A ‘Before You Go’ guide with a packing list, approximate driving distances and more tips to plan for your day ahead.
A series of four envelopes that will make up your day’s itinerary with recommended roadside stops along the way.
Exclusive 'Guess Where' discounts and incentives at select businesses.
Restaurant, attractions and activity recommendations based on your trip style.
Mailed version: includes 5 printed booklets (a Before You Go and 4 surprise stops) and shipping
What's Not Included:
Transportation and gas.
Entrances and parking fees for some of recommended attractions (the majority of stops are free).
Food, beverages and gratuities.
PDF version: does not include printed booklets, itinerary is emailed
How it Works
What is Guess Where Trips?
At Guess Where Trips, we specialize in self-guided one-day surprise road trips. Leave the stress of planning to us! We design each road trips around a general theme, so you will have an idea of what you might get up to during the day, but you won’t know where we’re sending you! We love finding new small businesses, hidden gems, cute cafes, and picturesque towns.
Need us to take even more stress off of the planning and help you choose a trip?
Fill out our quiz here to help you decide on a trip!
How do I know where I'm going?
Our road trips are intended to be surprises, but there are a few ways to get a better idea of where you'll be going:
1. Check out our Trip Map! This allows you to see the general area of where each trip ends.
2. Frequently Asked Questions: Each trip has its own set of frequently asked questions. These are located bottom of the specific trip page. Please read this section for a list of approximate round-trip driving distances from nearby cities.
3. Ask us! We're always here to help with any questions you might have. Start a chat with us or send us an email with your departure area and travel interests, and we'll send you our trip recommendations.
What is the difference between a mailed trip and a PDF trip?
Mailed Trip: This is most popular option. With a mailed trip, you will receive 5 sealed envelopes including 4 well-curated surprise stop envelopes and a “Before You Go” envelope which will give you just the right amount of details, without ruining the surprise stops. On the day of your road trip, your surprise stops will be revealed to you as you open each envelope.
PDF Trip: These are great for road trippers who don’t want to wait for their package in the mail. Our PDF trips are the same road trip as the mailed option just in a digital format. Once you purchase a PDF trip, you will receive an email with a link to download your trip.
Note: There are no surprise envelopes with the PDF option. All of the stops are in one digital file, so scrolling through the document will reveal the surprise stops.
What is included in my package?
Your road trip includes a well-curated itinerary for the day with a focus on small businesses, cute shops, hidden gems, and unique locations.
What's not included: Food, drinks, gas, and admission (if there is a fee!) are not included in the price of our trips.
How do I book my road trip?
Surprise! Nothing needs to be booked with us!
We have designed our itineraries to be flexible in regard when you take your road trip. Since they are self-guided trips, you can decide which day works best for you and your travel mates. You just need to follow what season and days of the week we recommend in the Before you Go booklet! Otherwise, most of our trips do not require any type of booking unless specified in the Before You Go booklet (some farm visits or national parks require advanced bookings).
I’m travelling with a group of people. Does each person in our group need to purchase a trip?
If all road trippers are taking the road trip together, you only need to purchase one trip.
How long are your road trips?
Our road trips are designed to be one day trips. Each trip takes roughly 6-8 hours to complete - this includes time spent at the recommendation and driving.
In the Before You Go booklet, we will tell you what time we recommend leaving for your road trip. Keep in mind that the later you leave, the less time you may have to spend at each stop.
Do you have any overnight trips?
While our road trips are designed to be one day trips, there is always the option of turning it into an overnight getaway. Keep an eye out for your confirmation email! In it, we will send you a list of our favourite hotels in the end destination if you would like to extend your trip.
How do I prepare for my road trip?
Before you head out for your surprise adventure, read the "Before you Go" booklet. This will give you all the important information about your day ahead, without spoiling the details.
Always be sure to check out our Travel Updates the day before you head out, in case there are any last-minute updates to your trip.
Do your road trips expire?
We recommend taking your road trip within 6 months of purchase.
You are always welcome to do your trip after 6 months of purchase, however, due to the ever changing nature of our business, we cannot guarantee that our recommendations will be up-to-date.
Do you plan custom road trips?
Unfortunately, not! Custom getaways were something fun we tested out but this year our focus is on our one day road trips (as well as some exciting new launches!)
We always send accommodation recommendations in the confirmation email in case you would like to turn your road trip into an overnight getaway.
If you're interested in doing a few trips to make it a longer getaway, send us an email at email@example.com and we can suggest trips that work well to do together.
How much are shipping costs?
For orders over $50, we will ship your package for free via expedited mail. Our expedited option takes between 5-7 business days.
