By Brian French | NaplesBusinessNews.com | October 12, 2026
Quick Answer
Fly into Southwest Florida International (RSW) or, if you fly private, Naples Airport (APF), and plan your meetings before Thanksgiving, when seasonal residents fill tables and tee sheets. Client entertaining runs along Fifth Avenue South, Third Street South, Waterside Shops, Mercato and the Vanderbilt Beach corridor. Note that Naples Grande Beach Resort’s rooms are closed for renovation through the end of 2026, and the Naples Pier is still under construction.
Why Naples Is a Different Kind of Business Trip
Most Florida business trips are about volume: conventions, plant tours, sales calls. Naples works on trust. The people who fly in this fall are mostly wealth managers, private bankers, trust officers, estate attorneys, custom home builders, physicians and medical practice executives, and luxury real estate brokers. Nearly all of them are here to see a small number of clients with large balance sheets, many of whom split the year between Collier County and somewhere colder.
That changes how you plan. The meeting itself is often the least important part of the visit. What counts is the lunch on Third Street, the round at the client’s club, the dinner where a spouse is present, and the follow-up coffee at Mercato two days later. A good Naples trip is set up around the client’s schedule, the client’s neighborhood and the client’s club. It is not set up around a convention center, because Naples does not really have one in the way Orlando or Tampa do.
Timing matters as much as place. In October the town is quieter, reservations are easy to get, and many full-time residents and early returners have time. From mid-November on, the population rises, traffic on U.S. 41 and Airport-Pulling Road gets heavy, and the best tables and tee times go to members and regulars. If you can choose, October and early November give you more of the client’s attention for less hassle.
Getting In: RSW, APF and the I-75 Run
Southwest Florida International (RSW)
RSW in Fort Myers is the commercial gateway for Naples. The airport handled a record 11,154,458 passengers in 2025, up 1.1% from 2024, according to Gulfshore Business. The Lee County Port Authority’s September 2026 air service update lists nonstop service to more than 80 destinations on 15 airlines. Domestic carriers include Allegiant, Alaska, Avelo, American, Breeze, Delta, Frontier, JetBlue, Southwest, Sun Country and United. International carriers include Air Canada and Air Canada Rouge, Porter, WestJet, Discover and Cubazul.
Several routes start or come back for the season this fall. Breeze adds Atlantic City and Dayton in October and Lansing in November. Avelo adds Concord, North Carolina, and McKinney, Texas, in November. Delta adds Austin and Raleigh-Durham in November, and Alaska brings back Seattle the same month. For the Northeast and Midwest money centers that send many advisers here, nonstop choices get better as the season goes on.
The terminal is a construction zone. Work began in October 2024 on a $1.1 billion expansion that includes a new Concourse E with 14 initial gates, room for 19 later, and a nine-lane consolidated security checkpoint. WGCU reported a late 2027 opening target. An earlier phase to expand the existing terminal ran into contractor disputes and cost overruns in 2025. In practice, leave extra time for security, especially on Sunday and Monday mornings once the season starts.
Naples Airport (APF)
Many clients who fly private use Naples Airport, a short drive from downtown and Park Shore. It has no scheduled airline service. It is run by the Naples Airport Authority, an independent government agency funded mostly by fuel sales and hangar rentals rather than local taxes. Naples Aviation, the airport’s own fixed-base operator, was ranked eighth among U.S. FBOs in the 2026 Professional Pilot PRASE survey. U.S. Customs and Border Protection is on site, which matters if clients fly in from the Bahamas or Canada. Naples Jet Center opened a new terminal in early 2025 as part of a $15 million redevelopment. NetJets proposed its own private terminal at APF in late 2025. That proposal still needed city and aviation approvals at last report, so do not count on it this season.
The Drive South
From RSW it is a straight run south on I-75. Collier County’s tourism office says RSW is about 40 minutes from Naples. Plan on less time to North Naples and Bonita Springs and more time to Old Naples and Port Royal, especially during the afternoon rush in season. Inside Naples, U.S. 41 (Tamiami Trail) and Goodlette-Frank Road carry most north-south traffic. For a downtown lunch followed by a meeting in North Naples, plan on at least 30 minutes between them in season.
| Arrival Option | Best For |
| RSW (Fort Myers) | Commercial flights, rental cars |
| APF (Naples) | Private and charter clients |
| I-75 from Miami | Drive-in from South Florida |
Where Deals Get Done: The Districts
Fifth Avenue South
Fifth Avenue South is downtown Naples’s main street and its most public business setting. It is lined with restaurants, outdoor tables and boutiques, and it is where a portfolio manager takes a new prospect to lunch to be seen in town. Expect conversations to carry; if the topic is sensitive, ask for a corner table or go inside.
