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Guest Post: Four Things I've Learned from Traveling with Girlfriends

I'm excited to feature a guest post by my great friend Stephanie! We've known each other for ages and she's my partner in crime for many of the fun times you see here on Sage & Serendipity! Steph and I love talking all things the Royal Family, taking spinning classes, and finding yummy new restaurants in the city. We've taken several trips together and have many (many) more planned for the future!

I'll toss it over to Stephanie!


I'm a single gal who loves exploring new cities. My favorite travel partners are my girlfriends. In the past few years we've explored the streets of New York City, rode ferries in Seattle, and strolled the beaches of Florida. I'm lucky to have girlfriends who love to travel and explore new cities. But, as with most groups of friends, we aren't without our disagreements or spats of drama. A trip with your girlfriends can be awesome or disastrous. Here's a few things I've learned during my past few years of traveling with friends:  

1. Set clear expectations.

Is this trip about seeing the sites? Or is it about relaxing by the pool/beach? Whether it's a loose schedule or detailed itinerary some expectations need to be set on what each lady should expect for the trip. While planning, the group should discuss the objectives of the trip (exploring vs. relaxing), the money you're expecting to spend, and the activities you'd like to do. This will look a little differently for different friend groups. For some trips we've had a detailed itinerary of activities with restaurant reservations and color coding. You may not get that detailed, but at least discuss a little of what you'll do each day. Otherwise you might be in a new city with four different opinions on what do that day, or worse four ladies who each don't have an opinion.

Cocoa Beach, FL

Cocoa Beach, FL

2. Don't be afraid to speak up.

A few weeks ago I went to Savannah with some college girlfriends. Prior to the trip it was recommended to go to the Juliette Gordon Low Birthplace. As a former Girl Scout, I really wanted to tour the house. So, when I arrived I told my friends that it was something I at the top of my list. None of them had been Girl Scouts, so the tour probably wouldn't have been their first choice. But, I asked and they obliged. They made it fun because they knew I loved it. And in return, when my friend Jillian said she wanted to visit Bonaventure Cemetery -- a site I wouldn't have chosen -- I obliged and had fun. Don't miss a site or activity you wanted to see because you're afraid to rock the boat and then leave disappointed. If you're into it your friends will get into too.

3. Address the drama.

Last summer, Logan and I headed with two friends to NYC (note from Logan: find all those trip recaps in my NYC section here!). On day two we planned to explore Brooklyn. We mapped out an agenda that included shopping, pizza and a walk across the Brooklyn Bridge. A few hours in we had walked miles more than we expected, were tired, cranky and hungry. It could have been a breaking point. Instead, we addressed it. Our solution: for 30 minutes we need to just sit in the air conditioned restaurant and not talk. So we sat silently in a pizza place playing on phones. It allowed us to all take some deep breathes, to relax and recover. After some silence (and food) all our moods improved and we could move on drama free. Don't let crankiness ruin a trip. Address it head on, find a solution and go back to having fun.

Brooklyn, NY

Brooklyn, NY

4. Be prepared for the unexpected.

I've missed a connecting flight, our car has overheated, and one lady spent the night on the bathroom floor. And that was just one trip! Something will go wrong. It's inevitable. Despite your best planning you might have to miss one of the most beautiful beaches to sit in Roy's Autoshop in St. Augustine, Florida (highly recommended by the way). Make the most of it: walk to Target, read funny cards and get slushies. Download Head's Up on your phone and be the loudest in the airport. Enjoy the times with your friends, turn attitudes around and laugh together. You won't regret making the unexpected fun AND you'll have a good story for later.


Stephanie is twenty-something gal. When she’s not trying new restaurants in Chicago, she’s exploring a new city or kayaking at her lakehouse. She's an avid reader, podcast listener and foodie. Follow her on Twitter or Instagram @stephaniehermes.