Self-Guided Adventures

One Day Mystery Road Trips

Our ultimate goal is to create a memorable experience that will inspire you to try, see, and do something you've never done before. We encourage you to step out of your comfort zone and take the road!

How it Works Our Trips
AS SEEN ON

Dragons' Den

All the dragons loved our mystery road trip experiences when Guess Where Trips' founder (Jessica Off) made a memorable appearance on Dragons' Den. Discover what had the dragons hooked – take a Guess Where Trip and experience the magic for yourself!

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Road Trip Quiz

Find Your Perfect Trip

Take our quiz to find the best mystery road trip to suit your location and interests!

Take the Quiz

AS SEEN ON

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  • The Globe and Mail Logo
step-by-step

So, How Does it Work?

Our itineraries include a 'Before You Go' package and four surprise stops. Each stop is packed with a new destination, specific recommendations, maps, travel tips and fun facts.

1

Select your trip.

Choose a day trip based on your location and interests, or take our quiz to narrow down options.

2

Get your package.

Choose between a beautifully crafted package by mail or a PDF version sent to your inbox.

3

Hit the road!

Each package includes a 'Before You Go' booklet with essential information that won't spoil your surprise destinations.

View All Trips Check our FAQs page

What Will You Get?

All mailed trips are $65
What's included
  • A handy before-you-go guide
  • Four surprise booklets with curated travel recommendations
  • Shipping is included
  • Optional: Gift wrapping with a tote bag for an additional $15
DELIVERY

Receive your trip in the mail within 2-6 business days.

Choose Your Trip
All digital trips are $39
What's included
  • Digital version of the itinerary
  • A convenient document that can be viewed on your phone
  • No delivery fees
DELIVERY

Received immediately via email after payment

Choose Your Trip
All gift cards are $74
What's included
  • All gift cards cover the the full price of a mailed road trip as well as taxes and shipping
  • Upgrade to a Road Trip Gift Box to receive the gift card gift wrapped with a tote bag and game pack
DELIVERY

Choose between a digital road trip where the recipient can receive the gift card immediately, or a mailed gift card.

Choose Your Trip

Popular Departure Cities

Greater Toronto Area
Greater Toronto Area
New York Area
New York Area
Chicago Area
Chicago Area
Los Angeles Area 
Los Angeles Area 
Miami Area
Miami Area

Choose Your Day Trip Starting Location

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Our Trip Map

Our interactive map allows you to search for a trip's ending destination. Simply type in your city or address to see the closest trips to you.

Guess Where Trips Envelopes and Folders
Woman Opening Guess Where Trips Envelope

CAN'T DECIDE?

Take our road trip quiz!

Enter your departing address, select your interests, and preferred driving duration to find the best trip for you.

Take Our Quiz
Product shot of Guess Where Trip box

Why day trips make a great gift

Perfect for the avid adventurer or the person who has it all, let them choose their own path with the help of Guess Where Trips. With each envelope comes a new exciting destination and locale to explore with none of the long hours of planning.

Let customers speak for us

from 1363 reviews

Markets to Mountains

Jessica Law
Markets to Mountains
Muskoka Meandering

My husband and I got this as a Christmas gift. We used it last weekend and it was an absolute blast! The bakery was definitely a highlight, the donuts were the best ! So many beautiful hikes! Lunch was absolutely delicious. We can’t wait to order another Guess Where Trip! 😊

BB
Guess Where Trips®
A Lovely way To spend the Day

Revisited some familiar spots, and discovered a few we didn't know existed. This was a nice excursion for my husband and myself. There was a nice variety to our stops, not just shopping. Plenty of outdoor beauty to enjoy.

kelly mclean
Local Markets and Picturesque Towns
Sweet & scenic

We had a great time on our Trip. Directions and Instructions were well planned and written. Bonus was getting some discounts at some of the stops when we told them we were doing the Trip. Didn't get to do everything based on the weather the day of our trip but we have the places and can go back another time when the weather is better.

Christina
Guess Where Trips®
Amazing way to spend time as a family

Today we did the chasing waterfalls adventure to celebrate my husband and my 3rd wedding anniversary and it did not disappoint. We have a 17 month old and day to day can be exhausting, especially what to cook for dinner and what activities to do for the day. So this having everything planned for us was a dream. We took our little one with us in a hiking carrier and also brought the furry family member along too. Can honestly say that today was one for the books, we had so much fun and made some great memories as a family. Can’t wait to try another one.

Natasha
Chasing Waterfalls
Great first adventure

This was a Christmas present, we decided to try this adventure! The stops and choices we had were a pleasant experience, the host and people we met on the way were amazing Thank you!

Anonymous
Quirky Adventures
Fantastic views and lots of fun

We really enjoyed our trip and would highly recommend it.

N.F.
Down by the Bay
Nice day trip

I really enjoy using these trips wtih out of town guest. They take the planning off the shoulders of the host and guest are on board. I enjoyed Quirky Delights, the only thing I would update is the quirky art portion and Bynum Bridge, a little unsafe feeling in area. I did see areas I had no idea about win/win for everyone.

Kathy Roberge
Quirky Delights

Wonderful scenic areas and quaint small towns. Lovely day!

Anonymous
The Whimsical Route
So much fun!

We had a great time getting away for the day for our anniversary. One thing to be aware of is one of the locations at the 3rd stop is temporarily closed and one of the locations at the second stop has changed owners and is now just a restaurant, not really a market anymore. Despite these small hiccups we had an amazing day and can't wait to try another trip soon!

A.M.
The Small Town Charm Trail

Love this company.

Andrew
Spooky Sights & Ghostly Tales
Great Fun!

This trip was so much fun! Lots of laughs and great sights and places to sip some cold beer!

Jenna Elliott
An Adventure is Brewing
Great day

This was incredible. I loved every second! Would def do another trip.

Kathy Iwanicki
Hudson River Hideaways
Great Day!

Got this trip as a gift for my mom for Mother's Day and it was the perfect way to celebrate. We have made this an annual tradition!

Holly Thompson
Taste of the Country
Meandering Marvels

What a great day, excellent stops for short walks with big viewing rewards. Wasn’t keen on one recommended food stop but left a suitable review there. Will most definitely recommend Guess Where Trips to all friends and family.

H.W.
Muskoka Meandering

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