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Guess Where Trips We create one day, self-guided, surprise road-trips in Canada and the United States.
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📌 SAVE THIS POST ⁣These are the best road trips to help you soak up all the festive vibes—think twinkling lights, cozy t...
06/11/2024

📌 SAVE THIS POST ⁣

These are the best road trips to help you soak up all the festive vibes—think twinkling lights, cozy towns, and Christmas shopping.

🎄 Swipe through for magical trips that’ll have you feeling the holiday spirit in no time.

♥️ COMMENT “FESTIVE” for a link to these trips ♥️

Travel Tip: These trips are available year-round, but are extra magical this time of year.

All Things Merry & Bright is the ultimate way to get in the holiday spirit ♥️ TORONTO AREA TRIP!✨Can be done from Novemb...
01/11/2024

All Things Merry & Bright is the ultimate way to get in the holiday spirit ♥️ TORONTO AREA TRIP!

✨Can be done from November 16th to December 22nd✨

This year there are two ways to explore the festivities:

1️⃣ Mailed self-guided road trip ($65). Digital trips are not available.

https://guesswheretrips.com/products/all-things-merry-bright?_pos=1&_psq=merr&_ss=e&_v=1.0

2️⃣ TOUR BUS! For the the first time ever we’re offering a fully guided mystery trip ($170 pp)

https://guesswheretrips.com/products/rural-routes-all-things-merry-bright?_pos=3&_psq=mystery&_ss=e&_v=1.0

Trip Highlights:
🍪 Seasonal sweet treats like gingerbread, pepper mint brownies and maple lattes.
🎄A Christmas tree farm with the cutest barn market
🎁 Artisan shops to check items off your holiday gift-giving list
💫 Optional close-by light displays for the evening

TODAY IS THE DAY!! Jess walks into the Den, but will she walk out with a deal? You’ll have to tune in to Dragons’ Den at...
31/10/2024

TODAY IS THE DAY!!

Jess walks into the Den, but will she walk out with a deal? You’ll have to tune in to Dragons’ Den at 8 pm EST on CBC to find out🐉❤️

While you wait with bated breath, read all about our founder’s experience in the blog post below!

https://guesswheretrips.com/blogs/trips/dragons-den?fbclid=PAZXh0bgNhZW0CMTEAAaYrocWPQNyjMj9LfRj2hpRaVrsWoM4VnZD-SifUqdY2J7pxdNwQdW21lZY_aem_sbFYygnYtYxQ-WQ209tUbA

The inspiration and experience of pitching to the Dragons on CBC's hit TV show Dragons' Den.

SAVE THIS POST 📌We’re visiting some of Ontario’s most festive holiday markets this year, and we can’t wait to see you th...
28/10/2024

SAVE THIS POST 📌

We’re visiting some of Ontario’s most festive holiday markets this year, and we can’t wait to see you there! 🎄✨

It’s the perfect chance to grab a Guess Where Trip for everyone on your list and support local artisans who make the season extra special. 🎁

Scroll through to see if we’re popping up at a market near you!

We faced the fire, and there’s just one week left to wait to find out if we got a deal in the Den!Tune in on October 31s...
24/10/2024

We faced the fire, and there’s just one week left to wait to find out if we got a deal in the Den!

Tune in on October 31st at 8pm EST on CBC to see what happens👀

We’re going all out with our viewing party, making it spooky, halloweeny, and dragon themed. Here’s how we’re setting the mood:

🐉 We have FIVE 10 foot inflatable dragons for the front yard. The trick-or-treaters will love it!
🍹 Dragon themed drinks made with dry ice for that special touch
🌫 Fog machine + fire light for setting the mood
✨ And of course, we’re making dragon costumes a requirement

If you have any other dragon themed party ideas, let us know!

Code Details Below ⇩ Applies to Mailed Trips, Physical Gift Cards, Road Trip Gift Boxes only! 💥Buy One, Get One 50% off ...
10/10/2024

Code Details Below ⇩

Applies to Mailed Trips, Physical Gift Cards, Road Trip Gift Boxes only!

