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.

Browse all trips

  • Road Trip Gift Card

    Road Trip Gift Card

    $80.00 CAD
    Give the gift of a one-day surprise road trip with Guess Where Trips®! Valued at $74, this voucher covers the full cost of any of our mailed road trips, including tax and standard shipping. The recipient can choose any surprise road trip that suits them, and it will be shipped right to their door. These gift cards never expire.
  • Detour Diaries: Ontario

    Detour Diaries: Ontario

    $49.00 CAD
    The ultimate travel companion that transforms Ontario's most-travelled highways into unforgettable adventures.
  • BEST SELLER
    Outdoor Adventures & Scenic Roads

    Outdoor Adventures & Scenic Roads

    $65 CAD
    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
  • BEST SELLER
    Wine Time and Hidden Gems

    Wine Time and Hidden Gems

    $65 CAD
    Craving rolling vineyard views, artful little towns, farm markets and that breezy, laid-back feel only lakeside moments can deliver? This is the trip for you! It’s the kind of place that deserves more than a quick visit...make it a weekend if you can!
    • Dog-Friendly
    • Accessible
    • Kid-Friendly
    Can depart from: Toronto Area, Kingston Area
  • BEST SELLER
    Woman looking out of car window.

    All the Pretty Things

    $65 CAD
    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.
    • Kid-Friendly
    Can depart from: Kingston Area, Ottawa Area
  • best done spring-fall
    A scenic view of a body of water with trees on the banks under a clear sky.

    Views & Secret Stops

    $65 CAD
    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
  • Digital Download Only
    Aerial view of Toronto cityscape during sunset, showcasing various buildings and the CN Tower.

    Toronto Gems

    $39.00 CAD
    Explore all of Toronto's downtown gems in a completely new way - ditch the car and walk or bike while you explore! This trip is best for anyone who isn't super familiar with the Toronto core, plus there's an optional “scavenger hunt" so there is something for you to find and decode at each stop!
    Can depart from: Toronto Area, Kitchener-Waterloo Area, London Area
Three women walking through tulip fields
Winding roads through mountains at sunrise

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Woman on road trip leaning out window

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!