+ What exactly is SkipTown?

SkipTown is a travel agency licensed to sell travel in all 50 states. We specialize in booking accomodations + transportation for short getaways with a twist...your destination is a surprise until the day of departure!

+ Where are you sending me?

If we told you that would spoil the surprise!

Having said that, the part of the secret we can let you in on is that we send clients to a variety of places around the United States, ranging from larger urban cities to mid-size towns. A lot of what plays a role in determining your destination has to do with departure location and survey response. Typical transit times are between 2-4 hours for air and up to 6 hours for road trips.

Don't worry though- we will not send you anywhere truly remote. No matter where your SkipTown getaway takes you, there will always be more than enough fun to be had to keep you busy for your 3- or 4-day vacation!

+ How long are getaways?

Standard getaways are 2 nights / 3 days. We also offer an extended option that is 3 nights / 4 days.

+ How do I choose a budget? What’s the difference between the different options?

There are many variables that go into budget choice. The budget, along with your survey, are the major determining factors for your destination, accommodations, and your method of transportation. Due to several different variables, we cannot say exactly what will come with each different budget level, but we can provide examples and recommendations.

Two main things to keep in mind when choosing your budget are travel dates (are you thinking of traveling over a major holiday weekend like Memorial Day?) and your departure location. If there are fewer flight/train options nearby, or you are wanting to travel over a busy weekend, we recommend choosing a higher budget ($800+/person). Some things are just out of SkipTown’s hands!

Here’s an example: Say you choose a budget of $600 per person and are flying out of Denver International Airport. It’s unlikely you would skip town to the Florida Keys and stay in an all-inclusive resort. You may however fly to Chicago…or maybe even Seattle… or possibly San Francisco…for your getaway and stay in a boutique hotel! A fun foodie tour, or other type of activity would likely be included if you’re into that sort of thing!

SkipTown would like to emphasize that no matter your budget or your getaway destination, you will not be staying in mediocre accommodations. Every aspect of your trip will be designed to fit you. A higher budget opens up more options when it comes to booking. Please do not hesitate to reach out if you need further guidance in choosing a budget option.

+ Does my budget include food + activities?

Transportation and accommodations are the only guaranteed inclusions in your budget. However, after transportation and accommodations are booked, and after charging our service fee, if there is leftover in your budget, we may use the funds to book extras, like restaurant gift cards, activities, etc. Extras are not guaranteed due to the variables mentioned in the previous question.

+ Does my budget include transportation to/from the airport? What about gas for road trips?

No, SkipTown does not include transportation to/from the airport or money for gas. Airport transfers can become messy to coordinate; some folks like to be at the airport earlier than others, flights are sometimes delayed, etc.

+ Are kids allowed to come on SkipTown getaways? What about babies?

Of course! Bring your kids! There is so much value to traveling as a family and these types of trips are some of our favorites to plan. Please be sure to mention your children when you are filling out your survey. Let us know of their ages and any specific likes/dislikes that your children have so that we can make sure to include lots of family-friendly and age-appropriate recommendations!

As far as babies…even better! If your baby is under the age of 2, they travel free! Lucky! You do not need to factor them in to your total number of travelers, but do make sure to provide their travel information, like full name and birthdate, when filling out the survey. In your survey please let us know what accommodations you need, such as a crib, extra bed, or anything else special, and we will make the requests for you.

+ Why are the solo trips more expensive than the multi-traveler options?

The long story short is that a hotel room costs the same amount whether one or two people are staying in it. After booking transportation, much of your budget is put toward booking accommodations, so in this sense traveling in groups is more cost-efficient. The price of getaways is lower if you have a travel buddy, which is why the costs for solo travelers are just a bit higher.

+ Can travelers in the same group depart from different cities?

Yes! - as long as you choose a plane/train getaway. Group travel is so fun, but also can be a challenge to coordinate when travelers are coming from different destinations. SkipTown makes this easy for you; all you need to do is indicate each traveler’s departure address and we’ll find the perfect meeting grounds for you! SkipTown makes traveling with groups simple and more enjoyable!

*Road trips must depart from the same location.

+ How far in advance do I need to book my getaway?

Sooner is always better. That way we have more time to hunt out the best deals for you. The absolute latest that you can book a trip is up to four weeks before the departure date. This is the amount of time we need to plan a personalized itinerary of recommendations for you and to make all of the reservations.

+ Can I travel over a holiday weekend?

