Naples doesn't slow down in late January, if anything, it gets better.
This week is stacked with easy wins: a great meal, a sunny stroll, and live music that feels like a mini-vacation.
Pick one or two from the list below and lock them in before the good spots (and good moods) get taken. |
We recommend confirming details with event hosts for the most current information. |
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🍽️ Food & Dining |
🔗 2nd Annual Winter Wine Festivus For The Rest Of Us
📅 Date: Thursday, January 29, 2026
⏰ Time: 5:45 PM
📍 Location: Rebecca's Naples
✨ Details: A cozy winter wine night with pours, bites, and plenty of good conversation. |
🔗 Stone Crab Saturdays at Celebration Park
📅 Date: Saturday, January 31, 2026
⏰ Time: 10:00 AM
📍 Location: Celebration Park Naples
✨ Details: A laid-back Saturday stop for stone crab and waterfront food-truck vibes. |
🔗 Chef Gaspard's Beef Wellington
📅 Date: Sunday, February 1, 2026
⏰ Time: 11:00 AM
📍 Location: 1234 8th St S, Naples, FL, United States, Florida 34102
✨ Details: A special dining feature built around a classic Beef Wellington-perfect for a treat-yourself night. |
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👨👩👧👦 Family Activities |
🔗 SW FL Muscle Car Show
📅 Date: Saturday, January 31, 2026
⏰ Time: 9:00 AM
📍 Location: North Collier Regional Park, Naples
✨ Details: A fun walk-through of classic cars and proud local owners-bring your camera. |
🔗 Art In The Park
📅 Date: Saturday, January 31, 2026
⏰ Time: 10:00 AM
📍 Location: Cambier Park
✨ Details: A relaxed park stroll with local art, vendors, and that easy Naples weekend energy. |
🔗 ❄️🐾 Winter Pet Fest is Coming! 🐾❄️
📅 Date: Saturday, January 31, 2026
⏰ Time: 12:00 PM
📍 Location: Smilin' Dog Bakery
✨ Details: A pet-friendly afternoon with vendors, treats, and plenty of wagging tails. |
🔗 Interpreted Show: Agatha Christie's The Mousetrap
📅 Date: Saturday, January 31, 2026
⏰ Time: 2:00 PM
📍 Location: Gulfshore Playhouse
✨ Details: A night at the theater with Agatha Christie's famous whodunit-full of twists and suspicion. |
🔗 Naples Gators Football & Cheer Conditioning Event
📅 Date: Saturday, January 31, 2026
⏰ Time: 4:00 PM
📍 Location: Fleischmann Park
✨ Details: A high-energy session for football and cheer-great for shaking off the week and getting moving. |
🔗 SWFL Critical Mass Naples Ride
📅 Date: Saturday, January 31, 2026
⏰ Time: 7:00 PM
📍 Location: Gordon River Greenway Parking Lot 1596 Golden Gate Pkwy Naples, FL 34105
✨ Details: A group ride that turns the streets into a moving block party-lights and helmets recommended. |
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Adventure outside the ordinary |
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Trusted specialty outdoor retailer, REI Co-op, has teamed up with the world's largest adventure travel company, Intrepid Travel, to create a collection of active trips. From farm stays in Costa Rica to sunrise summits on Kilimanjaro, each trip is led by a local expert with small group sizes capped at 16. |
Find your next adventure |
For T&Cs and to view the full collection of trips in 85+ destinations, visit rei.com/travel. |
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🎶 Concerts & Live Music |
🔗 The Real Macaw Welcomes back The Kennedys as part of the Winter Concert Series 2026
📅 Date: Monday, January 26, 2026
⏰ Time: 7:00 PM
📍 Location: The Real Macaw
✨ Details: Live music from The Kennedys-classic-rock energy and a great crowd. |
🔗 The Kennedys in Concert
📅 Date: Monday, January 26, 2026
⏰ Time: 7:00 PM
📍 Location: 3275 Bayshore Dr, Naples, FL, United States, Florida 34112
✨ Details: Live music from The Kennedys-classic-rock energy and a great crowd. |
🔗 Pickle Money LIVE! at Whiskey Park on Fri, Jan 30 at 8pm
📅 Date: Friday, January 30, 2026
⏰ Time: 8:00 PM
📍 Location: Whiskey Park
✨ Details: A loud, upbeat live set-expect a packed room and strong Friday-night energy. |
🔗 WORSHIP NIGHT | NAPLES
📅 Date: Saturday, January 31, 2026
⏰ Time: 6:00 PM
📍 Location: 2132 Shadowlawn Dr, Naples, FL 34112-4847, United States
✨ Details: A warm community night with live worship music and space to reset. |
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🔗 Olde Naples Hotel Job Fair
📅 Date: Monday, January 26, 2026
⏰ Time: 11:00 AM
📍 Location: Edgewater Beach Hotel
✨ Details: A straightforward chance to meet recruiters, ask questions, and explore open roles. |
🔗 LCBW WOMAN ON THE MOVE - Naples Chapter
📅 Date: Tuesday, January 27, 2026
⏰ Time: 11:30 AM
📍 Location: Carrabba's Italian Grill (4320 N Tamiami Trail, Naples, FL)
