so much you’ll learn about your new match planning that first vacation together. The Kelleher International matchmakers have a few suggestions to help set you up for success.

Decide Where You Want To Go and Why

As with most things in life, set and setting are key. Is this a romantic getaway, an active adventure, or an opportunity to unplug and destress? Will you travel solo or with couple-friends or family? Setting expectations and determining your “why” will make sure you’re both on the same page from the get-go.

Don’t Make Assumptions About Who’s Footing the Bill

Since money can be a sensitive subject, it’s important to discuss how you’ll split the costs of your first vacation together. If one of you offers to cover the trip expenses, that’s lovely. But make sure you discuss any time and budgetary constraints in the early planning stages.

Discuss Your Travel Styles

It’s essential to understand each other’s travel styles before embarking on your first vacation together. Is one of you a planner who appreciates booking tours, meals, and activities in advance? Arriving with an itinerary can feel like work to someone who likes to unwind and fly by the seat of their pants on holiday.

Kelleher International CEO, Amber Kelleher-Andrews advises, “If you learn you don’t have the same travel personas, that’s okay! Your relationship isn’t doomed. That just means it’s important to make time for together things and leave space for “me time” and individual exploration. Spending every moment together on your first vacation isn’t necessary. In fact, you’ll both appreciate the pockets of free time to recharge and reflect on how things are going.”

Test Your Negotiating Skills

Planning your first vacation together will test your ability to compromise as a couple. Be present during this process and remember that give-and-take is part of making any relationship successful.

If you’re the planner and have an overwhelming need to organize activities, go ahead and make your list. Jot down all of the sights you’d love to see, restaurants you want to try, fun couple activities, and some solo ones. Together you can collectively decide on a couple of things from each category and make a few reservations. That will give “the planner” some semblance of an itinerary. 

After that, let everything else on the wishlist simply be a guide of suggestions. You’ll have peace of mind knowing you’ve created a fallback list of things to do if necessary. The goal is to be in the flow with your partner. Enjoy discovering new places together and more about each other. 

On Your First Vacation As A Couple

If you’re traveling with a group, be sure to create some alone time activities with your partner. 

Make time for a special dinner and periodic alone time. It’s important to check in with each other on how the trip’s going. During the early stages of a relationship, it’s a good idea to connect on pacing and expectations. Get comfortable talking about what’s working and what’s not. The goal is to build a healthy foundation, and transparency will help you do that.

Sweet gestures or small gifts are a playful way of sharing your feelings of adoration and appreciation for your partner.

Don’t take yourself too seriously. We all have little quirks, and you might find yourself feeling vulnerable from time to time on your getaway. You both will likely experience some insecurity and anxiety around being together 24-7 for an extended time.

A great way to handle these feelings of insecurity is to be kind and complimentary to yourself and your partner. If there’s a disagreement or little quarrel, don’t let it take down your entire day, or first vacation together for that matter. A sweet note or small gesture can help you acknowledge whatever it was and keep up the momentum. Make memories together, and don’t sweat the small stuff.

Traveling can bring out the good, the bad, and the ugly in someone. And it can seal the fate of a relationship.

Kelleher’s director of matchmaking, Kimberly Colgate, shares her insight, “Some Kelleher clients use the first vacation together to determine long-term compatibility. Having a conversation around how you like to travel and setting collective expectations helps to ensure a more pleasurable and relaxing time together. I remember one client telling me how impressed she was with the way her new love interest navigated the airport. While experiencing flight delays, he made the best out of a stressful situation. She said it showcased his character, watching him deal with real-life stressors. She said he made a point to put her at ease and just handled it, so she didn’t have to worry.”

Holidays as a couple are an enjoyable part of being in a relationship. But that first vacation together needs some extra attention.

If you’re planning a trip with your new significant other and have questions, the Kelleher Matchmaking team is here to help. Ask your questions in the comments section below.