Yes- but here are a few things to keep in mind if you are thinking of traveling over a holiday weekend:

• Choose a higher budget. Cost of travel + accommodations typically are higher during peak travel season.
• If you would like to extend your getaway since it is a holiday weekend, send us an email and we can help you set that up!
• We vote for traveling over a non-holiday weekend if you can, and here is why. Less crowds and typically lower prices. Holidays (Memorial Day, Labor Day, New Years, etc.) tend to be busier, which makes airports more crowded and overall prices higher versus non-peak travel dates. SkipTown is all about creating an experience that you will LOVE, so if you’ve got some flexibility maybe think about a non-holiday weekend.
• Don’t stress too much…no matter what your availability, you will enjoy leaving all the planning stress of a getaway up to us!

+ Do I have to travel Friday-Sunday?

No way! Getaways can leave any day of the week, just tell us what day works best for you. Trips are either 3-days / 2-nights or 4- days / 3- nights depending on the option that you choose no matter the departure date.

+ What if I know where I want to go?

SkipTown is all about mystery and surprise…so we encourage you to play along! Trust us, surprise is good for the soul. Some of the best adventures are found by chance. If you know you want to visit Portland, for example, and are not up for a little adventure of trying out somewhere else, then plan a trip to Portland! SkipTown cannot guarantee that we will send you to Portland, however.

+ What if I don’t want to go where you send me?

We certainly hope you don’t feel that way! Try to keep an open mind and to not judge a destination without giving it a chance! SkipTown truly believes that every city and town have something special to offer. With your personalized itinerary as a guide, we are sure that you will encounter a hidden gem no matter your destination…and who knows…you might even fall in love with someplace new!

+ Can I choose a weather preference for my destination?

If you are traveling during the winter months and are hoping to escape the cold, please specify that in your survey…you’re not the only one! Keeping in mind that a lot of people are hoping to warm up on a beach in the middle of January, we would recommend choosing a higher budget, and we will do our best to accommodate your requests. The same goes if you are the opposite and are wanting to embrace the cold and hit the ski slopes, for example!

Remember that even warmer locations may be chilly during the winter months and that weather is unpredictable! We’ll work our hardest to find a location that is warmer than your hometown!

+ How do I know what to pack for my trip?

One week before departure you will receive an email with the weather forecast for your SkipTown getaway! If anything changes between that time and your departure date, we will make sure to send you an update.

All getaways include a personal item and a carry on for each traveler, meaning you can bring a smaller bag, like a purse or a backpack that fits under the seat in front of you, and a bag/suitcase that is 22 inches x 14 inches x 9 inches (standard size that fits into the overhead compartment).

+ Is a checked bag included?

No, a checked bag is not included. You are more than welcome to check a bag when you arrive at the airport, however. You will be responsible for any fees, which are typically around $50-$100 per checked bag.

+ How do I receive my boarding passes?

You will receive your boarding passes the morning of departure via email. You will also receive all of your flight information that you need in your envelope. Don’t worry about checking in for your outbound flight…we’ll take care of this for you!

*Please note, you are responsible for checking in for your return flight.

+ Can I bring a pet on my getaway?

The short and sweet answer is no. As much as we love pets, they make surprise travel tricky…so they’ll have to sit this one out.

+ How does payment work when I book my getaway? Are there any hidden fees?

Once you have added your getaway to the cart, you will be prompted to take the survey. When you finish the survey, you will be taken to the payment page where you can enter your credit card information. We accept Visa (credit & debit), MasterCard (credit & debit), American Express or Discover. We understand that your trip may be months away, but because we cannot save your payment information to charge at a later date, your card will be charged immediately for the full budget amount.

The budget you select is the budget you select, meaning there are no additional fees or taxes. If you choose a budget of $600 for two people, you will pay $1,200.

Wondering if SkipTown makes any money? Yes, of course…otherwise we wouldn’t be able to offer this service! Our service fee for booking an incredible getaway on your behalf is 20%. Outside of that amount, every cent goes into your vacation.

If you are still curious how this works, or have further questions, send us a message and we would be happy to share all the reservation receipts from your getaway!

+ Can my travel buddies and I pay separately?

Unfortunately, we are not able to offer this option at this time due to our website payment system. One payment per getaway please!

+ Can you use my frequent flyer miles or hotel points?

Good question! We don’t want to ruin your surprise…so the answer is…not quite. You see, if we accepted frequent flyer miles/ hotel points you would be able to visit your account and find out where you are going. No fun! However, what you can do with the majority of airlines & hotels is add your loyalty number after your trip and still get all your points from your getaway!

+ When do I receive my envelope?

SkipTown will put your envelope in the mail one (1) week before your departure date. This means it should arrive somewhere between two (2)- four (4) days before departure. What you will receive is a USPS mailing package. It is okay to open this…the envelope itself is inside. Wait to open the sealed SkipTown envelope until the day of departure…this is the envelope that will reveal your mystery destination!

+ What about if there are travelers coming from different addresses? Then where does the envelope go?

One surprise destination envelope will be mailed to Traveler #1 from your pre-trip survey. If you have a certain traveler that you would like to receive the envelope, make sure to fill that person out as Traveler #1… especially if they are celebrating something special!

+ Can I get a refund if I need to cancel my trip?

Plans change and emergencies happen…we get that! There is a 48-hour cancellation window from the time you book your trip. Unfortunately, after that we are unable to offer refunds as it is possible that hotel and airline bookings are already taking place. See TERMS OF SERVICE for more information.

Please call or email if you believe you need to cancel your trip. Even though we are not able to offer a refund after 48-hours, maybe we can offer a date change if travel details are not entirely finalized.

+ Is a surprise getaway the right kind of trip for me?

Surprise travel is really wonderful for anyone that wants to go on a trip but does not necessarily want to participate in all the back and forth of planning, researching, and updating travel itineraries (which on average takes 5+ hours!). When considering a surprise trip, ask yourself if you would benefit from stepping out of your daily routine? Could you or someone you know stand to give their inner control-freak a little break? Would you like to make your friends envious? Do you need to recharge a romantic spark? Or perhaps steer clear of decision-paralysis? Do you want to take a trip that is out of the ordinary from the typical vacation? If you answered yes to any of those...a surprise getaway is calling your name!

If the idea of not knowing where you are traveling to until the day of departure give you any overwhelming anxiety, or stresses you out rather than excites you...well..then maybe a surprise getaway is not for you after all.

+ Still not convinced? Here are 7 reasons why you should go on a surprise getaway…

1. Step out of your usual. How often as adults are we truly treated to a surprise? I think it's safe to say hardly ever...if ever! Unless someone plans something on our behalf it is impossible! By skipping town to a mystery destination, not only are you allowing yourself to be surprised, but also you may encounter new experiences that you would have never thought of before! All you have to do is sit back and savor the excitement.

2. Recharge a romantic connection. Sharing a feeling of suprise is the ultimate connection. It has been shown that couples that partake in new activities and adventures together feel a stronger attraction toward one another, and in the long run have a happier relationship.

3. Give the inner control-freak some breathing room. We get it. You're a rock star planner. That's awesome! But...just for once give yourself a break so that you too can just sit back, relax and enjoy your vacation as much as those that you typically plan it for. PhD psychologists and authors of "Surprise: Embrace the Unpredictable and Engineer the Unexpected", Tania Luna and Leeann Renninger, wrote that “so long as we fear vulnerability, we play it safe and stop ourselves from exploring”. Let yourself be vulnerable. Set aside the plan and see what you encounter by chance.

4. Find yourself. Without all the stress that comes with planning an epic trip you create space to enjoy and have extra time to take a look at your inner self.

5. Make your friends totally envious. Have you ever seen a friend post something that made you think, "wow s/he is so adventurous and brave"? Have you ever wished that could be you? You can be brave and adventurous...and SkipTown is here to help...by sending you to a surprise location. Once your friends see your amazing photos of an incredible getaway they will be wishing they had the guts to skip town for a weekend into the unknown.

6. This or that? Steer clear of decision-paralysis. How many decisions do you have to make in a day? It's constant right?- from what to cook for dinner every night, what to wear to work, how to respond to an email at work... even down to the to what TV program to choose on Netflix. Let yourself be spoiled. SkipTown will take the decision of where to vacation off your hands. We'll make all the tough decisions for you...and you get to have all the fun!

7. Science. If none of these reasons have made you a believer in surprise getaways, well then how about science? Research on the effects of surprises on the brain tell us that, simply put, it feels good to be surprised. In fact, according to researcher Tania Luna, when we are surprised our pleasure centers in the brain are activated and flooded with dopamine. During a 2015 episode of The Takeaway, she mentions that "when we're surprised our emotions intensify up to 400 percent. If we’re surprised with something positive, we’ll feel more intense feelings of happiness or joy than we normally would have absent the surprise". It's safe to say that travel is positive, so why not combine travel and surprise!