All Products

152 Products

Sort by:

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.

NEW

(3)

Road Trip Box

London Day Trip Box

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

$65

A woman standing on a desert road holding a sign.

Ends Near Joshua Tree, CA

(2)

Classic Road Trip

Joshua Tree Journey

Cowboy towns, desert trails, and offbeat art on the way to Joshua Tree.

$50

Ends Near Fredericksburg, TX

(1)

Classic Road Trip

Hill Country Harvest

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

$50

The Day Trip Deck

Build your own day trip, anywhere: draw a few cards, find the spots and hit the road.

Shop Now Shop

Ends Near St Croix Falls, WI

(2)

Classic Road Trip

Walk on the Wild Side

Riverside hikes, a wildlife park, and a well-earned winery stop.

$50

Ends Near New Ulm, MN

(2)

Classic Road Trip

Creatures & Quirks

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

$50

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.

NEW

(3)

Road Trip Box

Toronto Day Trip Box

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

$65

Ends Near Solvang, CA

Classic Road Trip

Solvang Splendors

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

$50

Aerial view of a pier stretching into turquoise water.

Ends Near West Malibu, California

(2)

Classic Road Trip

Tastes & Trails of Malibu

Under-the-radar finds and epic viewpoints along the coast.

$50

NEW

(3)

For the Road

The Day Trip Deck

Build your own day trip, anywhere: draw a few cards, find the spots, and hit the road.

$30

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

(1)

Classic Road Trip

Lakeside Treasures

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

$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.

NEW

(3)

Road Trip Box

Ottawa Day Trip Box

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

$65

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.

NEW

(2)

Road Trip Box

Washington DC Day Trip Box

20 day trips from DC: Virginia wine country, Civil War history, and Chesapeake towns.

$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.

NEW

(1)

Road Trip Box

Orlando Day Trip Box

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

$65

Vancouver Day Trip Box by Guess Where Trips, illustrated with mountains, evergreen forest, a waterfall, a suspension bridge and a ferry.

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

NEW

(1)

Road Trip Box

Vancouver Day Trip Box

20 day trips from Vancouver: waterfalls, Fraser Valley farms, and mountain towns.

$65

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

Marlena W.

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.

NEW

(3)

Road Trip Box

Boston Day Trip Box

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

$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.

NEW

(1)

Road Trip Box

New York State Getaway Box

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

$65

Austin Day Trip Box by Guess Where Trips, illustrated with Texas Hill Country, a winding road, small-town storefronts, a Texas flag and bluebonnets.

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

NEW

(1)

Road Trip Box

Austin Day Trip Box

20 day trips from Austin: Hill Country wineries, swimming holes, and Texas barbecue.

$65

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.

NEW

(3)

Road Trip Box

Bay Area Day Trip Box

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

$65

The Ultimate Road Trip Game Pack book cover by Guess Where You Go, featuring a retro orange background with a blue and cream Volkswagen Beetle illustration.

A close-up of a printed 'Road Trip Bingo' card or booklet page with red title text and pink game instructions on white paper, photographed on a light fabric surface.

(0)

For the Road

Road Trip Game Pack

This 50+ page road trip game bundle is an essential add-on for any surprise trip. It was truly...

$6Regular price ~~$12~~

(0)

For the Road

Road Trip Tote Bag

An essential tote bag for your road trip ahead. Carry everything from your surprise package to all the...

$5Regular price ~~$20~~

Showing 133-152 of 152 products

200,000+ Road Trips Sold200,000+ Road Trips Sold200,000+ Road Trips Sold200,000+ Road Trips Sold

All Products

London Day Trip Box

Joshua Tree Journey

Hill Country Harvest

The Day Trip Deck

Walk on the Wild Side

Creatures & Quirks

Toronto Day Trip Box

Solvang Splendors

Tastes & Trails of Malibu

The Day Trip Deck

Lakeside Treasures

Ottawa Day Trip Box

Washington DC Day Trip Box

Orlando Day Trip Box

Vancouver Day Trip Box

Boston Day Trip Box

New York State Getaway Box

Austin Day Trip Box

Bay Area Day Trip Box

Road Trip Game Pack

Road Trip Tote Bag

Give Us a Follow!

Get a mystery discount!

Our Trips

Help & Info

Company