After years of braving the icy grip of Connecticut winters, I can say with confidence: Naples, Florida feels like stepping into a dream. My move from the Northeast wasn’t just about swapping zip codes—it was trading snow shovels for sunsets, icy commutes for sandy toes, and gray skies for year-round sunshine.
In Connecticut, winter always overstayed its welcome. December to June felt like one long stretch of gray skies, slush, and bone-chilling cold. Sure, fall had its charm—crisp air, vibrant leaves—but it was short-lived, and by November the snow boots were back out. Now? I can still get my autumn fix on a quick trip north, but I no longer have to endure the six-month freeze.
Holidays, Naples Style
Forget snowdrifts and frozen sidewalks. The holiday season here has its own kind of magic. Naples glows with palm trees wrapped in white lights, festive displays across neighborhoods, and events that make you forget snow was ever part of the equation.
Highlights I look forward to every year:
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Snow on Third Street South (yes, they make it snow in December—minus the frostbite).
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The Naples Holiday Boat Parade, where yachts and sailboats sparkle with lights while music drifts across the water.
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Outdoor shopping and dining in perfect 70-degree weather—no heavy coats required.
The Summer Question
People often ask: But what about the heat? Yes, Naples summers are hot and humid—but so are summers in New York, Boston, and Connecticut. The difference? Naples living adjusts with ease. Mornings and evenings are prime time for walks, bike rides, or the beach. Afternoons are for pools, AC, or catching a matinee. Plus, that summer heat is a trade I’ll happily make for mild, breezy winters when the rest of the Northeast is shoveling driveways.
Hurricanes: The Reality Check
Let’s not gloss over it—hurricanes are part of Florida life. But they’re also something you prepare for. Communities here have systems in place, from shutter installations to evacuation plans. Living through Hurricane Ian was sobering, but it also revealed something powerful: the resilience and togetherness of the Naples community.
The Lifestyle Upgrade
Looking back, moving to Naples is one of the best choices we ever made. We’ve embraced outdoor living—beach mornings, sunset happy hours, boating with friends, pickleball, golf, and so much more. We’ve built a circle of incredible friends, and our days feel fuller, lighter, and brighter. My only regret? Not making the leap sooner.
Thinking About Your Own Winter Escape?
If you’re stuck in another Northeast winter, bundled in layers and dreaming of warmth, Naples may be exactly the reset you need. Whether it’s a cozy condo for seasonal escapes or a full-time home by the beach, this paradise is ready when you are.
