At Guess Where Trips®, we specialize in self-guided one-day surprise road trips. Leave the stress of planning to us! We design each road trips around a general theme, so you will have an idea of what you might get up to during the day, but you won’t know where we’re sending you! We love finding new small businesses, hidden gems, cute cafes, and picturesque towns. 

Need us to take even more stress off of the planning and help you choose a trip? 

Fill out our quiz here to help you decide on a trip!

Our road trips are intended to be surprises, but there are a few ways to get a better idea of where you'll be going:

1. Check out our Trip Map! This allows you to see the general area of where each trip ends. 

2. Frequently Asked Questions: Each trip has its own set of frequently asked questions. These are located bottom of the specific trip page. Please read this section for a list of approximate round-trip driving distances from nearby cities. 

3. Ask us! We're always here to help with any questions you might have. Start a chat with us or send us an email with your departure area and travel interests, and we'll send you our trip recommendations.

Mailed Trip: This is most popular option. With a mailed trip, you will receive 5 sealed envelopes including 4 well-curated 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.

PDF Trip: These are great for road trippers who don’t want to wait for their package in the mail. Our 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.

Note: There are no surprise envelopes with the PDF option. All of the stops are in one digital file, so scrolling through the document will reveal the surprise stops.

Your road trip includes a well-curated itinerary for the day with a focus on small businesses, cute shops, hidden gems, and unique locations.

What's not included: Food, drinks, gas, and admission (if there is a fee!) are not included in the price of our trips.

Surprise! Nothing needs to be booked with us!

We have designed our itineraries to be flexible in regard when you take your road trip. Since they are self-guided trips, you can decide which day works best for you and your travel mates. You just need to follow what season and days of the week we recommend in the Before you Go booklet! Otherwise, most of our trips do not require any type of booking unless specified in the Before You Go booklet (some farm visits or national parks require advanced bookings).

If all road trippers are taking the road trip together, you only need to purchase one trip.

Our road trips are designed to be one day trips. Each trip takes roughly 6-8 hours to complete - this includes time spent at the recommendation and driving.

In the Before You Go booklet, we will tell you what time we recommend leaving for your road trip. Keep in mind that the later you leave, the less time you may have to spend at each stop.

While our road trips are designed to be one day trips, there is always the option of turning it into an overnight getaway. Keep an eye out for your confirmation email! In it, we will send you a list of our favourite hotels in the end destination if you would like to extend your trip.

Before you head out for your surprise adventure, read the "Before you Go" booklet. This will give you all the important information about your day ahead, without spoiling the details.

Always be sure to check out our Travel Updates the day before you head out, in case there are any last-minute updates to your trip.

We recommend taking your road trip within 6 months of purchase.

You are always welcome to do your trip after 6 months of purchase, however, due to the ever changing nature of our business, we cannot guarantee that our recommendations will be up-to-date.

Unfortunately, not! Custom getaways were something fun we tested out but this year our focus is on our one day road trips (as well as some exciting new launches!)

We always send accommodation recommendations in the confirmation email in case you would like to turn your road trip into an overnight getaway.

If you're interested in doing a few trips to make it a longer getaway, send us an email at questions@guesswheretrips.com and we can suggest trips that work well to do together.

For orders over $50, we will ship your package for free via expedited mail. Our expedited option takes between 5-7 business days.

If you need your order earlier, there is an Xpresspost option for $10 USD / $12 CAD, which will take 2-5 business days.