Ontario Road Trip Boxes
Free shipping over $100
20 adventures per box
Self-guided & fully flexible
3 Products
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(7)
Road Trip Box
London Day Trip Box
20 day trips from London: Lake Huron beaches, theatre towns, and farm stands.
$65
(8)
Road Trip Box
Ontario Getaway Box
20 getaways across Ontario: cottage country, Niagara wine country, and beach towns.
$65
(6)
Road Trip Box
Toronto Day Trip Box
20 day trips from Toronto: Mennonite country, lakeside towns, and hidden trails.
$65
“From the coffee shop, to the towns locals giving us some fun history ... was amazing!”
Marlena W.
200,000+ Road Trips Sold
200,000+ Road Trips Sold
200,000+ Road Trips Sold
200,000+ Road Trips Sold
200,000+ Road Trips Sold
200,000+ Road Trips Sold
200,000+ Road Trips Sold
200,000+ Road Trips Sold
Frequently Asked Questions
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.
There is some overlap between our Day Trip Collection Boxes and our Classic Road Trips, as they explore similar regions. The amount of overlap will vary depending on which box you’re looking at and how many classic trips you’ve already completed in that area.
That said, each box contains 20 cards with a variety of stops to explore, so even if you’ve done a number of our classic trips, there will still be new destinations, travel tips, and more to discover; it’s a whole new experience!
If you’ve already completed several of our Classic Road Trips and aren’t sure which box is the best fit for you, feel free to reach out to us directly, we’re happy to help point you in the right direction!
How much of the trip is a surprise?
As much as you want it to be! Before opening an adventure, we'll give you just enough information to help you choose — including the general direction, best season and a few other helpful details. Once you've chosen, unseal the envelope to reveal where you're going and what you'll be doing along the way. You can look at this in advance or open it the morning of.
Where do I start and how do I find driving directions?
Each adventure will tell you where to begin and guide you from there. You'll also find a QR code inside your envelope that takes you to your digital itinerary and interactive map, making it easy to navigate between stops throughout the day.
Are there additional costs during the trip?
How long does each road trip take?
Can I bring my kids or dog? Are the trips accessible?
Customer reviews
55 reviews5 4 3 2 1 Write a reviewLatestOldestHighest ratedLowest ratedMost helpfulAll1 star2 stars3 stars4 stars5 starsKelly GVerified buyer14 days agoSo fun!!!We struggle to find things to do on the weekends. These are perfect and well thought out!!Response from Guess Where Trips®Thank you so much for leaving a review! :) We can't wait to hear about all of your adventures around Toronto! Would recommendHelpfulH E15 days agoWell-designed and lots of...Well-designed and lots of trips to choose from - the map card makes it easy to see where all fo the trips take place. Very giftable!Response from Guess Where Trips®Thank you so much for leaving a review! Would recommendHelpfulUri W28 days agoThe Gift That Keeps On Givinnnn!The gift that keeps on giving! My wife and I were celebrating an anniversary, long weekend and birthday in 3 succeeding weeks, and, this was a PERFECT way to spend our time and make memories together! We left from Vaughan and the day trips were perfect. Amazing photos, long lasting memories and an adventure we didn't expect.
THANKS Guess Where Trips!!Response from Guess Where Trips®Awww we love this so much! Thank you for making Guess Where Trips part of your special celebrations :) We're so glad that you are enjoying your Toronto Day Trip Box - be sure to tag us in your adventures @guesswheretrips! Would recommendHelpfulB28 days agoI live in Kitchener...I live in Kitchener and reached out to ask which box I should buy - they said both London and Toronto would work great, they did say London would be better but I decided to get both! I can't wait to use them!Response from Guess Where Trips®The KW area definitely works for both boxes, we're glad you're going to try them both out! Be sure to tag us in all of your adventures! Would recommendHelpfulJessica O28 days agoExactly what we needed!We live near Toronto and are always saying we should explore more. I love having a collection of day trips ready to go instead of spending forever looking up ideas.Response from Guess Where Trips®Thank you so much for leaving a review! We're so glad you're loving our new Toronto Day Trip Box - be sure to tag us in all of your adventures! Would recommendHelpfulReviewed on
What People Love About Our Road Trip Boxes
Rated 4.9/5.0 stars
A perfect little gift for travelers
The itineraries are thoughtfully curated, well-planned, and so convenient to follow. It’s such a fun way to discover hidden gems and experience a city in a whole new way.
