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®! Valued at $74, this voucher covers the full cost of any of our mailed road trips, including tax and standard shipping. The recipient can choose any surprise road trip that suits them, and it will be shipped right to their door. These gift cards never expire. -
Quaint Corners
$65 USDCozy cafes, countryside drives, gorgeous lookouts and quirky roadside stops are just some of the things you'll discover on your surprise road trip!- Accessible
- Dog-Friendly
- Kid-Friendly
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Wacky Wonders
$65 USDA little funky, a little unexpected, and totally unforgettable—this road trip is a whirlwind of colorful folk art, quirky roadside stops, scenic detours, and bites worth savoring. The only rule? Embrace the unexpected. -
A Drive Back in Time
SaleRegular price $39.00 USDUnit price perThe perfect day for the more leisurely road tripper. A Drive Back in Time isn't too far from the city and is full of cute towns, cafes, funky photo ops and so much more.- Accessible