Woman holding four Guess Where Trips envelopes while on road trip

Our Trips

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

  • MOTHER'S DAY PICK
    Patio table filled with beers.

    An Adventure is Brewing

    $65 CAD
    This 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
  • STAFF PICK
    A person walking on a trail surrounded by tall trees

    Vistas & Caves

    $65 CAD
    This 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
  • BEST SELLER
    Weird & Wonderful Things

    Weird & Wonderful Things

    $65 CAD
    This road trip takes you north towards beautiful sights, unusual attractions and secluded waterfalls.
    • Kid-Friendly
    • Dog-Friendly
  • BEST SELLER
    Water reflecting forest and blue sky.

    Muskoka Meandering

    $65 CAD
    Muskoka 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
  • BEST DONE SPRING-FALL
    The Waterfall Route

    The Waterfall Route

    $65 CAD
    Explore 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
  • BEST SELLER
    Outdoor Adventures & Scenic Roads

    Outdoor Adventures & Scenic Roads

    $65 CAD
    Outdoor Adventures encompasses everything you could possibly want in a road trip getaway. Scenic roads, cool attractions and good food!
    • Accessible
    • Kid-Friendly
    • Dog-Friendly
  • BEST DONE SPRING-FALL
    Hops, Hikes & History

    Hops, Hikes & History

    $65 CAD
    There 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
  • RETURNS THIS FALL
    Historic Haunts

    Historic Haunts

    CAD
    This 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
    Sold out
  • BEST SELLER
    Spring forest trail

    Quirky Adventures

    $65 CAD
    Quirky 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
  • RETURNS THIS FALL
    Spooky Sights & Ghostly Tales

    Spooky Sights & Ghostly Tales

    $65 CAD
    Explore 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
    Sale
  • MOTHER'S DAY PICK
    Wine Time and Hidden Gems

    Wine Time and Hidden Gems

    $65 CAD
    Craving 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
  • MOTHER'S DAY PICK
    Woman holding hands with small child on the beach in front of the ocean.

    From Country to Coast

    $65 CAD
    Meander along country roads, explore waterfall wonders, & visit local 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
    Sale
  • HIDDEN GEMS IN THE NIAGARA REGION!
    The Sweet & Scenic Route

    The Sweet & Scenic Route

    $65 CAD
    A little sweet, a little scenic - this road trip blends cozy cafés, local wines, and maple treats with easy trails, waterfalls, and serene ponds. Perfect for a girls' getaway or a romantic day trip! *Note that this trip can be taken in the summer months; however, the waterfalls may slow to a trickle in the hot weather!
    • Accessible
    • Dog-Friendly
  • SCENIC ROUTE
    Spooky black and white photo of a road on a foggy day.

    Beautifully Haunted

    $65 CAD
    This outdoorsy, story-filled road trip blends spooky legends with beautiful scenery along a rural driving route. A few local eateries and trails are sprinkled throughout the day to keep your energy up while ghost hunting. Most haunted sites are best enjoyed from the outside, so bring your curiosity and imagination to make the ghost stories come alive.
    • Dog-Friendly
    • Kid-Friendly
    Sale
  • MOTHER'S DAY PICK
    Sister and brother hugging on a boardwalk.

    Bridges to Beaches

    $65 CAD
    Picturesque 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
    Sale
  • Best done spring-fall
    A boardwalk leading to a beach with the sun shining brightly in the sky.

    Southern Express

    $65 CAD
    Think cozy bakeries, swim spots, easy hikes, and wine with a view, all wrapped up in one charming escape. You’ll wonder how this area stayed off your radar for so long!
    • Kid-Friendly
    • Dog-Friendly
  • MOTHER'S DAY PICK
    Two women on a beach looking out at the water

    Bayside Wonders

    $65 CAD
    The 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
    Sale
  • BEST SELLER
    Two people walking in a field with a mountain in the background.

    Quirky Gems

    $65 CAD
    Our best-selling Calgary road trip! 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
  • best done spring-fall
    A scenic view of a body of water with trees on the banks under a clear sky.

    Views & Secret Stops

    $65 CAD
    Views 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
  • PERFECT OVERNIGHT GETAWAY
    Lighthouse overlooking the water

    Curiosities & Coastlines

    $65 CAD
    Wander through eerie ruins, stop at offbeat roadside finds, explore historic small towns, and relax by the shores of Lake Huron. This laid-back Bruce County adventure perfectly mixes local legends, great eats, and scenic spots!
    • Kid-Friendly
    • Dog-Friendly
    • Accessible
    Sale
  • AN ICONIC ROUTE
    Rocky Mountain Route

    Rocky Mountain Route

    $65 CAD
    One 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 extra suggestions on the 4th stop just in case.
    • Accessible
    • Kid-Friendly
    • Dog-Friendly
  • BEST SELLER
    Maritime boats and boathouses.

    Coastal Crawl

    $65 CAD
    Get 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
  • BEST SELLER
    Hudson River Hideaways

    Hudson River Hideaways

    $65 CAD
    An iconic road trip route with a twist! We've found countless hidden hideaways along the Hudson including: crumbling ruins, quaint towns, spooky cemeteries and more.
    • Dog-Friendly
  • BEST SELLER
    A large American flag hanging on the side of a red brick building with greenery in the background.

    Tiny Town Tour

    $65 CAD
    Meander 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
Three women walking through tulip fields
Winding roads through mountains at sunrise

CAN'T DECIDE?

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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!