Construction is coming to the east end. The Avenue, a mixed-use project at the gateway to the Fifth Avenue district, secured a $202 million financing package in July 2026, according to the Business Observer, with vertical construction next and completion expected in early 2028. Some detours and staging are likely near that end of the street.
The 52nd annual Christmas Walk and tree lighting was held the first weekend of December last year. If that pattern holds in 2026, the street will be crowded and festive that weekend, which is good for client goodwill and bad for quiet talk. Confirm 2026 dates with the Fifth Avenue South association before booking.
Third Street South
A few blocks closer to the Gulf, Third Street South is quieter and older-money in tone, with low buildings, courtyards and galleries. It sits near Port Royal and the Gordon Drive estates, where many of the area’s wealthiest families live. For trust and estate work, Third Street is often the better choice than Fifth: it is a walk from the client’s home and tends to be more discreet.
On Saturdays, the Third Street South Farmers Market runs from 7:30 to 11:30 a.m. in the Neapolitan parking lot behind the Tommy Bahama restaurant, according to the City of Naples. A Saturday coffee and a stroll through the market is an easy, low-pressure way to see a client who would not want a formal meeting on a weekend.
Venetian Village and Park Shore
Venetian Village sits on Venetian Bay at the north end of Park Shore, with waterfront dining and boutiques. Its customers are mostly Park Shore and Moorings condo owners, many of whom moved here from the Midwest and Northeast to retire. It works well for a sunset dinner with a retired client who does not want to drive far at night.
Waterside Shops and Pelican Bay
Waterside Shops, at Seagate Drive and U.S. 41, borders Pelican Bay, one of the densest areas of high-net-worth households in Southwest Florida. Its owner, The Forbes Company, has been pushing the center further into luxury retail. The Naples Press reported in April 2026 that Brunello Cucinelli opened late in 2025, Pottery Barn and Williams Sonoma opened in January 2026, and Dior planned a standalone boutique. Several long-time tenants, including Brio Italian Grille, left as their leases ended.
The dining options business visitors care about are changing too. Eddie V’s Prime Seafood was targeted for a summer 2026 opening on an outparcel. Buck & Rider, the Arizona seafood restaurant, is taking the former Brio space and was targeting late 2026. RH is building a gallery with a restaurant on the former Nordstrom site, also targeted for late 2026. Check opening status before you promise a client a table at any of the three.
Mercato and North Naples
Mercato, at Vanderbilt Beach Road and U.S. 41, is the North Naples meeting point: restaurants, a movie theater, offices and residences in a walkable layout. It is close to many of the newer gated golf communities east of U.S. 41 and to a large share of the medical and professional offices in North Naples. For a working lunch or a quick drink after a meeting, Mercato is practical and easy to park at, which matters more than it sounds in January.
Vanderbilt Beach
West of Mercato, Vanderbilt Beach Road ends at the Gulf, home to The Ritz-Carlton Naples and a row of high-rise condominiums. The Ritz-Carlton closed for more than nine months after Hurricane Ian in 2022 and reopened on July 6, 2023, with a new 14-story club-level tower, a redesigned lobby and pools, and new restaurants, according to Gulfshore Business and CoStar. It is where many out-of-town wealth teams hold client receptions and where families booking multigenerational planning meetings tend to stay.
| District | Typical Client Fit |
| Third Street South | Old Naples estates, trusts |
| Fifth Avenue South | Prospects, public lunches |
| Venetian Village | Park Shore condo retirees |
| Waterside / Pelican Bay | Luxury, high-rise owners |
| Mercato | North Naples, medical, golf communities |
| Vanderbilt Beach | Receptions, family meetings |
Where to Stay This Fall: Recovery and Renovation
Hurricanes Ian in 2022 and Helene and Milton in 2024 left Naples’s coastal hotels with long rebuilds. Here is what a fall 2026 visitor should know about the major beachfront properties.
The Ritz-Carlton Naples (Vanderbilt Beach) has been open since July 2023 after its post-Ian restoration and expansion. Its sister property, The Ritz-Carlton Naples, Tiburón, is a golf resort inland. Tiburón will host the 2027 Naples Winter Wine Festival on January 29 to 31.
