There is far more to Key West than pub crawls on Duval Street and the nightly sunset celebration at Mallory Square. Soak in the Conch Republic’s year-round sunshine while exploring its beautiful beaches, outstanding restaurants, and noteworthy cultural and historic landmarks.

Ernest Hemingway Home & Museum

Ernest Hemingway’s legacy looms large on Key West. The renowned author resided for most of the 1930s in this refined two-story home and estate, built in 1851 and remodeled by Hemingway and his second wife, Pauline, to include an extravagant in-ground swimming pool rimmed by lush gardens. Now a National Historic Landmark, the property is open every day of the year for self-guided and guided tours of memorabilia- and cat-filled rooms (nearly 60 six-toed cats reside here) and the studio where Hemingway wrote portions of “A Farewell to Arms” and “For Whom the Bell Tolls.”

Fort Zachary Taylor Historic State Park

There’s something for everyone at this 87-acre state park. Its gorgeous beach is considered one of the island’s best, with a café, and chair and umbrella rentals. The marine life attracts snorkelers and anglers. Scout for iguanas and birds along the nature trails. Guided tours at the namesake Fort Zachary Taylor, a National Historic Landmark, recall its role in the Civil War and Spanish-American War. The fort is also a popular spot to catch the legendary Key West sunsets.

Harry Truman’s Little White House

Florida’s only presidential museum, this former naval officer residence on Front Street served as the Winter White House for President Harry Truman. The 33rd president spent 175 days in residence, savoring some sunny rest and relaxation amid the immense pressures of the executive office. While Truman’s name graces the house’s marquee, five other presidents and other luminaries have stayed here as well. Thomas Edison lived here during World War I while researching depth charges for the US Navy; President Dwight D. Eisenhower recuperated here after a heart attack in 1956; President John F. Kennedy hosted the British prime minister here during the Bay of Pigs incident. An hour-long guided tour walks visitors through the house’s 124-year history and its presidential pedigree.

Blue Heaven

You don’t need a reason to dine at the iconic Blue Heaven, but there are several compelling ones to pick from: colorful Key West history, live music, a fun and funky atmosphere, delicious Caribbean and Creole cuisine, and the eatery’s famous Key lime pie.

Latitudes

Accessible only by boat, Latitudes on Sunset Key is arguably the ultimate romantic fine-dining destination in the Conch Republic. You’ll need to book reservations several weeks in advance to enjoy its solid wine list paired with a local surf-and-turf menu.

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When it comes to making memories and celebrating good times, it’s tough to think of anyplace better than the Florida Keys. These islands are known for kicking back and relaxing all year round—and during the winter holidays, they take the fun to a Frosty-worthy level.

No, there’s no snow here; typical temperatures during December are in the mid- to high 70s. But that doesn’t stop merry-makers from Key Largo all the way down to Key West from getting their Santa on. The island attitude blends with the holiday spirit like a finely mixed cocktail of joy.

Arguably, the event that best epitomizes this spirit within the boating community is the annual Schooner Wharf Lighted Boat Parade on Key West. This will mark the 31st year of the event, on December 11, starting at the Historic Seaport and continuing past the Schooner Wharf Bar for judging.

All kinds of boats, from kayaks to schooners, typically participate, with a backdrop of island musicians belting out holiday tunes and other fan favorites. Never heard “Santa Claus Is Coming to Town” played by a steel-drum band? Well, then, you’re in for a treat.

Boaters who participate in this parade often go for the gusto with their decorations. In recent years, boaters have decked out their decks with giant inflated characters, glistening mermaids and fish, fake forests full of twinkling white lights, “dolphins” pulling Santa’s toy-filled sleigh, and a Rudolph so big that it filled the entire bow of a U.S. Coast Guard boat. Real, full-size Christmas trees are sometimes set up in cockpits for paradegoers to peruse along the docks, and boaters, of course, lend their own musical signature to their displays, sometimes with competing speaker setups.

Yes, there are some other lighted boat parades in Florida, but Key West, as with so many things, always puts its own spin on the fun. As they say at Schooner Wharf, “We don’t need snow to make our holidays bright.”  

