The Pressure of Planning the First One
When we first started planning the first USA Local Guides meetup, I hoped people would come. Then I hoped they would enjoy it. Then, as the event got closer, I started worrying about every little thing.
People were buying flights, booking hotels, arranging rides, and choosing to spend their time and money to be part of something we had only imagined. That is a lot of pressure. I wanted this meetup to be more than organized. I wanted it to feel worth it. I wanted it to feel welcoming, meaningful, and fun.
I also wanted something bigger than one weekend in Key West. I hoped this first meetup could help us learn what worked, what didn’t, and what future USA meetup hosts could build on. In some ways, we were not just planning an event. We were trying to create a starting point.
Most of all, I wanted this to be the first of many.
This Was Never a One-Person Effort
And let me be very clear: this was never a one-person effort.
I may have been the on-the-ground taskmaster saying, “Come on, folks! This way!” but the entire team was herding right along with me — herding cats, I mean Local Guides.
@Rednewt74 Alfred brought the planning brain, the spreadsheets, and the systems that helped keep us organized. He also made the scavenger hunt work with easy submissions and real-time leaderboards — and honestly, who doesn’t want to win a trophy after seeing them displayed Thursday night?
@Twyla Twyla was everywhere with video, encouragement, and creative energy, helping capture the weekend while also nudging everyone into those fun video moments we will be so glad to have later.
@jayasimha78 Jay and Anju were constantly checking in with people, making sure everyone felt engaged, included, and happy. “Anyone need anything?” was not just a question — it was part of how they cared for the group.
@SoniaK Sonia was always smiling, always helping gather people into group photos, always counting, and always making sure we were not accidentally leaving someone behind.
@JustJake Jake was our FUN guy. Whether he was making people laugh, staying toward the back of the crowd to make sure nobody got left behind, or somehow ending up under Marilyn’s dress for the photo, Jake brought the kind of joy every meetup needs.
And @AdrianLunsong Adrian — from outside the USA — gave us so much more than we ever could have expected. He created the logos, artwork, and web application, and he kept advising us from his experience with the yearly European meetups. He did not have to jump in the way he did. He just wanted to help, and his guidance helped us imagine what this first USA meetup could become.
This team made the weekend happen. We all had different roles, different strengths, and different ways of keeping the group moving, smiling, and connected.
Thursday Night: Before the Event Even Officially Started
And then Thursday happened.
Before the official walking, mapping, touring, photo-taking, and scavenger hunting even began, we gathered in a private clubhouse (Bluewater Key RV Resort) just for our group. Everyone arrived however they could — separately, together, by carpool, with guests, with friends, and with a whole lot of excitement.
Within minutes, the room changed.
I loved seeing the 3D-printed name tags in action. I designed them with big readable names, each person’s state shape, and +1 guest tags, because remembering names is always one of the hardest parts of meeting a new group. That small detail helped everyone feel included.
People who had only known each other through Connect, Telegram, comments, posts, and profile photos were suddenly laughing together like old friends. We had hamburgers, hot dogs, chips, snacks, drinks, and so many things people brought to share. There were handmade items, thoughtful items, funny items, and special little pieces of the meetup already spread across the tables before the event had even officially started.
It felt like the memories were multiplying faster than we could take photos of them.
There was laughter. There was dancing. And then came the tutus.
Bringing out the tutus Thursday night was one of those silly ideas that instantly became a memory. Everyone started picking their color, laughing, comparing, posing, and suddenly our first group photo had a whole extra layer of personality. It was fun, ridiculous, colorful, and absolutely perfect for Key West.
That first tutu group photo set the tone: this meetup was going to be organized, yes — but it was also going to be playful, joyful, and not afraid to be a little silly together.
There were people showing each other what they had made, packed, printed, carried, shared, or brought from home. I had spent so much time worrying about whether the meetup would feel successful, and suddenly I could see it happening right in front of me.
The event had not officially started, and we already had memories.
