You bring the people and the purpose.
I’ll help take care of the travel.
You can picture them already: the conversations over breakfast, the place you’ll explore together, the moment someone says, “We should do this again.”
Then come the questions. Where should we go? What will it cost? How do bookings work? Who answers everyone’s travel questions?
That’s where I come in. I’m Carrie, the travel advisor behind The Milestone Society. I work with leaders and organizations to turn a promising group idea into a travel experience that makes sense for the people coming along and for the person bringing them together.
Who is this for?
Perhaps you’re a coach planning a retreat, a speaker who wants to bring her community together, or a wellness professional with an idea that deserves more than another afternoon workshop. Perhaps you lead a women’s network, club, workplace group or community whose members would love to travel together.
You don’t need a finished itinerary before reaching out. You do need a reason to bring your people together and a willingness to be part of making the trip happen.
A food and culture trip? A retreat with breathing room? A chance for women with shared interests to see somewhere new together? Tell me what you’re imagining.
Two people, different strengths
The Milestone Society handles travel inquiries and bookings through Enjoy Travel. You stay the voice of your community without becoming everyone’s travel agent, payment collector and emergency spreadsheet keeper.
You know your people
You shape the purpose of the experience, lead any workshops or programming you offer, make decisions with me, and invite your community to take part.
I know the travel side
I help assess what’s possible, research suitable travel options, coordinate suppliers, establish the booking process, and support travellers with the details they need before departure.
What Could We Create Together?
A trip built around your program
You bring the reason everyone is gathering; we build the travel around it. That could be a wellness retreat with workshops and time to rest, a writing retreat with room to explore, or a food-focused trip led by someone who loves bringing people to the table.
You lead your program and your community. I help plan and manage the travel that makes it possible.
A trip for a group that already belongs together
Some groups don’t need a program. They just want to go somewhere together. Think a knitting circle exploring the wool traditions of Scotland, a wine club tasting its way through Portugal, or a group of friends finally taking the trip they keep talking about.
I’ll help you find the right destination and travel style, then take care of the bookings and details so the group can enjoy being together.
How It Begins
1. Tell me the broad idea
Share who the trip is for, why you want to bring them together, roughly when you hope to travel, and anything you already know about the destination or group size.
2. We’ll talk about fit and readiness
If the idea looks promising, I’ll send a short partnership questionnaire. Then we’ll discuss your community, the travel possibilities and what each of us would need to do.
3. We’ll choose a sensible next step
If your community is ready, we can discuss paid group development. If you’re still testing interest, we can start with Group Readiness. You’ll receive a clear scope and professional fee before detailed research begins.
A good group trip takes more than one enthusiastic announcement. We’ll be honest about the work, the numbers and the timing so you can decide whether this is the right moment to move forward.
Starting Point
Introductory Partnership Rates
Group Readiness :
define the idea and test genuine interest before detailed trip planning
$295 + HST
Curated Group Development:
research an established cruise, tour or other principal supplier
$695 + HST
Custom Group Development:
design a retreat or trip with several coordinated components
$1,295 + HST
Curated Launch & Management:
set up and manage the approved group trip and traveller booking process
$595 + HST
Custom Launch & Management:
expanded launch and coordination for an approved custom trip
$995 + HST
These introductory partnership rates are available for my first three qualified group collaborations. We’ll confirm the right approach, what’s included and the fee before any paid planning begins.
Have a group trip in mind?
You don’t need a finished itinerary or a head count confirmed down to the last person. Tell me who you’d like to bring together and what you’re imagining. I’ll read your idea and get back to you about a conversation and the next sensible step.