Packing Essentials for Your Weekend Trip to Key West

Weekend Trip

Even the most experienced traveler can sometimes have a hiccup and flounder when it comes to packing for a short trip to Key West for a long weekend. Packing for a short vacation is actually more challenging because you want to bring only the essentials–it’s silly to lug a huge suitcase for three days filled with items you won’t use but feel the need to bring “just in case.” Instead, use this guide to pack light yet smart so you can save your energy for sightseeing, swimming and snorkeling, fine dining, and more. 

A Brimmed Hat and Sunglasses

While you may not use either of these things every day at home, the sun in Florida may be stronger than you’re used to. A sunburn will certainly take away from your enjoyment of Key West, and a peeling sunburn–especially if it’s on your scalp–is unsightly. Not only does it come in handy when simply walking around the city, but you’ll be relieved you packed it when you book a fishing charter excursion with All In Fishing Charters. Even a half-day on the water can leave you overwhelmed by the sun if you’re not protecting your skin and eyes. Consider taking a packable or crushable hat so it can be packed into the smallest corners of your suitcase, carry-on, purse or backpack. 

Comfortable Walking Shoes

Key West is a relatively small island city, just a few square miles. Many people bike around, and depending on where you stay, many attractions are accessible by walking. Pack a pair of sneakers, shoes or sandals that you can bike or walk in all day. You’ll want to be able to enjoy the food at Eaton Street Seafood Market and Restaurant or the small bites as part of a food tour or the spooky stories on your ghost tour. If your feet hurt, you’ll just be distracted and less likely to enjoy touring the Conch Republic. Consider picking a slip-resistant pair; this is especially important if you’re going to be on a boat, which is pretty likely in Key West. Among the top activities are taking charter sandbar, sunset or fishing trips and taking the ferry to Dry Tortugas National Park; slip-resistant shoes will reduce your chances of falling and getting injured–not how you want to spend your vacation.


It probably goes without saying, but a swimsuit should probably be the first thing you pack. You’ll need it of course if you’re going to Dry Tortugas National Park or one of the local beaches for snorkeling. But even if you prefer to stay on this side of the water, activities like kayaking can get wet, and even sunbathing, you’ll probably feel more comfortable in a swimsuit. If you have two, it’s smart to bring one you know you can be athletic in without it moving out of place, and another for casual, lounging wear. 

Dressy Clothes

While Key West is well-known for its laid-back vibe, it’s also home to a wide range of upscale fine dining restaurants, and short or a sundress aren’t going to cut it. If you think you may want to go out to dinner to celebrate an anniversary, birthday or just to rekindle the romance of your dating days, bring along a dress and suit or shirt and tie, at a minimum. The high-end ambiance and chef-prepared meals that showcase fresh-caught seafood are worth the effort of dressing up. 

Waterproof Pouch for Your Mobile Phone

Whether you’re swimming at Fort Zachary Taylor State Park, Dry Tortugas National Park or enjoying a sandbar charter, you’ll want to take pictures but still protect your phone. Find one that includes a lanyard so you can have your hands free if needed. Consider testing it–with something other than your phone, of course–at home before you travel because it would be awful to think you’ve got great photos of coral reefs and shipwrecks only to pull out a waterlogged mobile phone. 

A Crossbody or Belt Bag

Of course, traveling presents certain risks when it comes to pickpocketing or simply losing your wallet or purse because you fumble putting it away. A crossbody or belt bag allows you to keep your wallet and other valuables right in front of you, minimizing the potential for someone to lift them when you’re not paying attention or purposely distracted by a thief. These bags also come in handy when you want to go hands-free on a walking tour, fishing expedition or other kind of excursion. 

Avoid the hassle of being inconvenienced by going without or wasting valuable time shopping for essentials on your vacation by including these items in your suitcase or carry-on bag. While many of them appear to be common sense things, it’s easy to overlook even items you use everyday when packing. A list like this is a great way to make sure you are ready for every adventure and the joyful, last-minute opportunities that make travel so exciting.