Visitors to Florida’s alluring, semi-tropical islands sometimes get more than they bargained for … but in a holiday-enhancing way, because many of the better-known islands are linked by boat or bridge to nearby, lesser-known ‘piggyback islands’ that have their own appeal. Four of our writers describe their favourite duos.

SANIBEL & CAPTIVA – GULF OF MEXICO CHARMERS

For Mary Moore Mason, it’s Sanibel and Captiva, floating in the Gulf of Mexico just off Florida’s west coast. Not only are they easy to reach from the mainland, as Sanibel is linked by bridge with the appealing resort city of Fort Myers, but they also are tethered to each other by the short-but-scenic bridge over narrow Blind Pass.

Sanibel offers miles of powdery, white sand beaches, some of the world’s best sea shelling, narrow lanes lined with exotic trees and flowers, a laid-back lifestyle, and clusters of tempting little boutiques, artisan shops and art galleries. Unlike some resort islands, which are crammed with soulless, modern, high-rise hotels, it excels in comfortably-chic, low-rise, beach-front properties such as the Casa Ybel Resort. And its true sense of community and history are exemplified by its 1884 Point Ybel Lighthouse and quaint Historic Pioneer Village.

Sanibel and Captiva are ideal for scuba divers, family holidays and shell collecting, here seen with Sanibel’s 19th century lighthouse in
the background

Sanibel is also a special place for boaters, fishermen and bird watchers. You can canoe or kayak through the primeval mangrove swamps of the Ding Darling National Wildlife Refuge & Bird Sactuary, fish along its shoreline, or spend an hour or more in the fascinating Bailey-Matthews National Shell Museum, which is filled with exotic shells from Florida and around the world. Among them is a selection collected in Fiji by actor Raymond Burr, once a famous US TV detective in the series Perry Mason and Ironside. Better still, join other beach combers in the ‘Sanibel Stoop’ as you hunch over and search for exotic coquina, junonia, olive and lightning whelk shells.

Captiva, on the other hand, is almost entirely privately owned, its main point of interest being the luxurious 330-acre South Seas Resort. However, both the resort and McCarthy’s Marina serve as launch pads for Captiva Cruises into Pine Island Sound, where you may be accompanied by convoys of frolicking dolphins. One of the most popular islands along the way is funky little Cabbage Key, where the namesake inn and restaurant is perched on a huge mound of shells left behind by Native Americans.

Built by the family of 19th-20th-century novelist and playwright Mary Roberts Rinehart (sometimes referred to as the ‘American Agatha Christie’), it is best known for its rustic bar, where the walls are plastered with thousands of dollar bills, signed and left behind by thirsty visitors. It also was here, according to legend, that Jimmy Buffet was inspired to write one of his most-famous songs, A Cheeseberger in Paradise.

TRAVEL NOTES: Sanibel & Captiva can be reached by flights from London into Miami or Tampa, with onward travel in all cases by rental car.

HONEYMOON & CALADESI ISLANDS – PRISTINE BEACHES, ASSURED PRIVACY

Paul Wade found his divine duo farther up the coast, where the Dunedin Causeway terminates at Honeymoon Island State Park, about 45 minutes west of Tampa. With four miles of white beaches, privacy is assured as you watch for snowy plovers and pelicans, collect seashells and stroll along the nature trails through pine forests. Or you can just relax at Café Honeymoon or the South Beach Pavilion before hiring a bike or kayak and exploring farther afield.

If that is not sufficiently ‘away from it all’, you can board the little Caladesi passenger ferry from Honeymoon Island for the 15-minute ride to Caladesi Island. One of the few undeveloped barrier islands left in Florida, it was awarded the ‘Best Beach in the USA’ title by ‘Dr Beach’ back in 2008. There, too, you can rent a kayak or canoe and paddle through a tunnel of mangroves or out on to the Gulf of Mexico. Look out for osprey and bald eagles (large) and piping plover (small). Then enjoy a barbecue picnic, using one of the grills in the picnic area.

