Does a Trip of a Lifetime Exist Anymore?


I remember a text message I once received from someone I had just met. I had recently moved to Fort Lauderdale, and was in that stage of meeting new people, finding friends, and getting settled in a new place.

I remember telling this new neighbor of mine that I was about to embark on a 5-week trip to Europe, from London to Malaga to Bordeaux to Paris to The Netherlands and finally to Ireland for a family road trip.

I remember his reply reading, “Wow, that’s a trip of a lifetime.”

And I remember thinking, but is it?

Sure, it was long. But as I used to live in Europe, this was actually one of my shorter sojourns to the other side of the pond. I’ve talked about my thoughts on chasing the high  before, and have often pondered whether or not we ever get a bit blasé about travel. Whether we become a bit too hard to impress.

Then #CaptureAnguilla happened.

For those of you who saw the posts all over Instagram, you might have already seen what this was about. For those who haven’t, I’ll explain.

#CaptureAnguilla was a gathering of travel media rockstars who traveled to the Caribbean island of Anguilla to experience the island, share skills, connect with other creatives, and create memories.

What we ended up creating was Magic.

And this brings me back to the original question, does a trip of a lifetime exist anymore?

Previously, I might have been inclined to say no. But now, I’m singing a different tune.

Our stay in Anguilla was stamped with stays at both Viceroy Anguilla and Àni Villas, sunset sails with Tradition Sailing, painting classes with Lynne Bernbaum, sushi dinner at the CuisinArt Resort, a backstage glimpse into the festivities of Carnival, and more incredible activities that define the popular term “experiential luxury.” We were pampered, and it was fantastic.

But that’s only one part of what made this trip so incredible.

The first ingredient that made this the recipe for a trip of a lifetime: the people.

For me, it’s the people that make an experience, more so than the place. This group, most of us who had never even met before, connected in such a way that none of us doubted that our paths were meant to cross. Usually groups this big – 10 in total – meet, chat, share a few tips and stories and then fondly hug at the end and say they had a great time. And I’ll say it, usually there’s one or two people with whom you may not have gelled.

That’s what made this trip different.

There wasn’t a single person there that I felt like I didn’t connect with. That we didn’t have a chance to sit down, have a real conversation beyond the fluff, and return to Florida feeling like I’d known them way longer than five short days.

In the coming weeks I’ll be introducing you to each of these attendees, and writing about the experience in more detail. It’s far too much to squeeze into one post.

So for now I’ll leave you with this thought:

The trip of a lifetime certainly does still exist, if you leave yourself open to the magic.

 The #CaptureAnguilla Attendees

Kristen Kellogg | Lacy Colley YamaokaRachel Rudwall| Mu-Hsien Lee |  Chrissann Nickel

Jessica van Dop DeJesus |Nathaniel Boyle | Aysegul Stanford | Bonnie Bloom

{photo by Kristen Kellogg}

  • Elena Sonnino

    Beautifully written. And I could not agree more. My trip to Turkey in May – especially our short side trip to Urfa was made so memorable by the people I was with.

    • Thank you Elena! It really is up to the people. I was thinking today too, the road trip to Ireland with my family definitely qualified as a trip of a lifetime as well. Not just because it was Ireland, but because we all managed to gather together for 10 days and explore a new country. Those are moments that deserve to be recognized and treasured. 🙂

  • Looking forward to reading all your impressions! This was quite the experience!

    • Thanks Jess!! Love writing about our time there – it’s the closest we’ll get to reliving every moment! 😉

    • Same with yours!! And your photos are so much better than mine… you’ll have to teach me some basics when you’re here next month! 🙂

      • We all had great photos. Love the way how the same scene looked so different from each viewpoint… Yes! Let’s go on a photo spree of Miami/South Florida next month!

        • Yes lets!! Everyone really did have fantastic photos… I was inspired to pick up my Nikon D3200 when I got home, but so far all I can seem to shoot are photos that come out almost completely pitch black… oh learning curves! lol

  • It sounds like your Anguilla trip had all the right ingredients for a memorable trip :-). We look forward to hearing more about your experience!

    • It was an incredible trip!! Partly the destination, partly the group, and mostly because everyone was so open to sharing the experience fully. Really makes me want to organize more meet-ups with all the amazing travel media connections out there! 😉

  • NIce intro! Absolutely agree…the trip of a lifetime deserves to be told in many parts 🙂

    • Thanks Mu-Hsien!! Anguilla certainly qualified as one of my life lottery wins! 😉