Friday Morning: The Meetup Became Real
Friday morning came early. Very early.
After such a fun welcome party, we started at the Southernmost Point buoy at 8:00 a.m. People filtered in little by little, still waking up, still smiling, and ready for the first full day. And of course, we started with group photos — because who doesn’t love a group photo?
There was something special about standing there together at the edge of the continental United States. This was no longer an idea, a planning spreadsheet, a Telegram message, or a “maybe someday.”
We were there. The first USA meetup was real.
Butterflies, Smiles, and Nonstop Photos
From there, we headed to the Key West Butterfly and Nature Conservatory, and the smiles never stopped.
Everywhere I looked, someone was grinning, pointing, or lifting a phone for another photo. Butterflies floated right past our faces and landed so close that every few minutes someone seemed to be saying, “Wait… what? That butterfly is SO close!”
Our guide was wonderful and shared so much about the butterflies, birds, fish, turtles, and flamingos, but what I remember most is the joy in the room. The cameras never really went down because every step offered something new to notice. It was peaceful, colorful, beautiful, and full of those little details Local Guides love.
Herding Cats — I Mean Local Guides
One thing that made me laugh all weekend was how hard it was to keep a group of Local Guides moving through Key West.
Not because anyone was difficult — exactly the opposite. Everyone was having such a good time that every few steps turned into another photo, another selfie, another “look at this,” another conversation, another moment worth capturing.
“Come on, folks! This way!”
Then two seconds later: “Wait — hang on. Someone is taking selfies back there.”
And then: “Everybody wait here. I don’t want to lose anyone.”
There was also a lot of counting.
“1, 2, 3, 4…”
And then I would realize I did not actually know what number I was trying to reach.
“Wait. How many are joining us here? Do we have everyone? Does anyone know if someone is missing?”
That became part of the rhythm of the day. We were making the schedule — somehow! People could skip stops if they wanted to, and that flexibility was always part of the plan, but most stayed with us. We moved as a group, stopped for photos, waited for selfies, counted heads, and kept going.
Hemingway House: History, Laughter, and Cats in Charge
Next came the Hemingway House, where our tour guide was a retired clown — and yes, that was every bit as fun as it sounds. He kept us laughing while sharing the history of the home, the rooms, the grounds, and, of course, the famous cats.
The cats were everywhere, exactly where they wanted to be, because at the Hemingway House, the cats are clearly in charge. On benches, on walkways, inside, outside, stretched out like they owned every inch of the property — and honestly, they probably do.
Then Came the Rain
And then came the rain.
Not a sprinkle. Not a cute little Key West mist. A full downpour.
That was when keeping the group together became a little more challenging.
We left Hemingway House and headed out anyway — still walking, still laughing, still taking selfies, and still trying to stay together. The sidewalks were wet, the streets were puddled, umbrellas were popping up, and people were still finding things to photograph.
The rain could have stopped the fun. Instead, it turned the walk into an adventure none of us will forget.
That is when I realized this group was unstoppable.
We stopped at Mile 0 because, of course, we did.
“Everyone! Gather around the sign! Hurry! We can’t miss this!”
We were soaked; cars were going by; puddles were splashing; and somehow everyone was laughing.
And then there was Marilyn Monroe.
Was she a little out of the way? Yes.
Was it still pouring? Also yes.
Did that stop us? Absolutely not.
Who goes to Key West with a group of Local Guides and skips the Marilyn photo? Not us. So there I was, standing out in the street trying to take the photo while cars passed by and pushed puddle water right toward me. And still, everyone smiled.
We also stopped at the banyan tree, because even in a downpour, Key West has a way of making you pause and look around. The whole walk from Hemingway House toward lunch became less of a route and more of a shared adventure — messy, soggy, funny, and completely unplanned.
And somehow, that made it even better.
Garbo’s: Delicious, Soggy, and Unforgettable
Then came lunch.
