The Milestone Society

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The Milestone Society Solo travel, small-group experiences & meaningful adventures for women 30+
Let's talk travel click to book > https://calendar.app.google/VoxRcziJ4L8FbYa5A

10/17/2026

1st Day of the National Women’s Show here in Ottawa. It has been a full day and my feet are tires but so worth it.

Check it out! The Ultimate girls' day out!This weekend I will be at the National Women's Show - Ottawa sharing the Socie...
10/14/2026

Check it out! The Ultimate girls' day out!

This weekend I will be at the National Women's Show - Ottawa sharing the Society with thousands of women.

Cohere Centre
4899 Uplands Dr, Ottawa, ON K1V 2N6

Saturday, October 17, 2026 10:00 am – 6:00 pm
Sunday, October 18, 2026 10:00 am – 5:00 pm

I have 12 complimentary tickets if you are looking for something to do this weekend. First come first serve. Claim them below.

The Milestone Society is a travel company created for women who are curious about the world, even if they’re not quite sure they’re ready to explore it on their own.

Specializing in solo travel, custom travel planning and hosted departures, The Milestone Society helps women move from “I’d love to go someday” to actually going, with thoughtful planning, support and plenty of room for curiosity along the way.

Travel doesn’t have to mean being fearless. It can mean wandering down an interesting street, lingering over coffee, learning something unexpected, and experiencing a place in a way that feels like your own.

Meet The Milestone Society at the National Women’s Show in Ottawa this October and discover where your next chapter might take you.

themilestonesociety.com

What does it mean to be part of The Milestone Society?It doesn’t mean collecting passport stamps like they’re proof you’...
10/12/2026

What does it mean to be part of The Milestone Society?

It doesn’t mean collecting passport stamps like they’re proof you’ve lived an interesting life. It doesn’t mean being fearless, endlessly outgoing or ready to leap onto a plane tomorrow.

It means staying curious about the world, about other women and sometimes about parts of yourself you haven’t met yet.

It means making room for yourself in a life that will happily fill every available corner with work, responsibilities and other people’s needs if you let it.

It means celebrating another woman when she finally books the trip instead of treating life like a competition.

Some women will arrive ready to make friends with the entire airport. Others will quietly take everything in before saying a word. Some will want the hike, some will want the café, and some of us will want both with a snack tucked in our bag just in case.

You don’t have to become a different kind of woman to belong here.

Bring your curiosity, your dreams and your wonderfully weird self.

There is room for you in the Society.

Today I am celebrating my birthday and Thanksgiving at one of my favourite campgrounds. This has me thinking about next ...
10/11/2026

Today I am celebrating my birthday and Thanksgiving at one of my favourite campgrounds. This has me thinking about next year though...

Next year I will be celebrating in Scotland! Ghost tours, food, and castles in Edinburgh and Glasgow, and rolling hills and lochs in the highlands!

And guess what????

You can join me! Let me know if you are interested in exploring Scotland with me and yes there will be cake involved!

What does it cost to join The Milestone Society?Nothing. Not “free until you accidentally click the wrong button” free. ...
10/04/2026

What does it cost to join The Milestone Society?

Nothing. Not “free until you accidentally click the wrong button” free. Actually free.

There is no membership fee, subscription or initiation ceremony. No secret handshake either—although now I kind of want one.

You don’t need to have a trip booked. You don’t need an impressive passport or a collection of wild stories. And you certainly don’t need to prove that you’re adventurous enough to belong.

The trips themselves cost money, obviously. And if you hire me to plan one, there is a professional planning fee because research, comparison, organization and support are real work, not travel-agent fairy dust.

But being part of the Society? That costs nothing.

Come curious. Come nervous. Come ready to tell everyone your latest travel idea. Come quietly and take it all in for a while.

There is room for you here.

When I say “Society travel,” I don’t mean matching hats, mandatory bonding or being marched from breakfast to bedtime wi...
09/27/2026

When I say “Society travel,” I don’t mean matching hats, mandatory bonding or being marched from breakfast to bedtime with a clipboard.

Some women will arrive nervous and quietly take everything in. Some will arrive ready to make friends with the entire damn airport. Some will want company at dinner and silence beside the fjord.

All of them belong.

Society trips won’t all look the same. Sometimes I’ll host. Sometimes I’ll plan the trip and send you off without me. We may join a tour, board a cruise or travel as our own small group. You can come alone or bring someone you already enjoy travelling with.

What will stay the same is clarity, support and room to be yourself.

I spent too long waiting for the right person, the right time and enough courage. The Society exists so other women don’t have to keep waiting, but it also isn’t here to make anyone prove how independent she is.

Travel can be wonderful, tiring, hilarious, awkward and occasionally a pain in the ass. We can make room for all of that, too.

Which traveller are you: quietly curious, packed and ready, or mostly waiting to see where the good snacks are?

Do I have to be a solo traveller to join The Milestone Society?No.Come on your own, or bring a friend, sister, mother, d...
09/18/2026

Do I have to be a solo traveller to join The Milestone Society?

No.

Come on your own, or bring a friend, sister, mother, daughter or another woman you enjoy travelling with.

Already have a group that wants to travel together? I can help you plan something specifically for your group, too.

The Milestone Society isn’t about proving you can travel alone. It’s about making sure you don’t have to keep waiting to travel.

Would you come on your own or bring someone with you?

09/14/2026

So many places to go in the world! Where would you go next? Where would you put your pin?

Thank you to everyone who came to visit me today, especially my Mom, sister and niece who are always a great support. An...
09/13/2026

Thank you to everyone who came to visit me today, especially my Mom, sister and niece who are always a great support. And to all the new women I met today I am so looking forward to the adventures ahead!

All set up and ready to meet all or you! Come on out to BeYoutiful Women's Expo - Ottawa today to visit me and see all t...
09/12/2026

All set up and ready to meet all or you! Come on out to BeYoutiful Women's Expo - Ottawa today to visit me and see all the other wonderful women owned businesses and speakers and events.

Address

C/o Enjoy Travel 469 Dundas Street West
Trenton, ON
K8V3S4

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