Island-hopping along The Beaches of Fort Myers & Sanibel (2019)

Find your island by land or water!

LEE COUNTY, Fla. -- Most of us dream about it. A tropical vacation. Island-hopping from one exotic, off-the-grid island to another. Not a care in the world. Leaving all of your worries (and maybe even your phone) at home.  If this is what you would like to turn into reality, pack up your T-shirts and flip flops and head to The Beaches of Fort Myers & Sanibel on the Gulf of Mexico.  Here, you can take the time to unplug. Find your island in this Southwest Florida paradise by land or by water.  

In Jimmy Buffett style, you may spend days doing absolutely nothing or engaging in serious exploring of these award-winning islands.  The Florida of days long past, with unspoiled white sand beaches, exotic wildlife and lush subtropical foliage, can still be found here and it is the perfect oasis where visitors can “get away from it all” and yet still be close to all of the modern amenities.  Many of the area’s 100 coastal islands are uninhabited mangrove clusters, while others take visitors' breath away with their beautiful beaches. From shelling to kayaking to beautiful sunsets, visitors come to this destination and find their island creating wonderful vacation memories.  

Save the date!

The sixth annual Island Hopper Songwriter Fest returns Sept. 20-29, 2019. The popular event brings music back to the beach with new artists and new events.  The festival takes place over 10 days and offers a range of star-studded performances. It kicks off on Captiva Island Sept. 20-22; moves to downtown Fort Myers Sept. 23-26; and ends at Fort Myers Beach Sept. 27-29. 

Visit for details as they are announced including artists, venues and great deals on accommodations for locals and out-of-town guests.

The festival is presented by The Beaches of Fort Myers & Sanibel, iHeartRadio, Cat Country 107.1 and BMI. It was named one of the top events for summer by the Southeast Tourism Society. Past performers include Parmalee, Thompson Square and Grammy Award winner Maren Morris.  The sixth annual event will continue to give fans the opportunity to meet the talented artists who write songs for country superstars including Tim McGraw, Miranda Lambert, Jason Aldean and Tricia Yearwood.

For more information visit Follow the festival hashtag #islandhopper on Twitter and other social channels.  

So many do you choose yours?

There’s just something about an island that spins romantic notions of independence, isolation, and escape. Whether it’s for a day trip, vacation, or rest-of-your-life commitment, getting out to an island is the ultimate experience at The Beaches of Fort Myers & Sanibel! So, check out these suggestions and for more, visit

      Roughing it: If you’re pining for the scent of campfires and the embrace of a sleeping bag, head to Cayo Costa, all-natural and untethered to the mainland. Marinas on Pine Island and Captiva Island can provide water taxi service. Call far enough in advance and you may be able to reserve a cabin, which isn’t all that much more luxurious than tenting – meaning both options are primitive. You’ll have to pack everything you need in and out.      

      Plushing it: Captiva Island has some of the plushest accommodations the other side of the Intracoastal Waterway, so if you’re looking to do nothing but laze on the beach or maybe play a round of golf, reserve your room and luxuriate. Go ahead and have a massage while you’re at it.

      Going rural: Fruit and tree farms, no stop lights, miles of countryside, even a cattle farm.
Pine Island feels like you’ve traveled inland rather than out island. Long and roomy, its lack of natural beaches means less traffic (aside from sometimes bustling Matlacha) and more affordable dining and lodging. Great fishing. A haven birdwatchers. Hiking and paddling trails. Indian shell mounds. Art galleries to shop.

      Barefooting: If your idea of a getaway involves going shoeless the entire time, Fort Myers Beach has the perfect dress code for you. Okay, you may have to slip into some flip-flops from time to time, but the fine white sand and casual attitude give you permission to dig your toes in the sand and make a barefoot fashion statement.

      Old, classic Florida: Historic charm, cute shops and great restaurants are the formula that draws travelers off the main roads to Gasparilla Island, home of the sophisticated little beach town of Boca Grande. Browse shops, have lunch, and buy ice cream in historic venues such as a railroad depot and movie theater. Rub elbows with the locals at a beach bar, then, spend the night in the grande dame Gasparilla Inn, circa 1913, a member of Historic Hotels of America.

