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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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Mysterious Gems
$65 CADTruly 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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Cascades & Colors
$65 CADFunky colorful towns full of local eateries and shops, a few waterfalls that will leave you in awe and one of the most unusual gardens we have ever seen. You’ll want to get your camera out for this trip!- Kid-Friendly
- Dog-Friendly
- Accessible
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The Long and Unknown Road
$65 CADIf you love a long and interesting drive, this trip is for you! This trip is approximately 5 hours round-trip from Calgary, so we recommend leaving super early or extending your stay into an overnight getaway.- Dog-Friendly
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Secrets of Gettysburg
$65 CADExplore Gettysburg and its surrounding area in a whole new way. We’ve made this classic, All-American, bucket list destination easy and fun to do - whether it's your first or fiftieth time! Discover hidden gems and surprising stops while learning more about the turning point of the Civil War.- Kid-Friendly
- Dog-Friendly
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Boardwalks, Brews & Markets
$65 CADThe name really says it all! Explore marvelous markets with food stalls and local artisans, enjoy a couple brews, and stroll along easy boardwalk trails.- Accessible
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A Little Bit of Everything
$65 CADThe perfect distance from Charlotte! From little local shops to an old rail trail and everything in between, this trip truly has something for everyone.- Accessible
- Kid-Friendly
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Quaint Corners
$65 CADCozy cafes, countryside drives, gorgeous lookouts and quirky roadside stops are just some of the things you'll discover on your surprise road trip!- Accessible
- Dog-Friendly
- Kid-Friendly
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Charming Curiosities
$65 CADWith a few haunted stories, trails with a unique past, and charming historic mansions, we're confident you'll find new favorite spots to explore when you hit the road with this surprise trip.- Dog-Friendly
- Kid-Friendly
- Accessible
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The Southwest Quest
$65 CADPlenty of sun, strolls and citrus make this the ultimate Southwest Florida road trip. From unique eateries and boardwalk trails to an eerie ghost town and a sunset beach stop, there is truly something for everyone!- Kid-Friendly
- Accessible
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Coastal Connection
$65 CADFrom seaside strolls and spooky ruins to cider donuts and historic mansions, this charming coastal road trip is full of surprises. Whether you’re wandering a 17th-century town green, petting goats at a giant book barn, or soaking in saltwater views, you’ll fall in love with Connecticut’s quirkier side.- Dog-Friendly
- Accessible
- Kid-Friendly
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The Shore Explorer
$65 CADHop from shore to shore on this iconic beachside road trip just a short drive from the tri-state area. Alongside beaches, you'll also explore waterside boardwalks, age-old lighthouses, scenic viewpoints, and delicious local eateries.- Dog-Friendly
- Accessible
- Kid-Friendly
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Treasure Coast Explorer
$65 CADWe've recommended our favourite hidden gems within this iconic area of Florida. Beach hopping, easy walks, charming cafes, and historic spots. This trip really does have it all!- Accessible
- Kid-Friendly
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Waterfall Wanderings
$65 CADThe ultimate waterfall adventure not too far from home! Wander along historic paths, snap photos of four falls, enjoy a glass of local vino and explore a mysterious cave.- Kid-Friendly
- Dog-Friendly
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Large Road Trip Tote Bag
Regular price $24.00 Sale price $18.00 CADUnit price perTHE road trip bag for all your snacks and accessories! Larger than your average tote, this bag is perfect to carry all the necessities for a surprise road trip.Sold out -
Enchanted Adventures
$65 CADAround every winding road is a world of whimsical and enchanted adventures. This family-friendly trip is perfect for those who love easy trails, farm market stops, colourful photo ops and tasty treats.- Kid-Friendly
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Escape to the Cape
$65 CADThis road trip is full of Cape Cod charm. Think picturesque views, independent shops, heritage buildings, boardwalks and more. This trip focuses more on the hidden gems, quaint towns and history of the area.- Kid-Friendly
- Dog-Friendly
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A Taste of Amish Country
$65 CADEscape to quintessential Amish country for cheese tastings, sweet treats, craft shops, funky museums and some incredible historic photo ops.- Kid-Friendly
- Accessible
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Coffee, Canyons & Coastlines
$65 CADCoffee, Canyons & Coastlines - Oh my! Get your caffeine fix throughout the day to prepare for beachside moments and easy outdoor adventures. This is the perfect trip close to San Diego!- Kid-Friendly
- Dog-Friendly
- Accessible
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Groves, Gardens & Grapevines
$65 CADThis incredibly picturesque road trip is full of whimsical gardens, lookout points, wineries, and easy strolls along forest paths. We think it's an area you'll want to come back to time and time again.- Kid-Friendly
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The Road to Asheville
$65 CADGrab a sweet treat in a converted church, sip a beer beside a babbling creek, get your steps in on a couple local trails and so much more. This iconic North Carolina destination is the perfect weekend away, so we highly recommend booking a hotel!- Dog-Friendly
- Kid-Friendly
- Accessible
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Sweet Sensations
$65 CADBetween making a furry friend at a farm, enjoying local eateries, walking to quirky ruins in the woods and exploring the sweetest small town, this trip will make all five senses come to life all day!- Kid-Friendly
- Accessible
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A Drive Back in Time
$65 CADThe perfect day for the more leisurely road tripper. A Drive Back in Time isn't too far from the city and is full of cute towns, cafes, funky photo ops and so much more.- Accessible
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Picture Perfect Discoveries
$65 CADReady for a little mountain meandering? Picturesque historic spots, unique destinations to grab a bite to eat, and a couple charming towns are on your to-do list.- Kid-Friendly
- Dog-Friendly
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Endless Christmas Cheer
CADThis is the perfect trip for those of you who think that extra-festive feeling should be a year-round experience. Decorations, cozy wine stops, and covered bridges - oh my!- Kid-Friendly
- Accessible
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