Remember when you wanted to go to Tulum with your girlfriends, but it never happened? Or that crazy girls weekend at the Palazzo that you were all daydreaming about? Or what about that half-baked plan to get your high school besties together for a spa getaway in Malibu?

It’s easy to get excited about traveling with your friends, but harder to actually make it happen. Here’s a few tips from a pro (yours truly) on how to turn your dream girls trip into reality.

Rally your crew

Someone’s got to be the instigator. Maybe this person isn’t the one that ends up reserving the hotel or planning activities, but there’s got to be a dreamer in every group – that person who is liable to say something like, “I want to go to Chicago because I want to take a reflection picture in front of the bean. Let’s go!”

Consistent communication

Your big dream might start with an enthusiastic conversation over drinks, but if no one brings up the idea after that initial talk, it might as well be dead in the water. Bring it up the next day over breakfast and then start a group text. It can say as little as “Let’s plan Chicago!”

Get dates on the calendar

When everyone is spread apart and in their own routines is the hardest part of the planning. I call it the “sea of separation.” To survive through this, you have to take some serious action. Get a date on your calendars. It feels crazy, but this can be done as much as six months in advance. Using your handy group text, pick a set of days where everyone’s available. If there’s one person who just can’t seem to make any of the available dates, you might have to kick them off the proverbial island.

Pro Tip

For picking dates, consider non-weekend days!
They’re cheaper and less less booked out.


This crucial step can make or break a successful planning process. If your destination is too far, you risk losing a day of travel in each direction. If it’s too close, it might feel too much like a STAYcation. I alternate between “jaunts,” which are little trips within an hour flight or three hours drive, and “journeys,” which can take me and my friends around the globe.

Anchor your trip

This is where you reserve your flights or your accommodation. Just book something! It’s surprising how much this can make a difference in whether or not a trip happens. Now there’s some money in the game and a good amount of momentum. Congratulations! If you get to this stage your trip is probably going to happen.

Know your limits

Everyone’s got a budget, even Oprah. Know what yours is, and have a sense for what your friends’ budgets are too, in order to keep expectations in line with reality. The ability to split the bill evenly at dinner can make everything a lot easier.

Have a hook

I have the tendency to take care of everything myself, but I have found that if my friends have a role in planning, they’re more invested, happier, and more fun to hang out with when we’re traveling. Whether each person picks a restaurant, or one person books the train and the other gets the airbnb, people are excited when they can contribute. Having roles also seems to make a difference in how people act when they’re actually traveling. If they don’t make any planning decisions, don’t expect them to be taking charge while en route.

Never stop plotting

While all the tips above are important pieces, my secret weapon is the “nexter.” At the end of each trip, while everyone is together, beaming from your new experiences, and glowing a little from the afternoon rose’, select your next trip!

Thanks for reading! You’re well on your way and I can’t wait to hear about your next girls trip. Oh, and if all else fails, put a gummy bear in your rose’, and call it a day.

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