TRAVEL NOTES: These islands are most easily reached via Tampa and rental car. For further information on the two islands take a look at the Florida State Parks Website.

KEY WEST & GARDEN KEY – HEDONISM AND HISTORY

Kathy Arnold headed about 160 miles south of Miami, island-hopping by bridge and causeway to the tip of the archipelago known as the Florida Keys. There she found funky, fun-loving Key West, nicknamed ‘The Last Resort’ and long-known for its Bohemian residents and party scene – bars and cigars, sunset cocktails and Cuban rum. For buzzy nightlife, she recommends Duval Street’s Sloppy Joe’s and Irish Kevin’s Bar or nearby Captain Tony’s Saloon (the original Sloppy Joe’s). It opened on December 5, 1933, the day that Prohibition was repealed. For the next five years, Ernest Hemingway and his friends were near-permanent fixtures.

Key West Beaches

Key West has idyllic white sand beaches as well as a laid-back, bohemian lifestyle

But away from the main drag is a different Key West – with quiet lanes, houses wrapped with verandas and laid-back B&Bs. The abundance of palm trees, bougainvillea, ginger blooms and orchids creates a tropical-garden look.

Then there is the history. Who would imagine that such a small place could have such an intriguing past? President Harry Truman spent winters there; in the Little White House museum, rooms look much as they did in 1949. The Ernest Hemingway Home was a tourist attraction even while the writer was living there 80 years ago. Looking farther back in time is the Mel Fisher Maritime Museum, devoted to underwater archaeology – gold bars, silver pesos, bronze cannon and more from Spanish galleons that went down in the Caribbean.

Seventy miles farther west is Garden Key, one of a clutch of islets in the Dry Tortugas National Park. Looming large and visible from miles away is the massive Fort Jefferson. When it was built in the 19th century, the idea was to protect America’s Gulf Coast from Spain. Before it was finished, it was militarily obsolete.

Fort Jefferson Dry Tortugas National Park

Fort Jefferson in the Dry Tortugas National Park

It can be reached by ferry or a 40-minute flight. From 500 feet above the turquoise blue water, you look down on sea turtles, giant manta rays and wrecks. Once on the island, tour the fort with a park ranger. As well as the impressive statistics, such as the 16 million bricks used in construction and the 420 heavy guns that were never fired in anger, you learn about the fort’s recycled role as a prison – and its most famous inmate, Dr Samuel Mudd.

He was the physician, who treated the broken leg of John Wilkes Booth, President Lincoln’s assassin. Convicted of conspiracy, Mudd was sentenced to life imprisonment and shipped off to Fort Jefferson. But, during an epidemic of yellow fever, he redeemed himself by helping the sick; four years after his internment, Mudd was pardoned.

After the history lesson, snorkel lazily along the aquarium-like moat, with coral, tropical fish, sponges, starfish and conchs. But be prepared for your visit. This hot, exposed island has no shop or restaurant, and only composting toilets; take food, water and proper sun protection.

TRAVEL NOTES: Key West and the other keys are best-served via flights into Miami and rental car.

EXTRA TREATS: LITTLE TORCH KEY & LITTLE PALM ISLAND

So enarmored by the Lower Keys was Kathy that she sampled two other islands, reached by Marathon via the glorious Seven Mile Bridge. Small, enticingly sleepy and favoured by birders and fishermen, sea kayakers, boaters and scuba divers, Little Torch Key has no chain hotels or restaurants; visitors stay in cottages and simple resorts, and eat in beach-side bars. Nearby attractions are of the natural kind. Bahia Honda State Park offers unspoiled beaches and a snorkeler’s fantasy of tropical fish.

