If you haven’t figured it out by now, this column is all about the things that help make travel better and easier. Yes, the experiences you have and the people you meet along the way are far more important than any piece of equipment, but good gear can enhance those things by quietly doing its job and making your life easier.
When something doesn’t work right—a zipper breaks, a wheel on your roller bag falls off, a backpack strap digs into your shoulder—it can put a damper on your trip.
If you’re ready to quit dealing with your bags and spend more time adventuring, here’s the complete luggage system you should use.
Carry-On
Osprey Sojourn ($300)
I love because of how versatile it is. I’ve never had a problem fitting it in an overhead bin, and last year. The fact that it converts into a backpack is especially nice for off-the-beaten-path travel when you can’t wheel your suitcase. The suspension system, inspired by the company’s Anti-Gravity backpacks, makes it nicer to carry than any other convertible bag I’ve tried.
Backpack
Gregory Border 25 ($119)
There’s a reason I’ve written about the before: it’s my all-time-favorite travel backpack. It’s just the right size and has a really neat, clamshell-style laptop and tablet sleeve that opens easily for airport security. There are also plenty of pockets for organization, and the back panel can slide over the handle of your wheeled luggage. There’s nothing not to like.
Duffel Bag
The North Face Medium Base Camp Duffel ($139)
Duffel bags hold more stuff than their hard-sided counterparts, and they’re definitely the best way to pack for a road trip. The is my favorite, not only because of how bombproof it is but because the end cap’s zippered compartment allows you to separate wet clothes or dirty gear from the rest of your belongings. It’s super handy. This year’s version has been updated with new carrying handles that make it easier to schlep over short distances.
Large Rolling Suitcase
Eagle Creek ORV Trunk 30 ($379)
Everybody needs at least one giant roller bag. Whether you’re moving to a new city, heading out to explore another country for two months, or just have trouble packing light, they serve a purpose. I’ve used Eagle Creek gear for the last 15 years, and if you told me I could only choose one company to buy luggage from for the rest of my life, it’d be this one. Its is one of the best in the industry, but you may never need it because the stuff lasts. The is a beast of a suitcase. Smart features, like an expandable wet-dry compartment, padded sleeves for electronics, and an “equipment keeper” that holds gear to the top of the bag, make it perfect for big adventures.
Toiletry Bag
Topo Designs Dopp Kit ($34)
I prefer . Large, hanging ones with all the pockets and zippers are fine for some people, but those encourage you to bring too much stuff. This one is as minimalistic as it gets, with one main compartment that’s lined with water-resistant material. It won’t take up a lot of room in your bag, and the Cordura exterior means it’ll stand up to plenty of abuse.
Sea to Summit Traveling Light RFID Neck Pouch ($24)
I’m not a huge fan of neck pouches, those little bags hanging down like a big necklace, but they’re a great way to keep your passport and other important documents together when traveling overseas. has three pockets for organization, and it’s lightweight, unobtrusive, and lined with RFID-proof fabric.