Hawks Cay

This resort destination on Duck Key, in the Middle Keys, has a marina and fuel dock for boats up to 110 feet length overall. Holiday packages are available this winter, when you can go ashore for a few nights and celebrate the most wonderful time of the year. Santa’s Workshop is open for making Christmas ornaments.   gingerbread houses are available for decorating. Mrs. Claus hosts story time with hot chocolate. Carolers will come by a villa or hotel room and spread some holiday cheer for guests who sign up in advance. Elf tuck-ins are available for the kids, with Santa’s elves stopping by to offer a bedtime story and gift.

The Big Meal

Want to get out of the galley on Christmas Day? You can do it in Key West, where numerous restaurants are taking reservations for the holiday.   

• Prime Steakhouse at Conch Harbor Marina pairs steaks with local favorites such as lobster and Key lime pie.   
• LaTeDa on Duval Street serves up freshly caught fish, crabcakes, caramelized duck and more.   
• Four Marlins on Simonton Street is decorated like a 1930s fishing lodge. It offers main courses of fish, ribs, lobster ravioli and risotto with jumbo shrimp.   
• Grand Cafe on Duval Street is known for its wine list, which is 35 pages long. Favorite dishes include seafood pasta and steak frites.

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For Alan Maltz, a career in photography was quite literally a calling. While at his graduation ceremony at Long Island University in New York, “I heard a voice saying, ‘Pick up a camera,’” Maltz recalls. He’d never been interested in photography, but he handed his mother his diploma in psychology and, the following day, purchased a Miranda Sensorex camera and Kodachrome film. He boarded a plane to Europe, read the manual while in flight, and started snapping away upon landing.

He hasn’t stopped since. He migrated down to the Florida Keys and opened the Alan S. Maltz Gallery on Duval Street in Old Town Key West in 1999. He specializes in Florida’s iconic wildlife and scenery: a manatee blowing bubbles just below the surface of the water, loggerhead turtle hatchlings crawling into the surf, a Florida panther staring straight at his lens from its perch in the Everglades. “It can be just magical,” he says.

Explore More: Island Icons

For his talent and passion for nature, Maltz was designated the official wildlife photographer for the Wildlife Foundation of Florida. He has collected his work in six coffee-table books, with the latest, Old Florida: An Artistic Interpretation, expected to be out soon.

What makes Key West an ideal base for you and your photography? It’s a laid-back atmosphere—live and let live. It’s a great place for freethinkers. 

What is the key to a great wildlife photo? Be in the right place at the right time. An hour to an hour and a half after the sun rises or before it sets is a good time. Lighting is essential. Be patient. And know your subject and its habits. 

Where is a favorite photo spot of yours on Key West? Fort Taylor is great. I get incredible sunsets there. You can see the whole vista, with sailboats coming in and going out at sunset. And the old fort itself is a point of interest.  

Alan Maltz’s Must-Do List

La Trattoria Oceanside: This location is away from downtown. The food is excellent. I like their Caesar salad and sauteed hogfish. They also make a great cappuccino.  

Salute! On The Beach: The location on Higgs Beach and the food are fantastic. Everything about it is very funky: the bathrooms, the decor, the people. My favorite dish is the shrimp salad.

Hemingway Home & Museum: It’s a landmark. The whole history of the place is interesting.

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Often, the idea of visiting a cruising destination that’s only accessible by boat or seaplane becomes an endurance test on many levels. What makes the 100-square-mile Dry Tortugas National Park different is that it lies just 70 miles west of Key West, Florida. The seven small islands are accessible during a long weekend aboard all kinds of boats.

In fact, boats have been coming here for centuries. Explorer Ponce De León visited in 1513, and throughout the 17th and 18th centuries, pirates would hide out here to attack ships in the Gulf of Mexico and Straits of Florida. The US government, wanting to protect ships headed for the Mississippi River basin, began construction in 1846 of Fort Jefferson, which is part of the national park that boaters can tour today.

These days, the islands are serene and uncrowded outside of the most touristy days and times, but back then, they were crawling with some 1,700 soldiers and notorious prisoners of the era. Convicts who would stare out from the fortress and into the blue sea all around included Samuel Mudd, the doctor who treated the leg of John Wilkes Booth after he assassinated President Lincoln.

The military maintained a presence until 1874, when increasingly powerful weapons made the brick structure obsolete. Nature reclaimed the islands, and in 1908, all the nesting birds led to the designation of a wildlife refuge. The fort has been a national monument since 1935, and in 1992, the islands were designated as a national park. There are now picnic tables where soldiers used to perform their exercises, and the protected waters where warships used to patrol are currently home to blossoming coral reefs and active marine life.

