Parent and child opening a Guess Where Trips booklet on a picnic bench

Road Trips near Kingston

Choose a road trip that suits your driving and travel preferences from our selection below. Can't decide? Take our road trip quiz for personalized recommendations.

How does it work?

Our itineraries include a 'Before You Go' package and four surprise stops. Each stop is packed with a new destination, specific recommendations, maps, travel tips and fun facts.

See our road trips below, or check out our quiz and trip map to help find your perfect adventure.

  • 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
    A scenic road trip from Ottawa or Kingston with charming stops, historic sites, and wineries.
    • Kid-Friendly
    Can depart from: Kingston Area, Ottawa Area
  • Detour Diaries: Ontario

    Detour Diaries: Ontario

    $59.00 CAD

    Packed with 500+ of our favourite road trip stops across Ontario, Detour Diaries features 130+ detailed, user-friendly maps and over 300 pages organized by major highways to make planning effortless. You’ll also get bonus QR code access to an interactive mobile map for easy navigation on the go.

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