The Naples Retreat / Naples guides
Naples events calendar, 2026-2027
The festivals, tournaments and holiday events that bring visitors to Naples each year, month by month, with dates, venues and drive times from north Naples.
Naples' event season runs from October to April, when the weather is dry and mild. Big weekends fill fast, so it pays to know the dates before you book. Below is every major recurring event we track, with the next date we could confirm. Each one links to a full guide with tickets, parking and tips.
Drive times are estimates from north Naples (Pine Ridge Rd & Logan Blvd) without traffic. Winter traffic on US-41 and I-75 can add 10 to 20 minutes. Dates were checked in October 2026. Organizers change them, so confirm on the official site before you book.
October
| Event | Next date | Where | Drive |
|---|---|---|---|
| Naples Stone Crab Festival | Oct 23-25, 2026 | Tin City & Naples Bay | ~20 min |
| Florida Everblades hockey (home season) | Oct 17, 2026 - Apr 10, 2027 | Hertz Arena, Estero | ~25 min |
November
| Event | Next date | Where | Drive |
|---|---|---|---|
| CME Group Tour Championship (LPGA) | Nov 19-22, 2026 | Tiburón Golf Club | ~15 min |
| Third Street South tree lighting | Nov 23, 2026 | Third Street South | ~25 min |
| Night Lights in the Garden | Nov 27, 2026 - Jan 3, 2027 | Naples Botanical Garden | ~25 min |
| Art in the Park | Nov 28, 2026 | Cambier Park | ~20 min |
December
| Event | Next date | Where | Drive |
|---|---|---|---|
| Christmas Walk on Fifth Avenue | Dec 4-5, 2026 | Fifth Avenue South | ~25 min |
| Naples Christmas Parade | Dec 8, 2026 | Downtown Naples | ~25 min |
| Grant Thornton Invitational (PGA TOUR + LPGA) | Dec 11-13, 2026 | Tiburón Golf Club | ~15 min |
| Christmas Boat Parade | Listed for Dec 19, 2026 | Naples Bay | ~25 min |
January
| Event | Next date | Where | Drive |
|---|---|---|---|
| New Year's fireworks | Jan 2, 2027 | City of Naples shoreline | ~25 min |
| Naples New Year's Art Fair | Jan 2-3, 2027 | Cambier Park | ~20 min |
| Bonita Springs National Art Festival | Jan 9-10, 2027 (also Feb 6-7, Mar 6-7) | Riverside Park, Bonita Springs | ~25 min |
| Naples Boat Show | Jan 21-24, 2027 | Sugden Regional Park & City Dock | ~25 min |
| Swamp Buggy Parade & Winter Classic | Jan 23-24, 2027 | Downtown / Florida Sports Park | ~20-25 min |
| Naples Winter Wine Festival | Jan 29-31, 2027 | The Ritz-Carlton, Tiburón | ~15 min |
February
| Event | Next date | Where | Drive |
|---|---|---|---|
| Chubb Classic (PGA TOUR Champions) | Week of Feb 8-14, 2027 | Tiburón Golf Club | ~15 min |
| Red Sox & Twins spring training | From Feb 19, 2027 | Fort Myers | ~30-35 min |
| Naples National Art Fair | Feb 19-21, 2027 | Cambier Park | ~20 min |
| Everglades Seafood Festival | Feb 19-21, 2027 | Everglades City | ~45-50 min |
| Swamp Buggy Spring Classic | Feb 28, 2027 | Florida Sports Park | ~25 min |
March
| Event | Next date | Where | Drive |
|---|---|---|---|
| Spring training continues | Through about Mar 21, 2027 | Fort Myers | ~30-35 min |
| Collier County Fair | Mar 18-28, 2027 | Fairgrounds off Immokalee Rd | ~20 min |
| Naples Downtown Art Fair | Mar 20-21, 2027 | Cambier Park | ~20 min |
April
| Event | Next date | Where | Drive |
|---|---|---|---|
| Swamp Buggy Finals | Apr 3, 2027 | Florida Sports Park | ~25 min |
| US Open Pickleball Championships | Apr 17-24, 2027 | East Naples Community Park | ~25-35 min |
Tournaments all season
Paradise Coast Sports Complex hosts lacrosse, soccer and field hockey events from January to May. See our guide to tournament travel and team lodging.
Summer
Things are quieter from May to September. July 4th fireworks usually run from a barge off the City of Naples beaches while the pier is rebuilt. Summer is also the best time for lower rates and warm Gulf water.
Planning tips
- January to March is peak season. Event weekends book up first, so lock in dates early.
- Several events share weekends, such as Feb 19-21. A group can split up and meet back at the house.
- Downtown parking fills on festival days. Leave early, or take one car and drop people off.
The Naples Retreat is a private 2.5-acre pool home in north Naples, just off I-75, so most of these events are 15 to 35 minutes away. We sleep 13 in 4 bedrooms, with a pool, spa and pickleball court for the days in between.
Check dates & priceQuick answers
What events are in Naples, Florida this winter?
Highlights include the CME Group Tour Championship (Nov 19-22, 2026), the Christmas Walk on Fifth Avenue (Dec 4-5), the Naples Winter Wine Festival (Jan 29-31, 2027), the Naples National Art Fair (Feb 19-21) and the Collier County Fair (Mar 18-28).
When is the busiest time for events in Naples?
January through March. That is peak tourist season, with art fairs, golf, spring training nearby and most festivals.
What is there to do in Naples in April?
The US Open Pickleball Championships (April 17-24, 2027) and the Swamp Buggy Finals (April 3, 2027), plus warm beach weather before summer rains.