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August 2026
The August newsletter is live — SWFL July market snapshot, back-to-school happenings, The Gate Golf Club & featured listings.
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World-class beaches, 90+ golf courses, award-winning dining on Fifth Avenue South, and one of the most sophisticated coastal lifestyles in the United States.
Skip and Michelle Riddle aren't transplants who discovered Southwest Florida — they grew up here. They know this city the way only natives can: the neighborhoods that hold their value, the streets that flood at high tide, the clubs worth waiting for, and the hidden restaurants that don't show up in any travel guide.
Skip grew up on Marco Island — just 20 minutes south — attended school and lived throughout Collier County, and returned to Southwest Florida after 24 years as an Army officer and a West Point education. He came home because there's simply nowhere else like it.
Michelle was born and raised in Naples — she and Skip actually met here in high school. She graduated with honors in Education and spent a decade teaching before transitioning to real estate, where she brings a uniquely thoughtful, client-first approach. As a Certified Military Residential Specialist, she understands the relocation process firsthand — having moved multiple times as part of a military family. She also brings deep knowledge of home renovation, having worked closely with builders and contractors throughout Collier County.
Together, they cover every corner of Naples — from Port Royal to Golden Gate Estates — with the kind of layered local knowledge that no algorithm can replicate.
From the ultra-exclusive waterfront estates of Port Royal to the wide-open acreage of Golden Gate Estates — Naples offers a range of communities unlike anywhere else in Florida. Skip and Michelle know them all.
Naples' most prestigious address. Grand waterfront estates on a pristine peninsula with Gulf of Mexico views, deep-water boating access, and a private beach club. One of the most coveted zip codes in Southwest Florida.
Ultra-Luxury · Deep Water · Private ClubOver two miles of private beach, championship golf, tennis, and a private beach club — all within a beautifully landscaped master-planned community. High-rise condos, villas, and single-family homes with world-class amenities.
Private Beach · Golf · High-RiseA prime waterfront location along the Gulf with stunning views and easy beach access. Luxury high-rise condominiums, single-family homes, and villas — steps from Venetian Village shopping and dining.
Gulf Front · Condos · WaterfrontNestled between the Gulf of Mexico and Naples Bay with access to the private Moorings Beach Park. A diverse mix of luxurious single-family homes, condos, and waterfront estates in a centrally located, prestigious community.
Private Beach · Central LocationSpacious custom-built estate homes on larger lots surrounded by mature landscaping and nature. A serene, private environment — Mediterranean to contemporary — conveniently close to all Naples has to offer.
Estate Lots · Privacy · Custom HomesFifth Avenue South, Third Street South, the Naples Pier — walkable, vibrant, and sophisticated. Boutique shops, art galleries, gourmet restaurants, and a coastal village feel that makes this the most sought-after urban neighborhood in SWFL.
5th Ave South · Walkable · Village FeelBeautiful gated communities, top-rated schools, and easy access to beaches, Mercato, and Waterside Shops. A thriving mix of single-family homes and condominiums with every amenity nearby.
Gated · Schools · Active Lifestyle100,000+ acres of rural and suburban living with larger lots, real privacy, and room to breathe. Popular with outdoor enthusiasts, equestrians, and anyone who wants space without sacrificing proximity to Naples amenities.
Acreage · Rural · PrivacyA diverse and vibrant community east of downtown with shopping at Coastland Center, golf at Lely Resort, and easy access to the Naples Botanical Garden. A convenient, livable neighborhood with excellent value.
Value · Convenient · Lely ResortNot sure which neighborhood is right for you? Skip and Michelle have sold in every pocket of Collier County and can walk you through the trade-offs — lifestyle, price per square foot, HOA, flood zone, and resale — without the sales pitch.
Ask Skip & Michelle →Naples has a restaurant scene that rivals cities ten times its population — fresh Gulf seafood, acclaimed chef-driven Italian, and waterfront dining that makes every meal feel like an occasion.
One of Naples' most acclaimed restaurants — handmade pasta, local ingredients, and a wine list that takes Italy seriously. A beloved neighborhood staple on Fifth Avenue South that earned its reputation the hard way: exceptional food, every time.
Italian · 5th Ave South Visit Website →Sophisticated Northern Italian cuisine on Fifth Avenue South with a romantic courtyard that sets the standard for Naples dining. Fresh pasta, exceptional service, and an atmosphere that makes it the go-to for special occasions year after year.
Italian · Outdoor Dining · 5th Ave Visit Website →A contemporary seafood restaurant where the entire menu is built around artisanal salts from around the world. Premium Gulf fish, oysters, and raw bar selections in a refined setting. One of the most inventive dining concepts on the Gulf Coast.
Seafood · Contemporary · Raw Bar Visit Website →Arguably the best beachfront dining in Naples — right on the Gulf at Vanderbilt Beach. Sunset views, fresh seafood, and an atmosphere that captures exactly why people fall in love with Southwest Florida. Book well in advance.
