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how to hire a travel companion

Updated: Jun 10, 2023

Obviously there’s a lot more to a successful fly me to you date than the five things outlined here, but if you remember these key points, you should be golden. And as long as you’re concise and polite in your correspondence, you should be able to sort out all of the other details together. Just remember that the easier you make it for your provider, the more relaxed and excited they’ll be for your date. If they’ve had to suffer through 45 planning emails before they’ve even boarded the plane, chances are they’ll already be tired of you by the time they get there. Also, it goes without saying that every provider is different. This is a general guide, but many providers have their own specific policies and requirements. Do your own research before you ever reach out to someone to book a date. The better prepared you are when you start planning your trip, the smoother the whole experience will go and the happier you’ll be in the end. Luckily, once you understand the basics of booking a fly me to you date, you’re never more than a flight away from the time of your life.

Below is a portion of an original post written by the artist formerly known as, Ava St. Claire, a companion based out of Florida whom has since retired. I am lucky to still call her a good friend and in a recent text chat we were bemoaning the fact she hadn't saved any of her brilliantly sharp tongued and cheeky twitter posts, because they really were brilliant, and in fact I see a lot of girls posting similar but I know where they got the inspiration from first!

A photo on Ava's Twitter - her barefoot and the bare feet of a man next to her walking mid-stride on the sandy beach, jeans cuffed and wet from the surf and the caption reads: "this could be us, but you didn't want to to send me your pre-screening details".

A photo of her hand holding another lover's hand, his excellent taste in watches showing, their setting is that of floors seats to a sports game, captions reads: "this could be us, but you kept waiting for me to visit your city". A photo posted to Twitter of her lounging half clothed on a front porch of a vacation home, making serious eyes at the man behind the camera, post caption: 'This could be us, but you 'don't pay deposits'".

Pure gold. She is missed, but here is a bit of sage advice in her frank manner, that I had saved for a reblog, thanks for the tips sis.

1. Have your schedule sorted.

Fly me to you dates require more planning and coordination than most. A provider may have to arrange for childcare, find someone to watch their pets, take time off of their other jobs, or sort out any of a hundred other details in order to jet off to meet you. Make it easier on them by knowing exactly when you want to schedule your trip. We can’t exactly plan for a weekend trip “sometime next month” or promise that we’ll be available to visit you at some point “this summer,” so don’t contact us to book a fly me to you date until you actually have solid dates in mind. If your schedule is flexible, try to offer your provider a few options to choose from. For example: “I’d love to meet for 48 hours on either February 15-17, 25-27, or March 2-4.” I know it’s exciting to plan your dream getaway and have something to look forward to all winter, but it’s decidedly less exciting for us to spend a month emailing back and forth about a date that’s a “hopeful maybe” at best.

2. Know your “dealbreakers”.

It’s perfectly okay to have set expectations or limitations when it comes to planning a fly me to you date. Maybe you can only pay in cash and so you need to find a provider who has deposit options that allow you to do so. Or perhaps you’ve got your heart set on going scuba diving together, so you’re only interested in inviting someone who enjoys swimming. Whatever dealbreakers you may have, it’s important to know what they are and present them up front. As a part of your initial email, along with the date and time of your trip and whatever screening information might be required, be sure to include any other details that may influence your provider’s decision to join you. Be polite, but honest. For example: “I’d like to invite you to meet me in Puerto Rico from April 6th through the 9th. One of the things I’m most looking forward to is enjoying a horseback riding trip through the jungle together, so please let me know if that’s not something you’re interested in.” As always, if you and your provider aren’t in agreement, don’t force the issue. Sending another two emails extolling the virtues of the noble steed is probably not going to convince them to come, but it will annoy the hell out of them and possibly land you on their Do Not See list.

3. Research travel costs.

Most providers do not include the cost of travel and accommodations in their fly me to you rates. This means that, in addition to paying their regular travel rates, you’ll likely be expected to cover their: flight, ground transportation to/from the airport, and hotel room (if you aren’t spending the night together). If you have a strict budget for the trip, do yourself a favor and research what that might cost before you invite a provider. Having an idea of what your additional expenses will help you make an informed decision about whether or not you can afford the trip. If you’re a budget minded client, it might be a good idea to present travel suggestions to your provider at the time of booking. For example: “I saw that the Hyatt near the airport has rooms for $200 a night, if that works for you.” It’s also perfectly acceptable to tell your provider that you have a set budget for travel expenses. If they balk at not being given free reign to book whatever accommodations they’d like, that’s totally okay too. You’re just not going to be a good match for this trip. Whatever you do, don’t waste their time trying to convince them to settle for La Quinta if they’re looking for the Ritz-Carlton.

4. Pay your deposit promptly.

Every provider handles the financial end of their dates differently, but at some point you will probably be asked to pay a deposit to confirm the trip. A good client should already know what their provider’s deposit policy is (it’s usually on their website) and be prepared to pay it at the time of booking. If for whatever reason you aren’t able to pay the deposit right away, it’s a better idea to hold off on booking the date until you can. Asking a provider to reserve time for you in her schedule without any kind of guarantee from your end is just unfair. Not to mention, failing to pay your deposit promptly only delays your provider’s ability to buy their airline tickets, book their room, and finish planning the trip, since most providers rely on your deposit to do so. A good rule of thumb is to be prepared to pay your deposit within two business days of booking your trip. Whatever you do, do not put your provider in the uncomfortable position of having to remind you to pay. I’m sure a “debt collector and the broke guy” role-play scenario can be super fun in the right context… but this isn’t it.

5. Plan for private time.

Whether you’re booking a quick 6 hour getaway or a week-long excursion, at some point your provider will probably need to poop. Or call their kid. Or perform salah. Or do something that doesn’t involve you. Be a gracious host and plan at least some time for them to enjoy a few moments of privacy. On shorter dates, that may just mean offering to step out of the room for a 20-30 minutes (go get a drink at the bar, take a walk around the block, or even just read in the lobby of your hotel for a little while) so that they can do whatever they need to do. It’s less awkward than it sounds. Between activities you might say something like, “I’m going to step out for a little bit. You relax. I’ll shoot you a text message when I’m on my way back up to the room.” This also gives you a little time to handle any personal things that might need your attention. Sure beats the hell out of hiding in the closet so you can call your wife, right? And let’s be honest, that’s not the only thing that I’m sure your provider would prefer that you do elsewhere, if you receive my meaning. On a longer date, expect that your provider may want a couple of hours a day all to themselves. Don’t think about it as time that you’re losing from your date, think of it as time that’s set aside to ensure that your provider is able to be at their very best for you the whole time that you’re together. It’s safe to assume about 30 minutes of private time for every 4 hours that you’re together. Small price to pay for having an amazing provider at your beck and call for the other 210 minutes of your time together."

and this piece of advice are from yours truly:

6. Life is short. book her.

For those of you who are currently in the search and planning phase for a long deserved holiday; go take a look at my curated list of once-in-a-lifetime travel experiences, pick one, and let's go there!


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