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(Courtesy of Eagle Creek)

Upgrade Your Luggage

These four picks are built for smooth travel.

by Chris Caswell
April 22, 2025
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I admit it: One of the best things about jet charters is that you and your luggage are treated with equal respect. From the crew hand-stowing your bag on board—no tossing from 50 feet away—to the careful removal and placement at your car on arrival, your luggage travels first class.

It’s your call on hard-side or soft, but you won’t have to worry about the airline saying your bag is (check one): too big, too heavy or too expensive. Several of the following recommended bags are great options for your travel luggage, with some available as sets with matching carry-ons—so you look good coming and going. 

Mark & Graham Terminal 1 (Courtesy of Mark & Graham)

Mark & Graham Terminal 1
11.9 pounds, $369 (31-inch)

As part of Williams Sonoma, this company appreciates quality, and its Terminal 1 luggage is my personal favorite. Also available as a carry-on, the Terminal 1 stands out for its luxurious leather detailing, TSA-approved locks, polycarbonate toughness and oversized wheels. An expandable zipper is optional and every Terminal 1 comes with a lifetime warranty. If you (or an airline) break it, they’ll replace it. 

 

Lands’ End Travel Checked Rolling Luggage Bag (Courtesy of Lands’ End)

Lands’ End Travel Checked Rolling Luggage Bag
11.1 pounds, $239  (28-inch)

As a sailor, I’ve long been a Lands’ End fan and still carry a decades-old canvas briefcase that is as indestructible as this nylon four-wheeled roller. Water-repellent with two cushioned grab handles and a retractable handle, the twin polyester-lined compartments with tie-down straps help you stay organized. 

Eagle Creek Gear Warrior (Courtesy of Eagle Creek)

Eagle Creek Gear Warrior
8 pounds, $489 (30-inch)

The name “Gear Warrior” says it all. Available in carry-on and checked sizes up to 30 inches, this rolling bag is water-resistant with multiple grab handles and all-terrain wheels to get you over cobblestones and stairs. A zippered expansion panel lets you bring home goodies from your trip, while inside, organizational pockets and straps keep your clothes in place. 

 

Moore & Giles Parker
Carry-On in Baldwin Oak (Courtesy of Moore & Giles)

Moore & Giles Parker Carry-On
11.5 pounds, $1,995 (22-inch)

Finely crafting leather since 1933, Moore & Giles’ signature piece is the Parker, borrowing design elements from classic steamer trunks. With four full-swivel wheels, an oversized exterior pocket plus a ticket pocket and zippered internal partitions for optimal organization, it comes in Baldwin Oak leather that exudes understated elegance. 

Check out these Must-Attend Tampa Bay Boating Events. Or if you’d like to advertise with us, click here.

Tags: Chris CaswellexploreJet travelluggageshoppingTop Pickstravelvacation
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