The birds are still all around too. Depending on the season, boaters can break out their binoculars to spot masked and brown boobies, double-crested cormorants, brown pelicans, frigate birds, Caribbean short-eared owls, shiny cow birds, warblers, thrushes, grosbeaks, cuckoos, and white-tailed tropic birds.

Fort Jefferson itself is on Garden Key and is open for tours. Boaters need to stop by the park headquarters to pay an entrance fee and receive a boat permit, and then they can explore the fort, which is slowly but surely succumbing to the saltwater environment. Wrought iron used in the fort’s construction has rusted and expanded, pushing apart the bricks and causing structural damage. The National Park Service is letting nature take its course, stabilizing instead of reconstructing parts of the fort so they’re safe to tour now and for generations to come.

It’s possible, for instance, to stand and stare out a hole in the brick that may have been a barred window back when Mudd was imprisoned here. Such spots combine American history and natural beauty in a way that’s hard to find anywhere else—all within a few hours’ cruising distance of modern civilization.  

Strategic Location

Though larger ships could avoid the biggest guns the US military ­installed at Fort Jefferson, they could not avoid the warships that patrolled the harbor and waterways all around.

Touring Fort Jefferson

Self-guided tours are available for Fort Jefferson year-round from sunrise to sunset, with interpretive signs around the structures. Numerous tour operators hold licenses to provide guided tours, not just of the fort but also of the surrounding waters for fishing, diving, snorkeling and viewing wildlife. Boaters can find more information at the Garden Key Visitor Center, which is open daily from 8:30 a.m. until 4:30 p.m. on the same island as the fort.

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The thing I remember more than anything else, is the feeling of being utterly, entirely alone. As I walked through the remains of the Fort Jefferson military outpost on Garden Key in the Dry Tortugas, I could run my fingers over the brickwork and look through holes in the crumbling walls, but it was the silence that captured my imagination. Not only weres there no other human beings around, but there were no sounds or smells of civilization, either. Not the faint hum of a generator, nor the distant rattling of rigging against a mast — the sound of me taking a deep breath and exhaling seemed somehow louder than a whistling offshore wind.

Solitude is something many of us desire, and it is what has long made the Dry Tortugas a place that we seek out. These islands’ history is a mix of good and bad “alone time,” so to speak; one reason Dr. Samuel Mudd was imprisoned here after setting the broken leg of President Lincoln’s assassin, John Wilkes Booth, is that no matter how loudly he screamed, his voice would echo across the Gulf of Mexico until the sound waves dissipated into the ether. Indeed, as I stood on the grass just outside the walls that once held him and other prisoners, I thought of shouting across the flat-calm water, much as I might holler into a big cathedral to hear my voice reverberate. Here in the Dry Tortugas, there would be no answer. It’s a realization both mesmerizing and humbling, a reminder that even in today’s go-fast world, we really can be alone sometimes.

Ferries and seaplanes come from Key West on day-tripper schedules, and yachtsmen can pick up a mooring at any time, plus the required free permit inside Fort Jefferson. A fisherman might come by while you’re on the hook, offering fresh lobster or other catch for the night’s supper, but after he goes, it might be just you, sitting in the harbor and looking up at the stars. Go ahead and shout across the water, back toward Key West. Expect no answers, and enjoy the silence.

What To Do

KAYAKS AND SNORKELS:

_{Some of the best fun to be had at Garden Key is on and under the water. Snorkeling is encouraged around the old fort’s moat. Kayakers are welcome with a VHF radio or other way of signaling their own boat for help.}

BY THE NUMBERS:

_{Fort Jefferson was built with more than 16 million bricks in a design intended to hold as many as 1,000 guns for protection. At its peak use, the fort housed close to 2,000 people.}

MORE THAN A FORT:

_{Garden Key, where Fort Jefferson is located, is just one of seven islets in the Dry Tortugas. The others are Loggerhead Key, Bush Key, Long Key, Hospital Key, Middle Key and East Key.}

A BIRDER’S PARADISE:

_{Bring your binoculars for a chance to see sooty terns, brown noddy birds, masked boobies and frigates. All are part of the seabird colony that calls the Dry Tortugas home.}

HAVE WHAT YOU NEED:

_{While Fort Jefferson is a National Park, there are no shops. Bring food, water and other supplies, and be prepared to carry out your garbage too.}

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