Guess Where? Surprise road trip packages include ‘Mysterious Gems’ of Florida.

ORLANDO, Fla. — Some road trips require meticulous planning, mapping and calculating to find the best roadside attractions, food stops and gas stations along the way. But for spontaneous, adventurous explorers, a travel company provides this puzzling riddle: Guess Where?

Geared toward families, friends and all-day dates, Guess Where Trips supplies self-guided itineraries that leave road trippers guessing right up until the moment they leave. The Canada-based company offers six surprise excursions in Florida that harken back to an earlier time in the Sunshine State’s history when car trips and roadside attractions were all the rage.

Some journeys help explorers delve into the past or embark on outdoor adventures, while others present quaint towns and local fare to eat. Near Gainesville, travel the “Old Florida Trail” or head to South Florida for “Treasure Coast Explorer,” “Mysteries of Miami,” “Outback Oasis” and “Adventure in the Glades.”

For an outing that promises “extraordinary destinations with strange stories and history,” order the “Mysterious Gems” itinerary, which is rated 3/5 for both accessibility and pet-friendliness and 2/5 for activity level. (Note: If you wish to avoid spoilers for this particular trip, stop reading now.)

Before getting in the car, open the (optional) gift box to see what’s in store. A folder with a neatly wrapped postcard and envelope awaits, plus a handy canvas tote bag. It’s wise to read the “Before You Go” envelope, which recommends traveling within six months of receiving the package. A section on the company’s website provides timely updates.

For this particular journey, the introductory pamphlet advises packing comfortable footwear, sunscreen, a bathing suit, a beach towel and other road-trip essentials like a GPS, cell phone...