Our Trips

  • Perfect Year round trip!
    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
    • Dog-Friendly
  • Best done late May-October
    An Adventure is Brewing

    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- October!
    • Accessible
    • Dog-Friendly
  • Best-selling gift | Fall Favourite
    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
  • 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
  • Perfect Fall & Winter Trip!
    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
  • Best-selling gift | Fall Favourite
    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
  • 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 Between June - October
    Secrets in the South

    Secrets in the South

    $39 USD
    From funky markets, scenic roads and the most picturesque towns. You'll love all the secrets you'll discover on this trip.
    • Kid-Friendly
    • Dog-Friendly
  • Best done spring-fall | Great for young families
    Country Farms & Furry Friends

    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
  • Best done spring-fall
    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
  • 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
  • Great Winter 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
1 of 12

Merch

  • Add On: Gift Box + Wrapping

    Add On: Gift Box + Wrapping

    Regular price $10 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.
  • Road Trip Gift Box

    Road Trip Gift Box

    Regular price $100 Sale price $90 USD
    Sale
    The ultimate gift for the road trip lover. Each box is beautifully wrapped and includes a gift card, tote bag and keychain.
    Sale
  • Road Trip Tote Bag

    Road Trip Tote Bag

    Regular price $8 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.
  • Gift Card [Mailed: $USD]

    Gift Card [Mailed: $USD]

    Regular price $65 USD
    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 $USD]

    Gift Card [Digital $USD]

    Regular price $65 USD
    Instantly send the gift of a one-day surprise road trip! Digital gift cards can be sent immediately or scheduled to be sent on a specific day.
  • Road Trip Hat

    Road Trip Hat

    Regular price $16 USD
    The perfect accessory for your road trip! Choose from a forest green or beige hat embroidered with the words "Road Trip".
  • Large Road Trip Tote Bag

    Large Road Trip Tote Bag

    Regular price $24 USD
    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 USD
    Spice up your key ring with this adorable metal 2" tall Road Trip key chain!
  • 'This Is My Road Trip' Tote

    'This Is My Road Trip' Tote

    Regular price $16 Sale price $8 USD
    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
  • Extra Roadtripper Kit

    Extra Roadtripper Kit

    Regular price $55 Sale price $35 USD
    Sale
    Hitting the road with the kids? Mini Jetsetter road trip kits are the perfect way to keep them occupied! Our Road Trip Kits come with one Mini Jetsetter Kit, but we recommend purchasing additional kits for additional kiddos.
    Sale
  • Mini Roadtripper Kit - Gift Card

    Mini Roadtripper Kit - Gift Card

    Regular price $135 Sale price $90 USD
    Sale
    This option comes with a gift card (that can be redeemed for the full price of any trip) and a Mini Jetsetter travel kit (colors vary), all wrapped up in a hand-tied gift box.
    Sale
1 of 11