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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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  • Valentine's Day Gift Box from Guess Where Trips

    Valentine's Add-On: Gift Wrapping with Tote Bag

    $22.00 $15.00 USD
    Let us gift wrap your trip or gift card for Valentine's Day with a tote bag and a Valentine's Day postcard. Add this on to any mailed gift card or mailed trip of your choice.
    Sold out
  • Gift Wrapping with Tote Bag

    Gift Wrapping with Tote Bag

    $22.00 $15.00 USD
    The ultimate addition if you're gifting a road trip or gift card to someone special! Let us carefully wrap up your mailed trip in our signature gift box, along with a Guess Where Trips® tote bag.
    Sold out
  • 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.
  • Valentine's Day Gift Box with Gift Card from Guess Where Trips

    Valentine's Wrapping with Gift Card

    $80.00 USD
    A gift wrapped gift card for Valentine's Day with a tote bag and a Valentine's Day postcard. Your Valentine can redeem the gift card for any of our road trips.
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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!