Waypoint Wild
3 trips Iโd plan from Winnipeg this fall ๐โ๏ธ
Not just flights.
Full trip ideas.
๐ Halifax + Cape Breton - coastal drives and Atlantic scenery
๐ฟ Panama + Boquete - coffee country, mountains and jungle adventure
โ๏ธ Dublin + the Di**le Peninsula - pubs, cliffs and small towns
The fall travel options from Winnipeg are just getting started.
Donโt just book the flight. Build the trip around it.
Which one are you choosing? ๐
13/07/2026
Flights Iโm watching this week ๐โ๏ธ
Some strong Winnipeg deals have popped up, and each one has a great adventure angle once you land.
๐ Halifax โ Cape Breton / Cabot Trail
๐ Anchorage โ Hatcher Pass
๐ฟ Panama โ Boquete
โ๏ธ Dublin โ Di**le Peninsula
๐น๐ญ Bangkok โ Kanchanaburi
๐ณ๐ฟ New Zealand โ Wฤnaka / Mount Cook
The flight gets you there.
The real adventure starts once you leave the crowds behind.
Think coastal drives, mountain roads, coffee country, small towns, riverside stays and bucket-list scenery.
Which one are you choosing? ๐
*Prices can change quickly and may vary by date, airline and availability.
08/07/2026
A client asked for Scotland.
But not just Edinburgh and a quick Highlands day trip.
They wanted countryside, coastlines, castles, villages, scenic drives and a trip that felt a little more their speed.
Thatโs where custom planning makes the difference.
For a Scotland road trip, the route matters just as much as the destination.
Borders Region.
Fife Coast.
Fort William.
Isle of Skye.
Highland roads.
Small towns.
Scenic stops along the way.
Itโs not just about picking places on a map.
Itโs about connecting them in a way that actually works.
Less rushing.
Better flow.
More of the moments you actually came for.
Thatโs the Waypoint Wild approach.
06/07/2026
The trip Iโd take next ๐
Northern Italy + Slovenia ๐ฎ๐น ๐ธ๐ฎ
This is exactly the kind of Europe trip I love.
Start with the Dolomites, Lake Garda, Verona and those unreal northern Italy road trip views.
Then keep going into Slovenia.
A lot of people donโt realize Slovenia actually borders Italy, which makes it an easy add-on to a Northern Italy itinerary.
Instead of flying somewhere new, you can turn one trip into an easy two-country road trip with alpine lakes, mountain towns, castles, caves, national parks and one of Europeโs most underrated capitals.
Most people stop at Italy.
Iโd add Slovenia.
You get incredible food, mountain scenery, unreal drives, fewer obvious stops and a trip that feels a little more adventurous than the usual Europe itinerary.
Would you do Northern Italy + Slovenia? ๐
03/07/2026
A travel advisor does a lot more than book flights and hotels.
The real value often shows up when plans change.
Flight delays happen.
Cancellations happen.
Missed connections happen.
Car rental hiccups happen.
Hotels make mistakes.
Even the best-planned trips can hit a few bumps.
My job isnโt just to help you choose where to go.
Itโs to help create a more frictionless travel experience from the first idea to the moment you get home.
Less stress.
Fewer unknowns.
Better options.
Someone in your corner when travel gets messy.
Because travel should feel exciting.
Not overwhelming.
01/07/2026
Waypoint of the Week ๐ฌ๐ช
Georgia might be one of the most underrated adventure destinations in the world.
You get huge mountain scenery, ancient wine regions, historic towns, incredible food, and road trip routes that feel completely different from the usual Europe itinerary.
Think Caucasus Mountains, Tbilisi, Kazbegi, Svaneti, Kakheti wine country, and views that make you wonder why more people arenโt talking about this place.
This is the kind of trip for someone who wants Europe, but not the same Europe everyone else is doing.
Mountains, wine, culture and a little hidden-gem energy.
Would you go to Georgia? ๐
29/06/2026
Flights Iโm watching this week ๐โ๏ธ
Some solid Winnipeg deals are popping up for summer and fall.
A few that caught my eye:
๐บ๐ธ Portland from $418
๐ฎ๐ช Dublin from $728
๐จ๐ฆ Halifax from $300
๐ฎ๐ธ Iceland from $520
๐ฉ๐ฐ Copenhagen from $870
๐ต๐น Lisbon from $745
๐ช๐ธ Madrid from $956
๐ฎ๐น Rome from $922
๐ฌ๐ท Athens from $985
The destination gets the attention.
But the real adventure usually starts once you leave the city behind.
Think coastal road trips, mountain towns, small villages, hikes, local food, and the places that donโt always make the first page of the guidebook.
Which one would you book? ๐
26/06/2026
Golf trips worth flying for โณโ๏ธ
A great golf trip is more than just the courses.
Itโs the road trips between rounds, the coastal views, the mountain backdrops, the small towns, the pubs, the breweries, and the memories made after the scorecards are put away.
From Cabot in Cape Breton to the links courses of Scotland and Ireland, these are the kinds of trips that turn into annual traditions.
So hereโs the question...
Your flight leaves tomorrow.
Where are you golfing? ๐
๐จ๐ฆ Cabot Cape Breton
๐บ๐ธ Northern Michigan
๐จ๐ฆ Banff & Canmore
๐ด๓ ง๓ ข๓ ณ๓ ฃ๓ ด๓ ฟ Scotland
๐ฎ๐ช Ireland
Fatherโs Day weekend hit a little different this year.
My sister flew in from Barrie, Ontario to surprise our dad, and it was a pretty special reminder of what travel is really about.
Itโs not always the big bucket-list trip.
Sometimes itโs a flight home. A weekend with family. A surprise visit. A memory youโll talk about for years.
Happy Fatherโs Day to all the dads out there. โค๏ธ
18/06/2026
You suddenly get a free week off work.
No planning. No excuses.
Which adventure are you choosing? ๐
๐ฎ๐ธ Iceland for epic road trips and waterfalls
๐จ๐ท Costa Rica for wildlife and tropical beaches
๐ต๐น Portugal for sunshine, food, and coastal towns
๐ต๐ช Peru for mountains and adventure
I'm taking Costa Rica right now... but Peru is a very close second. ๐
What's your pick? ๐
Click here to claim your Sponsored Listing.
Category
Contact the business
Website
Address
Georgetown