on a Whym


Whym's FAQ (frequently asked questions) about the process and how we plan you a perfect surprise vacation!

Frequently asked questions

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Getting Started

  • I'm ready to book, how soon can I leave?
    We require a minimum of one month's advance notice for a vacation.

  • I took the survey. What happens next?
    You’ll get a confirmation email from us, and then…you wait. No, we know that sounds ominious but trust us, it's fun. Nothing else is needed from you once we have your answers (and the credit card clears). Exactly 7 days before departure you'll receive a message with the 10 day forecast and a general packing guideline. 24 hours before your trip is to take place, we'll message you the time and location of your departure.

  • I'm traveling with a group - can we just all answer one questionnaire together?
    No, it's important for us to get a sense of everyone going on the trip, so we require everyone to answer their own questionnaire. Make your voice heard, sing out Louise!

  • I leave today, and I still have no idea where I'm going. Is something wrong?
    Nope, you’re right on track. You're told your point of departure and time 24 hours in advance, but the actual final destination won’t be revealed to you until about two to three hours before you leave.

  • I've already booked and I need to cancel. What now?
    We understand emergencies happen, so you have a 48 hour cancellation window for a full refund from the time of booking. After that unfortunately, there are no refunds as tickets and hotels may already be booked and underway.


  • How much does a Whym cost?
    Group trips start at $600 each for 2 nights and 3 days. Individual trips at $850 for two nights and three days. You can choose higher budgets starting there, but the minimum price increases for each additional night. Keep in mind, this budget is only for flights and hotels, so you should anticipate spending more on food, activities, transportation on the ground, and any other miscellaneous costs.

  • What’s included in my Whym reservation?
    Flights, hotels and a few surprises along the way are included in your initial package. Any transportation while there (Lyfts, subways, rental cars), meals, shopping, and attractions are additional once you arrive.

  • When do I pay?
    Once you choose your nights and budget and fill out your survey, you can head straight to checkout.

  • Is there an additional charge to travel over a holiday weekend?
    While there is no built in additional charge to travel during a holiday weekend, we recommend going up at least one to two price brackets or booking further in advance as often flights and hotels are significantly more expensive and rooms are more limited. A little bit more will go a long way in getting you the best possible trip.

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  • Can I go somewhere outside of the US?
    For the moment, we're only booking domestic travel within the United States of America. However, we're actively pursuing the ability to expand and will let you know as soon as we do!

  • Where are you sending me?
    What fun would it be if we told you that? That said, you’ll be traveling somewhere within the United States. We currently are not planning overseas trips, but we’ll let you know when we do!

  • Can I ask for a specific location?
    Nope - this is a total surprise. We will take your wish list into consideration, but have a little faith, we know what we're doing.

  • Is Whym a good option for solo travelers?
    Yes! The most rewarding experiences are often found on your own. We’ll put you in situations on your trip that will open you up to meeting new people or exploring a place you’ve never seen before

  • What if I’m traveling with a family? Is Whym a good option for us? How does that work?
    So many questions! You must be parents. Yes, Whym is an amazing way for families to travel together. You get all of the fun of a family getaway without the headache of having to plan anything. You show up and spend quality time together, we’ll arrange everything else. If you are traveling with kids 12 or younger, you will see a package especially for them under “Book Your Whym.” If the kids are 0-2, there is no additional cost to your trip as most airlines don’t charge for infant travelers. If they are 3-12, they have a reduced price point for their trips with a much more stripped down version of the survey so we can just collect the basic information. Please be sure to chose the package the same package for the children as chosen for the parents as far as dates & budget. Whym is a great way to make family memories without any of the work!

  • I love where you chose! (of course) What happens when I land?
    When you touch down, you'll receive a few more key details, such as where you'll be staying and how best to get there. Once you get to where you're going, you'll receive your itinerary which will lay out the rest of your trip. Within this itinerary however, you may notice a few grey squares. These are surprises - what we call Whymsies - and will remain surprises until right when it's about to go down. We want to keep you engaged and on your toes your entire trip.

  • Why should I trust you to know where I want to go?
    Well, we could try to prove ourselves via trust falls but the true answer is because we love to get it right. It’s true, the team here at Whym are competitive and live for getting the perfect trip built for the perfect person. In all seriousness, we’re a group of well traveled, anal-retentive planners who love to see the world and just want to help others do the same.

  • So tell me more about these surprises...
    We want your excitement to stay at a 10 your whole trip, so throughout the Whym, you'll have periods where you know you're going to do something but you don't know what it is exactly. We'll keep in touch with you via text messages/notifications to let you know about those "Whymsies" right when they're about to happen. These blocks are the only things on your itinerary that have hard and fast time rules - you'll be able to tell by the little clock in the corner of that area of the itinerary. Trust us, you'll love 'em.

  • I have free time on my itinerary but no idea how to spend it - what now?
    We want to give you time to explore, so from time to time, you will have whole periods of time all your own. Use this time to people watch, to wander a new neighborhood, to nap. We'll provide suggestions, don't worry, but carpe diem and seize this vacation.

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  • I don't like something on my itinerary, what now?
    Look, no one is going to show up and break your kneecap if you choose to skip something on the itinerary that doesn't sound like you but we encourage you to give it a try. Sometimes the things we would never choose for ourselves are the things that are the most memorable. We've built these itineraries meticulously. One plan leading to the next, things that are musts for the city you visit or things that are well kept neighborhood secrets. Like we said, you do not have to do anything that you don't want to, but be adventurous and give it a shot, trust us.

  • There is something wrong with my flight/hotel/reservation. What now?
    If you have any sort of emergency or issue with any of the accommodations or plans, feel free to reach out to us immediately and we will work to resolve it. However, please keep in mind we are a travel planning company, so we have no control over airline delays or a room issue. We will happily be the middle man to help solve any problems that arise but our influence is not all reaching, despite what we tell ourselves.

  • I've already booked and I need to cancel. What now?
    We understand emergencies happen, so you have a 48 hour cancellation window for a full refund from the time of booking. After that unfortunately, there are no refunds as tickets and hotels may already be booked and underway.

  • So wait - are you sure I can't just tell you where I want to go and you plan that?
    We promise, we're totally and completely sure.

  • I have a question that this incredibly long and detailed FAQ didn't answer - who do I contact?
    On our contact tab, you'll see all the myriad of ways to get ahold of us. Feel free to email or text or slide into those DM's, whatever is easiest for you! Please note the phone number is for texting only, phone calls will not be answered.