The Simmons Team’s
TOP 10 FAVORITE THINGS TO DO IN SOUTHWEST FLORIDA
There are so many things to see and do in the Southwest Florida area. Whether you are here for the first time or the tenth, if you have fallen head-over-”flip-flops”-in-love with all that Southwest Florida has to offer, we completely understand! At The Simmons Team, we are truly inspired by the natural beauty that surrounds us daily, and we are so glad you are too!
1) Beaches

2) Bicycling
Sanibel Island is one of Southwest Florida’s most tranquil locations for leisurely bicycling along winding pathways underneath canopies of trees. While cycling along the Sanibel Island Shared-Use Path — which includes trails through J.N. Ding Darling National Wildlife Refuge — you may encounter the occasional gopher tortoise munching on a hibiscus, or an iguana nestled in the trees. Riding along the pathways of tranquil locations, such as the Estero Preserve or Pine Island Bike Path, is a true escape from the day-to-day grind and a relaxing and enjoyable experience for the entire family.
3) Kayaking
Southwest Florida allows for the most breathtaking kayaking opportunities along the coastline of Florida. Visitors and locals enjoy gliding effortlessly through the mangroves along hidden waterways in places like Tarpon Bay, Matlacha, or the Calusa Blueway that encapsulate wildlife habitats and provide an escape from the sounds of day-to-day living. There are many locations positioned all along the coastline dedicated to ensuring your experience on the water is a safe and memorable one.
4) Boating
Boating in Southwest Florida is one of the many benefits of living on or near the Gulf of Mexico. Many locals and visitors enjoy the waterways of Florida and spend countless hours exploring the calm waters of the Gulf. If getting “salty” is your thing, there are many local businesses that offer sailing and boating courses that will help provide the information and licensing you and your family will need to safely navigate and charter the waters of Sanibel, Captiva, Cape Coral, Fort Myers Beach, Estero, Bonita, and Naples.
5) Golfing
It is no surprise that Florida continually ranks in the top 10 states for golfing in the U.S. for their abundance of golf facilities to suit any golfer. Included in this popular winter and summer vacation area are the cities of Fort Myers, Cape Coral, Sanibel Island, Estero, Naples, and Bonita Springs, all of which offer both public, semi-private and private golf courses. There is an abundance of golf courses available to travelers and residents alike, from championship-quality private courses with membership waiting lists to short par 3’s for the weekend novice.
6) Shopping
While taking a break from the sun and surf there are a multitude of boutiques, shopping centers, and indoor and outdoor shopping malls to help accentuate any wardrobe, as well as finding the perfect decor to make any house a home. Spend the day at Sanibel Island, where you will be captivated by the unique boutiques and shops such as Periwinkle Place, Tahitian Gardens, or Olde Sanibel Shoppes. For upscale shopping, you’ll want to visit Fifth Avenue South in downtown Naples or the Waterside Shops at Pelican Bay. Other destinations with a wide variety of shopping and dining options are Bell Tower Shops and Gulf Coast Town Center in Fort Myers and Coconut Point Mall, just to name a few.
7) Dining
Southwest Florida is a food destination paradise. The choices are endless when it comes to the places available to enjoy a great meal. Whether you are looking for a couples night out in downtown Fort Myers River District or a great family dining experience out on Sanibel and Captiva, you are sure to find it here, with restaurants offering great indoor dining experiences as well as outdoor and waterfront seating to enjoy Florida’s wonderful weather. Upscale and fine dining can also be found on Naples 5th Avenue as well as on Captiva.
8) Fort Myers Spring Training
Fort Myers is the spring training home to two professional baseball teams, the Boston Red Sox and the Minnesota Twins, offering a great time for families and friends during the best weather months in Southwest Florida. The fun does not stop after spring training, with these venues offering other events like concerts, car shows, festivals, and more. The Fort Myers area is also home to the Fort Myers Miracle minor league baseball team, exciting baseball fans all season long.
9) Museums & Parks
When searching for fun things to do with the whole family, Southwest Florida has you covered. Visit any of the great historical or natural museums, such as the Edison & Ford Winter Estates, Sanibel Historical Museum and Village, or even the Railroad Museum of Southwest Florida. You may also enjoy great art pieces from local artists found at the Alliance for the Arts in Fort Myers or the Tower Gallery in Sanibel, or simply enjoy the Florida weather at any of the area parks, such as Lakes Regional Park in Fort Myers and Cambier Park in Naples offering walking and biking trails.
10) Theater & Entertainment
Southwest Florida has become one of the leading destinations for Arts & Entertainment, with headlining shows appearing at the Barbara B. Mann Performing Arts Hall in Fort Myers, as well as Artis–Naples, home of the Naples Philharmonic. If you are seeking a more intimate and unique theater experience, The Broadway Palm Dinner Theater offers a dinner and show while the Florida Repertory Theatre is committed to providing a first-class regional theater for Southwest Florida.