Woman holding four Guess Where Trips envelopes while on road trip

South

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
    Treasure Coast Explorer

    Treasure Coast Explorer

    $65 CAD
    We've recommended our favourite hidden gems within this iconic area of Florida. Beach hopping, easy walks, charming cafes, and historic spots. This trip really does have it all!
    • Accessible
    • Kid-Friendly
    Can depart from: West Palm Beach Area, Miami / Fort Lauderdale Area
  • GREAT WEEKEND TRIP
    Wacky Wonders

    Wacky Wonders

    $65 CAD
    A little funky, a little unexpected, and totally unforgettable—this road trip is a whirlwind of colorful folk art, quirky roadside stops, scenic detours, and bites worth savoring. The only rule? Embrace the unexpected.
    Can depart from: Atlanta Area, Athens Area
  • Best done Spring - Fall
    Waterside Bliss

    Waterside Bliss

    $65 CAD
    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
  • 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 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
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!