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

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 charger, wallet and a full tank of gas. Leaving no stone unturned, Guess Where Trips even provides a playlist with modern-day hits and classics from Fleetwood Mac, Tom Petty, Billy Joel and The Beatles.

Stop 1: Haunted History

It’s recommended to depart between 9-9:30 a.m. for the first stop of the “Mysterious Gems” trip, DeLand in Volusia County. The town was founded in 1876 by Henry Addison DeLand, who envisioned building a citrus, agricultural and tourism hub.

Modern-day visitors can see well-preserved historic buildings on and around Main Street, some of which may be haunted. According to Guess Where Trips, the 1927 historic hotel now called the Artisan Inn may be the most haunted hotel in the state where a medium claimed to find 13 ghosts.

Other stops are steeped in history and folklore, including Stetson University, the Athens Theater, the Stetson Mansion and Old DeLand Memorial Hospital.

Step back in time to a century ago when the hospital used an operating room, early X-ray machines and iron lung devices to nurse patients back to health. A museum with eight galleries and exhibits showcases the hospital’s history along with displays of World War I and World War II artifacts.

Stop 2: Searching for Spirits

On a tour of Central Florida’s mysterious destinations, it makes sense to have a stop in Cassadaga, dubbed the “Psychic Capital of the World.”

Located about half an hour from Orlando, the town feels a world away, surrounded by trees and rolling hills. Cassadaga, founded in 1875 by medium George Colby, attracts visitors from far and wide in search of healing energy, as well as those who are just curious.

Today, the Cassadaga Spiritualist Camp welcomes visitors in search of healing and deepening their understanding of spirits. Guess Where Trips lists several stops in town, including the Devil’s Chair and G. Green’s Haunted History House and Museum.

The latter contains antique dolls, movie memorabilia and exhibits about the odd and uncouth. There are no jump scares, but it’s hard to avoid the feeling of being watched.

Stop 3: Milling About

Traveling through Volusia County on the way to the Atlantic Coast, there are two stops with history and legends abound.

The first is the Cruger-dePeyster Sugar Mill Ruins, a historical site that shares the story of a 600-acre sugar plantation and mill. In 1830, Henry Cruger and William dePeyster began their operation, relying on slaves for labor. Their business was short-lived and only survived five years before Seminoles burned it to the ground in 1835.

In New Smyrna Beach, a park serves as home to the Turnbull Ruins, a site founded by Scottish physician Dr. Andrew Turnbull. In 1768, he colonized the area for England and brought with him nearly 1,500 Greeks, Corsicans, Italians and Minorcans. Still, a lot of mystery surrounds the site and former colony built on coquina rock.

Stop 4: A Beachside Retreat

After spending a day among ghosts, history and legends, the final stop of the day brings with it the opportunity to unwind, relax and dip your toes in the sand.

Canal Street and Flagler Avenue have plenty of shops and restaurants to explore before or after hitting the beach.

Guess Where Trips recommends Smyrna Dunes Park or Bethune Beach, both of which are prime places for ending the day in oceanfront bliss.

If you go

• Mailed trip: With a mailed trip, you will receive five sealed envelopes, including four surprise stop envelopes and a “Before You Go” envelope, which will give you just the right amount of details without ruining the surprise stops. On the day of your road trip, your surprise stops will be revealed to you as you open each envelope. Cost: $65 plus tax for the mailed trip.

• PDF Trip: These are great for road trippers who don’t want to wait for their package in the mail. The PDF trips are the same road trip as the mailed option, just in a digital format. Once you purchase a PDF trip, you will receive an email with a link to download your trip. Cost: $39 for the PDF. Note: There are no surprise envelopes with the PDF option. All stops are in one digital file, so scrolling through the document will reveal the surprise stops.

• For more information, visit guesswheretrips.com.

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