✨ Details: A community meet-up focused on connection and momentum-perfect for a fresh start to the week. |
🔗 2026 Chamber Annual Meeting: Celebrating Together - Together in Spirit. Stronger in Purpose
📅 Date: Thursday, January 29, 2026
⏰ Time: 7:00 AM
📍 Location: Hilton Naples
✨ Details: A big community meet-up for local business leaders-updates, connection, and celebration. |
🔗 Grand Opening - Modern Wave Cabinetry & Design
📅 Date: Thursday, January 29, 2026
⏰ Time: 5:00 PM
📍 Location: 975 Creech Rd, Naples, FL, United States, Florida 34103
✨ Details: A grand-opening stop to meet the team, check out the space, and celebrate something new in town. |
🔗 CBIA Building Industry Panel
📅 Date: Thursday, January 29, 2026
⏰ Time: 5:30 PM
📍 Location: Hilton Naples
✨ Details: An industry conversation and Q&A-good for anyone who likes the 'why' behind what's being built. |
🔗 January Ladies Connect
📅 Date: Friday, January 30, 2026
⏰ Time: 6:00 PM
📍 Location: Wilshire Lakes Clubhouse & Pool
✨ Details: A friendly networking meet-up-come as you are, leave with a few new contacts. |
🔗 Now Touring Onsite, Walk The Homes, Feel The Space in Naples, Florida
📅 Date: Saturday, Jan 31 - Sunday, Feb 1, 2026
⏰ Time: All day / varies
📍 Location: Kings Lake Square Publix Plaza, 4888 Davis Boulevard, Naples, FL 34104
✨ Details: A touring weekend to walk through homes, get a feel for the area, and ask on-the-spot questions. |
🔗 Realtors Join Us OnsiteWalk The Homes Feel The Space
📅 Date: Saturday, Jan 31 - Sunday, Feb 1, 2026
⏰ Time: All day / varies
📍 Location: Kings Lake Square Publix Plaza, 4888 Davis Boulevard, Naples, FL 34104
✨ Details: A touring weekend to walk through homes, get a feel for the area, and ask on-the-spot questions. |
🔗 St. Sava Gala 2026
📅 Date: Sunday, February 1, 2026
⏰ Time: 5:00 PM
📍 Location: Glen Eagle Golf & Country Club
✨ Details: A dressed-up evening with community spirit-expect a lively room and a meaningful cause. |
⚠️ Please verify event details and availability with the respective venues or organizers, as schedules may change. |
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Naples, Florida News Highlights |
🔗 Conservation groups threaten lawsuit over Collier County development, cites risk to Florida panthers
Conservation groups say the proposed Rural Lands West project could violate the Endangered Species Act and shrink key panther habitat east of Golden Gate Estates, with plans that could bring roughly 9,000 homes plus a town center and commercial space. |
🔗 FWC confirms second panther death of 2026
State wildlife officials confirmed another Florida panther was killed in a vehicle strike in Collier County, underscoring how dangerous road crossings remain for the species. |
🔗 Naples approves Pride Fest permit for 2026, keeps indoor drag show requirement
City leaders approved the 2026 event permit while keeping the requirement that drag performances be held indoors, continuing a debate over how the festival is structured. |
🔗 2026 Naples St. Patrick's Day Parade makes official return following cancellation
Organizers confirmed the St. Patrick's Day Parade is officially coming back, bringing back a long-running tradition that had been canceled. |
🔗 Naples city leaders holding open house to discuss parks and recreation master plan
The city is updating its parks and recreation master plan and is inviting residents to a public open house to weigh in on priorities for amenities, programming, and future improvements. |
🔗 Supervisor of Elections Office Announces Canvassing Board Schedule for the City of Naples Election
Election officials published the Canvassing Board schedule (including the logic-and-accuracy test and ballot canvassing) and noted the meetings are open to the public at the elections office on Enterprise Avenue. |
🔗 1 injured after destructive house fire in East Naples
Fire crews responded to a destructive house fire in East Naples and officials reported one person was injured as investigators worked to determine what sparked it. |
🔗 Naples roommate killer kicked from courtroom for outburst before receiving life sentence
A Naples woman convicted of second-degree murder was removed from the courtroom after repeated outbursts and was sentenced to life in prison. |
🔗 Southwest Florida homeless coalition concerned about possible changes, cuts to federal funding
A regional homeless-services coalition said it's still waiting on two grants tied to Collier County and worries shifts or cuts in federal support could worsen homelessness pressures locally. |
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