Browse all trips
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Muskoka Meandering
$65 CADMuskoka Meandering is the perfect way to escape from the hustle and bustle of the city and immerse yourself in nature while enjoying delicious wines and beers, beautiful scenery and lookouts, and charming small towns.- Kid-Friendly
- Dog-Friendly
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Road Trip Gift Card
Regular price $74.00 CADUnit 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. -
Outdoor Adventures & Scenic Roads
$65 CADOutdoor Adventures encompasses everything you could possibly want in a road trip getaway. Scenic roads, cool attractions and good food!- Accessible
- Kid-Friendly
- Dog-Friendly
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Taste of the Country
$65 CADThis trip is just a short jaunt from Toronto and is perfect for foodies and families! You'll explore incredible farmers markets, cute small towns, a few local spots to grab a drink and an easy wooded trail.- Accessible
- Kid-Friendly
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Wine Time and Hidden Gems
$65 CADCraving 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
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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!