Florida

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United States Southern States Florida Gainesville Jacksonville Orlando Tampa

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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.

$89

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

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

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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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

Ends Near St. Augustine, FL

(2)

Classic Road Trip

Seaside Legends

Local legends, picturesque beaches, and tasty coastal eats, ending in an iconic town.

$65

A calm river reflecting trees and a blue sky.

Ends Near Bonita Springs, FL

(6)

Classic Road Trip

The Southwest Quest

Sun, citrus, boardwalk trails, and even an eerie ghost town.

From $39

A stylized map graphic showing an end destination with labeled locations: Gainesville 1 hr 50 min, Orlando 45 min, and Tampa 2 hr, connected by dashed brown lines to a central pin on a pale map background.

Ends Near Mt Dora, FL

(7)

Classic Road Trip

Boardwalks, Brews & Markets

Local markets, cool local brews, and a breezy boardwalk stroll to round out the day.

$65

Ends Near Gainesville, FL

(6)

Classic Road Trip

Old Florida Trail

Delightful small towns, local fare, and quirky roadside photo ops.

From $39

Ruins of an old building overgrown with trees and plants

Ends Near New Smyrna Beach, FL

(4)

Classic Road Trip

Mysterious Gems

Cemeteries, abandoned ruins, and historic homes with eerie local legends to discover.

$65

We had an amazing time! I highly recommend this trip for couples or groups of friends.

Cyndi G.

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

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The Day Trip Deck

Which Way? A Surprise Road Trip Card Game

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Orlando Day Trip Box

Lilac Road Trip Journal

Which Way? A Surprise Road Trip Card Game

Gift Cards

Mint Road Trip Journal

Seaside Legends

The Southwest Quest

Boardwalks, Brews & Markets

Old Florida Trail

Mysterious Gems

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Orlando Day Trip Box

Lilac Road Trip Journal

Which Way? A Surprise Road Trip Card Game

Gift Cards

Mint Road Trip Journal

Seaside Legends

The Southwest Quest

Boardwalks, Brews & Markets

Old Florida Trail

Mysterious Gems

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Our Trips

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