Vermont, without the guesswork
Private Vermont guided tours and custom day plans built around what’s actually worth your time.
What if Vermont doesn’t go as planned?
Most trips don't go wrong because people didn't try. They go wrong because the internet gives everyone the same (tired, inaccurate, boring) advice.
I know the roads, the timing, and the stops that don't show up on everyone's Top 10 list. You just show up.
5-star TripAdvisor& Google reviews. Limited weekend availability.
Why Vermont trips disappoint
Planning a day in Vermont should feel exciting. Instead, it often feels overwhelming.
Too many “must-see” lists. Untrustworthy opinions of what to do on social media. Routes that look simple online but waste hours in real life. Crowded stops that feel anything but special.
Vermont looks easy on a map. The roads around Woodstock, Killington, Ludlow and Weston don't behave the way Google suggests and the most crowded stops are often the least memorable.
No local insight into what’s actually worth checking out
Timing that quietly kills the mood
Popular spots that feel crowded instead of charming
Vermont is totally worth doing right!
In their own words
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"There is just no way we could have experienced such beautiful sites on our own."
—Fred G., TripAdvisor review
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"I was also glad to have one day where I was not in charge of the itinerary!"
— Patricia D., TripAdvisor review
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"This was hands-down one of the best day tours I’ve ever taken and I travel a lot. It felt personal, special, and completely unique."
— Martha J., TripAdvisor Review
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"We had a particular type of tour in mind and Aimee delivered perfectly."
—Val S., Google review
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"Aimee took us on backroads, through covered bridges and allowed for multiple photo ops while providing expert knowledge of the area. This was a 5 star experience."
— Thomas, Google review
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"We would highly recommend her tour to anyone looking for a relaxing, fun, enlightening, and memory-making day in Vermont."
— Mike, Google review
★★★★★ 5-star rated on TripAdvisor and Google ★★★★★
Here’s what a great day in Vermont actually feels like
Instead of rushing from stop to stop, your day flows.
Instead of second-guessing the next turn, the route makes sense.
Instead of fighting crowds, you find quiet stretches that feel like Vermont.
You tell me what you love. I handle the rest: the timing, the route, the backup plans for when a spot is busy. You get quiet bridges, open views, and stops that actually earn their place in the day.
No guessing. No rushed stops. No parking surprises. Just a day that feels unhurried from start to finish.
• The drive feels scenic, not strategic
• The timing works with the day, not against it
• Every stop earns its place
• You experience Vermont instead of managing it
Here's how it works
Step 1 Tell me your date and what kind of day you’re after
Step 2 I build a private route around your interests, with timing that actually works and a plan for whatever the day brings.
Step 3 Relax. Ride shotgun (or in the back seat). I’ll take it from there.
What every tour includes
Private tours only. No mixed groups, ever.
A custom route built around what you actually want to see.
Timing designed to avoid crowds and traffic.
Pacing that adjusts as the day unfolds.
Photo stops timed to light, weather, and season.
Local stories that bring each stop to life.
Flexibility to change course if something better comes along.
A private Ford Bronco. Comfortable, capable, and genuinely fun to ride in.
Pickup and drop-off included.
Clear pricing. No surprises.
Who is a day with Vermont Wayfinders for?
Not every traveler wants the same thing from Vermont. But there's a common thread. You’d rather experience the day than manage it.
The planner in the group who wants one day where they're not managing every decision.
Repeat visitors who've done Woodstock and Quechee and want something deeper and quieter this time.
Couples and small groups looking for a day that feels genuinely personal, not packaged.
Photographers who care about light, timing, and being in the right place at the right moment.
Independent travelers who love exploring but want a local to unlock the corners Vermont doesn't advertise.
Ready for a Vermont day that actually feels like Vermont?
Private. Thoughtfully planned. Designed around you.
No guesswork. No rushed stops. No crowded tour buses.
Still deciding?
Take the Vermont Anchor Day Quiz and see what kind of Vermont day is right for you.
