- Direct: 705-929-2538
- Email: [email protected]
It’s time to … look behind the curtain of my travel business
Most people think booking a vacation is simple:
Pick a resort.
Click a button.
Pack flip-flops.
Done.
And honestly? Sometimes social media makes it look that way too.
But the other day, I was in a meeting with a client who asked me what exactly I can do for his company: Flights, hotels, events, client travel, staff travel … what else?
On the drive home, it hit me: People only see the finished trip. They don’t see everything happening behind the scenes.
So, welcome to the organized chaos that is my travel business.
LEGAL DISCLAIMER:
If reading this article results in you sitting on your couch questioning my sanity while sipping wine, I cannot legally be held responsible for your therapy bills.
Now buckle up, buttercups.
We’re going behind the curtain. 😲
Research mode activated
Researching trips is probably the biggest part of my business — and definitely the most time-consuming.
And here’s the thing many people don’t realize:
I’m rarely researching just ONE trip at a time.
While one client is deciding between Mexico and Jamaica, another is waiting on pricing for Europe, another is travelling and messaging me from destination, another needs flights adjusted, and somewhere in the middle of all that, I’m standing in Costco watching a delayed flight app while silently threatening an airplane to PLEASE JUST TAKE OFF ALREADY.
Totally normal behaviour. 😜
Now, since we would all be here until Christmas if I explained the research process behind custom European itineraries, let’s stick to something “simple” — researching an all-inclusive vacation.
(And yes, I used air quotes around simple.)
Departure airports matter more than you think
Most of my clients are from Northern Ontario, so the first thing I need to determine is: Are they flying from their local airport or driving to Toronto?
That one decision changes EVERYTHING.
Some resorts and destinations won’t even appear depending on the departure airport. Then there’s flight timing, layovers, overnight connections, weather delays, hotel stays in Toronto, parking options, and whether the flights are realistic or if they’re taking what I call “the scenic cowpath route” across North America.
Because nobody wants to fly:
Toronto → Montreal → Somewhere else → Finally the Caribbean
… and arrive so late you can’t even find the buffet.
And if you’re connecting through Toronto during winter?
Ohhhhhh no!
You are heading down the day before.
I say this with love and experience … because Northern Ontario weather likes to wake up every morning and choose chaos.
I’ve seen flights delayed because of snowstorms, thunderstorms, fog, and probably strong negative emotions. 😒
So yes, while my clients are calmly packing swimsuits, I’m over here mentally calculating:
“OK … the delay is only 25 minutes … they still have time …”
“OK … now it’s 45 minutes …”
“WHY IS THIS PLANE STILL ON THE GROUND?!”
Sometimes those conversations stay in my head.
Sometimes they happen out loud in Costco. 🤣
Not all resorts are created equal
Once the departing airport is sorted out, it’s time to match the RIGHT resort to the RIGHT client.
And this is where experience matters.
Some clients want long beach walks.
Some want multiple pools.
Some want nightlife.
Some want peace and quiet.
Some want adults-only.
Some want food options.
Some want easy access to excursions.
And here’s the fun part:
Resorts LOVE using the same buzzwords.
“Adults-only” may actually mean:
Your building is adults-only.
One restaurant is adults-only.
But the rest of the property still includes families.
Oh, and my favourite: Oceanview!
Translation: You can “see” the ocean from your balcony … could be right in front of you, or, if you lean over the bars and look to the right — There is is!
The tiny details?
VERY important to know BEFORE booking.
Then there’s location.
A resort may check every box, until you realize the excursion the client REALLY wants is over an hour away.
Or the beach technically exists … but it’s so short your sunset walk looks like you’re pacing while waiting for bad medical news.
These are the little things clients often don’t discover until after they arrive.
My job is to figure them out BEFORE they book.
The research rabbit hole
Once I narrow down possible resorts, the real digging begins.
I go through feedback from my own clients, advisor groups, destination groups, supplier updates, site inspections, and travel agent communities.
I want REAL information. Not polished marketing photos where every beach is magically empty and every buffet looks like it was prepared by Gordon Ramsay himself.
Because resorts change.
Management changes.
Service changes.
Standards change.
And sometimes a resort that was AMAZING two years ago suddenly lands on my personal “Do Not Sell” list because too many trusted sources are reporting problems.
So, when I send resort recommendations to clients, understand:
I have researched the absolute snot out of those properties before they ever land in your inbox.
Let’s get some pricing
Once I’ve got the best resort options, it’s time to start pricing.
This is where I dive into the supplier system and compare inventory, flights, room categories, better departure date options, and overall value to find the best fit for my clients.
And here’s something many people don’t realize:
The price you see online?
That’s usually the most basic room category with the most basic flight option.
