Advice for Traveling with a Date for the First Time

Advice for Travelling with a Date

It’s difficult to travel with a date for the first time, here are some tips

When you are accustomed to traveling alone, traveling with anyone else can be a bit of an adjustment, especially when trying to get what you want out of the trip. If you are traveling with a date, a whole other layer of complication arises. You are more eager to find common ground, and you are less likely to agree to go your separate ways and meet up again later. The whole point is to spend time together.

What do you do when one of you wants to go hiking and the other wants to stay by the poolside sipping Mimosas? What do you do when your date agrees to go surfing with you, but thought that it would be for an hour or two, not five!? You are happy to have dinner at the affordable Ahi Taco truck that another traveler told you about, but they want to eat at a 4.5-star restaurant that they saw on Google.

Traveling with a date can make or break a relationship, especially if travel is an essential part of your life and they are going to need to fit into that. Depending on how far down the relationship path you are, this might also be the first time you are spending 24/7 with the other person and seeing how they truly operate, especially when they are outside of their comfort zone. Oh, and don’t forget, they will be looking at you and asking themselves all of the same questions! There’s nowhere to hide when you are traveling as a couple.

On a recent return trip from Hawaii with a date, I was vacant mindedly looking over the shoulder of a young guy at his smartphone screen. I couldn’t help but notice the notes he was making about as his trip. While I wasn’t trying to be nosey, it was clear that he was reflecting on his trip with his girlfriend, sitting next to him, and what he wanted to do differently next time. His notes read more or less:

  • Do more research and plan key activities ahead
  • Do your priority things right away and don’t risk running out of time
  • I want to do more rugged activities so go alone if needed

This also made me reflect on my trip with a date and compared what he was jotting down with my own experience. From this, and also casually listening to their conversation, it was clear that he really needed this holiday after an intense period at work, which was over a year since he started his company and got fundraising. He finally could take a breather.

Although I didn’t volunteer any advice to the young man, the questions played on my mind over the next few hours and I came up with some tips that would help him and me, and anyone else who wants to get the most out of their travel, and do so while balancing their needs with that of a travel partner.

Set Expectations & Discuss Desires
It is always risky to assume that you are on the same page as another person. Human beings are surprisingly diverse, and just terrible mind readers. It is better to have an explicit conversation with your travel partner about what you both want out of the experience before you set off (and maybe even before you buy your tickets).

You might be pleasantly surprised that you are both interested in the same things. They might also have some ideas that you hadn’t thought of that sound exciting. If there is more of a gap in your expectations, you can both start thinking about where you are going to compromise and how you are going to make the trip work for both of you.

Especially when rolling alone, it can be exciting to turn up at a place and just see what there is to discover. But when you need to coordinate your plans with another person, it is a good idea to know what is on offer. When you don’t know what to do and don’t have a plan, you are more likely to get pulled into plans that aren’t that appealing to you, such as staying by the hotel poolside or going back to that restaurant that you both liked.

While it is great to keep your options open, it is good to have a backup list for those moments when you aren’t really sure what you want to do, but know you want to make the most of where you are. Your date will appreciate the effort and it will help to budget your time to get the best out of it.

Book-In Important Items
If there is something in your mind that you absolutely want to do on this particular trip, book it in, and book it in early during the trip. If you leave it, you risk missing out as you try and book in everything that you both want to do.

More than this, the things that you do early on can set the tone of your trip. If you start with something strenuous like hiking, or something adventurous like paragliding, you and your travel partner are more likely to think of these elements as part of your trip and do more of them.

Fit More Into Each Day
Often when people plan trips, they say, “today I am going to do this”. But once that is done, what do they do with the rest of their day? You can have time to do a lot if you plan your days carefully. I recommend breaking the day up into thirds – the morning, the afternoon, and the evening – and having a plan for each part of the day.

If something overruns or you find that you are too tired to do something, it is not a big deal, if it is important you can do it another day (along as it is not one of your must-do booked-in items).

Be OK with Separate Activities Sometimes

Someone may want to work for a few hours, read, or surf. The other may not. So it’s important to set time aside for what you need, what makes you happy. Clearly schedule this time in and then schedule your together time. Communicate this upfront so there are no surprises.

Stay Extra Days
If you find that there is a serious disconnect between what you and your travel partner want to do, you may feel like you need more time to do some of the things that are on your list. If so, consider arriving at, or leaving, your travel destination a few days before or after your travel partner. That way you can spend time with you partner, and also do the things that you want to do.

Depending on your situation, it can be challenging to tell your partner that this is your plan. However, if you are honest and explain that you want to be able to focus on them while you are together, but also want to have time to do these other things, they should understand. If not, maybe they shouldn’t be your travel partner.

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