If you need your order earlier, there is an Xpresspost option for $10 USD / $12 CAD, which will take 2-5 business days.
Choosing a Road Trip
Help! I don't know what trip to choose.
We get it! It can be difficult to choose from our many road trips. We're here to help!
Here are some ways to help you decide on a trip:
1. Browse our trips under the "One Day Trip" section. Here, you can select trips by region. Read the Trip Highlights section to give you an overview of the trip!
2. If you know the area you'd like to road trip to, check out our Trip Map! This gives you the general area of where each trip ends.
3. If you know what activities you'd like to do, but don't know which trip to choose, fill out our quiz. Our quiz allows you to filter trips by activites, seasons, and general locations.
4. Email us! We love helping road trippers choose a trip. Send us an email with your starting location, your interests (wineries, breweries, trails, cafes, markets, animals etc), what time of year you'd like to take your road trip, and if you're travelling with kids or someone with low mobility (the more specific, the better so we can help you pick the best trip for you!).
Do I have to take my road trip on the weekend?
Most of our road trips are best taken on weekends because we work with small businesses and their hours are better on weekends. However, we do have a selection of trips that can be done throughout the week.
Please keep in mind that some small businesses and recommendations may be closed on weekdays and holidays.
Are your road trips kid-friendly?
Yes! Almost all of our trips are kid-friendly. Click here for our kid-friendly trips. (This will show you all of our kid-friendly trips both in Canada and the US). We recommend choosing trips shorter in driving distance to ensure it’s a pleasant drive for everyone. Even on our trips with adult activities (breweries and wineries), we usually recommend alternative options.
Are your road trips dog-friendly?
Many of our trips are dog-friendly! Click here for our dog-friendly trips (This will show you all of our dog-friendly trips both in Canada and the US). The trip page itself will let you know if it is okay to bring your pup or not. To find this information, go to the page of the trip you're interested in and scroll down to the faqs at the bottom of the page.
Note: Most restaurants and stores do not allow dogs inside, so most of your day will be spent outdoors if you bring a furry friend along.
Are your road trips accessible for people with lower mobility?
Yes! We have a variety of trips that are wheelchair accessible and good for people lower mobility. Click here to browse our wheelchair accessible trips. (This will show you all of our wheelchair accessible trips, both in Canada and the US).
Do you accommodate food allergies and preferences?
We understand how important it is to find food you can enjoy. Unfortunately, due to changing menus, we cannot guarantee that any establishment on our road trips will have a certain type of food. With food sensitivities, preferences and allergies, we always suggest that our travellers pack snacks just in case. You can never have too many snacks 😊
Gifting a Road Trip
Help! I want to gift a trip to someone.
Can’t find the perfect gift? Our road trips, road trip gift boxes, and gift cards make the perfect gift for every occasion!
We have 3 gifting options:
1. Choose a specific trip for the recipient. This option is $65 + tax (or $39 for the PDF). If you would like to add a gift box with a note, you can find it under the "Merch & Gift Cards" menu. In the mail, the recipient will receive a gift box, with the physical trip inside of it (5 envelopes - 4 surprise stops and 1 Before you Go envelope). Note: We cannot gift wrap PDF trips.
2. A gift card: A gift card is a great option that allows the recipient to pick out their own road trip. We offer two gift card options: a mailed gift card (sent in the mail) or digital gift card (sent immediately to the recipient's email address). We can also add a gift box with a note to a mailed gift card.
3. A Road Trip Gift Box: Our Road Trip Gift Box comes with gift card ($74 value) and a tote bag ($8 value) beautifully wrapped. The gift card is fully redeemable for any of our mailed trips. This option is great if you would like to let the recipient select their own trip from our website. Once they redeem their gift card, they will receive the 5 envelopes (4 surprise stops and 1 Before you Go envelope) in the mail.
What does the gift card cover?
Our gift cards cover the cost of any mailed trip including taxes and shipping. If you use a gift card to purchase a PDF trip, you will have money remaining on the card.
Why is the cost of the gift card more than the trip?
Our gift cards cover the cost of any mailed trip including taxes and shipping. The person you are gifting it to will not have to pay anything additionally when they redeem their gift card.
Can I send the gift card or trip directly to the person I'm gifting it to?
Absolutely! At checkout, be sure to put the recipient's address (or email address for digital trips) as the shipping address.
I accidentally sent the digital gift card to my email address. How do I send it to the recipient?
This happens frequently! No problem - You can just forward the email with the gift card code to the recipient's email address!
Can I include a gift note?
Yes! If you would like to let the recipient know who the gift is from, please make sure you write a gift note in the “special order instructions” box before checkout.
Note: Gift notes can be a maximum of three sentences and can not include emojis.