That “great deal” may technically exist … but it could also involve three airport stops, a 14-hour travel day, and arriving at your destination emotionally unwell.
When I research pricing, I go much deeper than the first screen. I check:
Because many times, the minute you proceed further into the booking system: “PRICE CHANGE!” 🙄
And trust me … nobody enjoys that pop-up.
The proposal stage
Once I have everything organized, I send clients what I call my “READ ME FIRST” email. This includes:
Then I send the full itinerary links so clients can explore the resorts in more detail.
This part is important because I’m not just throwing random resorts at people and hoping for the best. Every recommendation is based on:
Because yes, client saying: “I really love a walkable beach” actually matters.
“Book it, Danno!”
Once clients decide which resort they want, I go back into the system and pull up the exact package I quoted.
Then I re-check EVERYTHING.
Pricing.
Flights.
Availability.
Room category.
Timing.
EVERYTHING!
Because travel pricing changes constantly. If the package jumps significantly in price, I always reach out before proceeding.
Then it’s finally time to book.
And honestly?
That’s the part most people THINK would be where my job ends.
In reality, booking is just one small piece of everything happening behind the scenes.
What happens after booking?
Now the real multitasking begins.
Because while one client has officially booked their vacation, another client is still researching options, another is travelling, another needs payment reminders, and another may have just messaged me from an airport.
This business is basically organized chaos with a computer and coffee (and the afternoon dip into the snacky-snack drawer).
Once the booking is confirmed, I start coordinating all the moving pieces:
If I’m booking multiple rooms together, I often reach out directly to my supplier contacts or Business Development Managers to request adjoining rooms or preferred locations.
Nothing is ever guaranteed, but I do everything possible to make sure my clients’ requests reach the right people.
And then there are payment plans.
Many clients appreciate being able to spread payments out over time, so I help organize payment schedules and send reminders before processing anything.
Basically: I become part travel advisor, part project manager, part human reminder app. 😎
Almost time to leave!
As the departure date gets closer, my clients receive one of my favourite things to create: My signature travel booklet.
For many of my clients, this booklet is one of the things that first made them reach out to me. 😍
Yes, I do send you digital travel documents from suppliers and the proper links to entry forms, but this booklet is completely different. It includes:
Basically, it’s the “don’t panic, I’ve got you” guide to travelling.
And of course …
Mini Sherri also makes an appearance.
Mini Sherri: Tiny traveller, big impact
For those unfamiliar with Mini Sherri:
Yes, it’s literally a tiny version of meI 🤣
And yes, she travels VERY well.
Clients take Mini Sherri along on vacation, snap photos of her around the resort, and send them back to me.
Now, besides being adorable and making me laugh, those photos actually help me maintain relationships with suppliers and resort contacts.
I send the photos along to my reps and supplier partners, thank them for taking care of my clients, and — believe it or not — Mini Sherri helps keep me top of mind.
She may be tiny … but she’s basically my unofficial marketing department.
Clients also receive my VERY bright luggage tags so they can spot their bags without having to tackle someone at the carousel by accident.
While you’re away, I’m still working
Once my clients leave for vacation, my job doesn’t suddenly stop.
If anything, I become even more alert.
I monitor flights, weather systems, delays, airport issues, and supplier updates while clients are travelling.
If storms are developing, I’m already thinking ahead about possible backup plans before clients even know there could be an issue.
And yes … I absolutely monitor flights obsessively.
When my clients are travelling, I’m checking:
I don’t fully relax until my app tells me my clients have safely landed.
So, while my clients are relaxing poolside with a pina colada, I’m somewhere in Northern Ontario refreshing flight apps like it’s a competitive sport.
When things go sideways
Travel doesn’t always go perfectly. 😭
Flights get delayed.
Weather happens.
Systems fail.
Borders close.
Things change.
And when that happens, my job is to stay calm and help clients navigate through it.
The biggest example of this was March 2020.
When the world started shutting down, I had clients all over the place:
Groups travelling.
Families travelling.
Clients in Europe.
Students travelling without parents.
People trying to get home while countries were rapidly changing rules and closing borders.
For one solid week, my entire job became: Get everyone home safely.
I spent my days coordinating flights, communicating with clients, updating families, monitoring border changes, and constantly adjusting plans as situations changed by the hour.
And when my final client finally texted me to say: “We landed.”
I did what many travel advisors did that week.
I sat on the floor and cried. 😭 😭
That was one of the hardest moments of my career, but it also reminded me exactly WHY I continue to do what I do … Because when things go wrong, my clients know they are not alone — I got them!
Thank you to all who put their faith in me to look after their adventures! 😍
I am truly blessed and grateful.
Correspondent and Avid traveller