Woman holding four Guess Where Trips envelopes while on road trip

Windsor-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

    $74.00 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.
  • MOTHER'S DAY PICK
    Secrets in the South

    Secrets in the South

    $65 CAD
    With funky markets, scenic roads and the most picturesque towns, you'll love all of the secrets you discover on the road. This trip is best enjoyed between June - September as there are a handful of fabulous seasonal suggestions.
    • Kid-Friendly
    Can depart from: Sarnia Area, London Area, Kitchener-Waterloo Area, Toronto Area
  • Best done spring-fall
    A boardwalk leading to a beach with the sun shining brightly in the sky.

    Southern Express

    $65 CAD
    Think cozy bakeries, swim spots, easy hikes, and wine with a view, all wrapped up in one charming escape. You’ll wonder how this area stayed off your radar for so long!
    • Kid-Friendly
    • Dog-Friendly
    Can depart from: Windsor Area, Detroit Area, Sarnia Area, London 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.

  • A LITTLE BIT OF EVERYTHING!
    A box of assorted donuts with different toppings and glazes.

    Treats & Trails

    $65 CAD
    Is there anything better than a leisurely day sipping coffee, enjoying tasty treats and meandering along easy boardwalk trails? We think not, and you'll find all of that and more in this Michigan road trip!
    • Kid-Friendly
    • Dog-Friendly
    • Accessible
    Can depart from: Detroit Area, Toledo Area, Windsor Area
  • MOTHER'S DAY PICK
    Sweet Sensations

    Sweet Sensations

    $65 CAD
    Between making a furry friend at a farm, enjoying local eateries, walking to quirky ruins in the woods and exploring the sweetest small town, this trip will make all five senses come to life all day!
    • Kid-Friendly
    • Accessible
    Can depart from: Detroit Area, Toledo Area, Windsor Area
  • YEAR-ROUND JOY
    A festive Christmas-themed miniature village display with snow-covered houses and a large Christmas tree in the center.

    Endless Christmas Cheer

    $65 CAD
    This is the perfect trip for anyone who thinks that extra festive feeling should be a year-round experience. Decorations, cozy shops and eateries, and a picture-perfect covered bridge - oh my!
    • Kid-Friendly
    • Accessible
    Can depart from: Detroit Area, Windsor Area, Sarnia Area
Three women walking through tulip fields
Winding roads through mountains at sunrise

CAN'T DECIDE?

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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!