Woman holding four Guess Where Trips envelopes while on road trip

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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

  • Road Trip Tote Bag

    Road Trip Tote Bag

    $20.00 $5.00 CAD
    Sale
    An essential locally made tote bag for your road trip ahead. Carry everything from your surprise package to all the snacks and goodies you'll pick up throughout your day.
    Sale
  • Road Trip Game Pack

    Road Trip Game Pack

    $12.00 CAD
    Keep the young ones busy with a fun game pack to play with on the road! Dozens of games and activities to keep kids of all ages entertained.
  • Gift Card [Digital $CAD]

    Gift Card [Digital $CAD]

    $74.00 CAD
    Want to email this directly to someone else? Don't add it to your cart just yet! Click the photo above for more options, including scheduling the gift card for a date in the future.
  • Person holding the Which Way Card game in front of a green background

    Which Way? A Surprise Road Trip Card Game

    $22.00 CAD
    A surprise road trip game where the entire point is to get lost!
  • Mint Road Trip Journal

    Mint Road Trip Journal

    $25.00 CAD
    Track all your local adventures - big or small!
  • Detour Club Bundle

    Detour Club Bundle

    $106.00 $89.00 CAD
    Sale
    The ultimate travel companion that transforms Ontario's most-travelled highways into unforgettable adventures.
    Sale
  • Lilac Road Trip Journal

    Lilac Road Trip Journal

    $25.00 CAD
    Track all your local adventures - big or small!
  • Toronto Play Day Passport

    Toronto Play Day Passport

    $59.00 CAD
    Discover fully planned, kid-friendly days out across Toronto and the GTA. Just scratch a card to reveal a complete outing - with a destination, bonus stops, food spots, and tips all figured out for you.
    Can depart from: Toronto Area, GTA
Three women walking through tulip fields
Winding roads through mountains at sunrise

CAN'T DECIDE?

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

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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!