This mystery trip company plans a day of adventures. We tested it.

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Guess Where Trips plans day-long road trips that are easy to reach from home, with several stops and multiple options on each leg.

A “Before You Go” envelope includes a recommended time to leave and general information about all four spots, including driving time from one stop to the next. Information about closures on certain days and a list of what to pack were important for planning purposes.

Because my life is chaos, I didn’t open this pre-trip envelope until the day before our departure, only to discover an option on one of the stops would be closed the next day. For future trips, I would read this information as soon as the package arrived, in case I wanted to adjust the timing. A list of fast facts about the destination mentioned architecture, historical facts, famous foods such as crab cakes and films and TV shows that were shot there, including “Patriot Games” and “House of Cards” — a fun way to set our expectations. We headed to the recommended restaurant, the bustling, waited for seats at the high-top counter overlooking a harbor and ordered the recommended dishes .

 

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