The first Monday of the year always feels like a fresh start—a blank page waiting to be filled with new adventures, new memories, and hopefully a lot more travel. As I sip my coffee in New York City, bundled in layers against the bitter chill, I can’t help but find myself daydreaming about sandy beaches and balmy breezes. Naturally, my browser history is already filled with flight searches to sun-soaked destinations. Because let’s be honest: when winter tightens its icy grip, a girl has to escape somehow.
This time, my heart is set on Puerto Rico.
It’s been years since I last visited, and even longer since the devastating hurricane reshaped the island. Returning now feels both exciting and meaningful—I can’t wait to see how the island has rebuilt and to explore treasures like Vieques, Flamenco Beach in Culebra, and the lush El Yunque National Forest. And while the sights, sounds, and flavors of Puerto Rico are enough to entice anyone, you know me: part of the thrill is also planning what to wear.
So as I prep for my five-day, four-night escape to San Juan, I thought I’d share what’s in my virtual shopping cart—just in case you, too, are plotting a winter beach getaway.
The Travel Mindset
Packing for a tropical vacation in the dead of winter is an instant mood booster. There’s something wonderfully defiant about folding breezy dresses and swimsuits while snow falls outside your window. Resort wear is colorful, light, and joyful—the exact opposite of the black puffer coats and knit scarves that dominate New York streets this time of year.
For me, vacation style is about two things: versatility and ease. Every piece has to pull double duty—something I can wear while exploring during the day but also style up for dinner or a night out. And, of course, it all has to fit neatly in a carry-on.
Resort Wardrobe Essentials
Here’s what I’m bringing along to San Juan:
1. Breezy Day-to-Night Dresses
Nothing says vacation like a dress that takes you from sightseeing to sunset cocktails. I’m packing lightweight maxi and midi styles in bold colors and tropical prints. Think breathable fabrics that move with the breeze—perfect for wandering Old San Juan or dining alfresco by the beach.
2. Chic Swimwear (and Lots of It)
Let’s be real: swimsuits are the backbone of any beach trip. I’ve stocked up on both one-piece suits with playful cutouts and mix-and-match bikinis in bright shades. A good cover-up or two is a must—something sheer enough for the pool but chic enough for a beachside café.
3. Sandals That Do It All
Shoes can easily weigh down your suitcase, so I’m keeping it minimal: one pair of flat sandals for strolling, one dressier pair for dinners, and a pair of espadrilles for when I want a little extra height without sacrificing comfort.
4. Statement Accessories
Oversized sunglasses, woven straw hats, and bold earrings are not just outfit-makers—they’re space savers, too. A few key accessories can completely transform a simple sundress, so they’re always the first things I toss into my bag.
5. Activewear for Adventure
Puerto Rico isn’t just about lounging on the sand. With hiking trails in El Yunque National Forest, I’ll need breathable leggings, supportive sneakers, and a light rain jacket. Packing these ensures I’m ready for every kind of experience, from rainforest treks to waterfall dips.
Dining, Dancing, and Dressing Up
Part of my excitement about returning to Puerto Rico is indulging in its vibrant food scene. San Juan is buzzing with incredible restaurants, and I plan to dress for the occasion. For evenings out, I’m bringing flowy midi skirts, silky camisoles, and one standout dress for a fancier dinner. With the right heels and a swipe of red lipstick, even a simple dress becomes vacation-ready glam.
And of course, I’m leaving room in my suitcase. Puerto Rico is known for its artisan markets and local boutiques—I fully intend to come home with a few new treasures.
The Joy of Planning
Half the fun of travel, for me, is in the anticipation. Curating outfits, planning adventures, and picturing myself stepping off the plane into warm Caribbean air gives me the energy to push through New York’s frostbitten mornings. It’s not just about the clothes; it’s about preparing for a mindset shift—a chance to slow down, explore, and savor every moment without the rush of daily routines.
And after years of longing to return, Puerto Rico feels like the perfect place to begin a year of travel with intention and joy.
Final Thoughts
If you’re also dreaming of escaping the cold, I hope this little packing list inspires you to book that trip—whether it’s to Puerto Rico, Miami, or another sunny escape. Don’t overpack, choose versatile pieces you love, and remember: the goal isn’t to have the “perfect” wardrobe but to feel free and comfortable wherever your adventures take you.
As for me, I’ll be the one in a breezy caftan, sandals in hand, sipping a margarita while the waves lap at my feet. And trust me—when the New York chill feels unbearable, nothing warms you up faster than knowing your next beach getaway is only a flight away.
