We didn't set out to build a travel company. We were simply the friends you asked before a trip.
We're going to Nashville. Where should we stay?
We're in San Diego for three days. Where should we eat?
We're celebrating an anniversary. Where would you go?
Those texts happened over and over. Because for as long as we can remember, we've loved planning trips almost as much as taking them.
How it started
It started with a friendship.
Us, obviously
Best friends first. Travel planners second.We've been planning trips together since we were kids. The Five On It just gave us a way to share that obsession with everyone else.
We've been best friends since we were kids. Long before any of this existed, we were building restaurant lists, comparing hotels, mapping neighborhoods, hunting down the hidden bar, and figuring out how to squeeze the most out of every single trip.
One of us is always the first to find the next incredible restaurant. The other is already working out the smartest route, the right neighborhood, the perfect timing. We just fit that way, and somewhere along the line, planning trips quietly became our favorite thing to do together.
Then we noticed
Everyone else was drowning in tabs.
Somewhere along the way, planning a simple weekend turned into a second job. Dozens of open tabs, endless TikToks, reviews that contradict each other, Reddit rabbit holes, the same five influencers naming the same five places. People were spending more time researching the trip than getting excited for it.
There weren't too few recommendations. There were too many.
So we built it
The thing we always wished existed.
Not about finding everything. About finding the few places actually worth your time, the ones we'd text a friend without thinking twice:
The restaurant you'd send your closest friends to.
The rooftop worth making a reservation for.
The neighborhood that's just right for your trip.
The hotel you'd book again tomorrow.
Because five is enough. Enough to compare, enough to feel sure, enough to plan a weekend you'll actually remember, and not so many that choosing becomes another chore.
We do the research. You enjoy the trip.
And now, you
Welcome to The Five On It.
What started as picks for friends and family has grown into something bigger. Now we get to share them with you, built the exact same way we'd build them for the people we love most.
We're so glad you're here. Let's plan something worth remembering.
