How to plan a trip as a couple June 9, 2019

We were only a few days into planning our first real trip together and Holly was in tears. This was the first time I had ever seen her cry!

Tears! by Our Cruising Life

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We were trying to book flights and plan out our days for a long weekend getaway to New York City.

"I just want everything to be perfect..." she said, as she looked up at me from behind watery eyes.

"We'll be in NYC together... It will be perfect no matter what, I promise!"

We were both trying to be too overly accommodating to the other.

Though we instantly bonded on our love for travel, Holly and I realized very quickly that our planning styles couldn't be more opposite. She likes to have everything buttoned up well in advance, knowing where we'll be at what times on what days and prearranging tickets for tours or excursions. Me on the other hand.. I'm happy if I have a flight and a hotel to stay in (and sometimes I'm o.k. not even having a room booked!).

Holly likes to spend plenty of time researching the places we're going to visit, making a list of all the must-do's and tracking flights to make sure we get the best deal. I, on the other hand, prefer to land in a country, talk to the locals asking for recommended things to see or places to eat and casually explore after I get there. I'd also prefer to check flights from some reliable sites I've used in the past (check out our secrets to cheap flights post here!) and just book without looking back.

Needless to say, we have very different travel styles; something we had to figure out how to use to our advantage as a couple (who now host a travel blog!). Neither way of doing things is 'right' or 'wrong', we're just have different personalities in this regard. But we figured it out! And here's what we learned:

Since Holly is a planner and I enjoy being surprised, Holly takes the lead on planning out our day-to-day itineraries. If there are any must-do's on my list (things I already know about or that have been recommended to me) I'll let her know in advance, otherwise it's all up to her what we see and do at each location. She's also awesome at baking in some time to just explore on a whim (which sometimes leads to pretty interesting and unexpected stories), which I love to do.

My responsibilities include coordinating flights and finding hotel suggestions for each leg of the trip. Before booking, I'll usually get Holly's opinions on a few different lodging options so she feels comfortable with where we're staying.

Basically it boils down to deciding where we'd like to go as a couple, then taking a divide and conquer approach to planning out all the details. This works for Holly because she can sleep knowing we've thought of all the logistics and covered all our bases, but also works for me because it leaves a lot to be discovered on my end, since I'm usually still pretty unfamiliar with what our destination has to offer and most everything we end up doing is a surprise!

Our Cruising Life

When Holly and Andrew first met, they instantly connected over traveling. Since then, the trips haven't stopped. They realised pretty quickly that they love cruising!

Our Cruising Life