Eastern Canada

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A map-style destination graphic showing a central pin over Kitchener, with dashed lines and labels to Toronto (1.5 hr), Hamilton (1 hr 15 min), and London (2 hr) under the heading 'END DESTINATION'.

Ends Near Elora, ON

(207)

Classic Road Trip

Local Markets & Picturesque Towns

Historic towns, local markets, and plenty of under-the-radar finds.

$50

The Surprise Which Way? Road Trip Game box on a light cream textured background. The packaging features a bright orange top and bottom band with white text, and a central white panel decorated with cute illustrations of cars, a backpack, a coffee cup, and a suitcase, all framed by a dashed orange border.

A hand holds a mini card with a travel-themed mystery question, surrounded by promotional text callouts on a warm off-white background.

(4)

For the Road

Which Way? A Surprise Road Trip Card Game

Go on your own mini surprise trip with Which Way. Simply pick a card to reveal your next...

$22

Ontario Getaway Box by Guess Where Trips, illustrated with lakeside cottages, red Muskoka chairs on a dock, rocky island bluffs and a boat.

What's included in the Ontario Getaway Box: 20 sealed trip envelopes and a map of all 20 trip areas.

(8)

Road Trip Box

Ontario Getaway Box

20 getaways across Ontario: cottage country, Niagara wine country, and beach towns.

$65

Gift Cards

Not sure what to get them? Our digital gift cards are sent when you want, to whoever you want, in any amount you want.

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Toronto Day Trip Box by Guess Where Trips, illustrated with the CN Tower skyline, a red barn, a waterfall and a winding country road.

What's included in the Toronto Day Trip Box: 20 sealed trip envelopes and a map of all 20 trip areas.

(5)

Road Trip Box

Toronto Day Trip Box

20 day trips from Toronto: Mennonite country, lakeside towns, and hidden trails.

$65

London Day Trip Box by Guess Where Trips, illustrated with a lavender field, a gazebo, a small-town main street and a lakeside lighthouse.

What's included in the London Day Trip Box: 20 sealed trip envelopes and a map of all 20 trip areas.

(7)

Road Trip Box

London Day Trip Box

20 day trips from London: Lake Huron beaches, theatre towns, and farm stands.

$65

A stylized map graphic showing an end destination with a red pin marker and travel times to London, Kitchener, Hamilton, and Toronto. The map has a light gray land area, pale blue water, and dark green title text reading 'END DESTINATION'.

Ends Near Stratford, ON

(107)

Classic Road Trip

The Small Town Charm Trail

Blink-and-you'll-miss-it towns packed with hidden charm and funky finds.

$50

A travel map graphic showing an end destination with labeled locations: Toronto (1 hr 15 min), Kitchener (1 hr), Niagara Falls (1 hr), and London (1 hr 20 min), connected by dashed lines from a central pin marker on a pale map background.

Ends Near Ancaster, ON

(53)

Classic Road Trip

Spooky Sights & Ghostly Tales

Spooky ruins, haunted mansions, and a genuinely haunted lunch spot.

$50

End destination map: Kitchener 45 min, London 1.5 hr, Hamilton 1.5 hr, Toronto 2 hr.

Ends Near Millbank, ON

(46)

Classic Road Trip

Historic Haunts

Eerie legends, haunted towers, ruins, and cemeteries. Must love history!

$50

Ottawa Day Trip Box by Guess Where Trips, illustrated with a river and tour boat, canal locks, small-town storefronts, a church steeple and a red barn.

What's included in the Ottawa Day Trip Box: 20 sealed trip envelopes and a map of all 20 trip areas.

(6)

Road Trip Box

Ottawa Day Trip Box

20 day trips from Ottawa: Rideau canal towns, Gatineau Hills, and Quebec villages.

$65

A stylized city map showing an end destination with a red pin marker and dashed route lines to labeled locations: Toronto (1 hr 45 min), Kitchener (50 min), Hamilton (1 hr), and London (45 min).

Ends Near Woodstock, ON

(27)

Classic Road Trip

The Cheese & Charm Trail

Flower farms, dairy stops, and can't-stop-snacking energy.

$50

A map-style destination graphic showing a central pin near Ontario, with labeled nearby locations: Barrie, Peterborough, Oshawa, and Toronto, each with travel time annotations.

Ends Near Fenelon Falls, ON

(20)

Classic Road Trip

Butter Tarts, Boos & Brews

This autumn road trip mixes haunted tales with scenic drives, eerie landmarks, farm markets, local brews, and ooey-gooey butter tarts

$50

A stylized map graphic showing an end destination with labeled travel times to Toronto (1 hr 40 min), Hamilton (55 min), and London (1 hr 10 min). The map has a light gray land area, pale blue water, and a dark green banner at the top reading 'END DESTINATION' above a red location pin.

