Washington, D.C. & Maryland Day Trips
Ready to escape the hustle and bustle of the capital? The areas around D.C., Maryland, and Virginia are a day-tripper's dream, packed with history, culture, and natural beauty. Explore charming towns, dive into outdoor adventures, or uncover historical gems – all just a short drive from Washington, D.C. Whether you're in the mood for a peaceful retreat or a cultural deep dive, a one-day surprise road trip in the DMV area is the perfect way to mix things up!
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. -
Whimsical Wonders
$39 USDEscape to hidden gem destinations that make you feel like you've stepped into a fairytale world. Lucious gardens, charming towns and whimsical photo ops make this the perfect road trip.- Kid-Friendly
- Accessible
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Tiny Town Tour
$39 USDMeander along scenic roads while stumbling upon charming tiny towns! This trip has endless photo opportunities, easy outdoor adventures, and plenty of fantastic spots to shop, drink and eat.- Dog-Friendly
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Winding Roads & Historic Gems
$39 USDDiscover photo-worthy hidden gems along winding roads as you make your way to an iconic road trip destination.- Kid-Friendly
- Dog-Friendly
- Accessible