I had picked Garbo’s, which is wonderful — but also mostly outdoor seating. Because apparently I like to test people’s flexibility.
By the time we arrived, the inside bar area was already full of people escaping the rain, so our group adapted. People ordered from the Airstream, stepped in and out of the rain, found tiny tables, bar seats, covered corners, and whatever dry-ish spaces they could.
Was it the smooth, sunny lunch stop I had pictured? Absolutely not.
Was it memorable? Oh yes.
We did not all make it to the Truman Little White House after that. The rain was just too much. But @JessicaBerg and @DustinBerg still went, and honestly — go them! That is true Local Guide dedication.
Half Shell: Regrouping at the Historic Seaport
After all that rain, Half Shell Raw Bar felt like exactly what we needed.
Half Shell sits right on the water at the Historic Seaport, and it was our planned happy hour stop — a place to regroup, relax, dry out a little, and let the day slow down. Once again, I asked everyone to wait while I went inside to see what I could do.
Somehow, we managed to set aside a whole section where everyone could stay together. Some people sat. Some mingled. Some ordered food. Some kept taking photos. Conversations flowed as if these were old friends who had known each other for years, rather than people who had just met in person the night before.
And then came the half-price appetizers.
Honestly, that is the way to eat dinner in Key West.
After a morning of tours, downpours, puddles, and improvised lunch seating, it felt good to have space for everyone to settle in. The group did not need much by then. Give them a place to gather, and the laughter, stories, and photos took care of themselves.
And yes, the tutus came back out.
They had started Thursday night with that first colorful group photo, and by Half Shell, they already felt like part of our meetup personality. Because apparently, once a group of Local Guides chooses tutu colors together, tutus are no longer optional.
Mallory Square Sunset
Sunset at Mallory Square was not until 8:15, and after the rain, not everyone made it that long. I was one of the people who did not make it, and yes, I am still sad about that.
But those who did go said the sunset was amazing — and the photos prove it.
That feels like Key West, too. Not everyone’s day ended in the exact same place, but everyone had their own version of the adventure.
What I Will Remember Most
Looking back on Thursday night and Friday, what I remember most is not that every plan went perfectly.
It didn’t.
What I remember is that everyone kept showing up with joy.
They laughed through the welcome party. They smiled through the Butterfly Conservatory. They laughed through Hemingway House. They took selfies in the rain. They posed at Mile 0 in a downpour. They walked out of the way for Marilyn. They ate wherever they could fit. They wore tutus to happy hour. They stayed flexible, open, kind, funny, and ready for the next moment.
As one of the planners on the ground, that meant everything to me.
I had worried so much about whether people would have a good time. I wanted this first USA meetup to matter. I wanted people to feel welcomed. I wanted the weekend to feel worth the trip. I also wanted us to walk away with lessons — not because everything had to be perfect, but because this first meetup could help make the next one even better.
By Friday night, I knew.
It was working.
Not because every detail went according to plan, but because the people made it work. The team made it work. The group was unstoppable, the connections were real, and the laughter kept carrying us forward.
And this was only the beginning.
In Part 2, I’ll share more from Saturday and Sunday — the harbor stops, scavenger hunt moments, awards, goodbyes, and the memories that carried us through the rest of the weekend.
And in Part 3, I want to step back and share what we learned from planning the first #USAMeetup: what worked, what we would do differently, and what future USA meetup hosts may be able to build from.
Because Key West was never meant to be the only one.
It was meant to be the first of many.
Many of these photos came from our shared meetup album, because apparently when I was busy herding Local Guides, counting heads, watching the schedule, and trying not to lose anyone, I did not take nearly enough photos myself.
Thankfully, all of you did.
Thank you for sharing the smiles, selfies, soggy moments, tutus, cats, butterflies, sunsets, and everything in between. This recap would not feel the same without the memories everyone captured.
I had help turning my notes into something readable, but the stories, the worries, the laughter, and the “holy cow, this is actually working” feeling are all mine.
Love it!
