Our Story
We Spent Six Months Planning a Two-Week Trip. Never Again.
Twelve years ago, we met. Four years later, I asked Cali to marry me on a balcony in Manarola — overlooking the Ligurian Sea at sunset, in that exact spot you've seen in every Cinque Terre photo online. She had no idea it was coming. I'd spent weeks researching the perfect Airbnb, the perfect moment, the perfect view.
What we both didn't know? The six months of planning hell that came before it.
Manarola, Cinque Terre — where it all started
The Problem We Lived
Our 15-day Italy trip was incredible. But here's what no one tells you: planning a trip like that is a second job.
Rome, Florence, Siena, Venice, the Amalfi Coast, Capri — We dropped our bags and hiked all five Cinque Terre villages in a single day because we can't sit still. We averaged 40,000 steps daily. We found hidden speakeasies in Trastevere, ate our weight in pasta, and learned just enough Italian to get by.
Cali spent six months — six months — glued to her laptop. Browser tabs in the dozens. Spreadsheets tracking trains, hotels, restaurant reservations, museum tickets. WhatsApp messages to confirm Airbnbs. Downloaded apps for every city's transit system. Reddit threads about which neighborhoods were walkable. Blog posts that said take the bus to the Colosseum, but never mentioned which bus, where to buy tickets, or that you needed to go to paper stands and ask "due biglietti dell'autobus per favore" — then validate them ON the bus.
We still missed trains because the station signage wasn't in English. We spent our first two hours in Rome scribbling Italian phrases on a napkin because our Airbnb was just far enough outside the city center that no one spoke English. We sat on steps in Florence — during precious daylight hours — frantically Googling "what to do near Duomo" because we had an unexpected gap in our schedule.
"How was Italy?"
We said, "Amazing." What we meant was: "Amazing, but we're exhausted, and we definitely missed half the things we should've seen because planning was so overwhelming we couldn't possibly research everything."
Venice, Italy — this trip is why Ask Leif exists.
Why We Built This
Most people don't want to plan a trip. They want to take one.
Fast forward to 2026. We're planning another European trip — 14 to 21 days. We look at each other and think: here we go again…
Except this time, we don't start. We want to take the trip. We just don't have time to plan it.
So we looked at what exists... glorified spreadsheets and apps with drag and drop features. AI chatbots that spit out 50 dinner options for Monday night — and you still have to research all of them. A lot of tools that save you 10% of the work, but leave you doing the other 90%.
We thought: What if you could just say "I want to go to Rome for a week... love food, history, outdoor activities and have a moderate budget" — and someone just did the plan. A fully researched, day-by-day itinerary with specific restaurant names, museum ticket links, local tips and time-of-day suggestions — in 60 seconds?
That's Ask Leif.
Who We Are
Shane.
Cali.
She's the planner. I'm the builder.
Before Ask Leif, I'd spent 2 decades in sales — logistics, SaaS and fintech. I've always had to solve complex problems, think in systems, and figure out how humans actually make decisions (psychology degree helped). Cali's the one who taught me to travel. I'm the oldest of five; my family didn't take a ton of trips growing up. She's the middle of three; her parents drove them all over the country to national parks and east coast visits to family. When we met in 2014, she showed me what it meant to explore.
Since then, we've been all over: two trips to Italy (Florence is our favorite city on earth), Spain, and dozens of U.S. cities — Charleston, Savannah, Asheville, Nashville, Sonoma, Scottsdale, Reno, Fargo, DC and more. We're not the type to sit on beaches — we hunt down the coolest and most unique hole-in-the-wall places no one mentions, hike until our feet hurt, and ask the locals where they eat.
We're not professional travel bloggers. We're just two people who got tired of spending more time planning trips than taking them.
Why "Ask Leif"?
Named after the explorer who discovered new worlds.
Cali's family is Scandinavian, and Viking history has always intrigued us.
We named this Ask Leif after Leif Erikson — because this isn't just a "travel or guide" website... it's a companion.
Leif is the traveler who's been everywhere, knows everything, and is always ready to help. Want to know the best time to visit the Uffizi? Ask Leif. Need a vegetarian restaurant near your hotel in Bangkok? Ask Leif. Want to find a local cocktail bar within walking distance of dinner? Ask Leif.
The name is intentional. Because when you're standing in a foreign city with a few free hours and no plan, you don't need a spreadsheet. You need a friend who knows the answer.
What Makes Ask Leif Different
We've used every tool out there. None of them actually solve the problem. Here's what we built instead.
We do the research for you.
No vague lists — "50 things to do in Paris" with no context. We tell you the where, what and why... specific, opinionated recommendations. "Have dinner at the Olde Pink House restaurant, known for its refined southern cuisine in a beautifully preserved 18th century mansion. Reservations are essential, often weeks in advance. Request a table in the cellar for a more intimate, historic ambiance." With links to book.
We build the plan for you.
Day-by-day itineraries with time-of-day suggestions, walking routes, insider tips, budget breakdowns, where to stay and what to pack. Everything — in 60 seconds.
We let you customize without starting over.
Don't like our dinner suggestion? No offense taken... swap it. Found a speakeasy on Instagram you want to visit? Drop the link in. Leif weaves it into your day. Your trip, your way — we just do the heavy lifting.
We stay with you during the trip.
Leif isn't just a pre-trip planner. He's in your pocket. Rain on Thursday, need to change plans? Ask Leif for indoor alternatives. Finished lunch early? Ask Leif what's nearby. He's built for the moment you're standing on a street corner in a foreign city, wondering "what now?"
This is the tool we wish existed when we were sitting on those steps in Florence, burning daylight while we Googled.
Common Questions
A few things people ask before they start.
Is Ask Leif free to use?
Yes — you can generate a full itinerary for free. No credit card required to get started. We offer a free tier so you can see exactly what Leif builds before deciding if you want more.
What destinations does Ask Leif cover?
Ask Leif can build itineraries for virtually any destination worldwide — every U.S. state (covers multiple cities within each), plus international destinations across Europe, Asia, Latin America, and beyond. If it's a place people travel to, Leif can plan it. New destinations and guides are added continuously.
Do I need an account to generate an itinerary?
You'll need a free account to create, save and access your itineraries — takes about 30 seconds. Your trip plans are private by default. But if you want to share your itinerary with the Ask Leif community and help other travelers plan their own trips, you can do that too.
Our Promise
We're not trying to replace the joy of travel. We're trying to give you more of it.
Less time researching bus routes.
More time riding them to places that matter.
Less time comparing TripAdvisor reviews.
More time eating the pasta.
Less time planning.
More time going.
We've traveled enough to know: the best trips aren't the ones you spent six months planning. They're the ones where you showed up ready to explore — and didn't waste a single day figuring out what to do next.
That's what we built. That's Ask Leif.
— Shane & Cali
Travelers. Builders. Frustrated planners who got tired of wasting time on spreadsheets.