California Bear

Guess Where Trips: Make Your Next Weekend Getaway a Mystery Road Trip

Launched in the summer of 2020 when road tripping and exploring your local area were the only ways to travel, the woman-run, Ontario-based team at Guess Where Trips began piecing together road trip itineraries across the Canadian provinces and packaging them as mystery trips that spotlight hidden gems, quirky small businesses, local culture, and nature spots you never knew were there. The concept took off and Guess Where Trips now has surprise road trip itineraries available in four Canadian provinces and a growing number of U.S. states. California joined the list on February 1. 

Jessica enjoying her morning joe outdoors

The California launch was the result of several years’ worth of research by Guess Where Trips Founder Jessica Off and her small team. The 13 new California mystery trips include six leaving from the Bay Area, one from Sacramento, four from Los Angeles, and two from San Diego. “There are just so many scenic routes, hidden gems, and unique businesses scattered across the state,” Off shares. “It was a bit of a challenge putting these road trips together, but we did it and these routes make up the quintessential California day trip.”

Besides Ojai Oasis and Tastes & Trails of Malibu, most of the new California itineraries leave even the city names and other regional identifiers out, keeping titles and descriptions purposefully vague and with just enough information for you to choose your itinerary according to your tastes, adventure style, and requirements (kid-friendly, dog-friendly, accessible, etc.) alone. The rest is to be revealed when you hit the road. 

Here’s How it Works

Each itinerary is $65 (you only need to buy one per car) and includes four surprise stops, plus a “Before You Go” guide detailing all entrance fees you may encounter, what to pack for the day, what might be closed when, and driving distances between stops. You can choose your California road trip by region, season, theme, or accessibility, and if you’re still unsure you can take their trip quiz and be guided to the perfect road trip for you.

Most of the included four stops on the itinerary are free. When they aren’t, there’s always one or a few free alternatives suggested nearby that you can choose to do instead. Some itineraries even include exclusive “Guess Where” discounts and incentives at local businesses en route. Additionally, a list of recommended accommodations within the finishing area are provided, just in case you want to turn your day trip into a full-on overnight. Otherwise, each trip is designed to take about 6-8 hours to complete, which includes the driving time and time spent at each stop.

Once your trip is booked, you’ll receive a package in the mail within 4-10 business days. You can also have it delivered to your inbox in PDF format. The package includes the “Before You Go” guide as well as your four surprise stops, each sealed in its own envelope, that include maps, insider tips, fun facts, and a few nearby alternatives to swap in if anything’s closed or not what you had in mind. 

The California Trips We’ve Got Our Eyes On

Country Treasures

Escape to the country and visit tons of charming bakeries, get your steps in on easy trails, sip something tasty, and end the day in the most amazing small town. (Departs from the San Diego area)

Trip Highlights: 

  • Local wineries & breweries
  • A couple short trails
  • Try your hand at panning for gold
  • A seasonal family farm (weekends)

Colors & Wonders

This trip is full of colorful wonders – like a short hike to get your heart rate up before you relax with an afternoon beverage, support a local shop, or sip coffee & indulge in delicious baked goods. (Departs from the San Jose or San Francisco areas)

Trip Highlights: 

  • Meander below towering trees
  • A museum full of local legends and interesting theories
  • Two charming small towns
  • Photo ops at a United States record holder

Birds, Breezes & Cheese

Say cheese! This trip features a roundup of the best cheese shops and the most photo-worthy moments a road trip can have. You’ll feel the breeze in your hair as you walk down coastal trails and quaint streets. (Departs from San Francisco or Sacramento areas)

Trip Highlights:

  • Scenic coastal destinations
  • Ooey gooey cheese shops
  • A horror movie hotspot
  • Short picturesque trails
  • A winery with a view

Topanga Treetops to Beaches

Follow picturesque winding roads amongst the treetops while you shop, hike, and enjoy tasty bites. End the day meandering along the beach or sipping a glass of wine! (Departs from the Los Angeles area)

Trip Highlights:

  • The coolest photo-worthy vintage store
  • A funky lookout trail
  • Local eats at charming spots
  • A few easy trails (optional)
  • Get your toes in the sand

Share Story

Related Articles

  • Facebook
  • Twitter
  • Instragram
  • YouTube