Guess Where Trips

Guess Where Trips offers pre-planned surprise day trips from the Orlando area. Your day is a complete surprise until you hit the road! Destinations for each road trip are slowly revealed throughout the day as you open a series of envelopes that containing directions to hidden gems, picturesque stops, charming towns, and small businesses.

Unlike tours, guidebooks and blogs, Guess Where Trips’ itineraries offer a self-guided look at the world around us in the form of a one-day road trip from home.

How does Guess Where Trips work?

1. Select your trip:

Choose your own adventure near you by visiting Each trip is $50 USD, and you only need to purchase one (not two) for your date day.

Great for the Orlando-area:

  • Old Florida Trail: Go back in time and visit old Florida. You'll visit delightful small towns, dig into local fare and have a few outdoor adventures.
  • Mysterious Gems: Truly extraordinary destinations with strange stories and history. Cemeteries abandoned ruins, historic homes and so much more await on this mysterious road trip!

More to explore closer to Miami, West Palm Beach, and Naples:

  • Treasure Coast Explorer: We've recommended our favorite hidden gems within this iconic area of Florida. Beach hopping, easy walks, charming cafes, and historic spots. This is the perfect trip for any beach-lover.
  • Mysteries of Miami: If you're into true crime and mysteries then this is the trip for you! From murder mysteries and spooky cemeteries to ghosts and the supernatural, this Miami road trip is truly full of unusual destinations.
  • Adventures in the Glades: Scenic views, unique boardwalks and funky roadside attractions can all be found when you escape to the Everglades. Just make sure you keep your eyes peeled for those pesky gators!
  • Outback Oasis: This family-friendly road trip will have you escaping the hustle and bustle of Miami. A combination of easy outdoor adventures, farm markets, and hidden gems will make the perfect day out of the city.


2. Get your package:

You'll receive a package in the mail within 7-10 business days. A digital option is also available which is instantly downloadable.

Guess Where Trips

3. Hit the road:

Open the “Before You Go” envelope to help prepare for the day, and then get out there and explore the recommended stops!

Guess Where Trips

These trips also make fantastic gifts for those that ‘have it all.’ If you’re not sure which trip to choose, they have a gift card option that allow recipients to select a trip of their choice.

Happy roadtripping!


Check out More Things to Do in Orlando