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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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Bridges to Beaches
$65 USDPicturesque bridges to sandy beaches and everything in between. This trip takes you off the beaten path to some of our favourite places in Ontario.- Accessible
- Kid-Friendly
- Dog-Friendly
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Quirky Adventures
$65 USDQuirky 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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Beautifully Haunted
$55 USD SaleThis outdoorsy road trip is full of spooky spots set along a picturesque driving route. You'll definitely want to read all of the haunted stories to make the most of the day! 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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Road Trip Tote Bag
Regular price $12.00 USDUnit price perAn essential locally made tote bag for your road trip ahead. Carry everything from your surprise package to all the snacks and goodies you'll pick up throughout your day. -
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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From Country to Coast
$65 USDMeander along country roads, explore waterfall wonders, local wineries, breweries, farm shops, and beachside towns. This trip has something for everyone, from families to girlfriend getaways and seniors, you’ll find several hidden gems along the way.- Kid-Friendly
- Dog-Friendly
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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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The Whimsical Route
$65 USDGet ready for a road trip where nature, history, hidden gems, and a touch of cinematic magic come together for a perfectly whimsical escape just outside the city!- Kid-Friendly
- Accessible
- 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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Hidden Gems of Huronia
$65 USDDiscover the endless charm of a lesser-known area that is full of haunted history, picturesque trails, cute small towns and farm-fresh flavours. We're sure you'll want to keep coming back for years to come!- Kid-Friendly
- Accessible
- Dog-Friendly
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Gift Card [Digital $USD]
Regular price $65.00 USDUnit price perInstantly send the gift of a one-day surprise road trip! Digital gift cards can be sent immediately or scheduled to be sent on a specific day. -
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. -
Road Trip Game Pack
SaleRegular price $12.00 Sale price $9.00 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. -
Along the River
$65 USDMeander through tiny towns along the river that are brimming with hidden gems. There are countless photo-worthy moments and memories to make on this easygoing scenic road trip.- Accessible
- Kid-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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Whimsical Wonders
$65 USDEscape to hidden gem destinations that make you feel like you've stepped into a fairytale world. Lucious gardens, charming towns and whimsical photo ops make this the perfect road trip.- Kid-Friendly
- Accessible
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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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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 Fairy Tale Trail
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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Bayside Wonders
$65 USDThe perfect blend of charming small towns, farmers markets, and wine tastings mixed with epic waterfalls and a couple unique trails. Bayside Wonders is a bit further, which makes for an incredible weekend getaway! Please note: A few recommendations have been moved from The Waterfall Route to this new trip. There are still tons of new spots to explore!- 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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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
![Gift Card [Digital $USD]](http://guesswheretrips.com/cdn/shop/files/mockup-of-a-woman-working-on-a-macbook-2316-el1_7d0676c5-9738-4b80-bc5f-90c1d3e2e450.png?crop=center&v=1686682587&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!
