Woman holding four Guess Where Trips envelopes while on road trip

Kingston-Area Road Trips

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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  • Can be done in winter
    Outdoor Adventures & Scenic Roads

    Outdoor Adventures & Scenic Roads

    $65 USD
    Outdoor Adventures encompasses everything you could possibly want in a road trip getaway. Scenic roads, cool attractions and good food!
    • Accessible
    • Kid-Friendly
    • Dog-Friendly
    Can depart from: Toronto Area, Kingston Area
  • Can be done in winter
    Wine Time and Hidden Gems

    Wine Time and Hidden Gems

    $65 USD
    This trip requires a little more driving. We've found quite a few hidden quirks and gems along the route which we know you'll love.
    • Dog-Friendly
    Can depart from: Toronto Area, Kingston Area
  • BEST SELLER
    Woman looking out of car window.

    All the Pretty Things

    $65 USD
    Take in all the pretty views and things on this picturesque trip. The itinerary is packed with stunning viewpoints, historic attractions and delicious restaurants and wineries.
    • Accessible
    • Dog-Friendly
    • Kid-Friendly
    Can depart from: Kingston Area, Ottawa Area
  • best done spring-fall
    Views & Secret Stops

    Views & Secret Stops

    $65 USD
    Views for days and a scenic route that will take you there. This trip is perfect for anyone who's up for a more active day (but the views are worth it!).
    • Kid-Friendly
    • Dog-Friendly
    Can depart from: Kingston Area, Ottawa 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!