How does it work?
Our itineraries include a 'Before You Go' package and four surprise stops. Each stop is packed with a new destination, specific recommendations, maps, travel tips and fun facts.
See our road trips below, or check out our quiz and trip map to help find your perfect adventure.
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Road Trip Gift Card
Regular price $74.00 USDUnit price perGive the gift of a one-day surprise road trip with Guess Where Trips®! The recipient can then choose a surprise trip that suits them! -
Cascades & Colors
$39 USDFunky colorful towns full of local eateries and shops, a few waterfalls that will leave you in awe and one of the most unusual gardens we have ever seen. You’ll want to get your camera out for this trip!- Kid-Friendly
- Dog-Friendly
- Accessible
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A Taste of Amish Country
$39 USDEscape to quintessential Amish country for cheese tastings, sweet treats, craft shops, funky museums and some incredible historic photo ops.- Kid-Friendly
- Accessible
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Groves, Gardens & Grapevines
$39 USDThis incredibly picturesque road trip is full of whimsical gardens, lookout points, wineries, and easy strolls along forest paths. We think it's an area you'll want to come back to time and time again.- Kid-Friendly