While most of the country is bundling up for snowstorms, Naples, Florida offers a far more appealing winter forecast: 75° and sunny with a breeze off the Gulf. Known for its upscale charm, white sand beaches, and vibrant cultural scene, Naples is one of the most sought-after winter destinations in the country—and for good reason.
Whether you’re planning a quick holiday getaway or an extended winter stay, here’s everything you need to know to make your winter vacation in Naples, Florida both relaxing and unforgettable.
Thinking of spending more than just a vacation in Naples? Contact me HERE to explore short-term luxury rentals or investment opportunities for your winter escape.
Where to Stay in Naples This Winter
When planning your winter vacation, location is everything. Naples offers a wide range of luxury accommodations, from five-star beachfront resorts to private homes in gated communities.
Top Neighborhoods & Resorts:
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Old Naples: Walk to 5th Avenue South, dine al fresco, and catch nightly sunsets at the Naples Pier.
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Park Shore & The Moorings: Gulf-front condos with resort-style amenities and private beach access.
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Pelican Bay & Bay Colony: Known for their beach clubs, pristine landscaping, and proximity to Waterside Shops and Artis—Naples.
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The Ritz-Carlton Naples: A world-renowned resort with full beachfront access, luxury spa, and fine dining.
Looking for a private residence or seasonal rental? I have access to exclusive homes and condos not publicly listed. Get in touch with me HERE for curated options.
What to Do: The Best Winter Activities in Naples
Naples is more than just beaches—it’s a full-service luxury lifestyle destination.
Outdoor Experiences:
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Beach Days: Visit Vanderbilt Beach, Lowdermilk Park, or Barefoot Beach Preserve.
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Golf: Over 90 courses, including Tiburón (home to PGA and LPGA tournaments), Grey Oaks, and Old Collier.
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Boating & Fishing: Charter a boat for the day or enjoy sunset cruises out of Naples Bay.
Culture & Shopping:
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5th Avenue South & 3rd Street South: Luxury boutiques, art galleries, and restaurants.
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Artis—Naples: Catch performances by the Naples Philharmonic and Broadway-caliber shows.
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Mercato & Waterside Shops: Top-tier shopping, rooftop bars, and winter events.
Curious about the seasonal event calendar? Subscribe to my newsletter HERE for updates on winter happenings in Naples, Florida.
Where to Dine: Naples’ Culinary Scene Shines in Season
From fresh seafood to white-tablecloth fine dining, Naples offers no shortage of top restaurants.
Don’t Miss:
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The French (for champagne and deviled eggs)
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Sea Salt (on Third Street for upscale coastal cuisine)
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Baleen (for beachfront dining at LaPlaya)
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Osteria Tulia (Italian farmhouse flavors)
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Campiello (an Old Naples favorite with courtyard seating)
Want a local’s guide to the top restaurants in Naples? Check out my blog on dining hotspots or follow me on Instagram @NaplesJamie_RealEstate.
Tips for Planning Ahead
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Book Early: Winter is peak season in Naples, and properties go fast—whether it’s a rental, a tee time, or dinner reservations.
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Pack Smart: Think linen, sunhats, and sandals. Winter here means beach weather.
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Extend Your Stay: Many visitors fall in love with Naples and end up purchasing a second home or making the move full-time.
Considering a winter home in Naples, Florida? Let’s schedule a private consultation to explore your options. Click here to connect.
Final Thought
Planning your winter vacation in Naples, Florida isn’t just about escaping the cold—it’s about upgrading your lifestyle. From the moment you land at Naples Airport to the sunset on your final evening, every detail can—and should—be elevated. That’s what Naples offers: sun-drenched days, refined living, and effortless relaxation.
Start planning your winter escape today. Whether you're booking a stay or buying a home, I’m here to help you make it seamless.
📲 Contact me today
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