Skip to main content

Times of the Islands Magazine

15 Things To Do on Sanibel and Captiva Islands This September & October

Aug 31, 2018 03:11PM ● By Emma Eldridge
Looking for something to do in the Months of September & October? We've got you covered with an array of events including fall festivities, a variety of classes, and more.

Festivals and Fairs!

Who said the fun has to stop when the kids go back to school? There is still LOTS to do as the summer winds down and the fall starts up! Check out the 2018 ISLAND HOPPER SONGWRITER FEST and a Fall Family Candy and Costume Festival. Make sure to have fun!

2018 ISLAND HOPPER SONGWRITER FEST - start Sep 21 2018 0900AM


See you at the 5th Annual Island Hopper Songwriter Fest on The Beaches of Fort Myers & Sanibel! Captiva Island: September 21 - 23, 2018 Downtown Fort Myers: September 24 - 27, 2018 F... Read More » 

33rd Annual BaileyFest - start Oct 21 2018 1200PM

33rd Annual BaileyFest - Oct 21, 2018 12:00PM

Last year’s Baileyfest featured solo singers, bands and groups, dancers, a roaming magician, food, games and plenty of surprises. This year it’s going to be BETTER!Stop by Bailey’s Center... Read More » 

Fall Family Candy and Costume Festival - start Oct 31 2018 0500PM

Fall Family Candy and Costume Festival - Oct 31, 2018 05:00PM

Wear your costumes and have some fun at this fun carnival type festival. Family friendly food and more. Bag of candy is the entry fee. Read More » 

Creative Classes

Looking to take a note from the kids and take a class of your own? Great! Check out the Alcohol Ink Class and the Cooking with French Chef that the Sanibel Community Association is hosting. Just make sure to tell us what you learned :)

Alcohol Ink Class - start Sep 26 2018 0930AM

Alcohol Ink Class - Sep 26, 2018 09:30AM

Guests Back by popular demand Anita will be teaching Alcohol Inking! In this class you can practice all the different styles of inking such as Sticker, Stamping, Swiping, Blowing by straw... Read More » 

Cooking with French Chef - start Oct 05 2018 1000AM

Cooking with French Chef - Oct 05, 2018 10:00AM

This class will be hands on after the chef demonstrates the methods. With the puff pastry dough we will make ham and cheese appetizers, fruit tarts with fruit on pastry crème covered with... Read More » 

Something for the Whole Family

Grab the family and head on out for an adventure. We recommend checking out "Ding" Darling DaysCaptiva Memorial Library Apple Picking Time and maybe even Songwriter Saturday at 'Tween Waters Captiva Island for the tweens in your life.

Songwriter Saturdays - start Jul 07 2018 0300PM

Songwriter Saturdays - Sep 01, 2018 02:00PM

The hit sounds and hip artists of Nashville are coming to Captiva Island — as 'Tween Waters Island Resort & Spa continues our monthly and highly popular "Songwriter Saturdays" introdu... Read More » 

National Public Lands Day - start Sep 22 2018 0830AM

National Public Lands Day - Sep 22, 2018 08:30AM

J.N. "Ding" Darling National Wildlife Refuge & Tarpon Bay Explorers, are celebrating National Public Lands Day!"Ding" Darling National Wildlife Refuge:Wildlife Drive: FREE admission a... Read More » 

Captiva Memorial Library Apple Picking Time - start Oct 02 2018 0900AM

Captiva Memorial Library Apple Picking Time - Oct 02, 2018 09:00AM

Drop in for a book display featuring apples. From October 2-6 color a paper apple to add to our apple garland (to be hung in the Children's Room). From October 9-13 complete fun activity ... Read More » 

"Ding" Darling Days - Oct 12, 2018 09:00AM

“Ding” Darling Days’ Family Fun Day on Sunday, October 14, culminates a weekend of eco-activities with all-free refuge tram tours, live wildlife presentations, hot dogs, kids crafts, and ... Read More » 

Giving Back to the Community

Looking to give back to the community while having a bit of fun? Check out the F.I.S.H. of SanCap Friendly Faces LuncheonGalloway Captiva Triathlon Weekend 2018, and 10K Race 4 F.I.S.H.

FISH of SanCap Friendly Faces Luncheon - start Sep 11 2018 1130AM

F.I.S.H. of SanCap Friendly Faces Luncheon - Sep 11, 2018 11:30AM

The Friendly Faces luncheon is just that -- a luncheon surrounded by friendly faces. Everyone from the F.I.S.H. volunteer who greets the attendees at the door, the George & Wendy’s Sa... Read More » 

Galloway Captiva Triathlon Weekend 2018 - start Sep 15 2018 0900AM

Galloway Captiva Triathlon Weekend 2018 - Sep 15, 2018 09:00AM

The USAT-sanctioned adult sprint triathlon is a 1/4-mile swim, 10-mile bike and 3.1-mile (5K) run on Captiva Island, Florida. The swim will be in the open waters of the Gulf of Mexico, th... Read More » 


10K Race 4 FISH - start Oct 27 2018 0730AM

10K Race 4 F.I.S.H. - Oct 27, 2018 07:30AM

The 10K (6.2 miles) race will start and finish at the Sanibel Community House, 2173 Periwinkle Way, Sanibel Island. Parking will be available directly across the street from the Sanibel C... Read More » 


Ongoing Events

Don't forget about these weekly gems! There's Birdwatching Sanibel Sea School with  on Thursdays, Sunday Farmers Market & Native Plant Sale on Sundays, and SWF Critical Mass Cycling continuing on the last Friday of every month. A little something for everyone.

Sunday Farmers Market  Native Plant Sale - start May 13 2018 0800AM

Sunday Farmers Market & Native Plant Sale - Sundays thru December, 2018 08:00AM

The Sunday Farmers Market and native plant sale, 8 a.m. – 1 p.m., offers local and organic produce, fresh seafood, unique crafts, local honey, native plants, handcrafted jewelry, BBQ, Cub... Read More » 

Birdwatching - start Feb 01 2018 0900AM

Birdwatching - Thursdays thru November 2018 09:00AM

Each Thursday morning, we offer a walking tour to discover the birds of Sanibel Island's East End. During the walk we discuss basic bird biology and behaviors, as well as learn how to ide... Read More » 

SWF Critical Mass Cycling - start Jun 29 2018 0700PM

SWF Critical Mass Cycling - Last Friday of Every Month Thru February 2019 07:00PM

Southwest Florida Critical Mass is a collection of cyclists young and old, casual and competitive. We come together to enjoy riding bikes and sharing good times. You'll find fun and well ... Read More » 

Don't see your favorite included? Please share your event with us by posting to our calendar. It's free and a great way to spread the word!