OneTravel - Book cheap flights, hotels and cars!
Romance - Weddings

The Art of Traveling With Your Girlfriend

Written by Chris Osburn

This blog post was updated on July 16, 2019.

Going on a trip with your girlfriend can definitely prove to be a challenge. I mean, you do want to her to have a good time, but it’s also got to be balanced with some amazing experiences that the BOTH of you can share and enjoy. To get you heading in the right direction when you start planning your trip, here are a few simple tips to keep in mind.


Couple on rollercoast

Is this your first trip as a couple or your umpteenth? Are you going away for a bit of “R ‘n R” or are you planning to pop the question? Establish the “why” behind your trip before delving too deep into the planning. You’ll save yourself from unnecessary confusion (and potential arguments), and be able to create an itinerary suitable to her likes.

During the early days of dating, it might be best to take it light and easy with a short city break to somewhere new for you both to discover or maybe a visit to Orlando for action-packed theme park weekend. For longer-term relationships, consider planning your getaway around a destination that’s significant to you as a couple. Organizing for such a trip might include booking the exact table at a restaurant where you shared a special meal or staying in the same suite where you stayed on your first trip as a couple.

Pay Attention


Probably the best relationship advice anyone ever can give is to make sure you’re listening to your partner. This is definitely the case when it comes to making plans to travel with your girlfriend. Odds are, if you’ve been paying attention, your girlfriend has already let you know where she would like to visit and what kind of trip she would most enjoy – even if she didn’t realize it.

Does she have a favorite TV show? If it’s Sex and the City, maybe you can treat her to a Manhattan shopping spree. If it’s a less conventional series such as The Walking Dead, lurch your way down to Atlanta for a tour of filming locations.

Encourage Collaborative Input

Couple planning trip

Gauge your relationship. Do you believe it’s better to spring a surprise or to organize something jointly?

Designing a trip away with anyone without keeping that person in the loop can be fraught with missteps. Are you positive your partner doesn’t have obligations that will be hard to get out of? Are you sure she’ll be happily surprised with your choice? Are you even certain your partner isn’t orchestrating a surprise for YOU? If you are going ahead with a surprise trip, it’s probably wise in most cases to do so with flexible dates in mind or at least asking your girlfriend to keep certain dates free for going away.

Even if you want the trip to be a gift from you to your loved one, it can still be smart to allow some input. You might find out how to make the getaway better and more geared to pleasing your partner while limiting misunderstanding or ending up going somewhere that neither one of you actually wants to visit.

With the right attitude, coming up with a plan as a team might bring the two of you closer – and could be a romantic gesture in and of itself. Maybe you can go to your favorite local Italian restaurant to chat about going on vacation to Italy? Or perhaps you could give a guidebook as a gift with a note explaining how you’d like to create an itinerary jointly.

Maximize Your Time Together

Couple in Venice
Key to planning a successful romantic getaway is making sure you and your girlfriend get to spend as much time together doing things you both mutually enjoy. This might mean setting off on a camping trip to the Smoky Mountains of North Carolina or Tennessee or hopping a flight for an all-inclusive resort holiday in Jamaica. Whatever the case, be sure you plan your getaway intent on the two of you having as much fun with each other as possible.

To maximize quality time during a romantic getaway, choose relaxing activities you and your girlfriend can enjoy with each other. Is there a spa nearby where you’ve been meaning to go? Booking a few nights at a relaxing resort might be just the thing to put you both in the mood, and a couple’s massage could prove a wonderful opportunity to relax together. Need more inspiration? How about a cooking class or an overnight foodie pilgrimage to a famous restaurant?

Got any other tips to share on how best to plan for time away with your girlfriend? Drop a comment below and share your insights. 

About the author

Chris Osburn

Chris Osburn is a freelance writer, photographer, consultant, and curator and the driving force behind the long running and award winning blog, Originally from the American Deep South, Chris has lived and worked all over the world and has called London home since 2001.

Leave a Comment

1 Comment