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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.
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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 trial.- Accessible
- Kid-Friendly
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Beautifully Haunted
$65 USDBeautifully eerie and oh so haunted! This outdoorsy road trip is full of spooky spots set along a picturesque driving route. A few local eateries and trails are sprinkled throughout the day to keep your energy up while ghost hunting.- Dog-Friendly
- Kid-Friendly
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Backroad Bliss
$65 USDThis trip is perfect for Ottawans, Montrealers, and everyone in between! From waterfalls and a more challenging hike to ridiculously cute towns, shops and restaurants, there is a little bit of everything when you hit the backroads. This trip takes you to great spots in Québec!- Kid-Friendly
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Southern Express
$65 USDThis 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
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The Fairy Tale Trail
$65 USDThis 'mini' trip is designed for families with children under 12. The variety of stroller-friendly and toddler-friendly activities make it a no-fuss day for everyone in the car. We've even included scavenger-style activities throughout the itinerary to keep your kids engaged.- Accessible
- Kid-Friendly
- Dog-Friendly
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Toronto Gems
$65 USDExplore all of the downtown gems in a completely new way. Ditch the car, and walk or bike while you explore what Toronto has to offer. This trip is best for Toronto tourists, those new to the Toronto area, and those who are not super familiar with the Toronto core. The trip has an optional “scavenger hunt" so there is something for you to find and decode at each stop. -
Quirky Gems
$65 USDOur best-selling trip from Calgary! Hit the road and visit some quintessential Alberta towns, eat at funky restaurants, support local businesses and explore picturesque hikes and natural attractions. All without venturing too far from the city!- Accessible
- Kid-Friendly
- Dog-Friendly
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Tiny Town Tour
$65 USDMeander along scenic roads while stumbling upon charming tiny towns! This trip has endless photo opportunities, easy outdoor adventures, and plenty of fantastic spots to shop, drink and eat.- Dog-Friendly
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Sandhills Sauntering
$65 USDPicturesque drives beneath towering trees make this an incredibly scenic trip. Sandhills Sauntering is full of epic places to eat, tons of photo-worthy moments and a hidden gem that will leave you speechless.- Kid-Friendly
- Accessible
- Dog-Friendly
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Winding Roads & Historic Gems
$65 USDDiscover photo-worthy hidden gems along winding roads as you make your way to an iconic road trip destination.- Kid-Friendly
- Dog-Friendly
- Accessible
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The Whimsical Route
$65 USDThis 'mini' trip is designed for families with children over the age of 5. This trip will take you on a number of easy outdoor adventures that provide a variety of kid-friendly options at each stop. We've even included scavenger-style activities throughout the itinerary to keep your kids engaged.- Kid-Friendly
- Accessible
- Dog-Friendly
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Gift Card [Mailed: $USD]
Regular price $65.00 USDUnit price perGive 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 costs. The recipient can then choose a surprise trip that suits them! -
Road Trip Game Pack
SaleRegular price $12.00 Sale price $6.00 USDUnit price perKeep the young ones busy with a fun game pack to play with on the road! Dozens of games and activities to keep kids of all ages entertained.Sale -
Hidden Hideaways
$65 USDThis trip is filled with so many hidden gems and charming towns. A countryside brewery or winery, riverside roaming, a seasonal sculpture garden, and unique photo ops galore! This is the perfect trip to do on the way from Ottawa to Montreal. -
Old Florida Trail
$65 USDGo back in time and visit old Florida. You'll visit delightful small towns, dig into local fare and have a few outdoor adventures.- Kid-Friendly
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Coastal Crawl
$65 USDGet out of town and feel the ocean breeze in your hair. This trip perfectly combines iconic Nova Scotia views with small town hidden gems.- Kid-Friendly
- Dog-Friendly
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Rocky Mountain Route
$65 USDOne of the most iconic road trips in the world with a few secret surprises along the way. Incredible mountain towns, tasty local brews and food and a ton of photo-worthy views! Want to keep going towards Jasper? We included a 'want to keep going' section just in case.- Accessible
- Kid-Friendly
- Dog-Friendly
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Haunts, Hikes & History
$65 USDFrom haunted happenings to easy strolls and historic hot spots, this trip has a little bit of everything for everyone!- Kid-Friendly
- Dog-Friendly
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Views & Secret Stops
$65 USDViews for days and a scenic route that will take you there. This trip is perfect for anyone who's up for a more active day (but the views are worth it!).- Kid-Friendly
- Dog-Friendly
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Mysterious Gems
$65 USDTruly extraordinary destinations with strange stories and history. Cemeteries abandoned ruins, historic homes and so much more await on this mysterious road trip!- Dog-Friendly
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Waterfront Wonders
$65 USDWe'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
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The Taste Trail
$65 USDThis road trip will take you to some funky eateries, family farms, wineries, cideries and a whole lot more. To offset the treats, we've included a few whimsical hikes to end your day.
- Accessible
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'This Is My Road Trip' Tote
SaleRegular price $16.00 Sale price $8.00 USDUnit price perSave big on our "This is my Road Trip Bag" tote bag! Great quality, with an interior pocket to keep small items organized.Sale
![Gift Card [Mailed: $USD]](http://guesswheretrips.com/cdn/shop/files/FINALgiftcardwithenvelopeontable_24a9f159-fa44-43c7-916d-7caa5dd85839.jpg?crop=center&v=1691420728&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!
