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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
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Local Markets & Picturesque Towns
$65 USDOne of our best-selling trips, and for a good reason. Stops include historic towns, local markets, eateries and hidden gems. This trip makes a great gift because of its versatility.- Accessible
- Kid-Friendly
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An Adventure is Brewing
$65 USDA summer road trip within driving distance of Toronto, Hamilton, Kitchener, and London with beaches, wineries, and hidden gems.- Accessible
- Dog-Friendly
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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. -
The Small Town Charm Trail
$65 USDYou know those towns that are described as 'blink-and-you'll-miss-it'? They often have the most amazing hidden gems! Get to know a few small pockets of Ontario with this surprise road trip.- Accessible
- Kid-Friendly
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Road Trip Gift Box
SaleRegular price $118.00 Sale price $89.00 USDUnit price perThe ultimate gift for the road trip lover. Each box is beautifully wrapped and includes a gift card, game pack, and tote bag.Sale -
Free Add On: Road Trip Gift Wrapping
SaleRegular price $14.00 Sale price $0.00 USDUnit price perA reusable gift box with magnetic closure - perfect for presenting their surprise trip and storing souvenirs after the adventure.Sale -
Vistas & Caves
$65 USDThis road trip is a quick jaunt north of Toronto and is perfect for the outdoor enthusiast. It really is the perfect mix of everything.- Accessible
- Kid-Friendly
- Dog-Friendly
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Weird & Wonderful Things
$65 USDThis road trip takes you north towards beautiful sights, unusual attractions and secluded waterfalls.- Kid-Friendly
- Dog-Friendly
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Country Farms & Furry Friends
$65 USDAlpacas, donkeys and goats - oh my! Start your day off at a funky country market, before hanging with the birds and ending the day with some furry friends.- Kid-Friendly
- Accessible
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Funky Florals and Fine Wines
$65 USDThis pretty little road trip offers quite a few hidden gems combined with a few iconic attractions. Must enjoy: wine, food and flowers.- Accessible
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Muskoka Meandering
$65 USDMuskoka 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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Riverside Roaming
$65 USDStart your day in a picture-perfect town by the river before strolling along boardwalks, dining at a funky distillery, indulging at farm shops and so much more. This trip is a nice distance from the city and can be done year-round!- Kid-Friendly
- Accessible
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Markets to Mountains
$65 USDFrom cute markets to mountainside hikes, Markets to Mountains provides you with all the stops for a cozy yet adventurous day trip in Ontario. We highly recommend booking a hotel at the finishing stop for the ultimate weekend getaway.- Kid-Friendly
- Accessible
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The Waterfall Route
$65 USDExplore a variety of waterfalls, charming towns, funky restaurants and several photo ops throughout the day! This trip is perfect for spring - fall travellers. Waterfalls may dry up in extreme heat.- Kid-Friendly
- Dog-Friendly
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Outdoor Adventures & Scenic Roads
$65 USDOutdoor 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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Hops, Hikes & History
$65 USDThere is so much more to this trip than the name implies. From hidden local breweries to unique trails and scenic sights, this trip will take you to a few unknown areas that you’re sure to love!- Kid-Friendly
- Dog-Friendly
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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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Quirky Adventures
$65 USDQuirky cafes, funky little shops, forested nature trails, old mills, outdoor adventures, furry farm friends, and even a haunted ending. This is definitely an Ottawa-area favourite and for good reason!- Kid-Friendly
- Dog-Friendly
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Taste of the Country
$65 USDThis 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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Historic Haunts
$65 USDThis haunted history route blends eerie legends and unusual attractions. Visit spots with documented haunted pasts — from towers and ruins to cemeteries — while uncovering the fascinating tales behind them. Please Note: This trip begins in Cambridge and takes place in the same area as Local Markets & Picturesque Towns.- Accessible
- Dog-Friendly
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Wine Time and Hidden Gems
$65 USDCraving 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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All the Pretty Things
$65 USDA scenic road trip from Ottawa or Kingston with charming stops, historic sites, and wineries.- Kid-Friendly
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Spooky Sights & Ghostly Tales
$65 USDExplore spooky ruins, abandoned buildings, and haunted mansions tied to eerie legends, with a mix of walkable trails, photo ops, and even a chance to dine in a haunted restaurant. Please note: some parts of this trip take place within the city of Hamilton, travellers may encounter some traffic.- Dog-Friendly
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Escape to Nature
$65 USDExplore tiny towns and easy outdoor adventures before cozying up at a local cafe or brewery. Optional wintery activities include ice skating and snowshoeing! Please note: this trip is similar to the Sport Chek Winter Trek for Toronto.- 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!
