Greater Toronto Area

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Canada Ontario GTA K-W / Hamilton Southwestern Ontario Barrie / Muskoka Eastern Ontario

17 Products

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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

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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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

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 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

(28)

Classic Road Trip

Escape to Nature

Tiny towns, easy year-round outdoor adventures, and a cozy cafe to finish.

$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

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 travel map graphic showing an end destination with a red location pin near Kingston, with dashed lines and labels pointing to Peterborough (1 hr 50 min) and Oshawa (1 hr 45 min).

Ends Near Picton, ON

(38)

Classic Road Trip

Wine Time and Hidden Gems

Rolling vineyard views, farm markets, and laid-back lakeside vibes.

$50

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 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

A map-style destination graphic showing a central pin near Toronto with dashed lines pointing to nearby cities and travel times: Barrie 1.5 hr, Peterborough 1 hr, Oshawa 35 min, and Toronto 1 hr 15 min.

Ends Near Port Perry, ON

(52)

Classic Road Trip

Taste of the Country

Farmers' markets, cute small towns, and an easy wooded trail to round out your day.

$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: Peterborough 50 min, Oshawa 1 hr 20 min, Kingston 1.5 hr.

Ends Near Campbellford, ON

(44)

Classic Road Trip

Outdoor Adventures & Scenic Roads

Scenic roads, cool attractions, and really good food make this the ideal day trip.

$50

I've lived here for over 20 years and had never even heard of these places. Now we want to come back!

Meredith Z.

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

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

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

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Greater Toronto Area

Toronto Day Trip Box

London Day Trip Box

Ontario Getaway Box

Gift Cards

Which Way? A Surprise Road Trip Card Game

The Sweet & Scenic Route

Escape to Nature

Riverside Roaming

Funky Florals and Fine Wines

Wine Time and Hidden Gems

Vistas & Caves

The Whimsical Route

Taste of the Country

Spooky Sights & Ghostly Tales

Outdoor Adventures & Scenic Roads

Local Markets & Picturesque Towns

Historic Haunts

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Greater Toronto Area

Toronto Day Trip Box

London Day Trip Box

Ontario Getaway Box

Gift Cards

Which Way? A Surprise Road Trip Card Game

The Sweet & Scenic Route

Escape to Nature

Riverside Roaming

Funky Florals and Fine Wines

Wine Time and Hidden Gems

Vistas & Caves

The Whimsical Route

Taste of the Country

Spooky Sights & Ghostly Tales

Outdoor Adventures & Scenic Roads

Local Markets & Picturesque Towns

Historic Haunts

An Adventure is Brewing

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Get a mystery discount!

Our Trips

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