Hey there, Travellers, 

Can you believe that today is officially our TENTH birthday! That’s double digits. We’re big kids now.

Apparently, the appropriate gift for a tenth anniversary is tin or aluminium. While we’d love to receive lots of tin cans in the post, I have another suggestion: gift yourself a trip in one of those tin cans in the sky instead.

As we’re in quite the festive mood, here are ten reasons to celebrate Jack’s 10th birthday:

1. Ten years on, we’re still doing the hard graft of digging up amazing fares so you don’t have to…
   
   
2. But if you fancy trying your hand at a spot of flight finding, we’ll gladly share our tips and tricks.
   
   
3. We are completely independent and member funded - the only time we send you a Flight is when we would actually take it ourselves.
   
   
4. What started as one guy sending his mates emails from a basement in the UK has grown to an international club of over 4 million intrepid Travelers across Europe and North America.
   
   
5. Our team loves to travel just as much as you… and then give you all their recommendations.
   
   
6. Your experiences and stories are just as important as ours - that’s why we shout about them on the Postcards wall!
   
   
7. Jack still practices what he preaches - we’re never really sure where in the world he’ll pop up next! The last known sighting was somewhere in the jungle…
   
   
8. Our members save an average of 40% on airfare every time they book. For those cheaper short-haul routes, that might only equate to a tasty meal and the local craft brew, but for those long trips around the world, that’s a whole extra week’s accommodation.
   
   
9. As we’ve aged, our tastes have gotten a little fancier. Economy Flights may crop up most frequently, but the best savings come on those reduced premium economy, business class, and even first class fares. So of course, we’ve launched a new membership tier for even the bougiest of savvy Travellers!
   
   
10. Experiencing more of the world, meeting new people, tasting new foods and and learning about different ways of life opens our minds. I personally might never have visited some of the places I’ve been if it weren’t for Jack’s, and my life is richer for it.

As always, we'd love to hear where your Jack's Flight Club membership has taken you - whether a cheap weekend trip, a mega saving on your family's summer getaway, or somewhere in between, let us know in the comments.

Happy travels and safe landings,

Katy - Editor of The Detour

By Olivia

San Diego native Olivia left home three years ago to live on the road. Since then, she's had homebases everywhere from Quebec to England to New Orleans, but she always ends up back on the West Coast. When she's not hiking through the desert or the woods, she can usually be found exploring her current city and scoping out the best bars and coffee shops.

The misty, windswept coast of Oregon state stretches on for 362 miles (583 km) of beaches, cliffsides, and lighthouse-strewn capes. Plenty of states happen to have a coastline, but Oregon’s is special – due to some early pioneer history and 20th-century pushes for preservation, it’s been elevated to a protected, beloved region.

Thanks to its dramatic views, rock formations, lush woods, and towering sand dunes, it’s become quite a popular road trip route. US Highway 101 (the West Coast’s premier scenic route) traces along its edge, guiding you through beach town after beach town.

Cruising down that road is one of the main things I wanted to do during my year in the Pacific Northwest, and I’ve finally made the journey! 

What I learned was that (while the views are just as dreamy as the photos would have you believe) there’s actually quite a bit more logistics involved than I expected. I hoped my road trip experience would make it easy to breeze through my jam-packed itinerary, but the 101 is a fickle beast and your plans need to account for its chaos. 

That’s what I’m here to help you do! There’s no shortage of listicles online detailing “things to do on the Oregon Coast,” but after getting stranded for hours in the rain, losing an entire day of sightseeing, and screaming at the backs of RVs driving 15mph while the daylight rapidly disappeared, I wished I’d spent less time bookmarking viewpoints and more time researching the nitty-gritty facts required to build a more realistic itinerary.

So before you answer the siren call of Haystack Rock or Newport Aquarium, here’s what you need to know about road tripping the Oregon Coast.

How to start building your Oregon Coast itinerary

The Coast is covered in fun stops and eye-catching scenery, so it’s easy to overbook yourself. With so many hiking trails, cool beach towns, and picture-perfect overlooks, it’s tempting to star every single item on the map and devise an itinerary that has you stopping every 100 yards. But thanks to the 101’s shenanigans (more about that below), this is definitely one of those places where you want to pick fewer stops and spend more time at each one.

