Our Trips

  • MOTHER'S DAY PICK
    Local Markets & Picturesque Towns

    Local Markets & Picturesque Towns

    $65 CAD
    One of our best-selling trips, and for a good reason. Stops include historic towns, local markets, eateries and hidden gems. This trip makes a great gift because of its versatility.
    • Accessible
    • Kid-Friendly
    Can depart from: London Area, Toronto Area
  • 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
    Can depart from: London Area, Kitchener-Waterloo Area, Toronto Area
  • STAFF PICK
    The Small Town Charm Trail

    The Small Town Charm Trail

    $65 CAD
    You know those towns that are described as 'blink-and-you'll-miss-it'? They often have the most amazing hidden gems! Get to know a few small pockets of Ontario with this surprise road trip.
    • Accessible
    • Kid-Friendly
    Can depart from: Sarnia Area, London Area, Toronto Area, Kitchener-Waterloo Area
  • 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
    Can depart from: London Area, Kitchener-Waterloo Area, Toronto Area, Barrie Area
  • 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
    Can depart from: Toronto Area, Kitchener-Waterloo Area, Kingston Area, Barrie Area
  • GREAT FOR YOUNG FAMILIES
    Alpaca behind a fence, being fed a carrot.

    Country Farms & Furry Friends

    $65 CAD
    Alpacas, donkeys and goats - oh my! Start your day off at a funky country market, before hanging with the birds and ending the day with some furry friends.
    • Kid-Friendly
    • Accessible
    Sale
    Can depart from: London Area, Kitchener-Waterloo Area, Toronto Area
  • STAFF PICK
    Bikes parked in front of a flower shop.

    Funky Florals and Fine Wines

    $65 CAD
    This pretty little road trip offers quite a few hidden gems combined with a few iconic attractions. Must enjoy: wine, food and flowers.
    • Accessible
    Can depart from: London Area, Kitchener-Waterloo Area, Toronto Area
  • 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
    Can depart from: Kitchener-Waterloo Area, Toronto Area, Barrie Area
  • MOTHER'S DAY PICK
    Woman sitting on a rocky shore overlooking a river.

    Riverside Roaming

    $65 CAD
    Start your day in a picture-perfect town by the river before strolling along boardwalks, dining at a funky distillery, indulging at farm shops and so much more. This trip is a nice distance from the city and can be done year-round!
    • Kid-Friendly
    • Accessible
    Can depart from: Toronto Area, London Area, Kitchener-Waterloo Area
  • GREAT OVERNIGHT GETAWAY
    Markets to Mountains

    Markets to Mountains

    $65 CAD
    From cute markets to mountainside hikes, Markets to Mountains provides you with all the stops for a cozy yet adventurous day trip in Ontario. We highly recommend booking a hotel at the finishing stop for the ultimate weekend getaway.
    • Kid-Friendly
    • Accessible
    Can depart from: Kitchener-Waterloo Area, Toronto Area, London Area, Barrie Area
  • 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
    Can depart from: Kitchener-Waterloo Area, Toronto Area, Barrie Area
  • 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 depart from: Toronto Area, Kingston Area
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Merch

  • Road Trip Gift Card

    Road Trip Gift Card

    $74.00 CAD
    Give the gift of a one-day surprise road trip with Guess Where Trips®! Valued at $74, this voucher covers the full cost of any of our mailed road trips, including tax and standard shipping. The recipient can choose any surprise road trip that suits them, and it will be shipped right to their door. These gift cards never expire.
  • Add On: Gift Wrapping

    Add On: Gift Wrapping

    $14.00 CAD
    A reusable gift box with magnetic closure - perfect for presenting their surprise trip and storing souvenirs after the adventure.
  • Gift Card [Digital $CAD]

    Gift Card [Digital $CAD]

    $74.00 CAD
    Want to email this directly to someone else? Don't add it to your cart just yet! Click the photo above for more options, including scheduling the gift card for a date in the future.
  • Detour Diaries: Ontario

    Detour Diaries: Ontario

    $59.00 CAD
    The ultimate travel companion that transforms Ontario's most-travelled highways into unforgettable adventures.
  • Road Trip Journal

    Road Trip Journal

    $25.00 CAD
    Track all your local adventures - big or small!
  • Person holding the Which Way Card game in front of a green background

    Which Way? A Surprise Road Trip Card Game

    $22.00 CAD
    A surprise road trip game where the entire point is to get lost!
  • Road Trip Game Pack

    Road Trip Game Pack

    $12.00 CAD
    Keep 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.
  • Road Trip Tote Bag

    Road Trip Tote Bag

    $20.00 $5.00 CAD
    Sale
    An 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.
    Sale
  • Detour Club Bundle

    Detour Club Bundle

    $106.00 $89.00 CAD
    Sale
    The ultimate travel companion that transforms Ontario's most-travelled highways into unforgettable adventures.
    Sale
  • Guess Where Trips Gift Card Bundle

    Road Trip Gift Box

    $118.00 $95.00 CAD
    The ultimate gift for the road trip lover. Each box is beautifully wrapped and includes a gift card, game pack, and tote bag.
    Sold out
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