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. -
Outdoor Adventures & Scenic Roads
$65 USDOutdoor Adventures encompasses everything you could possibly want in a road trip getaway. Scenic roads, cool attractions and good food!- Accessible
- Kid-Friendly
- Dog-Friendly
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Wine Time and Hidden Gems
$65 USDCraving rolling vineyard views, artful little towns, farm markets and that breezy, laid-back feel only lakeside moments can deliver? This is the trip for you! It’s the kind of place that deserves more than a quick visit...make it a weekend if you can!- Dog-Friendly
- Accessible
- Kid-Friendly
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All the Pretty Things
$65 USDTake in all the pretty views and things on this picturesque trip. The itinerary is packed with stunning viewpoints, historic attractions and delicious restaurants and wineries.- Kid-Friendly