Waypoint Wild

You suddenly get a free week off work.

No planning. No excuses.

Which adventure are you choosing? 👀

🇮🇸 Iceland for epic road trips and waterfalls
🇨🇷 Costa Rica for wildlife and tropical beaches
🇵🇹 Portugal for sunshine, food, and coastal towns
🇵🇪 Peru for mountains and adventure

I'm taking Costa Rica right now... but Peru is a very close second. 🏔

What's your pick? 👇

Spent the weekend on a bachelor party golf trip and got a reminder that travel doesn't always have to mean boarding a plane.

A few friends, great golf courses, a cabin in the woods... and a curious bear 🐻

Sometimes the best trips are the simple ones.

What's the best golf trip you've ever done?

Flights I'm watching this week 👀 ✈️

This week's list includes:

🥾 Huaraz - Peru
🍷 Eastern Townships - Quebec
🌿 Uvita - Costa Rica
🌊 Flores Island - Portugal
🚲 Giethoorn - Netherlands
🏔️ Glencoe & the Highlands - Scotland
🌋 Snæfellsnes Peninsula - Iceland

The flight gets you there.

The adventure starts once you leave the crowds behind.

Let's get you off the grid

Which one are you choosing? 👇

What if Iceland wasn't the end of the trip? 🇮🇸🇫🇴

Most travellers spend a week exploring Iceland's Ring Road before heading home.

I'd add a few more days and hop over to the Faroe Islands.

Dramatic cliffs, tiny fishing villages, coastal hikes, and some of the most spectacular scenery in Europe.

The best part? Winnipeg now has direct flights to Iceland, making this adventure easier than most people think.

Iceland only... or Iceland + Faroes? 👀

Waypoint of the Week 🇫🇴

If Iceland, Scotland, and Norway had a wild little cousin, it might be the Faroe Islands.

Think dramatic cliffs, winding coastal roads, tiny villages, puffins, waterfalls, and some of the most spectacular scenery in Europe.

With direct flights from Winnipeg to Iceland and a short hop onward, the Faroe Islands are closer than they look. The dramatic scenery, quiet villages, and lack of crowds make the journey more than worth it.

Would you put the Faroe Islands on your travel list? 👇

Everyone travels differently, but I've learned something after a lot of trips:

The places I remember most are rarely the biggest cities.

They're the mountain towns, coastal villages, scenic drives, and places that make you slow down for a few days.

Agree or disagree? 👇

One of the most common questions I get:

“How far ahead should I book?”

The answer depends a lot on the type of trip… but in general:

The earlier you start planning, the better your options usually are ✈️

Especially for:

- Europe
- bucket-list trips
- direct flights
- unique accommodations

Good trips come together way easier before everything fills up.

Flights I’m watching this week 👀✈️

The best trips usually start once you get beyond the obvious stops.

Wine towns in Ontario.
Desert parks in Texas.
Coastal drives in Portugal.
Mountain loops through Utah.

The flight gets you there.
The real adventure starts once you leave the crowds behind.

Which one are you choosing? 👇

These are the adventure trips that lived up to the hype for me 🌍

Big scenery, epic hikes, incredible drives, mountain towns, great food, and places that feel a little different from the usual tourist route.

If I could rebook one tomorrow… it’d honestly be tough to choose.

Which one would you pick first? 👀

One of my buddies sent me this today and honestly… this is an elite trip concept 👍

Ski powder for a week. Then swap snow boots for golf shoes and sunshine.

Some combo trips that would actually work:

🇨🇦 Alberta + Phoenix
🇺🇸 Tahoe + Monterey
🇯🇵 Japan North to South
🇺🇸 Utah + Scottsdale
🇪🇺 Alps + Portugal

This feels very Waypoint Wild:

Big scenery. Active travel. Great food. Two completely different vibes in one trip.

What combo trip would you build? ⛷️🏌️🌴