Most Oregon Coast road trip routes include a few entries in each of these categories:

Beaches

Visit in summer, and you’ll almost definitely be spending some time laid out on the beach. There are a few loooooong stretches of sand (especially down in the dunes area), but the coolest beaches here are often secluded little inlets surrounded by dramatic rock formations. Cannon Beach is easily the most iconic spot and is pretty hard to beat, but you can pretty much pull up to any beach on the map and get one of those gorgeous, classic Oregon Coast views. 

If you’re taking a short trip, I’d schedule at least a few hours to relax at the beach, but you can often easily pull over and veg out for a bit whenever you need a break and see open parking spots.

Beach Towns

Scattered along the coast, you’ll find cute little beach town after cute little beach town. Most of them are pretty tiny, with a few hotels, a couple restaurants, and a gift shop or two. The largest hub in the area is Astoria (technically a riverside town and not a beach town, but it functions as the start of the Coast). Other popular towns include Seaside (touristy, beach boardwalk vibes), Newport (best known for its aquarium), Yachats (hippie central and my personal favorite), and Brookings (the last stop before California). 

These are the most fun and convenient spots to stay overnight (if you’re not camping), but they can also get pretty pricey in summer. If you stop in Yachats, check out the Drift Inn – I stayed in one of their hostel-style private rooms, and it was a good balance between affordability and fun beach town vibes.

Even if you don’t stay overnight in any towns, it’s worth taking the time to explore a few, grab a bite, and shop for local art.

Hiking Areas

There are trails snaking all around the region, including breezy beach walks, intense climbs to cliffside viewpoints, and a myriad of loops through a myriad of beautiful pine forests. Ecola State Park and Hug Point might be the most popular hiking stops in the area, but I’m also a big fan of the viewpoint trail at Cape Lookout. 

If you want to incorporate some hikes into your itinerary, I’d aim for variety – like one forest hike and one beach walk, or one dune trail and one cliff climb, etc.

Viewpoints

I can’t even begin to list all the ridiculously stunning viewpoints and overlooks along the Coast. There must be hundreds. Some of them are connected to short walking trails or picnic areas, and others are just simple pull-offs that take your breath away. If you look up images of the Oregon Coast, chances are that a lot of those views will fall into this category.

I made the mistake of showing up for my trip with a massive laundry list of viewpoints, which made some sections feel like I was just stopping and going, ticking off boxes. Instead, I suggest approaching them with more flexibility – there are so many pretty views that missing a few isn’t the end of the world. 

That said, there are a couple that I definitely recommend you try to hit. The Boardman Scenic Corridor is packed with them, and I think I’d pick Natural Bridges as my top stop there. Other favorite views include Depoe Bay, Devil’s Punchbowl, and Thor’s Well.

Keep reading for tips avoiding Oregon Coast pitfalls, and Olivia's suggested 5-day itinerary.

Ten bits of important (or silly, or strange) travel news from across the web this week.

• Pizza lovers rejoice, you can now find the world’s best pizzeria in none other than… London?
  
  
• Oasis fans are planning to travel half the world away to see the band on tour next year, with searches for travel to Glasgow up +2400%. 
  
  
• From South Korea to Morocco (and yes, also Glasgow), here’s where you’ll find the coolest neighborhoods to visit in 2026.
  
  
• Things aren't looking great for Latvian airline Air Baltic, who this week filed for Chapter 11 bankruptcy, nor for Canadian budget carrier Flair, after their $76 million federal bailout.
  
  
• But there is some good news for frequent-flying AmEx card holders - American Express has opened their first Centurion Lounge in continental Europe at Amsterdam's Schiphol Airport.
  
  
• Forget the Seven Wonders of the World (sorry Stevie), we’re on a mission to tick off the Seven Wonders of Northern England.
  
  
• Ever been disappointed when you splashed out on premium economy and all you got was a little extra wiggle room? Well, as usual, Emirates are aiming to go that extra mile with privacy screens even for that extra touch of fancy. Handy if you fall out with your travel buddy, we reckon.
  
  
• The world's largest electric ferry has just arrived in its new home port in Uruguay, where it will eventually provide a 3x daily service across the water to Argentina.
  
  
• It's the end of an era, as KLM says goodbye to the classic free cheese sandwich on their short-haul flights.
  
  
• And finally, good news for impulsive bookers: Frontier is allowing passengers to cancel their bookings up to 24 hours before departure (for free!) for any reason. Like we needed another excuse to book now, think later :-)