A welcoming scene at Little Palm Island Resort & Spa

Where Little Torch Key harks back to ‘Old Florida’, Little Palm Island Resort & Spa epitomises 21st-century luxury. Just three miles offshore, this private islet has no TVs, no telephones, no mobile phone coverage and no smoking. Paths of crushed white seashells wind among the 30 thatched-roof and air-conditioned bungalows, where even the mosquito netting looks stylish. Snooze in a hammock; laze in the spa; go for a swim; enjoy the cuisine in the dining room, rated among Florida’s best restaurants, or book a private table on the beach. The menu has a French-Caribbean accent – coconut lobster bisque and foie gras with a jalapeño pesto. From £500 per night, this is for VERY special occasions!

AMELIA & CUMBERLAND ISLANDS – A TWO-STATE ADVENTURE

Ever adventuresome, Chris Coplans opted to combine Amelia Island, the north-easternmost Florida island, with Cumberland Island just across the border in Georgia.

Amelia, he says, is a peach of a place whose charms have largely escaped the attention of UK visitors. It is a million miles away from the glamour and the glitz of southern Florida and is best-described as ‘island whimsical’ as the locals display a laid-back attitude to life.

Head first for the island’s west side, where the tiny city of Fernandina Beach faces the mainland (sunsets to die for). Although reached by a rather uninspiring, strip-mall-laden highway that then shrinks into a two-lane byway, it’s a delightful Norman Rockwellesque small town, complete with white picket fences, neatly-trimmed lawns and Southern Baptist churches.

The downtown area is a walker’s paradise – small leafy streets lined with Victorian clapboard houses, cafés, restaurants and small, privately-owned stores. At sunset, mosey over to Brett’s Waterside Inn, facing the marina, for a ration of ‘them mighty fine ’gator tails and a fresh brew’.

There are plenty of delightful small inns and B&Bs dotted around town. Opened in 1857, the Florida House Inn is claimed by locals to be the oldest in the state. Stellar guests included Ulysses S Grant, Henry Ford, Laurel and Hardy, and Mary Pickford.

The east, Atlantic, coast, is home to miles of glorious beaches ,with no shortage of motels, beach cottages, small hotels and family-style condos There are also some seriously-upmarket resorts such as the Ritz Carlton, which was named the country’s most child-friendly resort by Child Magazine.

Fernandina Beach Amelia Island

Horse and carriage rides pass the lovely old homes on Amelia Island’s Fernandina Beach

It is also home to American Beach, which was created in 1935 as the first resort for black Americans, and is now part of the Black Heritage Trail. In its heyday, thousands of African- Americans would arrive each week-end to hear such great musicians as Duke Ellington, Count Basie and Ray Charles play at the local club. For movie buffs, John Sayles’ shot his charming 2004 film Sunshine State mainly there and in Fernandina Beach.

Just a couple of miles north of Amelia is Georgia’s Cumberland Island, now mostly owned by the National Parks Service, although one or two of the old mansions are still the property of the wealthy Carnegie family. One of the most impressive is now an exclusive B&B, the Greyfield Inn, the only accommodation on the island other than camping. If you plan to stay at Greyfield, their boat will pick you up from Fernandina Beach; otherwise you need to take the ferry from charming St Mary’s a few miles up the Georgia coast.

Cumberland Island is a place of great natural beauty – tidal creeks, marshes and woodland, with beautiful mature oak trees dripping with Spanish moss and providing a glorious canopy over the trails. Wild horses roam all over the island as do deer, racoons, wild pigs and even the odd alligator. There are more than 16 miles of sandy beaches and no cars … and at the Greyfield Inn you get a glimpse into the private world of the American aristocracy at the height of their power. (The private Carnegie family cemetery was designed by Tiffany, no less.)

TRAVEL NOTES: The nearest airport to Amelia Island is Jacksonville International Airport, about an hour’s drive away, with connecting flights to Miami, Orlando and Atlanta, all served by direct service from the UK. Orlando and Atlanta are both about a four-hour drive.