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Ends Near Port Alberni, BC

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

A map-style destination graphic showing a location pin near Nanaimo, with a dashed line pointing to Victoria labeled 2.5 hr, under a dark label reading END DESTINATION.

Classic Road Trip

Valleys, Vistas & Falls

Rooftop goats, riverside pints, and iconic nature stops that are worth the detour.

$65

Ends Near Joliet, IL

Classic Road Trip

Eerie Escapes

Ghostly cemeteries, abandoned ruins, and stories that will make you shiver.

$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.

Shop Now Shop

A stylized map graphic showing the end destination from Victoria to Nanaimo, with travel time labels 'Nanaimo 1 hr 40 min' and 'Victoria 30 min' and a red pin marker between the two locations.

Ends Near Sidney, BC

Classic Road Trip

Seaside Sips & Strolls

Waterside strolls, blooming gardens, and storybook towns.

$65

End destination map: Lafayette 1 hr 20 min, Indianapolis 1.5 hr, Bloomington 1.5 hr.

Ends Near Rockville, IN

(5)

Classic Road Trip

Countless Covered Bridges

Quaint covered bridges and countryside charm, one stop at a time.

$65

Lilac Road Trip Journal with a Detour Diaries cover label.

A hand holding the Lilac journal outdoors against green trees.

For the Road

Lilac Road Trip Journal

Track all your local adventures - big or small!

$25

Ends Near Capitola, CA

Classic Road Trip

Colors & Wonders

Short hikes through the redwoods, local shops, and a beautiful beach ending.

From $39

A cluttered antique shop with vintage furniture.

Ends Near San Marcos, TX

Classic Road Trip

Strange & Spooky Sights

Haunted towns, peculiar museums, and genuinely eerie spots to grab a bite.

$65

Boston Day Trip Box by Guess Where Trips, illustrated with a New England harbour village, a white church steeple, colourful houses and a lighthouse.

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

Ends Near Dripping Springs, TX

Road Trip Box

Boston Day Trip Box

20 day trips from Boston: harbor towns, Revolutionary history, and covered bridges.

$89

A margarita and nachos on a patio with string lights.

Classic Road Trip

Cowboy Country Crawl

Wild West charm, cowboy photo ops, and a hidden swimming hole.

From $39

Ends Near Zionsville, IN

Classic Road Trip

Elegant Estates & Outdoor Art

Elegant estates, whimsical gardens, and colorful outdoor art to fill your camera roll.

$65

A lookout over a wide river valley framed by green trees.

Ends Near Red Wing, MN

(4)

Classic Road Trip

Art Trails & River Tales

Scenic riverside drives, quirky outdoor art, and charming towns that are worth the detour.

$65

Ends Near Highwood, IL

Ends Near Fredericksburg, TX

Classic Road Trip

Cinema & Scenery

Hidden art, movie-star moments, and a breezy waterside stroll.

$65

Ends Near Orangeville, ON

Classic Road Trip

Hill Country Harvest

Stunning wineries, a renowned distillery, and a wildflower farm.

$65

“From the coffee shop, to the towns locals giving us some fun history ... was amazing!”

Marlena W.

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

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

Ends Near New Ulm, MN

Classic Road Trip

Creatures & Quirks

Wild bison, waterfalls, towering sculptures, and pints with actual peacocks!

$65

Ends Near Solvang, CA

Classic Road Trip

Solvang Splendors

Rolling vineyard hills, local farms, and cute small towns.

$65

New York State Getaway Box by Guess Where Trips, illustrated with lakes, a waterfall, rolling hills and a small lakeside town.

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

Road Trip Box

New York State Getaway Box

20 getaways across New York: the Finger Lakes, the Hudson Valley, and the Adirondacks.

$89

Bay Area Day Trip Box by Guess Where Trips, illustrated with the Golden Gate Bridge, redwoods, a lighthouse and a coastal village.

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

Road Trip Box

Bay Area Day Trip Box

20 day trips from San Francisco: wine country, redwoods, and coastal towns.

$89

A map-style destination graphic showing a route from Minneapolis to St. Cloud, with a red pin marker at the center, orange labels for each location, and a dark green banner reading 'END DESTINATION'.

Ends Near Waconia, MN

Classic Road Trip

Lakeside Treasures

Lakeside towns, quirky art gardens, and the perfect patio pint.

$65

Orlando Day Trip Box by Guess Where Trips, illustrated with palm trees, a manatee and heron in a spring, Spanish-style buildings, a bell tower and an orange grove.

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

Road Trip Box

Orlando Day Trip Box

20 day trips from Orlando: crystal-clear springs, old Florida charm, and beach towns.

$89

Washington DC Day Trip Box by Guess Where Trips, illustrated with rolling countryside, a farmhouse, colourful row houses, vineyards and a horse fence.

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