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.

Browse all trips

  • BEST SELLER
    Whimsical Wonders

    Whimsical Wonders

    $65 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
  • GREAT FOR A WEEKEND AWAY
    Winding Roads & Historic Gems

    Winding Roads & Historic Gems

    $65 CAD
    Discover photo-worthy hidden gems along winding country roads as you make your way to an iconic road trip destination filled with history, charm, and scenic views.
    • 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

    $45 CAD Sale
    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

    $39.00 CAD
    Sale
    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
Three women walking through tulip fields
Winding roads through mountains at sunrise

CAN'T DECIDE?

Take Our Quiz to Find Out

Select your region and interests to find the best trip for you.

Take the Quiz
Woman on road trip leaning out window

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!