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. -
Secrets in the South
$65 USDWith funky markets, scenic roads and the most picturesque towns, you'll love all of the secrets you discover on the road. This trip is best enjoyed between June - September as there are a handful of fabulous seasonal suggestions.- Kid-Friendly
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Southern Express
$65 USDThink cozy bakeries, swim spots, easy hikes, and wine with a view, all wrapped up in one charming escape. You’ll wonder how this area stayed off your radar for so long!- Kid-Friendly
- Dog-Friendly
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Treats & Trails
$39 USDIs there anything better than a leisurely day sipping coffee, enjoying tasty treats and meandering along easy boardwalk trails? We think not!- Kid-Friendly
- Dog-Friendly
- Accessible