Our Trips

  • Perfect Year-Round Trip for Every Traveller
    Local Markets and Picturesque Towns

    Local Markets and 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
  • Best done late May-October
    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
  • Great year-round trip
    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
  • Best-selling gift
    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
  • Perfect Fall & Winter Trip! | Great gift
    Funky Florals and Fine Wines

    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
  • great year-round trip
    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
  • Great year-round trip!
    Muskoka Meandering

    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 | 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
  • Can be done year-round | Great gift
    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
  • Lots of outdoor attractions | 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. We included quite a few 'bonus stops' in case you'd like to turn this day trip into an overnighter. This trip is perfect for spring - fall travellers. Waterfalls may dry up in extreme heat.
    • Kid-Friendly
    • Dog-Friendly
  • Best done spring-fall | Great gift
    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
  • 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
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Merch

  • Guess Where Trips gift wrapping.

    Add On: Gift Box + Wrapping

    Regular price $10.00 CAD
    The perfect addition if you're gifting a road trip to someone special! Let us carefully wrap up your mailed trip in our signature gift box.
  • Road Trip Gift Box

    Road Trip Gift Box

    Regular price $116.00 Sale price $95.00 CAD
    Sale
    The ultimate gift for the road trip lover. Each box is beautifully wrapped and includes a gift card, tote bag and keychain.
    Sale
  • Gift Card [Mailed: $CAD]

    Gift Card [Mailed: $CAD]

    Regular price $74.00 CAD
    Give the gift of a one-day surprise road trip! The gift card covers the full price of one of our mailed trips, including taxes and shipping costs. The recipient can then choose a surprise trip that suits them!
  • Gift Card [Digital $CAD]

    Gift Card [Digital $CAD]

    Regular price $74.00 CAD
    Instantly send the gift of a one-day surprise road trip! The gift card covers the full price of one of our mailed trips, including taxes and shipping.
  • Road Map

    Road Map

    Regular price $6.00 CAD
    Everyone misses a good ol' traditional road map. This is an essential item for any road trip (and it looks great in photos).
  • Road Trip Tote Bag

    Road Trip Tote Bag

    Regular price $12.00 CAD
    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.
  • Large Road Trip Tote Bag

    Large Road Trip Tote Bag

    Regular price $24.00 CAD
    THE 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.
  • Road Trip Key Chain

    Road Trip Key Chain

    Regular price $8.00 CAD
    Spice up your key ring with this adorable motel-style Road Trip key chain!
  • Tote bag with red writing

    'This Is My Road Trip' Tote

    Regular price $16.00 Sale price $8.00 CAD
    Sale
    Save big on our "This is my Road Trip Bag" tote bag! Great quality, with an interior pocket to keep small items organized.
    Sale
  • Flatlay of Guess Where Trips tote bag, gift card, brochure, keychain and gift wrapping.

    Add On: Gift Box + Tote + Keychain

    Regular price $30.00 Sale price $16.00 CAD
    Sale
    The perfect addition if you're gifting a road trip to someone special! Let us carefully wrap up your mailed trip in our signature gift box.
    Sale
  • Road Trip Game Pack

    Road Trip Game Pack

    Regular price $12.00 Sale price $6.00 CAD
    Sale
    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.
    Sale
  • Mother's Day Add-On: Gift Wrapping

    Mother's Day Add-On: Gift Wrapping

    Regular price $23.00 Sale price $10.00 CAD
    Sale
    Let us gift wrap your trip or gift card for Mother's Day with a tote bag and a Mother's Day postcard. Add this on to any mailed gift card or mailed trip of your choice.
    Sale
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