Osprey's Transporter duffel-to-backpack convertible (on his back), Ex Officio's Double Haul Shorts (his), Nike's ACG Air Trigo (his), Timberland's Trek Compactor 30 (wheeled behind him), and Victorinox Swiss Arm E-Motion 360-Degree Trek Pack Plus
Here's my tripartite schlepping strategy for virtually any adventure journey: Pack one primary duffel, rolling bag, or convertible pack and check it. Pack a daypack with in-flight paraphernalia like books and spillover from the big bag, and wear it. Inside it, or dangling from a shoulder, is my nerve-center bag containing tickets, passport, camera, and notebook.
Wheeled bags make packing decisions easy: If you think you need it, bring it. At 7,100 cubic inches, the Gravis Convoy Roller ($299) is a beast of a duffel. The top flap peels away lengthwise to reveal the main compartment without any annoying flaps to hinder the search for your duds. Inside are niches for a toiletry kit and laundry bag (both included), while a separate lower compartment stashes two pairs of hiking boots with room to spare. JanSport's 28-inch Wheeled Footlocker Duffel (6,000 cubic inches, $180) utilizes a new cushy gel-filled shoulder pad and a different two-story configuration; beneath a midfloor is a full-length basement that isolates damp and smelly snorkeling gear from the upper tier, where your linen shirts store nicely. If you prefer one giant compartment, just zip away the divider. Timberland's Trek Compactor 30 (5,600 cubic inches, $200) has an inner structure that lends the bag rigidity when open, yet collapses flat for storage. No surprise that the Victorinox Swiss Army E-Motion 360-Degree 20-inch Trek Pack Plus (4,050 cubic inches, $325) has multiple "blades." It's a roller that converts to a backpack with sculpted, padded waist straps and an internal frame that follows the curve of the spine. Torso length is nonadjustable, but the bag comes in three sizes. Three docking bagsdaypack, lumbar pack, and shoulder bagattach to the mother ship. Osprey's Transporter (5,400 cubic inches, $134) duffel-to-backpack convertible is refreshingly simple. It uses foam-padded sidewalls to envelop one big compartment, and the harness is equally simplemaybe too simple, since it lacks waist-belt paddingbut it's easily adjustable for torso length. As for nerve-center bags, opt for one of these three. The Timberland Comrade II Shoulder Bag ($45) is just big (and padded) enough for a point-and-shoot and the usual travel ephemera, and it converts to a lumbar pack. The Gravis Checkpoint ($50) is bigger, and the "peat" color looks pleasingly like fish scales but is urbanized with pouches for cell phone, PDA, and minidisc. Patagonia's Atom ($70) raises the style bar for shoulder bags. It amounts to a teardrop-shaped half-daypack that you sling snugly over one shoulder a la bota bag.
Pack a quick-drying synthetic long-sleeve shirt and a pair of convertible trousers that zip down to shorts, and you've got yourself a full travel wardrobe. A good start: The North Face's T-Cargo Pant ($69) and A/T Ventilation Shirt ($79). The soft nylon pant features huge side cargo pockets and a zippered interior pocket that functions as a built-in passport pouch. The stretch-woven shirt has a smidgen of give and breathability, extra ventilation by way of armpit zips and a mesh back yoke, and a pass-for-dress-shirt look. Alternatives: The Sportif Wind Knot Shirt ($62) also has underarm zips and back yoke, with added utility in the form of roomy pleated pockets, roll-up sleeve tabs, and a sun-protective collar. The L.L. Bean Stretch Guide Pant ($125) lacks zip-off leggings, but its Schoeller Dryskin stretch-woven nylon (with CoolMax lining against the skin) is the ultimate travel-pant confection: light, breathable, and quick-drying. Or go with shorts like Ex Officio's peach-fuzz-soft, six-pocketed Double Haul Short ($48). For women, the svelte nylon Nike ACG Girl Convertible Skirt ($60) transfers the zip-off concept to a more feminine form. Whether you go ankle-length modest or short and gammy, you get pockets and a hidden security pouch. In the undergarment department, Ex Officio is reigning king: The ExO Active Tee ($38) is amazingly light and dressy, and the new ExO Give 'n Go Stretch Briefs for men and women ($18, $16) are the quickest-drying undertrou out there.