A weekly Southwest Florida newsletter featuring local life, waterfront living, things to do, upcoming events, real estate insights, and places worth knowing. Delivered every Friday.
This Week’s Feature
One of the things I enjoy about Southwest Florida is how much there is to see, do, and learn about the area. Even after more than 45 years of calling this place home, there's always something interesting worth sharing.
This week, I’m revisiting something I recently shared on social media that sparked quite a bit of interest. We’re also looking at some changes happening around Southwest Florida, a little good news for our natural environment, and the latest from our local real estate market.
And of course, there’s plenty happening throughout the area! I’ve included some upcoming events and local entertainment, giving you a little taste of what’s happening in Southwest Florida this weekend. Enjoy!
Local Life
Did You Know You Can Boat Across Florida?
From Cape Coral and Fort Myers, boaters can follow the Okeechobee Waterway across the state to the Atlantic coast near Stuart. The roughly 150-mile journey travels along the Caloosahatchee River, crosses Lake Okeechobee and passes through five locks, with marinas available for overnight stops along the way. It is a unique Florida boating adventure, but careful planning is essential—boat size, draft, lake levels and current lock conditions all need to be considered before making the crossing.
Around Southwest Florida
Two ranches covering nearly 1,300 acres and four miles of Peace River shoreline are being protected through Florida’s land-conservation program. The $7.5 million agreement prevents the land from being developed into subdivisions or commercial property while allowing it to remain privately owned. About half of the property consists of wetlands that naturally filter water flowing toward Charlotte Harbor, and both ranches are part of the Florida Wildlife Corridor.
Cape Coral Grove continues to take shape along Pine Island Road, with a new permit filed for a 42,696-square-foot fitness center. Plans for the development also include a grocery store believed to be Whole Foods, several smaller commercial buildings and a Cooper’s Hawk Winery & Restaurant expected to open in 2028. With dining, shopping and fitness all planned in one destination, this project is shaping up to be an exciting addition to Cape Coral.
This Weekend
Gather your crew and get ready for a full weekend of fishing and friendly competition on Fort Myers Beach. The event begins with a Captain’s Meeting on October 23, followed by the fishing tournament and awards ceremony on October 24 at Matanzas Inn.
Cape Coral Bike Night returns to Southeast 47th Terrace on Saturday, October 10, from 5 to 10 p.m. Enjoy motorcycles, food, local vendors and live music from Moonstone Riders and headliner Hairdaze, plus the popular Slow Bike Race at 8 p.m. Admission is free.
Discover an impressive collection of orchids during this American Orchid Society-sanctioned show at Edison and Ford Winter Estates. Judging begins Friday, October 9, at 1 p.m., and the show continues Saturday and Sunday from 9 a.m. to 4 p.m. The weekend also includes plant vendors offering orchids, cacti and tillandsias.
Wear your pink and run or walk for an important local cause at Bell Tower Shops on Saturday, October 10. The 5K begins at 8 a.m., followed by a one-mile walk at 8:10 a.m. Proceeds support Partners for Breast Cancer Care, which provides breast screenings, diagnostic testing and treatment to uninsured and limited-income residents across Southwest Florida.
Celebrate Oktoberfest on the waterfront at Sea-Craft Waterfront Tiki in North Fort Myers on Saturday, October 10, from 7 to 10 p.m. The evening will feature German food and drinks along with live music from Gone Coastal.
Bring your four-legged friend to Bell Tower Shops on Friday, October 9, from 6 to 8 p.m. This Halloween-themed Yappy Hour features live music, pet-friendly trick-or-treating and a costume contest. The monthly gathering benefits the Gulf Coast Humane Society.
Enjoy a creative evening at Azaleas on the Corner in downtown Fort Myers on Friday, October 9, from 6 to 8 p.m. Learn foundational watercolor techniques while creating your own fall-inspired artwork in a relaxed and welcoming setting.
Experience the timeless music of The Beatles performed by a live string quartet surrounded by the warm glow of candlelight. The 60-minute concert begins at 6 p.m. on Saturday, October 10, at the Music & Arts Community Center in Fort Myers.
Car lovers can enjoy an afternoon of classic cars, muscle cars, trucks, motorcycles and more on Saturday, October 10, from 11 a.m. to 3 p.m. at Roger Dean Chevrolet in Cape Coral. The show will feature awards, prizes, music, entertainment and food, with proceeds benefiting The Grateful Veteran.
Nationally touring comedian Carmen Ciricillo brings his self-deprecating and observational humor to Snappers Comedy Club in Fort Myers from October 8–10. Shows begin Thursday at 7:30 p.m., Friday at 7 p.m., and Saturday at 6 and 9 p.m.
From the Beyond the Waterfront Collection
Halloween, Southwest Florida Style
A little spooky, a little coastal and made for Halloween in paradise. This beach witch raglan brings together palm trees, salty air and vintage-inspired Halloween fun—perfect for warm fall days, waterfront gatherings or anyone who prefers tropical drinks over pumpkin spice.
Real Estate
Southwest Florida Home Sales Outpace State and National Trends
Southwest Florida’s housing market is showing some encouraging movement. According to FGCU’s October 2026 Regional Economic Indicators report, existing single-family home sales across the region increased 2.4% year over year, outperforming Florida and the nation, where sales declined.
At the same time, the number of active residential listings in Southwest Florida fell 17.3% from one year ago, showing that available inventory is tightening. Median home prices continue to vary widely across the region, ranging from approximately $350,000 in Charlotte County to $760,000 in Collier County.
From Carrie
Thanks for spending a little time with me this week. I hope you found something new, something interesting, or maybe something to add to your weekend plans.
I’m glad you’re here, and I’ll see you next week.
Carrie
Have a question or want to connect?
With 45+ years in Southwest Florida and more than two decades in real estate, I’m always happy to be a local resource.
Carrie Ciolino, REALTOR®
Royal Shell Real Estate
[email protected]
239-470-1546