Mani K.
Even Locals Will Find Something New
I thought I knew the area, but it took me to places I'd never heard of, even in places I'd already visited! Highly recommend for fun weekend plans.
Sofia M.
The presentation is great
The variety of trips is amazing and the little hint on the outside of each envelope makes choosing each adventure a perfect match for mood that day.
Cheryl L.
A perfect little gift for travelers
The itineraries are thoughtfully curated, well-planned, and so convenient to follow. It’s such a fun way to discover hidden gems and experience a city in a whole new way.
Mani K.
Even Locals Will Find Something New
I thought I knew the area, but it took me to places I'd never heard of, even in places I'd already visited! Highly recommend for fun weekend plans.
Sofia M.
The presentation is great
The variety of trips is amazing and the little hint on the outside of each envelope makes choosing each adventure a perfect match for mood that day.
Cheryl L.
A perfect little gift for travelers
The itineraries are thoughtfully curated, well-planned, and so convenient to follow. It’s such a fun way to discover hidden gems and experience a city in a whole new way.
Mani K.
Even Locals Will Find Something New
I thought I knew the area, but it took me to places I'd never heard of, even in places I'd already visited! Highly recommend for fun weekend plans.
Sofia M.
The presentation is great
The variety of trips is amazing and the little hint on the outside of each envelope makes choosing each adventure a perfect match for mood that day.
Cheryl L.
Road Tested by Our Team
Our team spends 40+ hours researching, driving, and vetting every route: talking to locals, discovering hidden gems, and making sure every stop is worth your day.
More Experiences You'll Love
2,328 verified reviews
See Where Our Road Trips Took Them
"Would you try a surprise day trip?"
“Each box is curated and packed with local intel."
"I love that I can just grab and envelope and we have the entire day planned.”
“None of them tell you where you're going, just when to open it!”
"Would you try a surprise day trip?"
“Each box is curated and packed with local intel."
"I love that I can just grab and envelope and we have the entire day planned.”
“None of them tell you where you're going, just when to open it!”
"Would you try a surprise day trip?"
“Each box is curated and packed with local intel."
"I love that I can just grab and envelope and we have the entire day planned.”
“None of them tell you where you're going, just when to open it!”
We Remember Experiences, Not Things.
Research consistently shows that spending time together creates more lasting happiness than buying more stuff. Every Guess Where Trip is thoughtfully planned to help you reconnect, explore, and create memories that last long after the day is over.
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As much as you want it to be! Before opening an adventure, we'll give you just enough information to help you choose — including the general direction, best season and a few other helpful details. Once you've chosen, unseal the envelope to reveal where you're going and what you'll be doing along the way. You can look at this in advance or open it the morning of.
Each adventure will tell you where to begin and guide you from there. You'll also find a QR code inside your envelope that takes you to your digital itinerary and interactive map, making it easy to navigate between stops throughout the day.
Yes. The cost of food, gas, accommodations, admission fees and any optional activities along the way are not included with your Road Trip Box. We try to provide as many options at each stop with a mix of free and paid recommendations so it can fit any budget!
Our Day Trip Collection adventures are approximately 4–6 hours, although you're always welcome to slow things down, add extra stops and make a full day of it.
Our Getaway Collection adventures are designed as overnight escapes and can be customized depending on how long you'd like to stay and explore.
Absolutely! Just keep in mind that depending on who you’re travelling with, you may not be able to experience 100% of every trip. We include a variety of options at each stop, so there should still be plenty to choose from. We recommend using the clues on the front of each envelope to help choose an adventure that’s the best fit for your group.
Another tip? Have the driver take a quick peek at the itinerary before you head out. They can help choose the activities and stops that work best for your family without spoiling the surprise for everyone else! And remember, there’s no pressure to do everything. You can always skip a stop, choose an alternative, or save something for another adventure.
