Woman holding four Guess Where Trips envelopes while on road trip

Alexandria, VA

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