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Kit: Cuba

Packing for three weeks of travel could easily balloon into roller bags, laptop cases and fanny packs. If you’re staying in luxury hotels and somebody else is handling your gear, fine.

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Packing for three weeks of travel could easily balloon into roller bags, laptop cases and fanny packs. If you’re staying in luxury hotels and somebody else is handling your gear, fine. Bring the sheepskin robe. But if you may have to spend full days carrying your luggage on your back, then you’re limited to the essentials. Here’s what I stuffed into my GORUCK GR2 for three weeks in Cuba.

50 Articles, 150 Gear Essentials, 1 Trek Across Cuba: Your Guide to Making Summer 2013 The Best Ever »


The second, larger bag from GORUCK, meant for overnights and longer. The best part about it is the maniacally efficient pocket system. See my full review here.

Buy Now: $395

GR2 Field

This is the field pocket for the GR2. It opens flat, with three internal compartments that are ideal for storing cables, headphones, flash drives and camera batteries — things that are otherwise easily misplaced. It has MOLLE webbing so you can attach it to the interior or exterior of the GR2.

Buy Now: $90

Brick Bag

It’s called the brick bag because it’s designed to carry bricks during the GORUCK Challenge, but it also serves a variety of other purposes. I used it as a camera bag in Cuba, rolling it up and stuffing it inside the GR2. If space is tight, it also also attaches to the outside of the bag via compression straps, which comes in handy if you’re using it as a dirty laundry bag.

Buy Now: $75

Straw Hat

One for mom, one for dad. I’m sticking with my backwards baseball cap.

Buy Now: $4

Asus VivoTab

Tablet plus Windows 8 laptop in one. Since there’s no wireless internet in Cuba I mostly used it to back up and sort photos. The display is razor-sharp.

Buy Now: $TBD

Canon Nifty Fifty

At $110 the Canon EF 50mm f/1.8 II is probably the best investment I’ve ever made. It’s not the best lens, and you can hear it auto-focusing from the next town over, but for the price it takes beautiful photos, especially portraits.

Buy Now: $110

Kodak Sport Disposable Camera

Obviously a better bet is a Scuba Suit, but there’s something charming and carefree about using a disposable camera. I picked this one up at a pharmacy in Mexico. They also sold Viagra there.

Buy Now: $12

Mophie Juice Pack

This is a no-brainer for travel. It doubles battery life and looks good. Sleek as it is, it does make the iPhone feel a little bulky, so I’d leave it behind on trips where there’d be guaranteed access to a power source every day.

Buy Now: $55

Snow Peak Lapel Torch

A clever alternative to a flashlight or headlamp, this handy light from Snow Peak has a magnetic clasp and a power source that clips onto your pocket.

Buy Now: $60

PocketMedic First Aid Kit

I’m always cutting myself or getting scraped up, so I pack a small first-aid kit. Doubles as a good place to store back-up cash.

Learn More: Here

Clif Shot Energy Gel

I swear by caffeinated nutrition supplements — but not so much for training (there are better alternatives). It turns out the combination of calories and caffeine makes them a good substitute for bus station breakfasts. Hey, I’m all for eating the local cuisine, but after getting sick on my last two trips I’d rather eat from a tube than collect stool samples for my doctor.

Buy Now: $1

Nuun Hydration Tablets

These are ideal if you’re traveling somewhere with unsafe drinking water. Add one iodine tablet and one of these and you’ve got safe drinking water that doesn’t taste like shit.

Buy Now: $25

Nau Carry-On Blazer

I’m not the type to travel with a blazer no matter where I’m going, but one that packs down and doubles as a water repellent bike jacket? I can get on board with that.

Buy Now: $225

Oakley Radar Path

I took heat from my friends for looking like I was going on a covert ops mission rather than vacation, but the reality is my Oliver Peoples shades haven’t seen the light of day since I got these sunglasses. They’re ultralight, customizeable for fit and lens color (pictured here with the G30) and highly impact resistant.

Buy Now: $180

Lomography Diana F+

The current iteration of a 120 format box camera from the 1960s. Light leaks and blurry photos are common — and, more to the point — the reason for using this camera.

Buy Now: $70

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