💥Buy One, Get One 50% off
‣ Code: GET2

💥 Buy Two, Get One FREE
‣ Code: GET3

https://guesswheretrips.com

⛑️ We have created a donation button for American Red Cross. Please consider adding to your order to support those affected by the hurricanes in the U.S. All donations will be matched by .

07/10/2024

I got to spend most of last week with 9 other female owned businesses who will also be aired on Dragons Den season 19! 🐲🐉🐲

We’ve all been selected as part of first ever fellowship program, and to kick it all off they treated us to:

1️⃣ Our poster being featured at Billy Bishop Airport. Has anyone seen us yet? 👀
2️⃣ Our company being advertised at the Toronto Stock Exchange 😎
3️⃣ I was interviewed by (this will be published on YouTube soon)
4️⃣ Our group went on stage at Elevate Festival with to announce the program

I think the best part of this experience was connecting with the other female entrepreneurs and learning about their companies. Can’t wait to cheer them on in the den this season! ⬇️⬇️⬇️

.ca

07/10/2024

Mystery road trips in Chicagoland 🚗 Would you try one of these?!

just launched SIX themed itineraries from the Chicago area and we tried the spooky one, Eerie Escapes!

✨ HOW IT WORKS ✨

1️⃣ Choose a road trip that matches your vibe—select your type, theme, and the region you want to explore.

2️⃣ You’ll get an itinerary with 4 mystery envelopes ($65). Keep them sealed until it’s time to start your journey!

3️⃣ Open an envelope at each stop to find out what’s next.

Not near Chicago?📍We have trips in Indiana, Michigan, and Ohio + other states across the U.S.

👻

📌 SAVE THIS POST If you’re looking for a spooky adventure this October! Comment a trip name and we’ll DM you the link 👻A...
04/10/2024

📌 SAVE THIS POST
If you’re looking for a spooky adventure this October!

Comment a trip name and we’ll DM you the link 👻

All haunted stories are full of eerie stories to read while exploring each destination. You could see anything from haunted buildings to spooky cemeteries!

1️⃣ HISTORIC HAUNTS
If you’re a fan of ghost stories and unusual attractions, this trip is for you! We’ve rounded up the spookiest attractions for a ‘Haunted History’ route.

2️⃣ SPOOKY SIGHTS & GHOSTLY TALES
Spooky ruins, abandoned buildings, and haunted mansions make up this ghostly road trip. Perfect for history buffs & paranormal seekers.

3️⃣ BEAUTIFULLY HAUNTED
This outdoorsy road trip is full of spooky spots set along a picturesque driving route. You’ll definitely want to read all of the haunted stories to make the most of the day! A few local eateries and trails are sprinkled throughout the day to keep your energy up while ghost hunting.

4️⃣ AN UNUSUAL ADVENTURE
This area is filled with all things unusual, spooky, and abandoned. You’ll also learn about some local legends, ghost stories and folklore throughout your day.

5️⃣ HAUNTS, HIKES & HISTORY
From haunted happenings to easy strolls and historic hot spots, this trip has a little bit of everything for everyone!

6️⃣ EERIE ESCAPES
Step into a day where every stop sends a shiver down your spine. Ghostly whispers in cemeteries, abandoned ruins, and wooded trails full of chilling stories will leave you wondering if any spirits followed you home.

7️⃣ OFFBEAT ODDITIES
Historic homes with peculiar stories, off-the- beaten-path eateries, and funky trails & ruins will keep you on your toes throughout the day.

01/10/2024

We got a request, and we delivered ✅

Did you know that we can add a note to any gift wrapping purchase? Like an old school tweet, please keep it under 150 characters. Or, if you’d prefer, Short n’ Sweet like Sabrina Carpenter🫶🏻

What cartoon should we have Marilu try next? Honestly so impressed with her skills!

✔️

01/10/2024

Guess Where we’re launching next 🇺🇸

Syd and Hannah are busy exploring a new state for our launch in November! Can you guess where by the clues below??

CLUES:

🩵 The bluebonnet is the state flower
👩🏼‍🚀 Home of the NASA training center
🥤 Dr. Pepper was invented here in the 1880s
📸 You can snap a photo of the world’s largest pecan.

05/09/2024

What's on your fall bucket list this year? Tell us in the comments!

