Island Hopping on the Coast of Florida

Three days — three different islands. It may sound impossible to most, but on the coast of Florida, particularly the Gulf Coast, it is as easy as one, two, three. The moment you touch down in the Sunshine State, you will be transported to island time on three very special islands.  

One of the easiest steps is just getting here, even if you’re far away, thanks to the Punta Gorda Airport (PGD) on Florida’s southwest coast between Sarasota and Ft. Myers. They offer flights with Allegiant Airlines, which provides low cost and non stop air service to almost 50 destinations.  

Day One: Gasparilla Island 

Less than an hour’s drive from PGD, this island is one of the best-kept secrets of Southwestern Florida. Its primary community, Boca Grande, gained popularity around the turn of the 20th century, and has remained an affluent area that has been enjoyed by residents and visitors for generations. Its Old Florida charm reminds one of the estates of the South, with lots of tall oaks and banyans covered in Spanish moss, elegant architecture with columns and expansive front porches, and a laid-back pace. Boaters can explore 750,000 acres of estuary — where freshwater and saltwater blend to provide nurseries for the oceans fish species. Dolphins, white pelicans, osprey, and manatees are only some of the unusual species you will encounter. The beauty of this island has provided many artists with inspiration, and the town’s art galleries feature many interpretations of the scenery and wildlife. At the Hughes Gallery on Park Avenue, you will find a variety of artists who present an array of works that include Boca Grande scenery. Stop in for monthly events and the opportunity to meet some of the artists! 
hughesgallery.net  

The beaches here are ideal for laying out, shelling, and long, scenic walks - particularly at the end of the island, where you can find the stately Boca Grande Lighthouse and Museum. This site is part of the Barrier Island Parks Society, who is dedicated to drawing visitors to Florida’s most natural and historical places. Enjoy a sunset together on the edge of the island, watching as the sky turns bright orange and pink.  
barrierislandparkssociety.org  

When the evening does come and you’re ready to rest for the night, the choice of accommodations are excellent; but one choice always stands out. The Gasparilla Inn & Club, built in 1911 and meticulously maintained to preserve its elegance. Accommodations at this resort range from rooms at the inn, to cottages, and their brand new Sharp Houses. Wherever you choose to stay will be decorated in a cheerful island style, and comes with great amenities and first-class service. The main attraction here is the golf course; designed by the renowned Pete Dye, there are water views from every hole, overlooking the Gulf of Mexico and Charlotte Harbor. Many golf lovers, including presidents, have come to enjoy the island-within-an-island course. 
the-gasparilla-inn.com  

While the main lodging attraction is the famous Gasparilla Inn and Club, some prefer an accommodation with less frills and more opportunity to feel at home while away from home. We recommend The Palmetto Inn, found within a beautiful historic house built in 1900 that sits on a quiet street just a block away from the beach and downtown shopping. 
thepalmettoinn.com 

Day Two: Sanibel Island 

Hop in the car to drive for just a couple of hours to Sanibel Island. You’ll need to go through the bustling city of Fort Myers - but that’s a whole other trip! Going over the long bridge to Sanibel (you’ll need about $5 in cash for the toll) you can marvel at the beauty of the surrounding water, and soak in the transition of leaving behind the tall buildings for little cottages. Sanibel is known for its shell-strewn beaches, created by a very specific geographical phenomenon that allows the many beautiful shells to wash up its shores, most intact and all colorful and unique. Sanibel is also intent on preserving its lush tropical foliage, with little shops, cottages, and inns tucked between. Its slow pace and many bike paths make it ideal for biking around.  

Your first order of business is to do as the locals do, and get yourself a set of wheels; no, not a car, a bicycle! Billy’s Rentals, located on the popular Periwinkle Way, offers bike and Segway rentals and bike repairs so you can wheel around with ease. Then you can wheel your way down Periwinkle, visiting the many shops and galleries located here. Don’t miss the chance to stop at the very cheery Blue Giraffe Restaurant, or to giggle at the cow themed decor of The Island Cow between bites of your burger. 
billysrentals.com  

After exploring Periwinkle Way, pedal over to the Baileys-Matthews Shell Museum, which houses all kinds of seashells and also features exhibits about conchology, malacology, and even the archaeological aspect of shelling! They also offer beach walks to search for shells, and be sure to visit their gift shop for shell-inspired jewelry, books, and gifts. 
shellmuseum.org  

Biking isn’t the only way to explore, so pick up a paddle! Become an explorer as you make your way through through the mangrove tunnels and sheltered bays on a canoeing, kayaking, or paddleboarding expedition. Launch from a local park or go on a guided tour, and get your rentals from one of the many great outfitters in the area. Kayak Excursions offers all kinds of fun paddle sports and even lessons, from kayak fishing trips to guided eco tours and more, with no-hassle customer service that includes free deliveries to your location. YOLO Board Adventures has many paddle rentals, but specializes in stand-up paddleboarding (SUP) with lessons from certified instructors for newcomers to the sport, and eco-tours that give you an up-close view of the area’s beautiful wildlife.  
kayak-excursions.com 
yoloboardadventuressanibel.com 

