Our Trips

  • BEST SELLER
    Woman looking at plants at a market.

    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 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
  • BEST SELLER
    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
  • 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
  • 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
  • EXPLORE NIAGARA
    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 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
  • BEST SELLER
    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
  • CAN BE DONE YEAR-ROUND
    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
  • 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
  • GREAT YEAR-ROUND TRIP
    Riverside Roaming

    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
  • Best done spring-fall
    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
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Merch

  • Gift Card

    Gift Card

    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.
  • Valentine's Day Gift Box from Guess Where Trips

    Valentine's Add-On: Gift Wrapping with Tote Bag

    Regular price $22.00 Sale price $15.00 CAD
    Let us gift wrap your trip or gift card for Valentine's Day with a tote bag and a Valentine's Day postcard. Add this on to any mailed gift card or mailed trip of your choice.
    Sold out
  • Mailed Trip Add On: Gift Wrapping

    Mailed Trip Add On: Gift Wrapping

    Regular price $15.00 CAD
    The ultimate addition if you're gifting a road trip to someone special!
  • Large Road Trip Tote Bag

    Large Road Trip Tote Bag

    Regular price $24.00 Sale price $18.00 CAD
    Sale
    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.
    Sale
  • 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).
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