What makes a great friends’ trip? 

Like all the best adventures, it starts with a beverage (or a few) and a late-night discussion that spins just a bit out of control. You will find many moments to share an adventure as you approach life’s many milestones—finishing your freshman year in college, celebrating landmark birthdays, and, yes, even retiring. 

Be sure to take the opportunity. As a wise friend told me, the best way to get to know someone is to hit the road together.

I’ve found that character and camaraderie are built in security lines, delayed flights, and the endless waits for checked bags. I also believe that amazing food, roaring laughter, and the brief escape from everyday responsibilities create some of the strongest bonds. 

There is no better way to maintain friendships and create memories that will last a lifetime. I’ve taken many “friends’ trips,” but three stand out. Let me walk you through them and, I hope, inspire you to take your own.

As our freshman year at Boston College started to wind down, four of us from the Class of ’89—Anita Cole, Lisa Contreras Wilkes, Chrissy Garvin, and me—committed to a two-week visit to our friend Andrea Soares, who was living in Bermuda. 

We scraped together money from our summer jobs to cover airfare, moped rentals, and other recreational expenses (like a visit or two to the Swizzle Inn and similar). Amazingly, we all made it.

Small hardly begins to describe our residence: Andrea’s dad’s apartment. A studio that felt even more cramped after bringing far too many clothes.

We learned a lot along the way, such as the yucky fact that Andrea likes raw bacon. I also learned the hard way that using baby oil on my fair skin was a mistake, no matter how tan I thought I was. We also discovered that if you choose to visit the beach at night (for whatever reason your imagination cooks up), you should make sure to lock up your rental moped.

My favorite memories include watching Andrea bartend, laughing until we cried, and having my parents walk right by me at the airport, as they had never seen me with a real tan.

Turning 50 is a significant milestone birthday. When my friend Lauren reached that marker, two of her friends, my middle child, and I decided to join her for a big celebration in Lisbon, Portugal. Safe to say, our accommodations far exceeded the studio apartment in Bermuda (a perk of getting older). 

I learned several fun things: If you sleep in a bit, the “bread fairy” quietly sneaks into the building and leaves warm rolls at the front door every morning. Lisbon challenges you with hills and staircases, but rewards you generously with food and drink. Pasteis de nata are best eaten when warm. And lastly, I discovered that fado music is not my favorite. 

There are moments from this trip that I’ll carry forever, like watching the sunset from a chartered sailboat, seeing the waves crash in Nazaré, and taking a wine tour with a handsome young tour guide we all developed a small crush on. And perhaps not my proudest moment—I joined a work conference call from a chapel made of bones (sorry about that, God, but it made for an interesting ice breaker with my client).

Lastly, one trip stands out: a gift from my husband. Frustrated by my complete lack of direction when it came to a birthday present, he leaned over one evening and said, “Duran Duran is on tour and coming to Madison Square Garden in October.” 

I looked up from my laptop and replied, “Oh, I would love to bring my three friends (Lori, Samantha, and Katrina) from high school to see them.”

Here is a bit of helpful backstory on why this trip meant so much to me. In 1984, the four of us somehow scored tickets to see Duran Duran (how we got them—and the post-concert shenanigans—remain a shared secret). We watched every music video and listened to their songs on the radio constantly. 

As young drivers, we also somewhat recklessly followed the band’s limo along the Mass Pike on its way to Worcester. I still remember the pulsating energy and pure excitement of seeing my favorite band perform live. 

So, 40 years later, we got the chance to do it all again. I hadn’t seen Samantha or Katrina since 1986, but we had reconnected on social media. Unsure of what would happen, I reached out—and sure enough—they all said yes.

They all stayed in my apartment in Manhattan, and beyond singing along to “Hungry Like the Wolf,” we toured the city, ate too much, and stayed out too late. We got snacks at Porchlight, went shopping, and wore tiaras as we saw Six on Broadway.

These trips helped me learn so many fun facts and gave me memories that will last a lifetime. They also taught me just how quickly you can reconnect, how some bonds transcend time, and how old friends remain so special. 

So please, start the conversation today, book the trip, and go. I guarantee you won’t regret it.