Go With Rosie Is Live: A Free Family Travel Platform
Go With Rosie is a free family travel platform that scores every venue 0 to 100 for real family-friendliness and helps parents plan a trip without the research spiral. Custom itineraries built around your kids' ages and pace. A Trip Wallet that keeps the whole trip in one place. We launched on March 18, 2026, it is still free, and we want families to shape what we build next.
What problem does Go With Rosie solve for parents?
You start with one search and end up deep in a research spiral. Hotels, restaurants, activities, forums, review sites, each one sending you somewhere else. A parenting thread says a resort's kids club is great, but someone in the replies says it doesn't take toddlers. A 4.8-star restaurant has a 45-minute wait and no changing table. "Family-friendly" is slapped on everything and means nothing.
Hours of research. Dozens of sources. And you're still guessing.
We wanted to know how big that gap actually was, so we analyzed 50,000 Yelp reviews across restaurants and activity venues. Only 3.5% mentioned kids at all. Only 0.3% mentioned a specific family amenity: a changing table, a high chair, a kids menu, stroller access.
50,000 reviews. 3.5% mention kids. 0.3% mention a family amenity. The information families need to decide barely exists in the places they are looking.
Then we talked to more than 100 parents before building anything. Every conversation landed in the same place: reviews come from people whose situations don't match yours, and every travel site out there is built around the booking rather than the trip. A bad vacation still counts as a sale on their end.
Family travel is a different kind of planning, with different variables, and nobody was building for it. So we did.
What is live right now?
The Rosie Score
Every venue gets a Rosie Score from 0 to 100 based on what families actually care about, weighted across six dimensions: age appropriateness, safety and supervision, educational value, weather independence, physical accessibility, and cost and value. The signals behind those dimensions are the specifics parents ask about, including stroller access, wait times, noise levels, and changing facilities.
The Rosie Score is not graded on a school curve where anything below 90 feels like a failure. An 80 or above is an excellent venue for families and earns our Rosie Approved designation; the Chicago Children's Museum was the first venue to earn it, at 81. A score in the 70s is still a good option. Every score breaks down into the dimensions behind it, so you can see exactly why a venue landed where it did. Maybe you care most about free admission or a place you can leave after 40 minutes. A venue scoring 60 overall might have standout marks in the dimensions that matter most to your family. The score gets you started. The breakdown helps you decide.
Custom itineraries and templates
Tell Rosie about your family (ages of your kids, what you're into, your pace) and she builds a custom itinerary from our scored venue catalog, with real data behind every recommendation. Don't want to start from scratch? Browse pre-planned itinerary templates built around destinations and family types. Every template drops straight into the itinerary builder, where you make it yours.
The itinerary builder
This is where everything comes together. Once you have an itinerary, whether Rosie built it or you started from a template, the builder lets you customize everything. Drag and drop to rearrange. Search for new venues and see their Rosie Score before you add them. Switch between calendar view, list view, and map view to see your trip from every angle.
Add smart blocks for the things other trip planners ignore: nap times, hotel time, travel time between stops. They are built into the scheduling, so your itinerary reflects how families actually move through a day.
Trip Wallet
Every trip generates loose pieces: hotel confirmations, flight details, packing lists, activity reservations, notes about what to bring. The Trip Wallet keeps it all in one place so you're not digging through email threads and screenshots when you need something. Right now you add things manually. Soon, hotel bookings, check-in times, and more will flow in automatically as we roll out booking integrations.
How is this different from asking a chatbot?
Fair question. A general-purpose chatbot can give you ideas for a family trip. The difference is where the answer comes from: text generated on the spot, or a trip built from real, evaluated data.
Go With Rosie starts with data, not prompts. We built a foundation of venue data evaluated specifically for family-friendliness, and every recommendation is grounded in that catalog of scored venues. A general-purpose text generator treats "family-friendly" as a keyword. We treat it as a set of measurable criteria.
That foundation lets us do something generic tools can't: capture what makes your family unique. Accessibility needs. Dietary restrictions. Nap time patterns. Whether your kids love museums or melt down in them. Over time, Go With Rosie learns what works for your family, kind of like how a streaming service figures out what you'll want to watch next, so recommendations get better and come from families like yours, for families like yours.
And even a chatbot with solid recommendations can't drop them into a customizable itinerary builder with calendar, list, and map views, add a smart block for nap time, or score a venue you found on your own and tell you whether it's worth the stop.
| What you need | General chatbot | Online travel agency | Go With Rosie |
|---|---|---|---|
| Family-friendliness rating | Keyword matching from text | Star ratings from all travelers | Rosie Score, 0 to 100, across six dimensions |
| Itinerary you can edit | A block of text | Not offered | Drag-and-drop builder with calendar, list, and map views |
| Nap times and drive time | Only if you ask | Not offered | Smart blocks built into the schedule |
| Trip documents in one place | No | Booking confirmations only | Trip Wallet |
| How it makes money | Subscriptions | Bookings, plus paid placements | Hotel booking commissions only, no paid placements |
Why is Go With Rosie free?
