By Wesley Owen, Florida broker · November 3, 2026 · 6 min read

Naples Festival of Trees 2026 and a Year-End Checklist for Agents

The Naples Players Festival of Trees runs Nov. 23 to Dec. 20, 2026, with free admission. Here's how Naples agents can use it to reach clients, plus a list of Florida year-end tax and homestead dates to check before December closings.

The holiday trees are going up in downtown Naples. The Naples Players Festival of Trees runs November 23 through December 20, 2026 at the theater on 5th Avenue South. Artists and designers decorate themed trees and place them throughout the renovated building. Admission is free.

It's a good family outing or a quiet break between showings. It also lands in the busiest stretch of the year for Southwest Florida agents. Seasonal residents are coming back, buyers want to close before January, and property-tax and homestead dates are close. This guide covers the event details, simple ways to use it in your client care, and a list of Florida year-end dates to check before your December closings.

The event at a glance

Sources: The Naples Players event page and the MustDo.com event listing. Hours can change by day, so check the theater's page before you send clients.

Why a free local event helps your business

You don't need a big budget to stay in touch with past clients during the holidays. A free, family-friendly event within walking distance of 5th Avenue South gives you an easy, low-pressure reason to reach out. Some ideas:

• Meet a past client. Offer to meet a past buyer at the festival, then get coffee nearby. It's a real visit without the cost of a hosted party.
• Break up a long showing day. If out-of-town buyers are touring downtown or Old Naples, a short stop between showings helps them picture life in the neighborhood.
• Make a local guide. Send a short holiday events email or social post that lists the festival with other community happenings. Helpful local content tends to get more engagement than another listing post.
• Shop local. The wreaths and mini trees for sale can double as small closing or thank-you gifts that support a local nonprofit theater.

Keep your promotion compliant

The usual Florida advertising rules apply to event posts too.

• Brokerage name. Under FREC Rule 61J2-10.025, real estate advertising must include the licensed name of your brokerage. It must also be clear to a reasonable person that they're dealing with a licensee. That includes social posts and emails that mention your services.
• Fair housing. Describe the event and the area. Don't describe who a neighborhood is "perfect for" in terms of family status, religion or any other protected class. "Great for a family outing" describes an event. "Perfect for families" next to a listing can raise fair housing questions.
• Get permission. Don't use the theater's logo or photos of the trees in ads without permission. Link to their event page.

Ask your broker if you're unsure whether a post counts as advertising.

Year-end dates to check before December closings

The festival covers the last four weeks of the year, which is also when many buyers rush to close. These Florida dates come up often in late-year transactions. They're general rules from the Florida Statutes. Confirm how each one applies to your file with your broker, the closing agent, an attorney or a CPA.

What these dates mean for your clients

1. Prorating taxes in a November or December closing. Florida property taxes are billed in arrears. Tax bills usually go out around November, so a late-year closing can land right when the current bill is open. Make sure your closing agent knows whether the seller has already paid, and how your contract tells them to handle the early-payment discount in the proration. Don't assume. Get the closing agent's answer in writing.

2. Homestead depends on January 1. A buyer who owns the home and makes it their permanent residence by January 1 may qualify for that year's homestead exemption. They still have to apply with the county property appraiser by March 1. For Naples buyers, that's the Collier County Property Appraiser. If a buyer plans to live in the home full-time, ask the closing agent or an attorney whether closing in December or January changes when the exemption starts. Then let the buyer decide with that information.

3. The buyer's tax bill will reset. Under Save Our Homes, the seller's assessed value may have been capped for years. After a sale, the property is reassessed at just (market) value as of the next January 1. That can make the buyer's tax bill much higher than the seller's. Tell buyers early, and send them to the Collier County Property Appraiser's online tax estimator rather than giving them a number yourself.

4. Portability for move-up buyers. Sellers leaving a homesteaded Florida home may be able to carry some of their Save Our Homes benefit to a new homestead. This is called portability, and it requires an application to the property appraiser. Rules and deadlines vary by situation, so refer clients to the property appraiser's office or a tax professional.

5. Hurricane season ends, insurance doesn't. The official Atlantic hurricane season ends November 30. Buyers still need a bound insurance policy before closing, and lenders still require one. Start insurance quotes as soon as you're under contract, especially for older homes or condos.

A checklist for December

Copy this into your notes for each December closing:

1. Confirm the seller's current-year tax status (paid or unpaid) with the closing agent.
2. Confirm how the contract tells the closing agent to prorate taxes and handle the early-payment discount.
3. Ask full-time buyers whether they plan to homestead, and note the January 1 and March 1 dates.
4. Send buyers the Collier County Property Appraiser link for estimating taxes after the reassessment.
5. Ask sellers moving within Florida whether they've looked into portability.
6. Start the insurance quote and binder process right after the contract is signed.
7. Check the closing date against holiday office closures for the lender, title company and county recording.
8. Put any client events, like a festival meetup, on the calendar with your brokerage name on all invitations.

Planning around the holiday rush

The hard part of December isn't any single deadline. It's keeping them all straight across several files while clients travel, offices close early and everyone wants to close before New Year's. Some brokers use transaction management software like Parcel to track key dates for each file.

In the meantime, grab a coffee, walk through the trees on 5th Avenue South, and invite a client or two to come along.

This article is general education, not legal or tax advice. Property tax, homestead and contract questions depend on the facts of each deal, so confirm with your broker, a Florida real estate attorney or a CPA.

This article is general information, not legal, tax or financial advice. Confirm the details with your broker, attorney or CPA.