TRAVEL & LEISURE | JANUARY 2026
What to Pack for a Resort Vacation This Winter?
All Things Tommy Bahama
When the temperature dips and your breath turns to mist, there’s no better feeling than jetting off somewhere warm. January and February are peak “escape months,” and a resort getaway offers the perfect antidote to chilly winds and gray skies. Before you slip into vacation mode, let’s talk about all the warm-weather getaway essentials to pack so you can transition from winter coats to mai tais in paradise.
Resort Style Tips for Sunny Days & Breezy Nights
Even in paradise, evenings can bring a cool breeze. Pack lightweight travel essentials—think a linen button-down or a soft cotton sweater—to layer over your daytime looks. During the day, easy-breezy linen shirts, relaxed shorts, and flowy sundresses will keep you cool and comfortable. Choose fabrics that breathe, dry quickly, and move with you from pool to bar.
Swimwear That Doubles as Style
A good resort wardrobe revolves around versatile swimwear (think reversible styles that play double duty). Pack at least two swimsuits so you always have a dry option. Pair them with a chic beach coverup for an effortless transition from lounging shoreside to grabbing lunch al fresco.
Footwear for Every Occasion
Sandals are a must—they’re comfortable for beach walks yet stylish enough for resort dinners, especially the ones from our partner in paradise, OluKai®. Add one pair of casual sneakers for exploring and flip-flops for poolside lounging. If your getaway involves upscale dining, pack dressier shoes or wedges to elevate your evening look.
Don’t Forget the Sun Protection!
You might have your OOO notifications on, but the sun doesn’t take vacations. Bring a wide-brim hat, polarized Maui Jim® sunglasses, and reef-safe sunscreen to protect your skin. If you plan on marking your spot in the sand, bring a lightweight beach towel, an easy-set-up beach umbrella, and a water bottle so you can call the beach your home for a couple hours.
Resort Vacation Packing List
Before you take off, save this list to ace your next tropical escape, whether it’s for a beach vacation or a resort getaway.
- Linen shirts and shorts
- Lightweight dresses
- Two to three swimsuits
- Beach coverups
- Wide-brim hat and polarized sunglasses
- Reef-safe sunscreen and aloe vera gel
- Sandals, flip-flops, and casual sneakers
- Lightweight sweater or wrap for cool evenings
- Beach towel
- Small crossbody bag for day trips
- Reusable water bottle for staying hydrated
With the best resort wear and tropical travel essentials for sunny destinations, you’ll be ready to trade snow boots for sandy toes and let your worries melt away under the sun. After all, paradise is just a packing list away.