Ontario Getaway Box

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Regular price $89

What's Inside 20 sealed surprise day trips
Adventure Length Approx. 4-6 hours each

Twenty surprise getaways across Ontario. One weekend you're settling into a cottage country town, the next you're spending a few days in Niagara wine country or slowing down in a Great Lakes beach town. Pick an envelope by mood, season or direction, reveal your itinerary, pack a bag and go.

  • $8 Flat-Rate Shipping
  • Free Shipping on Orders $100+
  • 30-Day Returns & Exchanges

Description

Inside each box, you'll find 20 sealed getaways, each designed to help you discover hidden gems, charming small towns, scenic spots, and local favourites across a state or province.

Every getaway is built around an iconic destination, with recommended stops, places to stay, and helpful details to make planning your adventure a breeze. Depending on where you're starting from, you might find a new favorite day trip close to home or the perfect excuse for a weekend away.

BONUS: Every getaway includes a QR code that unlocks an interactive map and a detailed digital itinerary, complete with recommendations and information we regularly update so you can make the most of every trip.

Product Details

  • Each box contains 20 sealed surprise getaways
  • Each getaway is planned for 1-3 days away
  • Each getaway includes 3 curated stops, plus recommendations on where to stay and what to see along the way
  • Choose your getaway based on season, mood and direction
  • Each envelope includes an overview of your getaway, plus a QR code to access additional trip details, maps and updates
  • Dimensions: 8.5 x 5.5 x 1.5"

Shipping & Returns

Buy with confidence! Return your product within 30 days.

Shipping: $8 flat rate, free on orders over $100.

Standard shipping takes 4–10 business days. Need it faster? Choose the fastest option at checkout for 2–4 business day delivery.

Exchanges: Want a different item instead? Email us at questions@guesswheretrips.com within 30 days of your order.

Read our full return policy →

Ontario Getaway Box

5.0 Physical Package

Here's How It Works

Each one shows the duration, best season to go, and a hint at the theme.

Reveal your day at a glance and scan the QR code for the full digital itinerary.

Follow your itinerary stop to stop, with maps and directions built right in.

Frequently Asked Questions

What’s the difference between the Road Trip Boxes and your Classic Surprise Road Trips?

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.

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?

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!

How long does each road trip take?

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.

Can I bring my kids or dog? Are the trips accessible?

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.

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.

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.