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  • Guess Where Trips gift wrapping.

    Add On: Gift Box + Wrapping

    $10.00 CAD
    The perfect addition if you're gifting a road trip to someone special! Let us carefully wrap up your mailed trip or gift card in our signature gift box (as shown).
  • 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
    Can depart from: Sarnia Area, London Area, Toronto Area
  • Gift Card [Mailed: $CAD]

    Gift Card [Mailed: $CAD]

    $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!
  • 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
    Can depart from: Sarnia Area, London Area, Kitchener-Waterloo Area, Toronto Area
  • Gift Card [Digital $CAD]

    Gift Card [Digital $CAD]

    $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.
  • 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
    Can depart from: Sarnia Area, London Area, Toronto Area, Kitchener-Waterloo Area
  • 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
    Can depart from: Toronto Area, Kitchener-Waterloo Area, Kingston Area, Barrie Area
  • 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
    Can depart from: London Area, Kitchener-Waterloo Area, Toronto Area
  • 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
    Can depart from: London Area, Kitchener-Waterloo Area, Toronto Area, Barrie Area
  • Road Trip Gift Box

    Road Trip Gift Box

    $108.00 $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
  • Guess Where Trips gift wrapping.

    Add On: Gift Box + Wrapping

    $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.
  • 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
    Can depart from: Kitchener-Waterloo Area, Toronto Area, Barrie Area
  • 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 depart from: London Area, Kitchener-Waterloo Area, Toronto Area
  • 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
    Can depart from: Kitchener-Waterloo Area, Toronto Area, London Area, Barrie Area
  • 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
    Can depart from: Kitchener-Waterloo Area, Toronto Area, Barrie Area
  • 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 depart from: Sarnia Area, London Area, Kitchener-Waterloo Area, Toronto Area
  • Road Trip Tote Bag

    Road Trip Tote Bag

    $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.
  • Best-Seller | Great year-round trip
    Wine Time and Hidden Gems

    Wine Time and Hidden Gems

    $65 CAD
    This trip requires a little more driving. We've found quite a few hidden quirks and gems along the route which we know you'll love.
    • Dog-Friendly
    Can depart from: Toronto Area, Kingston Area
  • 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
    Can depart from: London Area, Toronto Area, Kitchener-Waterloo Area
  • Great Winter Trip
    Outdoor Adventures & Scenic Roads

    Outdoor Adventures & Scenic Roads

    $50 CAD Sale
    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
    Sale
    Can depart from: Toronto Area, Kingston Area
  • Best Done Between June - October
    Secrets in the South

    Secrets in the South

    $65 CAD
    With funky markets, scenic roads and the most picturesque towns, you'll love all of the secrets you discover on the road. This trip is best enjoyed between June - October as there are a handful of fabulous seasonal suggestions.
    • Kid-Friendly
    • Dog-Friendly
    Can depart from: Sarnia Area, London Area, Kitchener-Waterloo Area, Toronto Area
  • 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
    Can depart from: London Area, Kitchener-Waterloo Area, Toronto Area
  • Great year-round trip!
    Escape to Nature

    Escape to Nature

    $65 CAD
    Explore tiny towns and easy outdoor adventures before cozying up at a local cafe or brewery. Optional wintery activities include ice skating and snowshoeing! Please note: this trip is similar to the Sport Chek Winter Trek for Toronto.
    • Kid-Friendly
    Can depart from: Toronto Area, Kitchener-Waterloo Area, Barrie Area
  • Best-selling gift
    Quirky Adventures

    Quirky Adventures

    $65 CAD
    Quirky cafes, funky little shops and adventures for everyone. Quirky Adventures is definitely the fan favourite within the Ottawa area.
    • Kid-Friendly
    • Accessible
    • Dog-Friendly
    Can depart from: Kingston Area, Ottawa Area, Montreal Area

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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!