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Venice to Naples: Part 2 of The Great Florida Retirement Trail

by Ryan Erisman | Updated: April 5, 2025

Maybe you've read our Parrish to Venice: The Great Florida Retirement Trail article, but you had to know we couldn't stop there.

While the Sarasota area covered in that article is the most requested area by our readers, Southwest Florida which we are defining here as the roughly 100-mile stretch from Venice to Naples is not far behind.

If you ever decide to explore this part of Florida, here are some great places you will find along the way.

Venice

We of course covered Venice in our Parrish to Venice article, but just to recap here, Venice sits in a sweet spot along Florida's Gulf Coast which makes it the perfect destination for anyone looking to make the most of 14 miles of stunning white sand beaches.

In addition to those beautiful beaches, Venice is also known for all kinds of exciting ways to enjoy the great outdoors. It is a fabulous destination for boomers interested in exploring arts and culture, boutique shopping, or a wide range of outstanding restaurant choices.

Some communities to explore in this area include:

Located just south of Venice in Sarasota County, Boca Royale Golf & Country Club offers a rare lifestyle that feels more like a vacation than the everyday. Residents of the gated 1,000-acre community enjoy a full line of fun and fitness amenities, including an 18-hole par 72 golf course. A beautiful amenity center and clubhouse round out the community. The community offers both single-family homes and attached villas.

Get More Information About Boca Royale

Grand Palm is truly a one-of-a-kind community! This beautiful, amenity-rich, nature-focused community in Venice, Florida is exactly what resort living should be like. Residents enjoy easy access to downtown Venice and beaches (20 minutes away) and a multitude of activities right in their own backyard with an on-site activities coordinator, state-of-the-art fitness facility, and large, resort-style pool with water slide. Attached villas and single-family homes are available.

Get More Information About Grand Palm

Discover a new brighter 55+ lifestyle at Brightmore at Wellen Park in Venice, Florida. This new gated community is nestled within popular Wellen Park, one the nation's premier master-planned communities. Brightmore will feature a rich array of resort-style amenities, including 2 pools, 8 pickleball courts and a competition court, and a 21,000 square foot clubhouse with gathering areas, bar/grill, fitness center, paw park and much more. A full activities and events calendar provides fun and social connections. Choose from 11 thoughtfully designed home plans, including villas and single-family residences.

Get More Information About Brightmore at Wellen Park

Port Charlotte and Punta Gorda

These two popular Florida cities sit right next to each other, separated by the Peace River.

One popular community you should check out when passing through this area is Kings Gate:

Located in the popular Port Charlotte/Punta Gorda area of Florida, Kings Gate offers easy access to beaches, marinas, wildlife sanctuaries, airports, and more, many within a 15-minute drive or less. A friendly, gated neighborhood community for residents age 55 and up, Kings Gate homeowners enjoy access to a recreation center, Olympic-sized swimming pool and spa, tennis courts, on-site activities director, and a variety of resident clubs and social events. Membership to the 18-hole golf course and facilities are additionally available. Prices start in the $200k’s.

Get More Information About Kings Gate

Babcock Ranch

The next stop along the way is Babcock Ranch, a solar-powered community situated on approximately 18,000 acres, adjacent to an extensive wilderness preserve.

The community is powered by and 870-acre solar farm. The neighborhoods within Babcock Ranch feature clubhouses, pools, golf courses, hiking and biking paths, greenways, and lakes perfect for outdoor adventures. Babcock Ranch was featured on 60 Minutes and in other news shows after it held up remarkably well despite a near-direct hit from Hurricane Ian a few years ago.

Located in Southwest Florida, Babcock Ranch has been designed to help residents live their happiest, healthiest life. Situated on 18,000 acres, adjacent to an extensive wilderness preserve, Babcock Ranch features hiking and biking paths, greenways, and lakes perfect for outdoor adventures.

America’s first solar-powered town, Babcock Ranch houses an 870-acre solar farm operated by Florida Power & Light, and the entire town is outfitted with fiber optic internet for a fully connected lifestyle.

Babcock Ranch features a variety of neighborhoods and home builders, and prices range from the $300's to over $2M.

Learn More About Babcock Ranch

Fort Myers

Known for offering the perfect combination of recreation and relaxation, Fort Myers contains an endless amount of options including white sand beaches, first-class golf courses, exciting deep-sea fishing, and outstanding shopping.

A few communities to check out here include:

Discover Valencia Harbor by GL Homes in Fort Myers – a new 55+ community featuring a clubhouse, resort pools, fitness centers, sports courts, dining, and social activities. New single-family homes start from the $300s. Join the VIP Interest List to be the first to explore this premium active adult community.

Get More Information About Valencia Harbor

Verandah is a beautiful, private, guard-gated golf course community in Fort Myers. Enjoy life among mature oak trees, meandering bike paths and walking trails, and breathtaking views of the Orange River. Verandah offers residents full-service dining options, social events and activities, fitness and recreation options, and 2 spectacular 18-hole championship golf courses: Old Orange, designed by Bob Cupp and Whispering Oak, designed by Jack Nicklaus.

Get More Information About Verandah

Del Webb Oak Creek is a new 55+ community that opened in Fort Myers in 2022. Here you’ll find pretty much the same floorplans and amenities offered in other Del Webb communities, but if Southwest Florida is where you want to retire, this place is definitely worth checking out. Prices start in the $300k’s.

Get More Information About Del Webb Oak Creek

Pelican Preserve is a 55+ community in Fort Myers with approximately 2,500 homes.

The Plaza Del Sol clubhouse for residents includes a state-of-the-art fitness center and dance studio, card room and art studio, a 100-seat movie theater, and more. Outside there is a resort-style pool, 12 pickleball courts, 8 tennis courts, a juice bar, a softball field, a basketball court, a beach area, a butterfly garden, a fishing pier, and more.

Pelican Preserve is also home to a 27-hole championship golf course and clubhouse. Golf membership is optional for Pelican Preserve residents.

Condos, villas, and single-family homes are available starting in the $300k’s.

Get More Information

Naples

As one of the most popular retirement locations in all of Florida, you can definitely count on plenty of options to choose from if Naples is the ultimate destination for you.

Here are a few recent additions:

Valencia Sky, GL Homes' newest 55+ community, combines luxury living with coastal convenience just 6 miles from downtown Naples. This Valencia community features a state-of-the-art clubhouse with pools, pickleball and tennis courts, gym, restaurant/bar, sports lounge, and event hall. Located minutes from 5th Avenue South shopping and Naples Pier. Request information today to learn more.

Get More Information About Valencia Sky

Set sail for the exciting adventures awaiting you and your family in one of Collier County’s newest communities. Neal Communities is pleased to announce SkySail, a serene home neighborhood located among 246 acres of crystal-clear lakes. This beautiful lakeside community offers a variety of beautiful amenities perfect for connecting with neighbors through outdoor relaxation or exciting activities.

Get More Information About SkySail

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