Created by Lori Richardson Published September 04, 2026 | Updated September 07, 2026 3 min read on Escorted or Guided Tour

Lori Richardson: The Advisor Who Overthinks in the Best Way

Lori Richardson: The Advisor Who Overthinks in the Best Way

What happens when a self-proclaimed overthinker and researcher channels that energy into planning your perfect vacation? You get a travel partner who genuinely cares from the first idea until you're home again.

I’ll Admit It — I Overthink

I’m a researcher. I’m a planner. And yes, I’m absolutely an overthinker.

But when it comes to travel, I think that’s a pretty good combination.

Because I don’t want to simply find you a vacation. I want to understand why you’re taking it in the first place.

Is it a honeymoon you’ve been dreaming about? A milestone birthday? A family vacation where everyone actually needs to be happy? A much-needed escape somewhere warm? Or maybe it’s a group trip where keeping everyone organized feels like a vacation in itself.

Those details matter.

I ask questions. I compare options. I read the fine print. I research the resort, the location, the flights, the room categories, the excursions and all those little details that can make the difference between “That was nice” and “That was exactly what we needed.”

And sometimes, yes, I probably think about your vacation more than I should.

But I’m okay with that.

It’s About More Than Finding a Deal

There is nothing wrong with looking for a great price. Of course we all want value.

But travel is about more than the number at the bottom of a quote.

The cheapest resort isn't necessarily the right resort. The prettiest beach isn't necessarily the best location. And the itinerary that looks perfect online might not actually work for the people travelling.

That’s where I come in.

My job is to listen to what you want, understand what matters to you, and then use my experience and research to narrow down the choices.

Sometimes I'll say, “I don't think that's the right fit for you.”

Sometimes I'll say, “I know this one costs a little more, but here's why I think it's worth it.”

And sometimes I'll get ridiculously excited because I found something I think you're going to love.

That's the fun part.

Travel Planning Should Feel Like a Partnership

I don't believe in handing someone a quote and saying, “Let me know.”

I want to have a conversation.

I want to know what you're excited about. What you're nervous about. What you've loved on previous trips — and what you'd never want to repeat.

Then we build from there.

Maybe we're looking at an all-inclusive in Mexico. Maybe it's a romantic escape to Costa Rica. Maybe we're planning a destination wedding with dozens of moving pieces. Maybe we're talking cruises, honeymoons, family vacations or that bucket-list trip you've been putting off for years.

Whatever the trip, I want you to feel like you have someone in your corner.

Someone who will research the options.

Someone who will tell you what they really think.

Someone who will notice the details.

And someone who will still be there when you're counting down the days to departure — and when you get home and want to tell me all about it.

The Best Part of My Job

One of my favourite parts of being a travel advisor isn't actually booking the trip.

It's watching the trip come to life.

It's the “We just booked!” excitement.

It's choosing the perfect room.

It's helping someone finally take that trip they've been talking about forever.

It's a couple getting excited about their honeymoon.

It's a group of friends celebrating a milestone together.

It's knowing that somewhere down the road, those travellers are going to look back at their photos and remember not just where they went, but how they felt while they were there.

That's what makes all the research worth it.

So, Yes… I’m Probably Going to Overthink Your Vacation

But I mean that in the best possible way.

I'll think about the details.

I'll research the options.

I'll ask the extra questions.

I'll challenge an idea if I don't think it's going to work.

And I'll get excited right alongside you when we find the one that does.

Because I don't want to plan a vacation for you.

I want to help plan your vacation.

And if you're looking for a travel advisor who genuinely cares about getting it right, I'd love to start the conversation.

Let's see where your next adventure takes you.

Lori Richardson Photo

Lori Richardson

Travel Associate

Meet The Agent

FAQ's

A dedicated travel advisor like Lori Richardson goes beyond finding a price by asking questions, reading the fine print, and researching resorts, room categories, locations, flights, and excursions. The goal is to match the trip to the traveller rather than simply presenting a quote. That level of detail can be the difference between a trip that was nice and one that was exactly what was needed.

Lori approaches honeymoon planning as a partnership, taking time to understand what the couple is excited about, what they may be nervous about, and what they have loved on previous trips. She researches options thoroughly and will flag when something looks good online but may not actually suit the travellers in question. Her aim is for the couple to feel genuinely supported from the first conversation through to their return home.

Yes — Lori Richardson specifically works with destination weddings and group travel, both of which involve many moving pieces and the challenge of keeping everyone organised and happy. She treats these trips as a conversation and a collaboration rather than a transaction, building the itinerary around what actually works for the people travelling.

Lori is direct about this: the cheapest resort is not necessarily the right resort, and the prettiest beach is not always the best location. When she believes a slightly higher-cost option is the better fit, she explains her reasoning clearly. Her focus is on value in the broader sense — ensuring the trip delivers what the traveller actually needs, not just a low number on a quote.

Lori works across a wide range of travel types, including all-inclusive vacations in Mexico, romantic escapes to destinations like Costa Rica, family holidays, honeymoons, cruises, milestone birthday trips, group getaways, and long-anticipated bucket-list journeys. Her approach centres on understanding the purpose behind the trip before narrowing down the options.

Lori describes her role as lasting from the first idea through to the traveller's return home. She remains engaged during the countdown to departure and welcomes the debrief when clients are back and want to share how the trip went. Her investment in the outcome does not end at the point of booking.

Lori Richardson's approach begins with a conversation rather than a quote. Prospective travellers are encouraged to share what they are excited about, what they want to avoid, and what the trip means to them — whether it is a long-overdue escape, a family milestone, or a honeymoon years in the making. From there, she researches the options and offers honest recommendations tailored to that specific traveller.
Lori Richardson: The Advisor Who Overthinks in the Best Way

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