      Family biking: Sanibel Island has more than 25 miles of shared-use bike paths. Most of the path is separated from roadway by vegetation, making it a safe trail for families to pedal along. It runs the length of the island – from beaches and nature attractions to shops and restaurants. The newest segment links two city parks away from all vehicular traffic.  And Cape Coral has been awarded the bronze level Bicycle Friendly Community (BFC) designation in recognition of the city’s accomplishments in creating a 90-mile network of interconnected bicycle-and pedestrian-friendly paths. It joins a distinguished group of only 351 communities in the nation recognized with this prestigious award.          

Check out the following tips for your island-hopping experience, whether you decide to travel by land or by water!

Island-hopping by land!

Few destinations have such an abundance of sandy beach coastline, much of it undisturbed by modern intrusions.  With a subtropical climate, a 590-mile shoreline and the warm waters of the Gulf, this area has all the components for a fantasy island vacation.  Each island has a character of its own and makes for an island hopping vacation that includes sunsets, shelling, great dining and picnicking, water sports, boating, biking and exploring.  Best-known are Sanibel and Captiva islands, connected to the mainland by an alluring three-mile causeway.  They are connected to each other, by a blink-and-you’ll-miss-it bridge at Blind Pass. 

Sanibel Island

Cross the magical Sanibel Causeway and all worries vanish!  Sanibel is known worldwide for its shelling and the associated posture referred to as the "Sanibel Stoop." Some shellers attach

flashlights to their heads, in an effort to be first in the daily search for top picks of the more than 400 varieties of shells found on the beaches, particularly after an especially high or low tide. For most visitors, however, shelling is merely a delightful excuse to enjoy hours of sun along some of the best shoreline in North America. 

U.S. News & World Report named Sanibel Island among the top 10 family beaches in the U.S.  The article says the island "is popular with families because its beaches have plenty of beautiful – sometimes unusual – seashells, which little ones love to collect." 

Huffington Post called Sanibel Island one of six Florida islands better than the Caribbean: “With no chain stores, no stoplights and a population of just about 7,000 people, this place is pure, quiet island bliss. Hunt for seashells on the beach, or chow down on chicken wings at the Lazy Flamingo.” included Sanibel Island in a roundup of America’s Most Beautiful Barrier Islands: “Sanibel epitomizes Old Florida. You won’t find a single traffic light on the island and its dark sky ordinances — meant to safeguard the turtles that nest here from May 1 through October 31—means that there are minimal streetlights. With its unique east to west orientation (most barrier islands are situated in a north/south pattern), the island is able to maintain beautiful sandy beaches that are prime spots for shelling. In fact, you can scoop up 250 different types of seashells on Sanibel’s shores. J.N. ‘Ding’ Darling National Wildlife Refuge is the place to go to spy roseate spoonbills, snowy egrets, cormorants, and other birds as well as alligators, bobcats, river otters, and manatees. Vacations here are all about swimming, walking, biking, kayaking, fishing, and boating.” 

The island’s main thoroughfare, Periwinkle Way, is picturesque and lush with foliage. Interesting shops and restaurants dot the road from the Sanibel Lighthouse to Tarpon Bay Road,

making it difficult to complete the distance without a half-dozen sightseeing stops at boutiques and art galleries. What you will not find:  Buildings taller “than the tallest palm tree.”   

Don’t miss:  The J.N. "Ding" Darling National Wildlife Refuge is home to many exotic species of birds and plants. A four-mile drive with access to walking and canoe/kayak trails offers abundant opportunities for naturalists to witness a raccoon washing up before breakfast, an alligator snatching a quick bite or long-legged wading birds stalking their prey. Visit or call 239-472-1100.  Also: Walk the boardwalk at Sanibel Lighthouse, bike along Periwinkle Way. Visit Bailey-Matthews National Shell Museum. Shop at the original Chico’s store in Periwinkle Place. Visit She-Sells-Sea-Shells. See a play at the Schoolhouse Theater, tour the Sanibel Historical Village and Museum.

Captiva Island

The main attraction on Captiva:  none.  And that is the attraction!  Many people wile away the hours in one outdoor endeavor or another. The natural beauty of the island is the draw.  It was here that Anne Morrow Lindbergh, wife of the famous aviator, wrote her best-selling book, "Gift from the Sea."  More remote than Sanibel, the island offers a laid-back pace, several great restaurants, sunset views and beautiful beaches.    