Ends Near Ayr, ON

(68)

Classic Road Trip

Riverside Roaming

A picture-perfect river town, boardwalks, and a funky distillery with incredible pizza!

$50

Ends Near Ancaster, ON

(65)

Classic Road Trip

Country Farms & Furry Friends

Alpacas, donkeys, goats, and a funky country market to start.

$50

A map-style destination graphic showing a central pin labeled 'END DESTINATION' with dashed lines pointing to four locations and their travel times: Parry Sound (1 hr), Barrie (1.5 hr), Newmarket (2 hr), and Peterborough (2 hr 15 min).

Ends Near Huntsville, ON

(87)

Classic Road Trip

Weird & Wonderful Things

Unusual attractions and secluded waterfalls that are worth the longer drive.

$50

We absolutely loved every stop along the way - it just kept getting better and better!

Jennifer U.

A travel map graphic showing an end destination with dotted lines and labels to nearby locations: Toronto (1 hr 20 min), Kitchener (1 hr 15 min), Hamilton (1.5 hr), and London (2 hr 15 min).

Ends Near Orangeville, ON

(80)

Classic Road Trip

Vistas & Caves

Hidden crevices, easy trails, and funky food stops perfect for lovers of the outdoors.

$50

A travel map graphic showing an end destination near Toronto, with dashed lines and labels pointing to Toronto, Kitchener, Hamilton, and London with travel times.

Ends Near Niagara, ON

(73)

Classic Road Trip

Funky Florals and Fine Wines

Must enjoy: wine, food and flowers for this pretty little road trip.

$50

A stylized map graphic showing an end destination with a red pin marker near the coast. Labels point to nearby locations: Sarnia, London, Kitchener, and Hamilton, with travel times written on orange boxes.

Ends Near Port Stanley, ON

(72)

Classic Road Trip

Secrets in the South

Funky markets, scenic roads, and the most picturesque small towns.

$50

A stylized map graphic showing an end destination marked with a red pin, with dashed route lines to three labeled locations: Barrie in 50 min, Toronto in 2 hr 15 min, and Kitchener in 2 hr 10 min.

Ends Near Collingwood, ON

(66)

Classic Road Trip

Markets to Mountains

Cute markets, mountainside hikes, and a cozy-meets-adventurous day.

$50

End destination map: London 1 hr 40 min, Kitchener 1.5 hr, Hamilton 1 hr, Toronto 2 hr 10 min.

Ends Near Port Dover, ON

(88)

Classic Road Trip

An Adventure is Brewing

Our summertime favourite: lavender fields, sandy beaches, and standout local breweries.

$50

A map-style destination graphic showing a red pin near Toronto, with labeled nearby locations and travel times: Toronto 1.5 hr, Kitchener 1 hr 45 min, Hamilton 1 hr, and London 2 hr 15 min.

Ends Near Fonthill, ON

(34)

Classic Road Trip

The Sweet & Scenic Route

Cozy cafes, maple treats, waterfalls, and scenic trails.

$50

A travel map graphic showing an end destination with location pins and travel times to Toronto, Hamilton, Kitchener, and London. The map has a light gray land area with pale blue water and a dark green banner at the top reading 'END DESTINATION'.

Ends Near Terra Cotta, ON

(30)

Classic Road Trip

The Whimsical Route

Nature, history, and a touch of cinematic magic, close to home.

$50

End destination map: Collingwood 1 hr 45 min, Barrie 1 hr 15 min, Peterborough 2.5 hr, Toronto 2.5 hr.

Ends Near Port Carling, ON

(70)

Classic Road Trip

Muskoka Meandering

Cottage-country wineries, scenic lookouts, and charming small towns.

$50

Showing 1-22 of 49 products

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Eastern Canada

Local Markets & Picturesque Towns

Which Way? A Surprise Road Trip Card Game

Ontario Getaway Box

Gift Cards

Toronto Day Trip Box

London Day Trip Box

The Small Town Charm Trail

Spooky Sights & Ghostly Tales

Historic Haunts

Ottawa Day Trip Box

The Cheese & Charm Trail

Butter Tarts, Boos & Brews

Riverside Roaming

Country Farms & Furry Friends

Weird & Wonderful Things

Vistas & Caves

Funky Florals and Fine Wines

Secrets in the South

Markets to Mountains

An Adventure is Brewing

The Sweet & Scenic Route

The Whimsical Route

Muskoka Meandering

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