Naples Grande Beach Resort (Pelican Bay) is the biggest change this season. A full renovation began in April 2026, and guest rooms, meeting rooms and event spaces are closed through December 2026, according to Hotel Management. Rhode’s End restaurant, beach service at Clam Pass and some villas stayed open, and Naples Grande Golf Club kept operating normally. A June 2026 update put the reopening in 2027. If your firm usually books its fall client event here, you will need another venue this year. The resort has also proposed changes at Clam Pass that some Pelican Bay residents oppose, a local issue worth knowing before you raise it with a client who lives there.
LaPlaya Beach & Golf Resort (Vanderbilt Beach) finished an 18-month restoration after Ian and unveiled it in May 2024, including renovated rooms, a rebuilt Beach House and a restored spa, according to Hospitality Net. Its owner later reported more storm effects from Helene and Milton in 2024, so ask when you book whether any work is still under way.
Hyatt Regency Coconut Point in Bonita Springs, just north of the Collier County line, has about 82,000 square feet of meeting space. It renovated its meeting and event areas in the second half of 2025. For a larger client seminar, it is one of the few full-scale meeting hotels near Naples.
Rates swing widely between October and February. Ask for the shoulder-season rate in October and early November. Book December and later stays well ahead, because group blocks for holiday parties and January events fill early.
| Property | Fall 2026 Status |
| Ritz-Carlton Naples | Open since July 2023 |
| Naples Grande | Rooms closed through Dec. 2026 |
| LaPlaya | Restored; confirm on booking |
| Hyatt Regency Coconut Point | Open; meeting space renovated 2025 |
Golf and Club Culture: The Rules Nobody Prints
Collier County has a very high concentration of private clubs, and for many wealthy residents the club is where their social life, their charitable work and their business relationships come together. An invitation to play or dine at a client’s club is a signal of trust. Treat it that way.
How Guest Policies Usually Work
Every club writes its own rules, so ask your host instead of assuming. Some practices are common across Naples clubs:
- The member pays. Guest green fees, cart fees and meals are usually charged to the member’s account. Do not offer cash or a card at the bar or pro shop; it embarrasses the host. Thank them afterward with a handwritten note or by taking them to dinner off-site.
- Guest limits tighten in season. Many clubs cap how often a non-resident guest can play, and some restrict guest tee times from January through March. A round that is easy to set up in October may be impossible in February.
- Dress codes are enforced. Collared shirts, tailored shorts or slacks, and no denim are the norm on the course. Clubhouse dining rooms often have stricter evening dress codes. Ask.
- Phones stay away. Many clubs ban phone calls in the clubhouse and on the course. Do not take a call on the fifth tee, and never pull out a laptop in the grill room.
- Do not pitch on the course. Let the client bring up business. The round is for the relationship; the business talk usually happens later in the day or the following week.
Public and Resort Options
If you are the host and do not have club access, resort courses close to Naples are the practical choice. The Ritz-Carlton’s Tiburón courses, Naples Grande Golf Club and LaPlaya’s golf course all take resort guests or outside players, depending on their rules. Booking a resort tee time lets you return the favor without asking a client to sign you in again.
Season Timing: October Versus December
Naples’s year has two halves. From about May through October the town belongs to full-time residents, and from about Thanksgiving through Easter the seasonal residents are back. For business travelers, the shift changes almost everything.
October is still hurricane season (it runs through November 30) and still warm and humid, with afternoon storms possible. Restaurants that close or cut hours in late summer are usually back to normal. Most clients who live here year-round have open calendars. This is the best window for introductions, annual reviews with full-time residents and site visits for builders and developers.
By mid-November the seasonal residents start to return, many after Thanksgiving, though many wait until after the holidays. Weekend dinner reservations at well-known downtown and Third Street restaurants get harder, and traffic grows. December brings holiday parties, charity events and family visits, which makes it a good time for receptions and a poor time for long working meetings.
January through March is peak season. Clients are in town but busy with charity galas, club events and guests. The Naples Winter Wine Festival, January 29 to 31, 2027, at The Ritz-Carlton Naples, Tiburón, is a fixture of the philanthropic calendar. If a client is involved, schedule around it rather than against it.
| Month | What Changes |
| October | Quiet, easy reservations, warm |
| November | Snowbirds return, traffic rises |
| December | Holiday events, receptions |
| January–March | Peak season, book weeks ahead |
Fall 2026 Events on the Calendar
Naples International Film Festival, October 22 to 25, 2026. Run by Artis—Naples, this is the 18th edition. It draws a cultured, local audience and is an easy invitation to extend to a client who likes the arts.
Third Street South Farmers Market, Saturdays. The City of Naples calendar lists it on Saturday, October 10, 2026, from 7:30 to 11:30 a.m.
