Penny Planner

Out & About

Your weekly guide to fun within an hour of Naples

Written by Penny Planner

Welcome to Out & About! Penny Planner is your go-to guide for things to do within an hour of Naples. Visiting grandkids? Penny's got you. Looking for a couples' day out? She's on it. Penny checks the weather, thinks about who you're with, and gives you real, practical suggestions — not tourist traps. Every pick includes directions, costs, and tips from someone who actually goes to these places.

What You Get Every Week

  • 2-3 top picks for adults and couples each week
  • Dedicated 'With the Grandkids' section every issue
  • Weather-aware suggestions (indoor when it's hot!)
  • Activities within 1 hour of Naples
  • Real costs, real directions, real tips
Your Sunny Guide to Fun: Out & About This Week!
Latest ColumnSunday, March 29, 2026

Your Sunny Guide to Fun: Out & About This Week!

Get ready for a fantastic week in Naples with perfect weather for exploring, plus some indoor gems for those sprinkles!

This week, Penny Planner has your guide to making the most of Naples' beautiful weather, from stunning gardens to thrilling airboat rides, and fantastic fun for the grandkids too!

Read the Full Column

Upcoming Events

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Art walks, farmers markets, festivals, and fun — all within an hour of The Quarry

Family FunToday Kid-Friendly

Naples Zoo Free Day – Collier County Residents

Naples Zoo at Caribbean Gardens opens free to all Collier County residents. Bring a valid ID showing your Collier County address. Explore the zoo, take a boat ride, and enjoy wildlife encounters.

9:00 AM – 5:00 PMNaples Zoo at Caribbean Gardens Free for Collier County residents More Info
Arts & CultureToday Kid-Friendly

Naples Art – Art in the Park

Outdoor juried art show featuring local and regional artists displaying paintings, sculptures, photography, glass, and jewelry in beautiful Cambier Park.

10:00 AM – 4:00 PMCambier Park Free More Info
Food & DrinkToday Select Saturdays

Feast on 5th: Naples Food Tour

Experience Naples' renowned Italian melting pot as you stroll 5th Avenue South, tasting diverse areas of Italy at distinctive restaurants that showcase the city's international fine dining reputation.

11:30 AM – 2:30 PMFifth Avenue South Ticketed More Info
Arts & CultureToday

9 to 5 – The Musical

An uproarious and uplifting musical by The Naples Players that will have you laughing, singing, and rooting for the underdogs. Based on the hit movie, this show is pure fun.

7:30 PM – 10:00 PMKizzie Theater (The Naples Players) $45–$55 More Info
Live MusicThu, Apr 9 Kid-Friendly

Evening on Fifth

Fifth Avenue South comes alive with live music, street performers, open-air dining, and a festive atmosphere. Stroll the avenue and enjoy the energy of downtown Naples.

6:30 PM – 9:30 PMFifth Avenue South Free More Info
Sports & RecreationSat, Apr 11 Kid-Friendly

US Open Pickleball Championships – 10th Anniversary

The world's largest pickleball tournament returns to Naples for its 10th anniversary. Watch top players from around the globe compete across all skill levels. Food vendors, exhibitions, and clinics available.

All DayEast Naples Community Park Spectator passes available More Info
Food & DrinkSat, Apr 11

Blooms & Brews

An evening of craft beer, local bites, and live music set among the stunning gardens. Explore themed garden areas while sampling brews from regional breweries.

6:00 PM – 9:00 PMNaples Botanical Garden Ticketed More Info
CommunitySat, Apr 11

Naples Social Club Sunset Social

Bring your friends and have fun at this casual sunset gathering. BYOB and bring your own food. Live music, games, and great company as the sun sets over the Gulf.

6:30 PMSeagate Beach Free (BYOB)