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

  • BEST SELLER
    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
  • FATHER'S DAY PICK
    Vistas & Caves

    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 and Wonderful Things

    Weird and 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
  • GREAT SUMMER ROADTRIP
    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
  • GREAT SUMMER ROADTRIP
    Hops, Hikes & History

    Hops, Hikes & History

    $65 CAD
    There is so much more to this trip than the name implies. This itinerary will take you to a number of unknown areas you'll fall in love with. The hops, hikes and history are just the added perks.
    • 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
  • CAN BE DONE YEAR-ROUND
    Historic Haunts

    Historic Haunts

    $65 CAD
    If you're a fan of ghost stories and unusual attractions, this trip is for you! We've rounded up the spookiest attractions for a 'Haunted History' route. Please Note: This trip takes place in the same area as Local Markets & Picturesque Towns.
    • Accessible
    • Dog-Friendly
  • Optional Scavenger Hunt Included
    Spooky Sights & Ghostly Tales

    Spooky Sights & Ghostly Tales

    $65 CAD
    Spooky ruins, abandoned buildings, and haunted mansions make up this ghostly road trip. Perfect for history buffs & paranormal seekers! We've even included a fun scavenger hunt! This trip takes place in a busier city, so travellers may run into some traffic.
    • Dog-Friendly
  • BEST SELLER
    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
  • BEST SELLER
    Woman looking out of car window.

    All the Pretty Things

    $65 CAD
    Take in all the pretty views and things on this picturesque trip. The itinerary is packed with stunning viewpoints, historic attractions and delicious restaurants and wineries.
    • Accessible
    • Dog-Friendly
    • Kid-Friendly
  • BEST SELLER
    Spring forest trail

    Quirky Adventures

    $65 CAD
    Quirky 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
  • BEST DONE MAY-OCTOBER
    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
  • GREAT SUMMER ROADTRIP
    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, 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
  • SCENIC ROUTE
    Spooky black and white photo of a road on a foggy day.

    Beautifully Haunted

    $65 CAD
    This 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
    Sale
  • Best done spring-fall
    Southern Express

    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
  • HIDDEN GEMS
    The Whimsical Route

    The Whimsical Route

    $65 CAD
    Get 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
  • BEST SELLER
    Quirky Gems

    Quirky Gems

    $65 CAD
    Our 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
  • SCENIC ROUTE
    Historic white house underneath a vibrant blue sky.

    Hidden Gems of Huronia

    $65 CAD
    Discover 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
  • best done spring-fall
    Views & Secret Stops

    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
  • GREAT WEEKEND GETAWAY
    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
  • HIDDEN GEMS IN THE NIAGARA REGION
    Couple holding hands on a forest trail

    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!
    • Accessible
    • Dog-Friendly
  • BEST SELLER
    Tiny Town Tour

    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
  • 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 a 'want to keep going' section just in case.
    • Accessible
    • Kid-Friendly
    • Dog-Friendly
Three women walking through tulip fields
Winding roads through mountains at sunrise

CAN'T DECIDE?

Take Our Quiz to Find Out

Select your region and interests to find the best trip for you.

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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!