Trips with Friends

Good friends follow you anywhere.

Winnie the Pooh

I love to travel and can’t remember a time when the anticipation of a trip didn’t make my days a little brighter. Growing up in the Southeastern United States far from extended family meant annual summer road trips to see them in New England. While our destination didn’t change, each experience was a little different and my best childhood memories include the salt water taffy and hydrangeas of Cape Cod.

Once I started working, my travel ambitions were only limited by vacation time and budget. By my early 30’s I had driven around Ireland with my friend Teffani, hiked in Costa Rica with Gayle, and cycled through Provence with Patty. When I started a family of my own, my trips were largely relegated to kid-friendly destinations. I relished the opportunity to create lifelong memories for my children as my parents did for me, but I missed the time spent away with friends.  

While time for travel with friends became less frequent, it never lessened in importance to me. With my bestie Sara and me living a plane ride apart, long weekend trips were a way for us to stay close and connect more deeply. Our trips to Georgia and West Virginia gave us an opportunity to explore new places and try new foods. Our stay at a spa in Western Massachusetts was the perfect venue for rest and reflection after some trying life experiences. Then our return to New York City nearly two decades after we had moved away involved the most thrilling celebrity sightings ever. These adventures were memorable, but the chance to talk for hours without having to think about the responsibilities of daily life was soul nourishing.

It doesn’t matter where you’re going, it’s who you have beside you.


As pandemic restrictions have eased, travel is once again picking up, and there’s no better time than summer to explore someplace new with a few friends. Travel has the potential to deepen friendships, but it involves a leap of faith, as well as a fair amount of planning. In April I had the opportunity to take a trip with a few local women I primarily knew from shared activities like book club and parenting 7th graders. I had tagged along with two of them on an overnight trip in the fall of 2020, and it went well enough to start thinking about other travels.

As I was a newer addition to this small travel group, I wanted to make sure they didn’t feel like they had to do all the work with travel planning, so I suggested a visit to my home state of Kentucky. They’d heard me go on about its beauty, and the idea became even more compelling when I suggested we go in April during Keeneland’s thoroughbred spring racing season.

Traveling with a few friends you’re still getting to know can be tricky, but I’ve learned over the years a few lessons that can set a trip with friends up for success:

  • Discuss expectations. This is such an important and often overlooked step when planning a trip. For our Kentucky weekend, it was important to make sure we were all up for the 6-hour drive and ok sharing rooms in our Airbnb. While we talked of inviting the entire book club, we settled on a smaller group to minimize the complexity of travel logistics.  Lumi loves to hike, so we made sure to incorporate a visit to Raven Run Nature Sanctuary. I have close family friends in Lexington, so I confirmed that everyone was fine with spending our Friday evening with the extended Thomas family on the outskirts of town.
  • Let someone lead. Since Kentucky is my home state, I led the planning, regularly checking in with my travel companions prior to making any big decisions. If it’s less obvious who should be in charge, discuss what needs to be done and identify who should plan what. While acting as trip lead may seem like a lot, one benefit is you get to hand off stuff you’d rather not do. I’m great with setting up Google sheets to track expenses but don’t love to be driving for hours on end. So we took my laptop and another friend drove.
  • Sweat the big stuff first and let the small stuff flow. Once we had a general sense for what the weekend should look like, we quickly locked in the dates, bought tickets to Keeneland and reserved a place to stay.  We had a general idea of where we wanted to eat and what sights to explore, but we were willing to be flexible as well. This led us to discover a new coffee shop and then enjoy a homemade breakfast Saturday morning at Lucretia’s home.

The Kentucky weekend was full of laughter and the making of new memories. And the trip definitely brought our growing friendships to a deeper level. I learned Julie drinks tea, not coffee, and Lumi and Shiva can’t get enough of hats (and selfies)! These may sound like small things but discoveries like these help us connect as individuals. We’ve started kicking around ideas for future adventures, and I’m looking forward to those. I’m also looking forward to my next trip with Sara. Although we’ve had some quick visits over the past few years, it’s been a while since we’ve taken a real trip, and there’s nothing like staying up late, talking about everything and nothing, away from it all with your dearest friend.

Julia and her friends hiking in Kentucky.

One thought on “Trips with Friends

Add yours

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s

Blog at

Up ↑

%d bloggers like this: