Resort escorting

When another polar vortex freezes North America, a girl’s fancy turns to sun and fun. Or a couple of weeks skiing during what may be one of the greatest snow seasons ever. Either way, the question an escort asks is,

How can I have a great vacation and still make money?

Many escorts tour. Think of it as an escort road show: basically they travel to another city for a few days and set up shop in a hotel. They book their dates using a site like and often make very good money simply because they are the new girl in town. It’s a great idea, but why not go somewhere warm? Or somewhere you can ski? Well, why not!

by Hannah Jay

In fact, as a pure business move, spending some time in the sun or near a chairlift can make very good business sense–particularly with a little foresight and planning.

The Resort Sort

The nicer resorts around the world cater to high income patrons. No longer just about white sandy beaches or powdery ski slopes, these destinations feature designer boutiques, world-class cuisine and all the high-end amenities the rich desire.

From an escort’s perspective, a prospective client pool of thousands of well-heeled gentlemen on a vacation offers ample business opportunity. All of which can make for a fun and profitable vacation.

However, resort escorting is not for every girl. Just as the clients who spend their time and money at luxury resorts have hit a certain level, girls who want to work in those resorts have to make sure they are up to it. Resort escorting is not a volume business. Exactly the opposite, really.


Whether you want the soft Maui breezes or the miles of vertical Whistler offers, getting out of town is not a spur of the moment proposition when upscale resorts are your target vacation market. Furthermore, leaving your escort business in the lurch is no small consideration so you are going to need to plan ahead to make your trip worthwhile. Think how long you want to stay? When during the season? Those are basic questions, but even more importantly is figuring out how can you make the most money in the shortest period of time.

The calendar is important because everything from flights to hotel accommodation is priced to reflect peak seasons. Plus, you don’t want to be sitting in Sun Valley during high school spring break when the place is overrun with kids and family men.

Planning a great winter vacation should start at least two months before you want to travel. A bit of flexibility is smart as there can be great deals on airfares to one spot while the rates are terrible to another. If your objective is sun does it matter whether it is the sun in Barbados, Palm Beach or Maui? Being willing to change course can result in considerable savings.

Which is going to come in handy, of course, because you have to budget money for your flights and accommodation. Obviously you have to cover the costs of your vacation even if you don’t manage a single date. It is a bit of a risk–there are just no guarantees. Don’t structure your trip based on a prospective escort income built in–in otherwords, have the cash to cover the expenses and think of any money you do make from escorting as a bonus. Either way, enjoy the sea, the sand, or the slopes. There are benefits from a time away which don’t necessarily show up on the bottom line.

As you are selecting your destination take a look at what advertising options exist where you are planning on staying. Most resorts will be covered at so that is a great place to start. But there is more to it than just a simple ad.


The sorts of girls who do well on resort escorting already have a significant web presence. Resort escorting is not a game for beginners. If you have a good website, you’ll probably also have a blog for updates and are hooked up to social media like Facebook and Twitter as well. Your smart phone is your business partner at home and especially when you are travelling.

Once you have picked your destination and the dates of your trip, you need to try to book some dates in advance. Will you be charging the same rates at your destination as you do at home? This is a decision which can go either way. On the one hand, gentlemen on vacation tend to expect higher prices; on the other, if your rates are relatively high already, there may not be much advantage to raising them even further. Check out the going rates for the area. No matter what you decide, it makes sense to offer incentives for early booking.

Use your website and social media to make sure that you give potential clients plenty of notice as to your plans. “Going to Maui? So am I. From February 15 to March 1,” gives a prospective client the opportunity to juggle his schedule to coordinate with yours.

While you may normally only advertise in your home town, if you are traveling it makes a lot of sense to advertise in major markets. People travel from all over North America to go to beach or ski resorts. You want to find them before they have left.

A simple ad, “There’ll be more to do in Vail than ski – I’m there from…” in five or six large markets will likely give you more than a few dates. Refer them to your website and make sure you have a page or a blog post devoted to your vacation experiences. Pics of a relaxed, bikini-clad you offer a glimpse of the enticements of encounters away.

It is sensible to request a 20% booking fee by way of PayPal if a gentleman wants to see you during your vacation. And, of course, you need to use the same screening procedures for your vacation clients as you would use if you were seeing them as out of town visitors to your own city.

The major difference between resort escorting and regular work is that you actually are trying to have a bit of a vacation as well, which means that you do not want to have too many dates. Much better to have one date a day for a couple of hours at a solid rate than try to do two or three. But that really does take a lot of marketing and pre-booking.

One other advantage to pre-booked appointments is that you are very unlikely to be subject to a sting by law enforcement or, frankly, to attract any serious attention at all for your pre-arranged dates.

Travel Tips

The best airline ticket is one which has been paid for by someone else. Many upper level businessmen have stupid numbers of frequent flyer miles. On some plans, these can be transferred. Check with your regulars and see if any of them happen to be frequent flyer miles heavy. What a lovely Christmas present!

Tempting as the Expedia room deals may be, you can often get the same deal from the hotel direct if you ask. The advantage to booking through the hotel is that hotels actually actively hate people who book through online discounters and you are likely to get a room with a view of the dumpster.

Remember the people at the front desk of a hotel have a good deal of discretion with their room assignments. You might not be able to wrangle an upgrade to a suite, but the combination of a designer outfit, nice shoes, a great bag and attractive luggage qualifies you for consideration for the nicest room in the category. So does a lovely smile, exquisite manners and a discreet $50 tucked under the registration card. So does a good story – “I’m celebrating my divorce/end of my engagement”. (Lots of tips here.)

However, a more discreet and often cheaper alternative to a hotel is to book a condo for your stay. The wonderful thing about condos is that they lack a nosy front desk. Plus, with a little imagination, you can make the space your own. Condos tend to need some lead time, but can usually be held with a deposit. Having the option to make a sandwich or a pot of coffee which a condo with a kitchen offers can save you money and be a relief from eating every meal out.

Renting a car will depend on where you actually are relative to the attractions of the resort. Google maps is your friend here. At the same time, if a car is going to cost you $30 to $50 a day it may make a lot more sense to pay for a more central location where you can walk or take public transit to where you want to go. If you have to travel for an out-call, most resorts have cabs.

What to Take

With your regular escorting, you are providing a reprieve from the stress and sameness of the day-to-day; resort escorting, in contrast, is about providing a delicious addition to all the amusements of a vacation. You know what to pack for your own vacation: what else do you need when a little work is in the mix?

Frankly, other than a slip or two and a pretty garter belt and a few pairs of stockings, nothing that you’ll want to take through airport security. Though, of course, they have seen it all. And there is always the issue of you and your baggage arriving at the same destination. So unless you are going to be miles away from civilization, every resort you are staying at has the lube, condoms and candles a girl needs for her date.

Now, it is always essential to have a little black dress and a pair of pretty shoes for a dinner date. And a sexy sheer robe takes up very little suitcase space. But there is no reason to overpack either. What girl doesn’t like to hit the shops and have something new to wear on vacation?

Regardless of whether you are going to the beach or the slopes, make sure you have really good sunscreen. A lovely radiant glow is awesome but a sunburn is not.

The Resort Date

Of course you could treat your dates at the resort or the ski area just the way you do at home. But why would you? Taking a break from you own routine is what a vacation is all about.

Of course the nature of your date depends on where you are: if you are at the beach you probably don’t want to greet your client in a seductive slip, stockings and black patent heels. Much more fun to have a pretty, sheer cover-up, bikini bottoms and strappy high heeled sandals. Up in the snowy mountains, a less casual approach is called for so think full black lingerie and pretty stockings–ideally in front of a blazing fire.

Some of your resort clients will want to have drinks or dinner as part of the package. And why not? You’re on vacation and going out is part of the fun. You’ve packed your little black dress in either tropical linen or chilly climate wool, so dressing is a snap. Just add a few accessories and a red toned lipstick. Resorts often have excellent restaurants so do your research to ensure your dates are in places you actually want to go to.

In most cases, your dates will be booked in the evenings but, for various reasons, it may be easier for your clients to take a break from their vacation in the afternoon or even the late morning. Being on a vacation schedule yourself, you should strive to accommodate them. But remember that part of a great vacation is having lots of time for your own activities and that ski instructor is only going to be available for so long, so be flexible but not a slave to the whims of others.

Filling Your Schedule

In a perfect world, you would have enough pre-booked dates to keep you busy throughout your vacation. However, if you have a few gaps there is nothing to stop you from booking dates right from your smartphone. Running an ad for your services on the page for your resort destination is easy.

The one purchase which will make sense while you are away is a very cheap “burner” phone to book appointments. You really don’t want roaming charges. You can use your smartphone using the Wifi in your hotel– check to make sure it is free or a fixed rate–or your condo; but to actually book appointments and screen clients you need a local phone.

If you are going to look for clients by local advertising, you need to get up to speed on the law enforcement situation as well as any other “negative externalities” which may be present. It is important to check the laws in the state and the municipality in which you are going to be working. There are some jurisdictions where the law is harsh and its enforcement nasty. This is even truer if you are vacationing outside your home country.

You can minimize your exposure in a number of ways. Set a hard limit on the number of “local” dates you will accept. If you have done your pre-booking well, you really will have very few openings in any event. Tailor your ads to an up-market clientele. Make sure you emphasize “select hotels” and “generous professionals”. Don’t be afraid to charge a premium for your local dates. Your risk factor is greater therefore you should be paid more.

Screen your local dates very carefully. In actual fact, you don’t want to see “locals” at all. You are really looking for clients who are there on vacation but who have somehow neglected to pre-book your services.


One of the delights of being on vacation is that you can be anyone you want to be. Yes, you are limited slightly by your website – unless you are clever with web design and put together a quick site just for vacation “you”. But even that constraint does not have to determine how you escort at your resort.

If you have been escorting for a while, you probably have a “date routine” where you do much the same thing, in much the same way, with almost all of your dates. A vacation is an ideal time to switch things up a bit.

From how you greet your date at your door, to how you wear your hair and your make-up: on vacation you experiment and see how well it works. Your conversational strategies are going to change simply because you are going to be talking about the resort and how your client’s vacation is going.

One thing about people on vacation, they tend to have fewer inhibitions than they would at home. With this in mind, an escort might include a bit more teasing, some role play, a bit of naughty talk: nothing terribly daring, just a little out of the ordinary.

While you are away, you can also try out some slightly different approaches to your escorting persona. Instead of you regular “game face”, try being a bit demanding, or slip into the role of the geisha, the hand maiden, attending to your client’s every desire. Simply putting your hair up and sliding a pair of glasses on can change how your client sees you and how you see yourself. Does the naughty librarian or salacious school teacher work for you? Well, while you are out of town is a great time to find out.

Remember that it is extremely unlikely that you will see any of your resort dates again–well they may book another session at the resort but that is about it–so you can play a bit without hurting your chances of gaining a regular. As well, you are less likely to run into hobbyists at a resort so you don’t need to be as conscious of reviews.

Business and Pleasure

It is all too easy to get caught up in the mundane routine of your escorting business. A well-planned escape with enough dates to pay for part, or all of, your trip is the break which allows you come back to your routine truly refreshed.

But that means you have to actually take time for yourself when you are on your vacation. Whether it is lying on the beach with an “airport novel” or getting tips on your form from Lars the hunky ski instructor, you are away from home to have some fun. If you are gone for ten days, make sure you book at least one luxurious day at the spa.

That lovely man body surfing at the beach? Or carving turns on the black diamond run? Well, you’re a girl. And a professional. Sometimes pleasure is entirely disconnected from business. That’s why they call them vacations.