ISSUE 59 · OCTOBER 30, 2026
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
There's some welcome news for Sanibel Island! The popular fishing pier near the historic Sanibel Lighthouse is getting closer to reopening, bringing back a favorite waterfront destination for residents and visitors alike.
Closed since Hurricane Ian in 2022, the pier is undergoing temporary repairs, with hopes of welcoming visitors back in late November or early December, pending construction progress and final approvals.
The restoration has received tremendous community support, with residents, businesses, and local organizations contributing approximately $380,000 toward the effort.
Meanwhile, plans are moving forward for a new, permanent fishing pier. In early October, Sanibel City Council approved a preferred location for the future structure, marking another step toward bringing this popular destination back for years to come.
Whether you're casting a line, enjoying the coastal scenery, or simply spending an afternoon exploring Sanibel, the return of the fishing pier is something to look forward to!
Also this week, I'm taking you along to explore a waterfront dining spot in downtown Fort Myers! And with Halloween falling on a Saturday this year, there's no shortage of things to do around Southwest Florida, from fall festivals and craft fairs to waterfront celebrations and costume contests.
Local Life
Waterfront Dining in Downtown Fort Myers
There's something special about dining along the Caloosahatchee River! This week, I'm taking you inside Oxbow Bar & Grill in the historic downtown Fort Myers River District. With indoor and outdoor waterfront seating, beautiful river views, and a charming boutique to browse, it's another great spot to enjoy the Southwest Florida lifestyle.
📍 1300 Hendry Street, Fort Myers
Take a look inside in my latest video!
Around Southwest Florida
Cape Coral City Council unanimously approved nearly $31 million in incentives on October 21 to help HCA Florida Healthcare build a $300 million hospital at 322 SW Pine Island Road, where its freestanding emergency room currently operates. The planned facility will include up to 100 beds, operating rooms, and a cardiac catheterization lab, bringing expanded healthcare services closer to home for Cape Coral's growing population. Construction is expected to begin in 2027, with an anticipated opening in 2029.
Cape Coral's newest outdoor destination officially opens Friday, October 30, with a 10 a.m. ribbon cutting at 3115 Del Prado Blvd. N. The preserve features nature trails, a fishing pond, disc golf, camping areas, and opportunities to enjoy local wildlife. Opening-day festivities include guided tours and animal encounters. Free and open to the public, with no reservations needed for the ceremony.
Up and Coming
The 23rd annual Great Calusa Blueway Kayak Slam Tournament is Saturday, November 14, on Lee County waters. Entry is $75 per angler, and the mandatory captain's meeting and registration is Friday, November 13, 6 to 7 p.m., at its new location, The Venue at Matlacha, 4130 Pine Island Rd.
This Weekend
More than 175 vendors fill Mike Greenwell Regional Park for Buckler's 34th annual Fall Craft Fair, 11831 Bayshore Rd. in North Fort Myers. Saturday, October 31, 10 a.m. to 5 p.m., and Sunday, November 1, 10 a.m. to 4 p.m. Admission is $6, good both days — bring a canned good for $1 off.
Start Halloween with a costumed 5K or one-mile fun walk at Eastwood Golf Course in Fort Myers, hosted by the Fort Myers Police Department. Saturday, October 31, at 7:30 a.m., with costume awards and finish-line treats. Proceeds support the department's Police Athletic League youth programs.
Stroll craft vendor booths, grab a bite and enjoy music at Edison and Ford Winter Estates — and climb the historic banyan tree or pick out a pumpkin. Saturday, October 31, 9 a.m. to 4 p.m. Free to attend, with a fee for each activity, so bring cash.
Margaritaville Beach Resort on Fort Myers Beach hosts a Halloween night party at License to Chill with live music by Rock Candy, cocktails and fire pits. Saturday, October 31, 7 to 10 p.m. Costume contest prizes include a cabana at Fins Up! Beach Club and a two-night resort stay.
Castaways at Fishermen's Village in Punta Gorda throws an all-day Gilligan's Island Halloween party on Saturday, October 31, with themed drink specials, island tunes and prizes for the best costumes. Come as Gilligan, the Skipper, Ginger or Mary Ann — or any castaway look of your own.
The Fort Myers Beach Community Foundation's second annual Halloween pub crawl starts at 5 p.m. Saturday, October 31. Tickets are $20, with games at each stop and $500 prizes for best individual and group costumes, awarded at Bayside Park at 8:30 p.m.
Southwest Florida Car Shows brings classic and custom cars to Ford's Garage at Miromar Outlets for a Halloween show with music, prizes and more than 300 people expected. Saturday, October 31, 10 a.m. to 2 p.m., at 10801 Corkscrew Rd. in Estero. Stroll the rows of cars, grab lunch at Ford's Garage — an automotive-themed burger spot — and browse the outlets while you're there.
The Punta Gorda Isles Civic Association marks its Diamond Jubilee with Halloween bingo, open to the public. Friday, October 30, 6 to 8 p.m. (doors 5:30) at 2001 Shreve St. Entry is $25 at the door for three cards and 10 games; food and drinks available.
Slipaway Food Truck Park & Marina caps Halloween week with Fright Night on Saturday, October 31, 5 to 9 p.m. Expect '80s hits from The Bango Bango's from 6 to 9, spooky cocktails at The Helm and a costume contest with a $1,000 cash prize, announced at 9 p.m.
From the Beyond the Waterfront Collection

Good Morning, Cape Coral
What better way to start your morning than with a little Cape Coral charm? Featuring three of our beloved burrowing owls on the front and an adorable baby owl on the back, this mug brings a little personality to your morning coffee. Perfect for anyone who has a soft spot for these feathered little locals!
Real Estate
Florida's homeowners insurance market continues to show signs of improvement. In September, state regulators approved rate reductions averaging about 7% across four insurers, affecting more than 62,000 policies at renewal. Insurance Commissioner Mike Yaworsky anticipates additional reductions heading into 2027. Meanwhile, Citizens Property Insurance has seen its policy count drop from 1.4 million in 2023 to approximately 266,000 as more homeowners move to private insurers. Another positive change: Florida's 1% FIGA insurance surcharge ended October 1 for new and renewing policies. With more options becoming available, even homeowners whose premiums haven't increased may benefit from shopping around.
Your Free Cape Coral Waterways Guide
Cape Coral has more than 400 miles of canals — and no two are quite the same. This free guide explains Gulf access, sailboat access, and freshwater canals, plus bridge heights, flood zones, seawalls, docks, and how long it takes to reach open water. Written by a 45-year local for anyone thinking about life on the water.
From Carrie

With Halloween falling on a Saturday this year, there's plenty of fun to be had around Southwest Florida! Whether you're dressing up for a costume party, enjoying live music with friends, exploring a local festival, or heading out for a waterfront dinner, there's something for everyone.
Whatever your plans, I hope you enjoy a little fun, good company, and all the things that make living in Southwest Florida so special.
Have a wonderful weekend, and I'll see you next Friday!
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















