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Local Markets and Picturesque Towns
$65 CADOne of our best-selling trips, and for good reason. Stops include historic towns, local markets, eateries, and hidden gems - all of which feel especially lovely when winter slows things down. This trip makes a great gift thanks to its versatility.- Accessible
- Kid-Friendly
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Gift Card [Digital $CAD]
Regular price $74.00 CADUnit price perInstantly send the gift of a one-day surprise road trip! The gift card covers the full price of one of our mailed trips, including taxes and shipping. -
An Adventure is Brewing
$65 CADThis road trip takes you on the perfect summer adventure filled with lavender fields, funky hidden gems, beaches and unique wineries and breweries. This is our featured summer trip and is best taken mid-May to early-October!- Accessible
- Dog-Friendly
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The Small Town Charm Trail
$65 CADYou know those towns that are described as “blink-and-you’ll-miss-it”? They often have the most amazing hidden gems - especially when winter slows things down and the crowds thin out. Get to know a few cozy pockets of Ontario with this surprise road trip.- Accessible
- Kid-Friendly
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Vistas & Caves
$65 CADThis 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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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. -
Weird and Wonderful Things
$65 CADThis 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 CADAlpacas, 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 CADThis 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 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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Riverside Roaming
$65 CADStart 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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Add On: Gift Wrapping
SaleRegular price $14.00 Sale price $7.00 CADUnit price perA reusable gift box with magnetic closure - perfect for presenting their surprise trip and storing souvenirs after the adventure.Sale -
Detour Diaries: Ontario
Regular price $49.00 CADUnit price perThe ultimate travel companion that transforms Ontario's most-travelled highways into unforgettable adventures. -
Markets to Mountains
$65 CADFrom countryside markets to mountain views, this trip delivers a relaxed yet adventurous day trip in Ontario. It’s an especially great pick for a slower-paced winter getaway, and we highly recommend booking a hotel at the finishing stop to turn it into a weekend escape.- Kid-Friendly
- Accessible
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The Waterfall Route
$65 CADExplore 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 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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Hops, Hikes & History
$65 CADThere 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 CADWith 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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Historic Haunts
SaleRegular price $65.00 Sale price $39.00 CADUnit price perThis 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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Spooky Sights & Ghostly Tales
SaleRegular price $65.00 Sale price $39.00 CADUnit price perExplore 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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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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Quirky Adventures
$65 CADQuirky cafes, funky little shops, beautiful boardwalks, old mills, outdoor adventures, and even a haunted ending! This is definitely an Ottawa-area favourite!- Kid-Friendly
- Dog-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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Escape to Nature
$65 CADExplore 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
![Gift Card [Digital $CAD]](http://guesswheretrips.com/cdn/shop/products/mockup-of-a-woman-working-on-a-macbook-2316-el1_55346c2b-32bf-480f-bb3e-ad6250bc479e.png?crop=center&v=1669307570&width=1100)
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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!