Christmas Walk on Fifth Avenue South, early December (to be confirmed). Last year’s 52nd Christmas Walk was held December 5 and 6, 2025, with the tree lighting at Sugden Plaza. Check 2026 dates with the Fifth Avenue South association.
Greater Naples Chamber events. The chamber lists Jingle & Mingle, a holiday networking event with a toy drive, among its signature events. 2026 dates were not posted when this guide was written; check the chamber calendar.
Naples Winter Wine Festival, January 29 to 31, 2027 (planning note). It is not a fall event, but auction lots, sponsorships and guest lists are often settled in the fall. Advisers whose clients take part should know that.
The Naples Pier and Other Recovery Notes
The Naples Pier, the city’s best-known landmark, was destroyed by Hurricane Ian. Reconstruction began on January 6, 2026, after a public groundbreaking the day before. Demolition of the old pier finished in April. On September 18, 2026, contractor Shoreline Foundation finished a mid-pavilion concrete pour that took the project past half of its total concrete. The city says the pier will be closed for about 18 months, so expect a reopening around mid-2027 at the earliest. The construction contract is $23.5 million. You can watch the work from the beach at the end of 12th Avenue South. It is a natural thing to talk about with a client who lives in Old Naples, many of whom followed the rebuild closely.
Beyond the pier, most of the waterfront has recovered, but some coastal homes in Old Naples, Port Royal and Vanderbilt Beach are still being rebuilt or raised. For builders, architects and insurance and lending professionals, that rebuild is the business opportunity. For everyone else, it is a sensitive topic: some clients lost homes, and many are still dealing with insurers.
Bonita Springs and Estero: The Northern Spillover
Many clients who once lived in Naples now live in Bonita Springs and Estero in Lee County, drawn by newer gated golf communities and easier access to RSW. Coconut Point in Estero has shopping and dining, and the Hyatt Regency Coconut Point is the main meeting hotel in the area. If a client lives in one of these communities, meeting near them saves both of you a drive down U.S. 41 at rush hour.
For visitors, staying in Bonita Springs or Estero makes sense if most of your meetings are in North Naples or Lee County, or if Naples beachfront hotels are full. It does not make sense if your clients are in Old Naples or Port Royal; that drive gets long in season.
Brian’s Take
I managed money for years before I started publishing, and some of my most important client meetings never took place in an office. Naples is the purest form of that kind of business I know. The clients here have already been sold to by everyone. What they are buying now is judgment, discretion and the confidence that you understand how they live.
My advice to any adviser, banker or attorney coming down this fall is simple: come in October, not February. In February your client is at a gala three nights a week, has houseguests from Chicago and is in a fight over a tee time. In October the same person has time to walk Third Street, have a long lunch and talk about the things that keep them up at night: the estate plan, the kids, the house that still is not rebuilt after Ian. That is when real relationships are built.
Second, respect the club. When a client signs you in, you are a reflection of them in front of their friends. Dress right, put your phone away and let them pay. You can return the favor later.
Third, watch the market changes. Naples Grande’s renovation, Waterside Shops’ move upmarket and the Fifth Avenue construction tell me money keeps coming here. Owners would not commit this kind of capital if they did not believe the wealth base was still growing. As a former money manager, I find that worth more than any brochure.
Frequently Asked Questions
What airport should business travelers use for Naples?
Most commercial travelers fly into Southwest Florida International (RSW) in Fort Myers, which Collier County’s tourism office puts about 40 minutes from Naples via I-75. Private and charter flights use Naples Airport (APF), which is closer to downtown.
Is the Naples Pier open in fall 2026?
No. Reconstruction began in January 2026, and the city expects the pier to be closed for about 18 months. Concrete work was past the halfway point in September 2026.
Is Naples Grande Beach Resort open?
Its guest rooms, meeting spaces and event spaces are closed for renovation from April through December 2026. Rhode’s End restaurant, Clam Pass beach service, some villas and Naples Grande Golf Club stayed open. A reopening is expected in 2027.
When do seasonal residents return to Naples?
Seasonal residents start returning in November, many after Thanksgiving, and the population peaks from January through March. Plan for heavier traffic and tighter reservations from mid-November on.
Can I pay my own way as a guest at a private club?
Usually not. Most private clubs charge guest fees and meals to the member’s account. Ask your host about the club’s rules and thank them with a note or an off-site dinner.
Where should I meet a client who lives in Pelican Bay or North Naples?
Waterside Shops and Mercato are the most convenient. Both have dining and easy parking, and Waterside is adding upscale restaurants including Eddie V’s and Buck & Rider.
What is the best month for a Naples business trip?
