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.

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  • Add On: Gift Wrapping with Tote Bag

    Add On: Gift Wrapping with Tote Bag

    $27.00 $20.00 USD
    Sale
    The ultimate addition if you're gifting a road trip to someone special!
    Sale
  • Large Road Trip Tote Bag

    Large Road Trip Tote Bag

    $24.00 $18.00 USD
    Sale
    THE road trip bag for all your snacks and accessories! Larger than your average tote, this bag is perfect to carry all the necessities for a surprise road trip.
    Sale
  • Gift Card [Digital $USD]

    Gift Card [Digital $USD]

    $65.00 USD
    Instantly send the gift of a one-day surprise road trip! Digital gift cards can be sent immediately or scheduled to be sent on a specific day.
  • Road Trip Game Pack

    Road Trip Game Pack

    $12.00 $9.00 USD
    Sale
    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.
    Sale
  • Mother's Day Add-On: Gift Wrapping

    Mother's Day Add-On: Gift Wrapping

    $27.00 $20.00 USD
    Sale
    Let us gift wrap your trip or gift card for Mother's Day with a tote bag and a Mother's Day postcard. Add this on to any mailed gift card or mailed trip of your choice.
    Sale
  • Road Trip Tote Bag

    Road Trip Tote Bag

    $12.00 USD
    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.
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!