After all of that exercise, you deserve a rest. Live the barrier island life at Sundial Beach Resort & Spa! Boasting miles of shell-strewn beach, this resort boasts spacious, fully-equipped condominiums so that you can have all the comforts of home while enjoying a tropical paradise. The living spaces come in various sizes for your secluded getaway or family vacation, and all are complete with kitchens, living rooms, and dining areas. Shop and dine directly onsite at any of the resort’s locations and enjoy high-end amenities such as tennis facilities, multiple swimming pools, children’s activities, and the Kay Casperson Lifestyle Spa and Boutique. 
sundialresort.com 

If you are looking for more local flavor, then enjoy a stay at Tarpon Tale Inn, a charming getaway located on the quiet east end of Sanibel Island in Old Town Sanibel. Each of the inn’s cottage-style accommodations is carefully decorated to exude its own charming style, the larger suites with kitchens and dining areas, and all with their own private patios and use of the inn’s complimentary bikes to explore the island. Nearby, you’ll find the famous island beaches, quaint shops, adorable eateries, the romantic Sanibel Lighthouse, and plenty more spots that are soon to become your favorites. 
tarpontale.com  

Day Three: Captiva Island 

This time, there’s barely a drive at all, since Sanibel and Captiva are connected as sister islands. Captiva is the smaller of the sisters, and has only one main road that runs through it. It is the perfect place to find serenity and relaxation, whether for a short visit or for the rest of your life - as many people have found home here. Part of the charm of the island is found in driving along Sanibel Captiva Road, spotting the different characteristics of the distinctive houses that dot the island.  

You can also sense the peacefulness that the island offers when visiting its natural areas. Marvel at the astounding beauty of this idyllic island with a visit to the 7,600-acre J.N. "Ding" Darling National Wildlife Refuge. This spectacular sanctuary is home to more than 245 bird species, 60 types of reptiles, 35 mammal species, paddling, hiking/biking trails, observation towers and a four-mile scenic drive (open every day except Friday). Be sure to stop by the visitor and education center to glean information about this marvelous refuge or to arrange informative, guided tours. 
dingdarlingsociety.org  

Arguably the best way to see Florida wildlife is from the water - so give kayaking and paddleboarding a shot. Launch and rental facilities are abundant near the water and many provide guided tours that can direct you to notable spots. The Great Calusa Blueway is a 190-mile water trail that threads through Southwest Florida, arguably the finest paddling trail in the U.S., and is a must-paddle for anyone able to stand on a board or sit in a canoe or kayak. It provides a closer look into the native habitats of resident birds and fascinating sea creatures. It’s an easy way to spot dolphins, osprey, and manatees, just to name a few! The pace is up to you — just pick one of the 80 access points to launch from and go with the flow. 
calusablueway.com 

Rest is also found at Captiva’s incredible accommodations, of course. If you’re traveling with the whole family, we must recommend South Seas Island Resort on Captiva. Between the gentle Gulf waters, nature preserve, numerous pools, and family activities available, this resort is like one big playground for you all to enjoy together. Whether you stay in an inn suite, condo, or vacation home, all of this resort’s accommodations are meant to suit a family vacation with spacious layouts, equipped kitchens, and amenities. Have a meal at one of their onsite restaurants, visit the activity center, or even play a round of golf together on their unique family-friendly course. 
southseas.com 

The ‘Tween Waters Island Resort & Spa has become a legend among Southwest Florida visitors since its beginnings in 1931, and is situated between the Gulf of Mexico and Pine Island Sound. This all-inclusive resort spans 13 acres, and offers 137 units and cottages that vary from standard guest rooms, studios and three bedroom suites to two and three bedroom historic cottages whose past guests have included famous historic characters like Teddy Roosevelt! Plan an outdoor adventure, bask in the luxury of the spa, dine at one of their onsite restaurants, swim in one of their beautiful pools, or be a part of one of their seasonal events. 
tween-waters.com  

Bonus Trip: Pine Island 

 Only 30 minutes from Fort Myers but a world apart, secluded Pine Island offers a quiet, laid-back atmosphere, plenty of great fishing, and lush natural environment. The waterways of Matlacha Pass and in the Pine Island Aquatic Preserve are excellent for kayaking and canoeing. The largest island off Florida’s Gulf Coast, Pine Island offers a small-town atmosphere amid mangroves, three aquatic preserves, and acres of palm, tropical plants and fruit groves. The waters of Pine Island Sound provide not only some of the finest fishing in Florida, but are a haven for birdwatchers and nature lovers. For many, vacation rentals are the choice accommodation - for longtime visitors, staple inns are the favorite option, like the iconic Tarpon Lodge that offers romantic Old Florida style and unforgettable views.  

We hope that on your last day of island hopping, you feel refreshed and relaxed - and also inspired to visit again! Perhaps you’ve fallen in love with the island life…and it’s time to extend your trip.