Don’t Miss:  The best sunset views at the Mucky Duck at the north end of Captiva on picturesque Andy Rosse Lane.  This popular hangout with locals and visitors is never short of cold beer and fresh seafood. An island sunset tradition since 1976.  Visit or 239-472-3434.  Also:  Dinner at the eclectic and delicious Bubble Room, shop art galleries on Andy Rosse Lane. 

Estero Island, Fort Myers Beach

Estero Island, home of Fort Myers Beach, has been long-recognized as one of the “world’s safest beaches” because of its gently sloping shoreline. The sand is particularly soft and white, like powdered sugar. During the winter, Estero Bay is home to an extensive shrimp and fishing fleet.  Visitors find every imaginable water toy, from windsurfer to catamaran and parasail. Numerous marinas operate boating and fishing charters. Local restaurants benefit from the catch, which generally include red snapper and grouper. 

Don’t miss:  Lovers Key State Park, just south of Fort Myers Beach.  The Travel Channel ranked this beautiful park fourth in the state of Florida.  This is one of the area’s most pristine parks.  Walk the boardwalk over tidal lagoons to a sandy, white beach with sea oats. Hike the nature trail, paddle a lagoon, and get married under the gazebo! 

Visitors understand why has listed Lovers Key among its Top 10 Romantic Retreats.  For information, visit or call 239-463-4588. 

Also:  Explore Mound Key Archaeological State Park, rent a kayak and paddle the estuaries around Lovers Key.

Pine Island

Step back in time on Pine Island to reminisce a period when fishing reigned as the area’s largest industry. Accessible by land via "the fishingest bridge in the USA" at Matlacha [Mat-la-chay], the island is 17 miles long with Pine Island Sound on one side and an aquatic preserve on the other.  Home to the Calusa Heritage Trail; the largest Indian shell mound in Southwest Florida.  For details, contact Randell Research Center at or call 239-283-2062. 

Don’t miss:  A stroll through Matlacha. This colorful Mayberry-like fishing village is filled with galleries of painters and sculptors.  Visit or call 239-283-0888.  Also:  Visit “Florida Creative Coast Weekends,” the second weekend of each month November through April. 

Gasparilla Island

Accessible by boat and car via a causeway, this island offers fishing, shelling and lots of family fun.  The island has five beaches with Gulf access. For information visit or call 941-964-0375. 

Travel + Leisure magazine named Boca Grande on Gasparilla Island, as one of its 50 Best Romantic Getaways. “This idyllic enclave on the Gulf of Mexico is a genuine glimpse of Old Florida. Whimsically named streets such as Damnificare, a postcard-worthy lighthouse watching over Gasparilla Island State Park, and long, quiet beaches lapped by gentle waves.” 

The island’s charming turn-of-the-century harbor town, Boca Grande, was founded by the wealthy DuPont family in the late 1800s.  This sleepy southern town comes with small shops, cozy restaurants, waterside accommodations and beautiful beaches. Former President George H. W. Bush, along with family members, enjoys an annual winter visit to Gasparilla Island, staying at the legendary Gasparilla Inn & Club.  The Inn dates back to 1911 and is a member of the Historic Hotels of America.  For information, visit or call 941-964-2201. 

Don’t miss:  The restored Boca Grande Lighthouse Museum, built in 1890.  For information, visit call 941-964-0060.  Also: visit the famous Boca Grande Railroad Depot, home to antique and gift shops, the Loose Caboose Restaurant and an ice cream parlor. The structure was the last depot for the Charlotte Harbor & Northern Railway. 

Island-hopping by boat!

With more than 100 barrier and coastal islands, there are many options to exploring the area by water.  Hop on a water taxi, rent a boat, and take one of the scheduled services for the outer islands.  Collect shells.  Visit a museum or historic site.  Have a “cheeseburger in paradise” at the Cabbage Key Inn.  Swim in the pristine waters surrounding tiny North Captiva Island.  Relax on a deserted beach at Cayo Costa. The options are as endless as the area’s award-winning beaches.  

Don’t miss:   Pack a picnic lunch and head for a favorite of area boaters, Picnic Island.  Visible from the Sanibel causeway, this island is located at mile marker 101 off the south end of Pine Island. Camping is allowed.  

