Ontario Trips & Adventures

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

47 Products

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End destination map: London 45 min, Kitchener 1 hr, Hamilton 1.5 hr, Mississauga 1 hr 45 min.

Ends Near St. Marys, ON

(1)

Classic Road Trip

A Cozy Countryside Christmas

Trade your holiday to-do list for a day of twinkling lights, cozy sips, and festive finds.

From $39

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

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

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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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

Lilac Road Trip Journal with a Detour Diaries cover label.

A hand holding the Lilac journal outdoors against green trees.

(2)

For the Road

Lilac Road Trip Journal

Track all your local adventures - big or small!

$25

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

(28)

Classic Road Trip

The Cheese & Charm Trail

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

$50

End destination map: Toronto 1 hr 20 min, Kitchener 1 hr 15 min, Hamilton 1.5 hr, London 2 hr 15 min.

Ends Near Orangeville, ON

Classic Road Trip

All Things Merry & Bright

If you're looking for a road trip that is full of festivity and holiday cheer, look no further!

From $39

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

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

Mint Road Trip Journal with a Detour Diaries cover label.

A woman holding the Mint journal in a sunny garden.

For the Road

Mint Road Trip Journal

Track all your local adventures - big or small - in one place with this fun road trip journal!

$25

A map-style destination graphic showing a red pin near the left side and dashed lines connecting it to labeled locations: Collingwood 2 hr, Barrie 2.5 hr, Toronto 3 hr, and Kitchener 2 hr.

Ends Near Kincardine, ON

(25)

Classic Road Trip

Curiosities & Coastlines

Eerie ruins, historic towns & bridges, and easy afternoons by the shore.

$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 map-style destination graphic showing an end point marked with a red pin, with dashed lines and labeled callouts to Kincardine, Barrie, Toronto, and Kitchener, each with estimated travel times.

Ends Near Owen Sound, ON

(34)

Classic Road Trip

Bayside Wonders

Farmers' markets, wine tastings, and waterfalls worth making it a weekend getaway.

$50

The entire day we talked about how much fun we had and enjoyed ourselves.

Maureen F.

A travel map graphic showing an end destination with a red location pin at the center, dashed route lines to Ottawa (30 min), Cornwall (1 hr 10 min), and Montreal (2 hr), plus a dark green label reading 'END DESTINATION'.

Ends Near Clarence-Rockland, ON

(9)

Classic Road Trip

Gardens, Trails & Local Ales

Under-the-radar breweries, easy trails, and quirky local shops close to home.

$50

A travel map graphic showing an end destination with a red location pin and dashed lines pointing to four labeled locations: Collingwood (1 hr), Barrie (45 min), Peterborough (2.5 hr), and Toronto (1 hr 45 min).

Ends Near Midland, ON

(34)

Classic Road Trip

Hidden Gems of Huronia

Haunted history, picturesque trails, and farm-fresh flavours.

$50

A map-style graphic with a red location pin in the center and dashed lines pointing to nearby labeled areas: Sarnia, London, Chatham, and Kitchener, each with travel time text. The top banner reads 'END DESTINATION'.

Ends Near Grand Bend, ON

(47)

Classic Road Trip

From Country to Coast

Waterfall wonders, local wineries & breweries, and beachside towns.

$50

A stylized map graphic with a red location pin near Toronto, showing three labeled destination options: Toronto 2 hr, Kitchener 1.5 hr, and London 1 hr 45 min, with the heading 'END DESTINATION' at the top.

Ends Near Cayuga, ON

(37)

Classic Road Trip

Beautifully Haunted

Spooky legends, rural scenery, and ghost-hunting energy all day.

$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

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

Showing 1-22 of 47 products

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Ontario Trips & Adventures

A Cozy Countryside Christmas

Toronto Day Trip Box

Ottawa Day Trip Box

Gift Cards

London Day Trip Box

Ontario Getaway Box

Lilac Road Trip Journal

The Cheese & Charm Trail

All Things Merry & Bright

Butter Tarts, Boos & Brews

Which Way? A Surprise Road Trip Card Game

Mint Road Trip Journal

Curiosities & Coastlines

The Sweet & Scenic Route

Bayside Wonders

Gardens, Trails & Local Ales

Hidden Gems of Huronia

From Country to Coast

Beautifully Haunted

Muskoka Meandering

Escape to Nature

Riverside Roaming

Funky Florals and Fine Wines

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