Whether you’re strolling through a charming small town, hiking a scenic trail, or discovering hidden gems along the backroads, there’s something about this time of year that makes everything feel like an adventure.

🍂 TORONTO: Vistas & Caves
🚗 LONDON: Bridges to Beaches
🍺 OTTAWA: Quintessential Québec

Special thanks to .travels & for the video clips of Vistas & Caves and Quintessential Québec ♡

Who’s up for a surprise road trip? 🚗We’re here to help you discover one-day SURPRISE road trips across Canada and the US...
28/08/2024

Who’s up for a surprise road trip? 🚗

We’re here to help you discover one-day SURPRISE road trips across Canada and the USA. Whether you’re craving picturesque views, hidden gems, animal encounters, outdoor adventures, or even a dash of haunted history, we’ve got a trip just for you!

Here’s how it works:

Pick your vibe: Choose a theme and departure city from our website. We’ve got everything from stunning attractions to quirky stops.

Get ready: Your trip includes four sealed surprise envelopes and a ‘Before You Go’ package.

Hit the road: Each envelope reveals a secret stop, complete with maps, route suggestions, fun facts, exclusive perks, and travel tips.

Our trips are self-guided, flexible, and ready when you are. Most of the stops are free or cost just a little. Grab a digital PDF instantly or have a physical version delivered to your door in our cute packaging.

Planning a group adventure? You only need one itinerary for the whole crew, but if you’re splitting up in different cars, we recommend getting one for each vehicle.

🎁 Pro tip: These road trips make awesome gifts for weddings, birthdays, anniversaries, or just because.

Check out our website at guesswheretrips.com or hit the link in our bio for more info!

19/08/2024

20% off PDFs for National Photography Day!

If you’re the friend that likes to capture everything, we’re giving you a chance to take way more pictures! 📸

Our digital trips are on sale from August 19th - 23rd! Use PHOTO20 at checkout to get 20% off your purchase.

Code: PHOTO20 🤳🏻

*this discount applies to pdf trips only and cannot be used on any other product on our website.

Did you know we test every surprise road trip when we launch in a new State? Since November 2023 we’ve been in 17 states...
16/08/2024

Did you know we test every surprise road trip when we launch in a new State?

Since November 2023 we’ve been in 17 states making sure our itineraries are the best that they can be.

BUT, things don’t always go to plan:

✨ Sometimes we find that certain stops aren’t as incredible as they seem when we’re first researching.

✨ Sometimes the drive isn’t all that great so we have to find a new picturesque route to get from A-B.

✨ Sometimes Jess brings her kids and the day turns to chaos.

✨ Sometimes Sydney thinks she can beat a giant thunderstorm, only to get caught in the rain and absolutely eat it (see last photo).

BUT we wouldn’t change it for the world! It fuels our sense of adventure and in turn, allows our wonderful travellers to have the best possible time 💛

Guess Where we’re launching next 👀This city’s name is derived from the Algonquin word meaning “onion field.” The land be...
15/08/2024

Guess Where we’re launching next 👀

This city’s name is derived from the Algonquin word meaning “onion field.” The land below all of the architecturally striking buildings was originally very marshy - the perfect environment for growing the tear-inducing vegetable. 🧅

✨SAVE THE DATE ⇨ September 12th✨

NAME THAT MOVIE 🎬 All of these filming locations can be found on one of our surprise road trips in the U.S. Can you gues...
12/08/2024

NAME THAT MOVIE 🎬

All of these filming locations can be found on one of our surprise road trips in the U.S. Can you guess all 5?? 👇🏻

1️⃣ Laurie and Amy reconnect following a tragic moment in this 2019 book to move adaptation.

‣ On: Scenic Sights & Tasty Bites

2️⃣ Luckily you can't go inside or you may have just gotten stuck in some b**b traps left behind by Kevin.

‣ On: 👀

3️⃣ The oceanfront residence of Maverick's love interest, Charlie.

‣ On: Coffee, Canyons, and Coastlines

4️⃣ Melanie walks down the aisle...well, halfway...to her fiance Andrew.

‣ On: A Drive Back in Time

5️⃣ Three doomed documentary students interview locals about a town legend while recording their own shots at the cemetery.

‣ On: Winding Roads & Historic Gems

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