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.

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  • BEST SELLER
    Secrets in the South

    Secrets in the South

    $65 USD
    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 - October 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
    Southern Express

    Southern Express

    $65 USD
    This trip takes you to some iconic stops and hidden gems in southern Ontario. It's the perfect combination of outdoor activities, funky restaurants, beaches and historic attractions.
    • Kid-Friendly
    • Dog-Friendly
    Can depart from: Windsor Area, Detroit Area, Sarnia Area, London Area
  • 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.
  • BEST DONE spring-fall
    Waterfront Wonders

    Waterfront Wonders

    USD
    We've recommended an incredibly scenic route that takes you to a variety of picturesque stops you'll fall in love with. The best part? There are hardly any crowds.
    • Kid-Friendly
    • Dog-Friendly
    Sold out
    Can depart from: Windsor Area, Sarnia Area, London Area, Kitchener-Waterloo Area
  • Can be done in winter
    Treats & Trails

    Treats & Trails

    $65 USD
    Is there anything better than a leisurely day sipping coffee, enjoying tasty treats and meandering along easy boardwalk trails? We think not!
    • Kid-Friendly
    • Dog-Friendly
    • Accessible
    Can depart from: Windsor Area, Detroit Area, Toledo Area
  • Can be done in winter
    Endless Christmas Cheer

    Endless Christmas Cheer

    $55 USD Sale
    This is the perfect trip for those of you who think that extra-festive feeling should be a year-round experience. Decorations, cozy wine stops, and covered bridges - oh my!
    • Kid-Friendly
    • Accessible
    Sale
    Can depart from: Detroit Area, Windsor Area, Sarnia Area
  • Great For Active families
    Sweet Sensations

    Sweet Sensations

    $65 USD
    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
  • BEST DONE MAY-OCTOBER
    Rivers & Rural Roads

    Rivers & Rural Roads

    $65 USD
    Riverside roaming strolls, historic highlights, scenic spots for sipping wine or beer, and some of the prettiest rural roads are just a few of the hidden gems you’ll discover on this trip!
    • Kid-Friendly
    Can depart from: Detroit Area, Toledo 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!