Woman holding four Guess Where Trips envelopes while on road trip

Road Trips in the DMV Area

Select a trip that works with your driving and travel preferences. If it's hard to choose, take our road trip quiz instead.

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  • Road Trip Gift Card

    Road Trip Gift Card

    $74.00 CAD
    Give 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.
  • BEST SELLING GIFT
    Whimsical Wonders

    Whimsical Wonders

    $39 CAD
    Escape 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
    Can depart from: Philadelphia Area, Trenton Area, Baltimore Area
  • BEST SELLING GIFT
    Tiny Town Tour

    Tiny Town Tour

    $39 CAD
    Meander 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
    Can depart from: Washington DC Area, Baltimore Area, Winchester VA Area, Alexandria VA Area
  • GREAT FOR A WEEKEND AWAY
    Winding Roads & Historic Gems

    Winding Roads & Historic Gems

    $39 CAD
    Discover photo-worthy hidden gems along winding roads as you make your way to an iconic road trip destination.
    • Kid-Friendly
    • Dog-Friendly
    • Accessible
    Can depart from: Washington DC Area, Baltimore Area, Winchester VA Area, Alexandria VA Area
  • PERFECT YEAR-ROUND
    Haunts, Hikes & History

    Haunts, Hikes & History

    $39 CAD
    From haunted happenings to easy strolls and historic hot spots, this trip has a little bit of everything for everyone!
    • Kid-Friendly
    • Dog-Friendly
    Can depart from: Washington DC Area, Baltimore Area, Alexandria VA Area, Winchester VA Area
  • BEST DONE SPRING-FALL
    Woman spinning on the beach.

    Waterside Bliss

    $39 CAD
    Beach breezes, coastal eats, and charming strolls await on this picturesque day trip. You’ll wander waterfront boardwalks, explore historic homes, and discover secret spots only the locals know - all with a side of sandy serenity and small-town charm.
    • Kid-Friendly
    • Dog-Friendly
    Can depart from: Washington DC Area, Baltimore Area, Alexandria VA Area
  • CAN BE DONE IN WINTER
    Charming Curiosities

    Charming Curiosities

    $39 CAD
    With a few haunted stories, trails with a unique past, and charming historic mansions, we're confident you'll find new favorite spots to explore when you hit the road with this surprise trip.
    • Dog-Friendly
    • Kid-Friendly
    • Accessible
    Can depart from: Washington DC Area, Baltimore Area, Winchester VA Area, Alexandria VA Area
Three women walking through tulip fields
Winding roads through mountains at sunrise

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Gift-a-Trip

The ultimate present for the avid traveller. Select a digital or mailed 'Gift-A-Trip' option that covers the full cost of one of our road trips. We promise you this will be one of the most memorable and unique gifts they'll ever receive!