Cayo Costa

If you want to be a castaway, this is your island! Cayo Costa ranks as one of Boating World magazine’s “Great Escapes.” 

The beach at Cayo Costa State Park was recently named among the world’s best “hidden beaches” by Condé Nast Traveler magazine’s Web site  The site described the beach on Cayo Costa island, which is accessible only by boat: “soft white sand, chill-out serenity, and nary a high-rise at the tide line.” 

The state park is also popular with day visitors for its snorkeling and fishing opportunities.  Heartier souls enjoy the primitive overnight camping in the 12 small cabins or 18 tent campsites.  No electricity.  Close to nature.  Beautiful.  The island is accessible only by private boat or passenger ferry.  For information, visit  or call 941-964-0375. 

Don’t miss:  Shelling at the south end of the island.  It is worth getting up at dawn to have the first pick of sea shells!  

Cabbage Key

A hidden paradise located on a unique 100-acre island reminiscent of days gone by.  Built by playwright and mystery author Mary Roberts Rinehart in 1938 on a Calusa Indian shell mound 38 feet above sea level, the original inn and restaurant features the famous dollar bill bar and cheeseburgers in paradise.  The restaurant walls, beams and ceilings are plastered with $1 bills, a tradition that began in 1941 when a fisherman signed and taped his last dollar to the wall.  When he returned, he would have money to buy a beer.  Visitors continue the custom today. Accessible only by boat, the inn has guest rooms and cottages.  For information, visit or call 239-283-2278. 

Access:  Private boat, water taxi service or scheduled boat service. 

Don’t miss:  Boaters love to stop in for a cheeseburger in paradise.  Also:  Explore winding nature trails with picturesque views. 

No boat?  No problem!

Adventures in Paradise offers daily cruises from Port Sanibel Marina and Sanibel Harbour Marriott Resort & Spa in Fort Myers. Canoe and kayak tours, shelling and sealife encounters, dolphin watch cruises and sunset champagne cruises.  For details visit or call 239-472-8443. 

Captiva Cruises offers trips from McCarthy’s Marina on Captiva Island to Useppa Island (  This exclusive, private island club allows access only by membership or Captiva Cruises.  Shelling, sightseeing and lunch tours visit the outer islands and Cabbage Key.  For schedule and details, visit

Tropic Star of Pine Island offers regular scheduled boat service from Pine Island to Cayo Costa State Park.  Sightseeing cruises include eco heritage and nature cruises, Cabbage Key and Cayo Costa nature cruises, overnight camping trips to Cayo Costa and a Calusa Indian heritage and mound tour.  For details, visit or call 239-283-0015. 

Island hop along the Great Calusa Blueway

Kayaking the barrier islands is a very popular way to see the area and its wildlife.  The Great Calusa Blueway Paddling Trail has launch sites and landings around the 190-mile marked trail, as well as easy access to rental kayaks and canoes.   One of Southwest Florida's most acclaimed nature-based attractions, the Blueway and the Fort Myers/Sanibel Island area have been recognized as one of the best kayaking destinations in North America by both Paddler and Canoe & Kayak magazines. The trail itself has garnered National Recreation Trail designation and is part of the evolving Florida Circumnavigational Saltwater Paddling Trail.  

Put-in sites are designated along the trail, as are other amenities, such as campsites, restaurants, marinas and cultural and historic sites of the ancient Calusa Indians, for whom the trail is named. The Caloosahatchee leg offers a lush, green, Old-Florida dimension to the Blueway, complete with moss-draped oaks along shores dotted with expansive preserve land.  On the trail, novice to experienced paddlers can get up close with outstanding flora and fauna while exploring back bays, aquatic preserves, wildlife refuges, creeks, bayous, rivers, and mangrove forests. Many of the trails follow the course charted some 2,000 years ago by the area’s earliest residents, the Calusa Indians.  For maps, kayak rental information and accommodations along the Blueway, visit




Editor's note: The Beaches of Fort Myers & Sanibel in Southwest Florida includes: Sanibel Island, Captiva Island, Fort Myers Beach, Fort Myers, Bonita Springs, Estero, Cape Coral, Pine Island, Boca Grande & Outer Islands, North Fort Myers, Lehigh Acres. For media assistance, visit

Francesca Donlan, Miriam Dotson