October and early November give you the most client attention, the easiest reservations and the lowest hotel rates. Weather is still warm and humid, and hurricane season runs through November 30.
Are there major business events in Naples this fall?
The Naples International Film Festival runs October 22 to 25, 2026, and the Greater Naples Chamber holds networking events, including its holiday Jingle & Mingle. The Naples Winter Wine Festival follows on January 29 to 31, 2027.
NaplesBusinessNews.com is part of the Florida Authority Network, a group of Florida-focused business news sites covering markets from the Panhandle to the Keys.
Sources and Further Reading
- Gulfshore Business, “RSW sets passenger record despite December dip” — https://www.gulfshorebusiness.com/gb-daily/rsw-sets-passenger-record-despite-december-dip/article_5b90a10e-e75e-49f6-9452-f0b78d274033.html
- Lee County Port Authority, “Air Service Update September 2026” — https://www.flylcpa.com/app/uploads/2026/09/ASU-September-2026-Final.pdf
- Lee County Port Authority, “Southwest Florida International Airport Fast Facts” — https://www.flylcpa.com/app/uploads/2026/06/Southwest-Florida-International-Airport-Fast-Facts-05-26.pdf
- Construction Dive, “$1.1B Southwest Florida airport expansion breaks ground” — https://www.constructiondive.com/news/terminal-e-breaks-ground-southwest-florida-airport/743116/
- WGCU, “RSW shows off work on new concourse while a previous expansion remains stalled” — https://www.wgcu.org/top-story/2025-03-12/rsw-shows-off-work-on-new-concourse-while-a-previous-expansion-remains-stalled
- WGCU, “Naples Aviation recognized as a top 10 operator in national industry survey” — https://www.wgcu.org/section/transportation/2026-04-29/naples-aviation-recognized-as-a-top-10-operator-in-national-industry-survey
- AIN, “Naples Jet Center in Florida Debuts New Terminal” — https://ainonline.com/aviation-news/business-aviation/2025-02-12/florida-fbo-debuts-new-terminal
- Naples News Now, “Private jet giant NetJets proposes new terminal at Naples Municipal Airport” — https://naples-news-now.beehiiv.com/p/private-jet-giant-netjets-proposes-new-terminal-at-naples-municipal-airport
- Visit Naples, Paradise Coast, “Anreise” (Getting Here) — https://www.paradisecoast.com/de/plan-your-trip/articles/anreise
- City of Naples, “Naples Pier Rebuild Project” — https://www.naplesgov.com/node/55986
- Hotel Management, “Naples Grande Beach Resort renovation to begin in April” — https://www.hotelmanagement.net/renovations/naples-grande-beach-resort-unveils-renovation-set-begin-april-2026
- Hotel Management, “Naples Grande Beach Resort plans early 2027 reopening” — https://www.hotelmanagement.net/renovations/naples-grande-beach-resort-plans-reopening-early-2027-after-redo
- CoStar, “Ritz-Carlton in Naples Reopens Next Month” — https://www.costar.com/article/1107266701/ritz-carlton-in-naples-reopens-next-month
- Gulfshore Business, “The Ritz-Carlton Naples to reopen July 6, plans to hire 300” — https://www.gulfshorebusiness.com/gb_daily/the-ritz-carlton-naples-to-reopen-july-6-plans-to-hire-300/
- Hospitality Net, “Naples’ LaPlaya Beach & Golf Resort Unveils Stunning Transformation” — https://www.hospitalitynet.org/announcement/41011092/naples-laplaya-beach-golf-resort-unveils-stunning-transformation
- Meeting Spotlight, “Hyatt Regency in Florida to Renovate Meeting & Event Spaces” — https://www.meetingspotlight.com/hotels/hyatt-regency-florida-renovate-meeting-event-spaces
- The Naples Press, “Ann Taylor and others close as Waterside shifts to luxury” — https://www.naplespress.com/tim-aten-knows/waterside-shops-moves-forward-with-luxury-tenant-strategy/article_0fc74d46-c0aa-4b08-a790-685e10c3730b.html
- Business Observer, “Naples project secures $202 million financing package” — https://www.businessobserverfl.com/news/2026/jul/27/naples-project-secures-financing/
- Gulfshore Business, “Naples Winter Wine Festival sets 2027 dates, theme” — https://www.gulfshorebusiness.com/gb-daily/naples-winter-wine-festival-sets-2027-dates-theme/article_1699ca96-596a-4620-9526-75d755c41d50.html
- Artis—Naples, “Naples International Film Festival” — https://www.artisnaples.org/niff
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