Custom travel itineraries created by travelers for travelers. Sounds too good to be true, right?
You know that feeling when you get back from a trip and see your friends for the first time. They want all the juicy details. You’re still buzzing — sharing the highs, the lows, the hacks, the meals you’re still dreaming about, and the experiences you’d repeat in a heartbeat. Everything is fresh. Your perspective has shifted. And during that time, your tips are gold.
That’s the magic most travel planning is missing.
Enter Pinerary.
This is exactly what Annie, founder of Pinerary, has set out to preserve.
Annie’s Defining Travel Moment
Annie was born in St. Louis, raised in Denver, and now lives in Chicago. When she was young, travel wasn’t always about luxury or ease. Her parents were divorced. Life oscillated between abundance with her dad and tighter moments with her mom.
At age 10, she was sent to Honolulu with her grandmother and stepmother. She still remembers walking into the Royal Hawaiian — the scent in the air, the colorful florals, the feeling that she had stepped into another world entirely.
It wasn’t just a vacation. It was an awakening. And to share it with her grandmother meant everything.
‘That was the moment,’ she told me. ‘I realized there’s a whole big world out there to see and smell.’
Then it was Mexico, her first international trip years later. First, as a spring break hustle (selling trips to fund her own), then later as a place she genuinely fell in love with. The culture, the people, the energy. Travel began to take on new meaning. It wasn’t escape, it was expansion.
The Five-Day Portugal Problem
Fast forward to 2018.
Annie’s husband was pursuing his MBA and had five days in Portugal for a class.
The entire fam headed east, with the kids in tow. They had five days. Not enough time to wander aimlessly. Not enough luxury to get it wrong.
She did what we all do. She started asking people.
Who’s been there? What should we do? Should we leave Lisbon? Is this museum worth it? What’s overrated?
She didn’t want Pinterest boards or a list of 47 must-dos. She wanted someone who had lived it to say — Here’s how I’d spend five days.
‘There needs to be a place,’ she thought. ‘Select five days. Select Portugal. See what to do from someone you trust.’
That gap between overwhelming content and a trusted boots-on-the-ground experience is where Pinerary was born. When Annie told her husband about the idea, he said — go for it!
Pinerary’s Custom Travel Itineraries Are Different
Pinerary stands for pinning an itinerary. Pin-er-ary.
But the concept is deeper than a clever name.
At its core, Pinerary is a storytelling platform built around custom travel itineraries. Day-by-day guides created by real travelers who have actually traversed the trip.
Real people sharing how their days unfolded.
The day-by-day format is intentional. Research shows travelers plan in blocks. Morning, afternoon, evening. Knowing when to move on, how long something actually takes, and what’s worth slowing down for.
That’s where lived experience comes into play.
And here’s the part I love most:
‘We are all creators on Pinerary,’ Annie told me.
Not just professional travel creators, not just influencers, and not just brands. Everyday travelers.
That philosophy changes everything. Anyone can create an account and begin sharing. This resonates with me because I look at my travels as a book of work, a lifetime of experience. To think anyone can document their travels in a fun way that helps others, without building a blog or personal brand, is a game-changer.
It’s free to sign up. All travelers are welcome. In minutes, you can begin creating an itinerary for your future trip, or share a trip you’ve already taken to help other readers.
Traveling Better, Not Just More
There’s another layer to Pinerary that feels especially relevant right now.
For Annie, sustainability isn’t marketing language. It’s personal. Movement creates a footprint. So how can travel be more mindful?
Better planning leads to better impact.
Annie believes that when you plan intentionally, you choose experiences that benefit the places you visit. You seek out independent boutique hotels, participate in cultural activities that give back, visit sanctuaries responsibly, and interact with people beyond just your server at the resort restaurant.
‘We are a vibe,’ Annie said, smiling. ‘I want to foster that vibe.’
It’s not about luxury isolation.
It’s about meaningful participation.
Custom travel itineraries built by travelers naturally lean toward this kind of awareness because they reflect real experiences rather than curated perfection.
Where AI Fits — Without Replacing People
Of course, Pinerary lives at the intersection of travel and tech. The AI question inevitably arises.
Annie’s stance is refreshingly balanced.
AI can help funnel ideas more quickly. It can make research faster. It can organize information based on what someone is looking for.
There’s a place for it, but never at the expense of people.
‘We trust real stories,’ she told me. ‘There’s room for both.’
Future features may include gamified milestones. Badges for itinerary writing, trip creation, and community contributions, but never in a way that compromises authenticity.
What Stays Protected
As Pinerary grows, what Annie feels most protective of is simple. People’s voices. The storytelling stays sacred.
The knowledge that what you’re reading came from someone who actually walked in those streets, ate at the prized taqueria, and climbed that mountain.
You can’t manufacture that.
In today’s digital world, where the lines between real and fake are increasingly blurred, trust is harder to earn.
At Pinerary, nothing is bought.
Looking Ahead
Next up for Annie? A mother-daughter trip to Miami. South Beach. A boutique hotel stay. A little Latin culture and a lot of beach time.
Because at the end of the day, this platform wasn’t built in a boardroom.
It was built from awe. From five-day time crunches, wanting to get it right the first time, and creating a place for stories to live somewhere lasting. Where their meaning expands with each read.
And that’s what makes Pinerary different. Because the best trips aren’t dreamed up from algorithms or tons of research. They’re built from being out in the world.
To browse and take a stab at creating your own custom itinerary, visit Pinerary.com.
Happy voyaging,
Bekah
PS ~ For a couple more travel hacks, learn how we stay around the world for free here and master international cell phone use here!