Beachfront · Sunset Views · Seafood Visit Website →An adventure in global seafood — Asian-inspired preparations meet Gulf-fresh fish in a lively, art-filled setting. One of the most creative kitchens in Naples, and consistently one of the hardest reservations to get. Worth the effort.
Asian-Fusion · Seafood · Creative Visit Website →Gulf-front dining at its finest — fresh seafood, perfectly prepared, in an elegant beachfront setting at La Playa Beach & Golf Resort. One of the most scenic dining rooms on the entire Gulf Coast. Sunday brunch is legendary.
Gulf Front · Resort Dining · Brunch Visit Website →Skip's take: "Fifth Avenue South and Third Street South have more great restaurants per block than anywhere I've ever been — and I've eaten in a lot of places. The dining scene in Naples is a genuine reason to move here."
Naples has more golf courses per capita than anywhere in the United States. From ultra-private members-only clubs to resort layouts open to the public, the range — and quality — is unmatched on the Gulf Coast.
Three championship courses — the Palm, the Estuary, and the Stadium — surrounding one of Naples' most prestigious residential communities. A full-service club with tennis, fitness, a beach club shuttle, and exceptional dining. The benchmark for Naples country club living.
Private · 3 Courses · Full-ServiceA rare and exclusive Tom Fazio design — pure golf without the residential development. One of the most beautiful and challenging courses in Florida, Old Collier is an invitation-only private club that represents the pinnacle of Naples golf.
Private · Tom Fazio · Members OnlyA storied private club with two championship courses and a warm, welcoming membership community. Extensive fitness, tennis, pickleball, and dining amenities. One of the most established clubs in Collier County with a strong social calendar.
Private · 2 Courses · SocialTwo Audubon-certified courses carved through pristine nature preserves in North Naples. A private community with a genuine commitment to natural beauty — bald eagles, wood storks, and Florida wildlife are part of the daily round here.
Private · Audubon Certified · North NaplesChampionship golf in one of Naples' most iconic master-planned communities, complemented by private beach access, tennis, and world-class amenities. One of the most complete club environments in the city — and the private beach club access is hard to beat.
Private · Beach Club · Pelican BayTwo Greg Norman-designed courses at the Ritz-Carlton Golf Resort in North Naples. The Black Course consistently challenges Florida's best players. Host of the QBE Shootout, it's one of the most recognized tournament venues in Southwest Florida.
Greg Norman · Ritz-Carlton · TournamentMany Naples neighborhoods are built around country clubs — which means your choice of golf club often shapes your social life, your neighborhood, and your home's value. Skip knows the clubs, the waitlists, the initiation fees, and which communities are right for which buyer.
Talk Golf with Skip →Naples has one of the most vibrant arts and culture scenes of any city its size in the United States — world-class performing arts, acclaimed museums, and a live music scene that runs year-round.
Home to the Naples Philharmonic and The Baker Museum — one of the finest arts complexes in Florida. World-class musical performances, major art exhibitions, and a year-round calendar of events that draws serious arts lovers from across the country.
Philharmonic · Baker Museum · World-Class Visit Website →One of the most significant automotive history museums in the world, right in Naples. Over 100 of history's most important automobiles in a museum-quality setting. A must-visit for anyone with an appreciation for engineering, design, or motorsport history.
Automotive Museum · World-Class Collection Visit Website →170 acres of stunning botanical collections, beautifully designed gardens, and unique exhibits showcasing plant life from around the world. A serene escape that's also a world-class horticultural institution — recognized among the top 10 botanical gardens in the U.S.
170 Acres · Top 10 in U.S. Visit Website →One of the most celebrated community theater companies in Florida, with a year-round season of Broadway-caliber productions. A vital part of the Naples cultural fabric — and consistently one of the best entertainment values in the city.
Theater · Community · Year-Round Visit Website →Southwest Florida's premier large-venue entertainment complex in nearby Estero — home of the Florida Everblades minor league hockey team and host to major touring concerts, family shows, and sporting events throughout the year.
Live Events · Concerts · Florida Everblades Visit Website →The Collier Museum at Government Center, Palm Cottage (Naples' oldest standing house), and the Naples Depot Museum preserve and celebrate the rich history of this extraordinary city — from the Calusa civilization through the railroad era to today.
History · Architecture · Local HeritageNaples has a shopping scene that consistently surprises first-time visitors — from internationally recognized designer boutiques to one-of-a-kind local shops, concentrated in some of the most beautiful streetscapes in Florida.
The crown jewel of Naples retail — a beautifully landscaped boulevard lined with upscale boutiques, art galleries, jewelry stores, and some of the city's finest restaurants. The social and commercial heart of downtown Naples. An evening stroll here tells you everything about why people love this city.
