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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Road Trip Gift Card
Regular price $74.00 USDUnit price perGive 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. -
Secrets in the South
$65 USDWith 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
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Southern Express
$65 USDThink 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
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Treats & Trails
$39 USDIs 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
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Sweet Sensations
$39 USDBetween 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
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Endless Christmas Cheer
$39 USDThis 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
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Rivers & Rural Roads
$39 USDRiverside 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
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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!
