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  • Guess Where Trips gift wrapping.

    Add On: Gift Box + Wrapping

    Regular price $0.00 USD
    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 USD
    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 USD
    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 USD
    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 USD
    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 USD
    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 USD
    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
  • Guess Where Trips gift wrapping.

    Add On: Gift Box + Wrapping

    Regular price $0.00 USD
    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 USD
    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 USD
    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
  • Lots of outdoor attractions | Best done spring-fall
    The Waterfall Route

    The Waterfall Route

    $65 USD
    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 be done year-round | Great gift
    Markets to Mountains

    Markets to Mountains

    $65 USD
    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 | Great gift
    Hops, Hikes & History

    Hops, Hikes & History

    $65 USD
    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
  • Road Trip Tote Bag

    Road Trip Tote Bag

    Regular price $12.00 USD
    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 USD
    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 be done year-round
    Historic Haunts

    Historic Haunts

    $65 USD
    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
  • Great Winter Trip
    Outdoor Adventures & Scenic Roads

    Outdoor Adventures & Scenic Roads

    $50 USD 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
  • Best Done Between June - October
    Secrets in the South

    Secrets in the South

    $65 USD
    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
  • Optional Scavenger Hunt Included
    Spooky Sights & Ghostly Tales

    Spooky Sights & Ghostly Tales

    $65 USD
    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
  • Great year-round trip!
    Escape to Nature

    Escape to Nature

    $65 USD
    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
  • Best-selling gift
    Quirky Adventures

    Quirky Adventures

    $65 USD
    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
  • best-seller | best done spring-fall
    Woman looking out of car window.

    All the Pretty Things

    $65 USD
    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 done spring-fall
    Sister and brother hugging on a boardwalk.

    Bridges to Beaches

    $65 USD
    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
  • Best-selling gift | can be done year-round
    Woman taking a selfie, showing the woman behind her taking the photo.

    Brews, Bites, and Everything Nice

    $65 USD
    This trip is very true to its name, the coolest brews, the tastiest bites and everything else is very nice.
    • Accessible
    • Kid-Friendly

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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!