This is the question everyone asks, so here's the direct answer. The entire experience is free right now: venue scores, the itinerary builder, the Trip Wallet, custom itineraries. No paywall and no premium tier.
Our business model is hotel booking commissions. We're in the final stages of integrating with a major hotel supplier, and when that's live, families will be able to book directly through Go With Rosie. That's how we'll make money.
| Promise | What it means |
|---|---|
| No data sales | Your family's information is yours. We don't sell it, share it, or monetize it |
| No paid placements | Advertisers don't pay to rank higher in our scores. If a venue is paying us for visibility, we can't also promise you an honest score. Those two things can't coexist |
| Same tools for every family | Not just the families booking a two-week cruise. The same honest recommendations for a road trip, a one-night stay, or a budget weekend |
How did we get here?
The startup story usually gets cleaned up for public consumption. Here's the actual version.
I'm a product manager by background. I knew what to build. But to prove this thing could work, I taught myself to code and built about 90% of the beta myself. It was the only way to move forward without the kind of funding that comes with strings attached.
The beta worked. Families found us with zero marketing spend and generated $30,879 in bookings. That was real validation. People wanted this.
The number one piece of feedback was hard to hear: families wanted to book everything through us. Hotels, activities, the whole trip in one flow. Without that, they saw us as a planning tool rather than a full travel experience. They were right.
So we shut the beta down. I found a small, tight-knit team I trust, people who care about building things the right way, and we rebuilt from scratch with real architecture, proper data security, and the booking integrations families asked for. It took longer than we wanted. We could have kept the beta running and patched things together, but scaling on a shaky foundation isn't how you build something that lasts.
What launched in March is what families told us to build. And it was built in Sheboygan County, Wisconsin, with help from the SCEDC and the Sheboygan County Innovation Council: that story is here.
What's coming next?
Hotel bookings are nearly ready. Families will be able to book directly through Go With Rosie with zero impact on scores or recommendations. Replan a Day is close behind: a feature that helps you pivot when plans fall apart (weather changes, someone has a meltdown, an attraction closes early) by rebuilding your day around your family's preferences, location, and your kids' ages. Activity bookings and road trip planning tools are also on the list.
What matters more than our roadmap is what you care about. The next features don't have to come from a product plan. They come from parents telling us what would make their next trip easier. That's how we've built everything so far, starting with those 100-plus parent interviews, and it's how we want to keep building. If you use Go With Rosie, tell us what's working and what's not at hello@gowithrosie.com.
Why does family travel need its own tool?
There are 33 million US households with children (Census Bureau). Every major travel site treats them as a checkbox filter rather than a category worth building for. Family travel is harder to serve: more variables, higher expectations, lower revenue per booking than the business and couples travel that drives most of the industry. The big players aren't going to do the work.
We are. That's the bet.
We won People's Choice at the Startup World Cup Regional hosted by the SCEDC, not because investors loved a pitch deck, but because a room full of real people connected with what we're building. That's the signal we keep coming back to.
If you're a parent who's done the research spiral, come try it. If you're an uncle or godparent trying to plan something great for your nieces and nephews, I built this for me too. It's free. It's live. And we're just getting started.
Questions families ask about Go With Rosie
What is Go With Rosie?
Go With Rosie is a free family travel platform that scores every venue 0 to 100 for real family-friendliness. It includes custom itineraries, a drag-and-drop itinerary builder, and a Trip Wallet for organizing travel details. Scores come from 50,000 analyzed venue reviews plus venue data, never from paid placements.
How does the Rosie Score work?
Every venue gets a score from 0 to 100 across six dimensions: age appropriateness, safety and supervision, educational value, weather independence, physical accessibility, and cost and value. An 80 or above earns Rosie Approved status. Every score breaks down by dimension so you can weigh what matters most to your family.
Is Go With Rosie really free?
Yes. The Rosie Score, itinerary builder, Trip Wallet, and custom itineraries are all free, with no paywall and no premium tier. Go With Rosie earns revenue through hotel booking commissions only. No data sales, no paid venue placements.
How is Go With Rosie different from asking a chatbot for trip ideas?
Go With Rosie starts with real, evaluated venue data scored specifically for families rather than text generated on the spot. Every recommendation comes from a catalog of scored venues, and it drops into an itinerary builder with calendar, list, and map views plus smart blocks for nap times and drive time.
Does Go With Rosie sell user data?
No. Your family's information is yours. Go With Rosie doesn't sell it, share it, or monetize it. Revenue comes from hotel booking commissions only, and venue scores are never influenced by advertisers or paid placements.
Where is Go With Rosie based?
Sheboygan County, Wisconsin. Founder Tyler Heilberger is a Sheboygan native, and the company was built with support from the SCEDC and the Sheboygan County Innovation Council through Accelerate Sheboygan County. The team remains small, tight-knit, and mostly Wisconsin-based.
What features are coming next?
Hotel bookings are nearly ready, letting families book directly through Go With Rosie with zero impact on scores. Replan a Day is close behind, helping families pivot when plans fall apart. Activity bookings and road trip planning tools are also on the list.
