Woman holding four Guess Where Trips envelopes while on road trip

Baltimore 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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  • BEST SELLER
    Whimsical Wonders

    Whimsical Wonders

    $39 USD
    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
  • GREAT FALL TRIP
    Winding Roads & Historic Gems

    Winding Roads & Historic Gems

    $39 USD
    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 USD
    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
    Waterside Bliss

    Waterside Bliss

    $39 USD
    Boardwalks, beaches and bites make this charming itinerary the ultimate road trip!
    • Kid-Friendly
    • Dog-Friendly
    Can depart from: Washington DC Area, Baltimore Area, Alexandria VA Area
Three women walking through tulip fields
Winding roads through mountains at sunrise

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