Florida downtowns ranked on the ‘Dumpy Scale.’ What made the list?

The serious hubbub over dire predictions by a few AI engineers that the digital brain network they helped develop could take over the world by 2030 or much, much worse, somewhat inspired today’s In the Know.

Read more Bus hits college sign in Sarasota County, 7 report injuries

It’s a topic that has the attention of Gov. Ron DeSantis, who warned last week that Republicans who don’t call for artificial intelligence regulations would get hurt electorally and be in a “losing position” in the mid-terms if they tried to protect tech companies.

So with AI on our minds, we essentially asked it to recommend Florida downtowns largely south of I-10 that aren’t dumpy.

Not only did it provide its own list, it created a “Dumpy Scale” ranking with 1.0 being the most pristine “while a 10 is a completely run-down, shuttered ghost town.” That then led to further In the Know research and editing to determine how the older, more conventional Southwest Florida downtowns compare, and whether local upgrades that we’ve been reporting and continue as we speak, have helped boost them in AI’s public eyes. Not that we necessarily agree with it all, but some downtowns were rated as falling short. However, improvements are planned.

Here’s what to know, or at least what AI wants us to know, with a local list first and then the Florida ranking of not so dumpy downtowns that will lead to a few debates including from me and whether we can depend on digital neurons and the biases Americans baked into them to guide us the rest of the way.

How did more historic SW Florida downtowns do on the “Dumpy Scale?”

1. Downtown Naples (Collier County) | Rating: 1.1 / 10

• The Vibe: Ultra-Luxury and Flawless.
• The Reality: Centered around Fifth Avenue South and Third Street South, this is the pinnacle of high-end Florida. Expect pristine Mediterranean architecture, perfectly manicured tropical landscaping, luxury boutiques, fine dining and zero signs of urban blight. It blends seamlessly into multi-million dollar residential avenues and ends directly at the beach.

2. Downtown Fort Myers: River District (Lee County) | Rating: 2.2 / 10

• The Vibe: Polished Historic Brick and Palms.
• The Reality: A stunning example of urban revitalization. The core features beautifully restored historic brick streets lined with towering royal palms. It is pristine, lively, highly walkable and packed with restaurants, bars and galleries.

3. Downtown Boca Grande (Lee County) | Rating: 2.3 / 10

• The Vibe: Exclusive, Old-Money Island Hideaway.
• The Reality: Located on Gasparilla Island, this tiny, historic downtown core is golf-cart centric, quiet and hyper-clean. It features upscale island boutiques, historic cottages and the historic Gasparilla Inn, completely isolated from mainstream commercial strip malls. But the bad news is new parking rules for beach visitors.

4. Downtown Sanibel (Lee County) | Rating: 2.4 / 10

• The Vibe: Elite, Eco-Conscious Coastal.
• The Reality: Centered along Periwinkle Way, this has been a low-profile, manicured island district recovering from 2022’s Hurricane Ian. A lot historically had been hidden behind lush, native canopy trees. The shell shops, boutiques and cafes are upscale, meticulously maintained and explicitly designed to blend with the environment.

5. Downtown Bonita Springs (Lee County) | Rating: 2.6 / 10

• The Vibe: Revitalized Old-Florida aesthetic
• The Reality: Historically, this area was a quiet, weathered highway corridor that might have scored closer to a 5.0. However, a massive multi-million dollar city revitalization initiative combined with heavy private investment is completely transforming it. It is becoming a vibrant, highly manicured, hip district filled with independent restaurants, craft cocktail lounges and modern music venues.

6. Downtown Matlacha (Lee County) | Rating: 3.4 / 10

• The Vibe: Ecclectic, Ultra-Colorful Artist Village.
• The Reality: A tiny, walkable island corridor bridging the mainland to Pine Island. It consists of brightly painted candy-colored art shacks, seafood spots and kayak launches. While structurally rustic and “salty,” it is a vibrant, clean tourist destination rather than an actual dumpy zone.

7. Downtown Fort Myers Beach (Lee County) | Rating: 4.2 / 10

• The Vibe: Post-Hurricane Transitional Coastal.
• The Reality: Historically a loud, heavily stepped-on beach party zone, it is currently undergoing massive, redevelopment after Ian. While pieces of it are beginning to shine, lingering construction spaces and vacant lots pull it into a transitional middle-ground.

8. Downtown Cape Coral (Lee County) | Rating: 4.8 / 10

• The Vibe: Sprawling Suburban Commercial Strip.
• The Reality: Tied to Cape Coral Parkway, this area struggles on the traditional “downtown scale” but redevelopment efforts are taking place. It is safe and features restaurants and bars, but visually it needs more work.

9. Everglades City (Collier County) | Rating: 5.2 / 10

• The Vibe: Time-Capsule Fishing Village Meets Wilderness Frontier.
• The Reality: Located at the literal end of the road where the gulf melts into the river of grass, Everglades City functions as a quirky, remote outpost rather than a manicured suburban destination. The downtown core is centered around a massive, grassy traffic circle featuring the historic courthouse. The town’s score reflects its intense vulnerability to challenging coastal conditions, which gives it a structurally weathered appearance.

10. Downtown Immokalee (Collier County) | Rating: 6.8 / 10

• The Vibe: Energetic, Working-Class Agricultural Crossroads.
• The Reality: This is the agricultural heart of Collier County. The walkable district features excellent, highly authentic Mexican taquerias, local markets, a pioneer museum and a vibrant, half-acre public town square. It sits on the higher side of the scale due to an aging infrastructure grid. Rather than being a leisurely outdoor shopping mall for tourists, it is an active transit hub for farmworkers.

