Guess Where Trips

06/12/2024

STARTS TODAY 🚨 CODE: BOGO25

Unwrap the thrill of new destinations, hidden gems, and unforgettable memories.

‣‣ Available on Mailed Trips & Physical Gift Cards ONLY! Gift wrapping available for both.

Tip: Our Road Trip Game Packs are sold out, so gift wrapped gift cards with a tote bag have been added as an option online.

28/11/2024

REMINDER 🔔

BOGO 50% off is still on until November 30th!
Code: GET2

Buy Two, Get One FREE started today 🖤
Code: GET3

✨ available on mailed trips, mailed gift cards, and road trip gift boxes!

26/11/2024

Not to fear - We’ve still got you covered! 📦

Your orders are in safe hands as we do not use Canada Post to ship our mystery road trips.

🖤 Take advantage of our Black Friday deal this week - Buy One Get One 50% Off.

Use Code ✨GET2✨ at checkout

‣ applies to mailed road trips, mailed gift cards and road trip gift boxes. Available until November 30th.

🖤 Buy Two, Get One Free starts November 28th and runs until December 5th.

22/11/2024

Tag your friends and expose their Black Friday vibe (because we all know a Treat Yourself Ta**us or a Bargain-Savvy Scorpio)! 🛍️

👀 Find your sign and let us know - did we get it right?

DEALS START TODAY:

🖤 November 22 - 30: Buy One Get One 50% Off
🖤 CODE: GET2

Travel Tip: Check our pinned Black Friday post for a breakdown of each week’s deal. Codes for future weeks will be released when the sale starts.

21/11/2024

✨SAVE THIS POST and make holiday plans✨

Let one of our mystery road trips take you there 💌

1️⃣ STRATFORD
With its twinkling lights and cozy charm, Stratford transforms into a winter wonderland during the holiday season. Stroll along the Avon River, enjoy festive picnics with seasonal treats, and explore tree-lined streets filled with holiday cheer.
🚗 The Small Town Charm Trail

2️⃣ ELORA
Explore the scenic gorge, browse holiday markets for unique gifts, and warm up in cozy cafes. Whether you’re enjoying a riverside walk or exploring local galleries, this town is a picture-perfect winter escape.
🚗 Local Markets and Picturesque Towns

3️⃣ NIAGARA-ON-THE-LAKE
During the holidays, this “Loveliest Town in Canada” truly lives up to its name. Wander through streets adorned with festive décor, sip on mulled wine in scenic vineyards, and enjoy the cozy glow of the season.
🚗 Funky Florals & Fine Wines

4️⃣ THORNBURY
Nestled along the shores of Georgian Bay, Thornbury transforms into a holiday haven. Explore boutique shops decked out for the season, enjoy warm cider at local orchards, and take in the snowy beauty of the Thornbury Dam.
🚗 Bayside Wonders

5️⃣ PORT PERRY
With views of Lake Scugog and a friendly small-town vibe, Port Perry is the perfect spot to embrace the holiday spirit. Pop into quaint shops for one-of-a-kind gifts and enjoy festive flavours like peppermint hot chocolate or gingerbread men at cafes.
🚗 Taste of the Country

🎄

20/11/2024

SIGN UP for early access to Black Friday deals!

Click the link below and become a subscriber📲

https://guesswheretrips.com/pages/subscribe

You’ll receive an email tomorrow that lets you shop before everyone else 💥

Here’s the lowdown on our deals:

🖤 November 22 - 30: Buy One Get One 50% Off

🖤 November 28 - December 5: Buy Two, Get One Free

🖤 December 6 - 12: Buy One Get One 25% Off

19/11/2024

Save the dates! Here’s the lowdown on our Black Friday deals 🔥

Your final reminder to sign up for SMS notifiations and get access TOMORROW!

🖤 November 22 - 30: Buy One Get One 50% Off

🖤 November 28 - December 5: Buy Two, Get One Free

🖤 December 6 - 12: Buy One Get One 25% Off

Travel Tip: Whether it’s one special gift or a full sleigh, shop the week that matches your list! 🎁

12/11/2024

The perfect gift for the adventure lover in your life! 🎁

🏷 Subtle? Never heard of her. Tag someone who needs this hint!

Our one-day mystery road trips are the perfect gift. Explore hidden spots, support small businesses, and make unforgettable memories—all close to home.

Bonus: Check out our add-on ideas for that perfect finishing touch. ✨

11/11/2024

Today, we take a moment to remember and honour the incredible people who have served our countries.

Their courage and dedication have shaped the freedoms we often take for granted, and for that, we are forever thankful.

To all the veterans and those still serving – we appreciate you, today and every day ♥️

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.

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

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.

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!

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!

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.

👻