Downtown · Designer Boutiques · DiningNaples' historic shopping district — charming, walkable, and filled with art galleries, specialty shops, and beloved restaurants. Home to the Saturday farmers market and some of the most distinctive locally-owned boutiques in Southwest Florida. A neighborhood unto itself.
Historic · Art Galleries · Farmers MarketAn open-air luxury retail center anchored by Nordstrom and Saks Fifth Avenue, with Tiffany & Co., Gucci, Louis Vuitton, and dozens of high-end retailers in a stunning tropical setting. The definitive upscale shopping destination in Southwest Florida.
Luxury · Open-Air · Saks · NordstromA unique waterfront shopping village set along Venetian Bay with boutiques, galleries, and waterfront dining in a European-inspired setting. One of the most picturesque retail environments in Florida — arrive by boat if you can.
Waterfront · Boutiques · GalleriesNorth Naples' premier mixed-use entertainment and retail destination — restaurants, a movie theater, specialty shops, and a vibrant nightlife scene all in one walkable complex. The main gathering place for North Naples residents.
North Naples · Dining · EntertainmentNaples is home to dozens of outstanding independent boutiques — Marissa Collections (one of the finest independent fashion retailers in the country), Ooh! Ooh! Shoes, Gretchen Scott, Cypress & Palm, Wind in the Willows, and many more that you won't find anywhere else.
Independent · Fashion · One-of-a-KindNaples consistently ranks among America's top beach destinations — pristine white sand, warm Gulf waters, and some of the most breathtaking sunsets on the continent. From protected state parks to private community beaches, the Gulf is always close.
The iconic heart of Naples beach life. The historic 1,000-foot Naples Pier stretches into the Gulf and has been a gathering place since 1888. The surrounding beach is immaculate — wide, white, and walkable. Parking at 12th Avenue South puts you steps from the water and the pier at sunset.
Iconic · Pier · Downtown AccessNorth Naples' premier beach — wide, busy in season, and surrounded by some of the best beachfront dining in the state. La Playa and Turtle Club are right here. Vanderbilt Beach Road gives you direct access; arrive early in season. One of the most photographed stretches of Gulf coastline in Southwest Florida.
North Naples · Beachfront Dining · SunsetA protected barrier island beach widely considered the most pristine in Collier County. No development, no crowds past noon — just clear water, gentle surf, and nesting sea turtles from May through October. Entry by the car load; arrive before 9am in season to guarantee a spot. Worth every effort.
State Park · Protected · Sea TurtlesA hidden gem tucked inside Pelican Bay — accessible via a tram ride or a scenic 3/4-mile boardwalk through mangrove forest that opens to a stunning Gulf beach. Less crowded than Vanderbilt, calmer water, and a natural tidal pass where kayakers and paddleboarders congregate. A local favorite.
Pelican Bay · Tram Access · KayakingThe most family-friendly beach in Naples — ample parking, restrooms, a volleyball court, a playground, and a snack bar all in one spot. Central location just west of downtown makes it convenient. A popular gathering spot for year-round residents and a great first beach stop for families relocating to Naples.
Family · Amenities · Central NaplesOne of the last undeveloped barrier islands on the Gulf Coast of Southwest Florida — protected by the county and beloved by locals. Nesting shorebirds, excellent shelling, and remarkable solitude compared to more accessible beaches. A short drive into Lee County but considered a Naples-area gem by anyone who knows it.
Preserve · Shelling · UndevelopedPrivate beach access matters when buying in Naples. Pelican Bay residents have exclusive access to two private beach clubs with attendant service, loungers, and dining. The Moorings has its own private beach park. Port Royal deeded beach access is among the most coveted amenities in all of Southwest Florida. When we evaluate a property with you, beach access — and the type of access — is always part of the conversation.
Ask Skip & Michelle About Beach Access →"Working with Skip and Michelle was nothing short of a revelation. The time, attention, and genuine care they brought is simply not what I've experienced from other real estate professionals. They bring an insider's knowledge of Naples that money can't buy."
— Andrew Monnot"I had an outstanding experience working with Skip and Michelle Riddle. Their knowledge of the Naples and Marco Island market was invaluable. They were always responsive, professional, and made what could have been stressful feel easy."
— Alvaro Hidalgo"Michelle was very responsive and goes above and beyond to help. She is very personable and professional at the same time. A person of integrity, and she was always available to answer our questions quickly and accurately."
— Alicia WilliamsSkip and Michelle Riddle work with relocating buyers every week — from out-of-state families choosing their first Florida home to retirees upgrading from a previous Naples property. They know the neighborhoods, the clubs, the schools, the flood zones, and the seasonal market rhythms that determine whether you get the right home at the right price.
No pressure. No canned sales pitch. Just genuine local expertise from agents who are invested in this community — because it's their community too.
Skip and Michelle personally respond to every inquiry. Whether you're six months out or ready to make an offer, start the conversation here.
We personally review every inquiry. Your info is never shared or sold.
Skip & Michelle Riddle · Compass Naples