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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

(3)

Road Trip Box

New York State Getaway Box

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

$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.

NEW

(3)

Road Trip Box

Boston Day Trip Box

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

$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

Gift Cards

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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

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 location near Boston, Providence, and Worcester with labeled travel times. The image includes a dark green banner reading “END DESTINATION” and orange callout boxes for Worcester, Providence, and Boston, with a red pin marking the destination.

Ends Near South Dartmouth, MA

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Classic Road Trip

Vintage Vibes & Views

New England charm, cozy cafes, and postcard-worthy beaches.

$50

A stylized map graphic showing an end destination near Boston, with dashed route lines and labeled travel times to Worcester (1 hr 40 min), Boston (1 hr), and Providence (2 hr 15 min).

Ends Near Newburyport, MA

(2)

Classic Road Trip

Scenic Sights & Tasty Bites

Bakeries, breweries, and scenic views for a well-rounded road trip.

$50

Ends Near Dennis, MA

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Classic Road Trip

Escape to the Cape

Picturesque views, heritage buildings, and Cape Cod charm.

$50

End destination map: Boston 45 min, Worcester 1 hr, Providence 1.5 hr.

Ends Near Concord, MA

(3)

Classic Road Trip

Funky Farms & Storybook Tales

A picturesque drive past farms, boardwalk trails, and quirky local history.

$50

My heart and soul were full of joy by the end of the day.

Melanie B.

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

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New York State Getaway Box

Boston Day Trip Box

Lilac Road Trip Journal

Gift Cards

Which Way? A Surprise Road Trip Card Game

Mint Road Trip Journal

Vintage Vibes & Views

Scenic Sights & Tasty Bites

Escape to the Cape

Funky Farms & Storybook Tales

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Massachusetts

New York State Getaway Box

Boston Day Trip Box

Lilac Road Trip Journal

Gift Cards

Which Way? A Surprise Road Trip Card Game

Mint Road Trip Journal

Vintage Vibes & Views

Scenic Sights & Tasty Bites

Escape to the Cape

Funky Farms & Storybook Tales

Give Us a Follow!

Get a mystery discount!

Our Trips

Help & Info

Company