How to Select the Perfect Guess Where Trip

How to Select the Perfect Guess Where Trip

How to Select the Perfect Guess Where Trip

A step-by-step guide to picking out an unforgettable road trip with Guess Where Trips

With dozens of amazing and exciting Guess Where Trips itineraries to choose from, it can be tough to pick the perfect one for you. Worry not, we’re here to help!

Below, you will find a very thorough guide to picking out your ideal trip. We've summarized it here for those in a hurry:

  • Use your area as a starting point to help narrow down the perfect trip (search by locationTrip Map, or Quiz).
  • Select your trip based on the highlights and description that appeal most to you. Pay attention the the "Available to Depart" section to make sure you can do the trip when you'd like to, and the "How Long Will It Take" question listed in the FAQs to make sure it isn't too far (or close!) to home - we recommend a trip that will be 2-3 hours round trip driving.
  • Decide how you want it delivered: by mail (best for gifts, or if you're planning on going in the future), or emailed (best if you want to go within the next week).
  • Purchase & hit the road (after checking our Travel Updates)!
Boy looking at map outdoors

Step one: Narrow down your options by your location

There are three easy ways to find the trips in your area. You can pick your area from the "One Day Trips" menu, look at our trip map and zero in on your location, or take our quiz.

One Day Trips Menu

Here, you’ll find all our regions broken down by cities and areas. You do not need to live in the city or drive to the city to start your trip - this just serves as an easy way to find the area you live in, and see which trips can be done from home.

For example, you do not need to live in Miami or Atlanta to do a “Miami area” or “Atlanta area” trip. If you live in Pickering, Ontario, look at the “Great Toronto Area” options, etc.

Trip Map

If you prefer a visual aid, play around with our Trip Map to see icons of cars that indicate the end location of our trips. Click on the car icons to see more information about the trip.


Our quiz makes it easy to filter trips by interests - like accessible trips with breweries that are good to do in the summer near Vancouver (hi Explore the Shore and Flora, Fauna & Farms!).

Step two: Pick a trip

Once you've narrowed down the trips in your area, take a closer look at the different trip names, descriptions, and highlights. While all our trips are mysteries, we like to provide you with enough details to get an idea of the theme of the trip. From "A Drive Back in Time" to "Wine Time & Hidden Gems," we try to give you enough information to help you find the perfect trip that appeals to you most, without revealing the destinations.

On the trip page itself, you will see a lot of key information. The "Available to Depart" section is very important, as it will tell you the best days of the week and seasons to do the trip in. We make these recommendations so that you take the trip on a day where the majority of the stops will be open. Taking it on a day we don't recommend, or in a season we don't recommend, can result in a lot of closures and a poor experience.

Section of website that says "Available to depart"

If you scroll down to the bottom of the page, you'll find the FAQ section. This section is unique to each trip and covers details like driving distances from major cities, what time to leave the house, and more.

FAQ section that tells you how far trips are, round trip

If your city or town is not listed in the driving distance section, it can be for one of two reasons.

One: your city/town is close to a larger city that we have included (example: you may not see Newmarket, Ontario, but you will see Toronto).

Or, two: the trip you are looking at is not recommended for your area (because our trips are one-day road trips, we would not recommend an Edmonton trip for someone who lives in Calgary).

Live in London, ON but want a Guess Where Trip to do while you're in Ottawa? You'll want to look at the Ottawa Area trips.

Step three: Receive it by mail or email

Once you've picked out your trip, you have two options on how to receive it. Our recommendation is the mailed option, which is the default option on every trip page. You can switch "Mailed" to "PDF Instant Download" on any trip if you prefer to receive it by email. You can find the drop down box to switch between Mailed and PDF Instant Download just above the "Add to Cart" button.

The same information is available in both versions of the trip, but the mailed version is the one that comes printed and packaged.

PDF instant download on phone screen

 Emailed (PDF) Trips

The PDF version is recommended for last minute road trips. We do not recommend printing the file (it is very large, about 40-80 pages), as it is best viewed on your smartphone. The PDF trips don’t make the best gift idea, as they are just a link to the document. If you are looking for a last minute gift, we recommend purchasing a Digital Gift Card so that the recipient can choose any of our trips (the gift card covers the shipping and tax on any mailed trip).

Mailed Trips

If you choose the mailed option, you also have the choice of gift wrapping it. Our gift wrapping only costs $10. This is a beautiful way to present the trip as a gift or to treat yourself to something fun to open when the mail arrives.

Mailed trip version

Shipping times depend on where you are located and the shipping speed you choose. All our trips are printed, packaged, and shipped from our office in London, ON. Shipping is faster if you live in a large city and a little slower if you live somewhere remote. In Canada, you can expect your package to arrive in 2 to 8 business days, depending on location and shipping speed selected (free vs Xpresspost). If you’re in the States, shipping times range from 5-10 business days. Just give us 1-2 business days to package your trip before calculating the delivery time.

Step four: Hit the road

Once you've received your trip, it's time to hit the road! Remember, you only need to purchase one trip per group. If you will be taking two cars, we recommend purchasing two of the same trip so that each driver can see the stops.

One of the most important steps to starting your road trip is checking our updates page. You’ll be reminded to do this, and tempted to skip it, but we cannot stress enough the importance of this step. As we recommend small businesses, things like hours and seasonality can greatly affect operating hours. We update our booklets often before printing our next batch, but you may order a trip, and 3 days later we learn that a cafe now opens at 11am instead of 10am. This is why you need to check the updates page, where we will make note of this change. We also suggest using the itinerary within 6 months of purchase so that you have the most up to date information.

Final Thoughts

Picking the right one-day road trip can be tough, but with Guess Where Trips, it's easier than ever. Whether you're looking for a fun day out with friends or a romantic getaway, we've got you covered.

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Tags: Guides