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®! The recipient can then choose a surprise trip that suits them! -
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
