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Our Frequently Asked Questions page holds many of the answers you're looking for. For everything else, we're here to help!

before emailing...

The answer to your question might be here:

What is different about the new Road Trip Boxes?

Our Classic Day Trips are a full day with 4 stops, and they keep the mystery going all day long. You'll open a new envelope at each stop, so every reveal is a surprise.

Our new Day Trip & Getaway Boxes flip that: open one of the 20 sealed cards and your whole itinerary is revealed at once. You get a little mystery up front, then a fully mapped-out itinerary, which is great if you'd rather plan ahead than wing it stop by stop.

Redeeming a Gift Card?

In order to redeem a gift card, you must click CHECKOUT.

On the checkout page, you can enter your 16-digit code in the 'Discount or Gift Card' field. On mobile, this can be found by tapping 'Apply Discount.'

More information about redeeming a gift card can be found here.

Shipping and Local Pick Up

Shipping:

Free on orders over $100

Shipping times:

4-10 business days with free shipping
Option to select 2-6 business days for a small fee.

We have a store at 100 Kellogg Lane in London, ON where you can choose to pick your order up - simply pick "Local Pick Up" at checkout and we will email you when it is ready.

Travel Updates

For Classic Road Trips:

Check Travel Updates the morning of your road trip.

  • If your road trip isn't listed, we don't have any updates to report.
  • If we mention "other options/recommendations," you'll find those listed in your trip, no need to reach out for them.

Your Before You Guide contains a QR code to access the digital version of your road trip. This, coupled with our Travel Updates, will give you the most up-to-date information for your day out. We recommend checking it out if you have an older road trip.

For Road Trip Boxes:

The digital itinerary (accessed by scanning the QR code) is continuously updated to hold the most current information.

Trip Recommendations

Our trip map can be used to find the perfect road trip. It can be filtered by interest, season, and more! It is also very helpful in visualizing the general area where the road trip takes place.

We highly recommend our new Road Trip Boxes if you are looking for more options, or for gifting. Rather than picking one road trip, you're receiving 20!

Hotels

All our recommendations can be found here.

Contact Us

Founder Jessica Off standing in front of the Guess Where Trips store at 100 Kellogg Lane

Come see us!

Have you heard? We opened our very first store - and we can’t wait to welcome you!

Stop by to shop our local trips in person, browse fun road trip accessories from a variety of great brands, and chat with our friendly travel experts to help find your perfect trip or gift!

Find us upstairs at 100 Kellogg Lane in London, right across from Starbucks.

Store hours: Wednesday to Saturday, 10am-6pm