Q: DO you charge a fee?

All of our planning fees are included within the trip’s price. The fee includes:

  • Expert Planning:  Each trip is individually designed based on the traveller’s preferences. This is not a ‘one-size-fits-all’ type of trip.

  • Zero Stress:  We understand how many hours it takes to plan a trip and how overwhelming the experience can be. With Guess Where the only work you have to do is filling out the questionnaire…you can leave the rest to us.

  • The ‘Surprise’ Essentials: We’ll send you a cute little travel package for you to open before you leave. This has everything you need for your trip ahead.

Q: how soon SHould I book?

The sooner the better! The further out you book the more options available to you. There are simply more hotels and flights available.

For Overnight Surprise Road-Trips and Flight & Hotel Getaways: Once you submit the survey, we’ll get back to you within 24 hours to let you know if there’s something available for your selected dates. If there is, we’ll send over an invoice and confirm the trip once we receive requested payment.

Q: Can I travel on a weekday or a weekend?

Either option is possible! There will be a lot more accommodation options available over weekdays, however we understand weekends are a more convenient option for travellers. For weekday travellers, we might be able to offer upgraded accommodation options or additional inclusions (included breakfast, an added activity etc.) as we’ll have more of a budget to fit this is.

Q: Can I travel over a holiday weekend?

We highly recommend travelling over a non-holiday period if possible. Travel costs are a lot higher over holidays and accommodations aren’t as available. If you can only travel over the holidays, please book 4-5 months in advance to ensure we have enough time to find the best accommodations for your trip. There is a fee of USD $50/night to cover the costs of inflated hotels over the holidays.

Q: What happens if you send me somewhere I’ve already been?

 Good question! Before booking you’ll fill out a survey which includes a section on where you’ve been recently and the types of destinations you don’t want to be sent to. We go over every questionnaire in detail to ensure we won’t send you back to a destination you’ve already been to.

Q: What if I know exactly where I want to go?

We can certainly still work with you to arrange a ‘non-surprise’ trip. This is common with families, and special occasions (engagements, honeymoons etc.) if one person wants to know the details while leaving the rest of the travel party surprised. When filling out a questionnaire please note this in the comments section.

Q: Can I bring my pet with me?

We unfortunately cannot accommodate this for our Flight & Hotel Getaways. However, our Road-Trips and One Day Roadtrips can accommodate pets for an additional price. This price depends on the accommodations’ pet fee which can vary from $10-$50/night. This fee is payable upon checking in at the hotel. We recommend leaving your pets at home as requiring ‘pet friendly’ accommodations significantly limits the options available for us to book.


Q:For Flight & Hotel getaways, Does the price include transportation to & from the airport?

No…with delayed or cancelled flights, airport transportation can be really tough to arrange in advance. We will provide you with recommended options in your trip details so you can decide how you would like to be transferred.

Q:What if something goes wrong while I'm away?

We don’t anticipate anything going wrong…but if it does we’re here for you. Our team is available 24/7 via email, phone or text. We’ll provide you with these emergency numbers in your booking confirmation.

Q: What happens if I need to Cancel?

Please let us know as soon as possible if you cannot make the trip. Each trip is cancelled and refunded on a case-by-case basis. For flights, you most likely won’t get all of your money back. Hotels can be a little more lenient depending on their policies. Guess Where also charges a $45 cancellation fee. Once our One Day Surprise Trips are sent, they are non-refundable.

Q:What if my envelope gets lost in the mail?

We send out our surprise packages in enough time for it to get to your address. If it hasn’t shown up within 3-4 days of departing, please let us know and we’ll send you over the information via email as soon as possible.