Beyond Southwest Florida, what are other not so dumpy downtowns?

The Ultra-Luxury and Flawless Gems (1.0 – 1.8)

These downtowns are hyper-manicured, incredibly wealthy, and feature zero blighted elements. They feel more like pristine movie sets than standard towns.

Read more GMOs, drones and radiation: Florida’s war on mosquitoes goes high-tech

• Palm Beach (Worth Avenue) | 1.0 – The absolute gold standard; flawless Mediterranean architecture, hidden courtyards, luxury designer boutiques, and immaculate cleanliness.
• Winter Park (Park Avenue) | 1.2 – Central Florida’s crown jewel; gas-lamp styled brick streets, a stunning central park, upscale boutiques, and a sidewalk cafe culture bordering a chain of lakes.
• Boca Raton (Mizner Park) | 1.3 – A pristine, pink-hued, outdoor shopping and dining estate designed in flawless Mediterranean Revival style.
• Sarasota (St. Armands Circle) | 1.4 – A gorgeous, upscale outdoor shopping circle right off the beach, filled with statues, high-end boutiques and chocolate shops.
• Coral Gables (Miracle Mile) | 1.5 – Historically preserved, lushly canopied, and completely upscale with historic stone architecture and high-end bridal and dining districts.
• Key West (Duval Street – Upper/Truman Annex) | 1.6 – Specifically the manicured, historic end; gorgeous Victorian-style mansions, pristine tropical flora and upscale Caribbean vibes.
• St. Augustine (Historic District) | 1.7 – The oldest city in America; flawless Spanish-colonial cobblestone streets, completely pedestrianized walking zone and deep historic charm.
• Delray Beach (Atlantic Avenue) | 1.7 – A vibrant, upscale beachside downtown stretching from the interstate straight to the ocean, packed with trendy boutiques and pristine sidewalks.

The Polished Waterfront and Coastal Walkers (1.9 – 2.4)

These towns perfectly blend stunning waterfront access with heavily invested, clean and charming commercial districts.

• St. Petersburg (Beach Drive / Central Ave) | 1.9 – A massive, gleaming waterfront park system bordering upscale high-rises, world-class museums, and a highly active, clean arts district.
• Dunedin (Main Street) | 1.9 – Clean, golf-cart friendly coastal hub with zero chain stores, an active pier and a vibrant Scottish-heritage craft beer and boutique scene.
• Venice (Miami Avenue / Venice Ave) | 2.0 – A beautiful, heavily landscaped historic downtown planned in the 1920s with Northern Italian architecture that dead-ends into the Gulf.
• Safety Harbor (Main Street) | 2.0 – Shaded by massive canopy oak trees, brick sidewalks, and boutique shops that lead straight to a pristine marina on Tampa Bay.
• Stuart (Historic Downtown) | 2.1 – Known as the “Sailfish Capital”; an impeccably clean, old-school coastal downtown with a beautiful wooden riverwalk and charming local shops.
• Punta Gorda (Historic District) | 2.2 – A quiet, highly polished waterfront downtown on Charlotte Harbor with pristine brick pathways, historic homes and zero clutter.
• Las Olas (Fort Lauderdale) | 2.3 – A highly stylish, clean, and energetic boulevard lined with palm trees, fashion boutiques and black-tie dining that weaves through canals.
• Cocoa Village | 2.4 – A riverside historic village with tree-lined streets, a beautiful waterfront park, historic playhouse and charming coastal gift shops.

The Picture-Perfect Inland and Lake Fronts (2.5 – 2.9)

These towns emphasize deep Southern charm, rolling hills, pristine lakes and heavy architectural preservation.

• Mount Dora | 2.5 – A stunning, hilly New England-style village in Central Florida known for massive oak trees, pristine antique shops and a beautiful lighthouse walk.
• Inverness (Downtown Core) | 2.5 – Beautiful courthouse plaza, pristine lakeside boardwalks and a bike-friendly park network.
• Lakeland (Munn Park Historic District) | 2.6 – Gorgeous historic brick buildings, antique shops and an immaculate, classic promenade wrapped entirely around Lake Mirror.
• Ocala (Historic Downtown Square) | 2.6 – The heart of horse country; a highly polished, historic town square complete with a central gazebo, upscale steakhouses and clean brick paths.
• DeLand (Main Street) | 2.7 – Consistently voted one of the best main streets in America; highly historic, immaculate murals, local bookstores and a highly vibrant collegiate energy.
• Dade City | 2.7 – Rolling hills, historic brick architecture, canopied streets and a haven for clean, upscale antique shopping and historic home tours.
• Winter Garden (Plant Street) | 2.8 – An incredibly clean, restored packing-district downtown with a historic theater, a fountain splash pad and the West Orange bike trail cutting right through the middle.
• Clermont (Downtown / Waterfront) | 2.9 – Set on rolling hills overlooking Lake Minneola; heavily invested waterfront trail, local breweries and clean, newly paved walking paths.

Writing In the Know for the USA TODAY Network, Columnist Phil Fernandez ([email protected]) grew up in Southwest Florida and has led Pulitzer Prize-winning efforts. Sign up for our free Breaking Ground growth and development newsletter. Subscribe to our News-Press and Naples Daily News apps.

This article originally appeared on Naples Daily News: Florida downtowns ranked on the ‘Dumpy Scale.’ What made the list?

Reporting by Phil Fernandez, Fort Myers News-Press & Naples Daily News / Naples Daily News

Read more GMOs, drones and radiation: Florida’s war on mosquitoes goes high-tech

USA TODAY Network via Reuters Connect

Copyright Reuters or USA Today Network via Reuters Connect

This story was originally published September 21, 2026 at 12:42 PM.