No matter what time of year you go to Sanibel Island in the sunny state of Florida (hence why it is called the aptly-named Sunshine State!), you will have a blast. But if you skip the busiest summer months and head to the Sunshine State during September, you might find that you have really hit the jackpot.

Instead of fighting people for blanket space on the sandy beaches, trying to find accommodation for you and your friends, or attempting to get a reservation to one of the many seafood restaurants, there are fewer people when you head here in September. Plus, you can still experience super long days filled with sunshine, bright skies, blue waves, and lush greenery. Talk about a relaxing and fun vacation!

We love coming to Sanibel Island for Labor Day weekend. Not only is there so much to do that is perfect for partying and having a few drinks with your pals, but this is a fun-filled weekend that has annual events you won’t find at other times. Head to Sanibel Island and visit nearby Captiva Island for LDW on September 4th, 2023, to have an unforgettable experience with your loved ones. Check it out!

Labor Day Sidewalk Sale

One of the best not-miss events that you can check out during your stay in Sanibel is going to the Labor Day Sidewalk Sale at Sanibel Outlets! If you need to buy a date night outfit, another bathing suit for surfing, or a souvenir to bring back home for your friends, head to the Sanibel Outlets in Fort Myers, FL, on September 4th and 5th, 2023. You can get multiple days of savings for your holiday weekend to kick off the holiday in the best way possible.

Willy Wonka

Are you a theater nerd? We mean nerd in the best way possible! And if the answer is yes, you are going to love the Willy Wonka showing at the nearby Fort Myers Theatre on San Carlos Boulevard in Fort Myers, FL. Since Sanibel Island is so close to the bustling and busy city of Fort Myers, you can easily get here in no time at all. And then, at the end of the show, you can retire to your quieter and more relaxing neighborhood. We love the sound of that!

Steel Drums

Listen to some tropical and island-type music by going to Rumrunners on Cape Harbour Drive in Cape Coral, FL, on September 4th at 1 pm. Listen to “Pan Dave” , an infamous local musician who is well-versed in the steel drums and can get people out of their seats and dancing in no time at all.

Have a Few Drinks in Sanibel Island for Labor Day!

One of the main events of Labor Day weekend is having a few drinks with your friends or family. Luckily for you, there is no shortage of bars, breweries, wineries, and fun restaurants for you to check out during your weekend stay in Sanibel. We recommend going to Doc Ford’s Rum Bar and Grille in Sanibel for Caribbean and Southern-style seafood dishes, like Cajun crab and numerous types of rum. Mix some rum and coke, or just have it plain for a fun way to kick off your evening!

Next, head to Island Time in Sanibel to enjoy this poolside bar for laid-back snacks and ice-cold drinks during a hot summer day. We love having a strawberry daiquiri, relaxing by the pool while the kids go swimming, and munching on some fried food. It is vacation, after all!

Lastly, you can’t miss Sanibel Grill if you are in the mood to catch a football game on TV or challenge your pal to a game of foosball or pool. Head here to chill out and eat some yummy seafood while you watch the latest NFL game on the different TVs scattered around the joint.

Take the Kids to the Beach

Last but not least, you can’t go to Sanibel Island, or Florida, without heading to the beach! Luckily, there are tons of beaches right outside of your doorstep that you can walk to in just minutes. We recommend going early and grabbing a spot at Bowman’s Beach to gaze at the miles of coastline and the endless waves. Or head to Sanibel Island Northern Beach to avoid the crowds and enjoy more solitude. You’ll also love going to Lighthouse Beach Park to swim in the ocean and relax with your children while they build a sandcastle.

As you can see, Labor Day weekend is THE perfect time to head to Sanibel Island in sunny Florida! And when you stay with us at Tropical Escape Sanibel, we guarantee you will have an unforgettable vacation. Just look online and find the perfect accommodation option for your needs. We know that you will have an amazing time with your friends and loved ones as you explore all that the Sunshine State has to offer.