Jet ski around Florida Keys

Florida Keys Travel Guide

By Tracey Minkin
March 02, 2021

The Florida Keys are like a coral kingdom: a 125-mile-long arcing chain of islands flung south from the tip of Florida with the ultimate island — Key West — resting  just 90 miles from the shores of Cuba. And with one narrow road (and 42 bridges) connecting the isles, just to travel the Florida Keys is to feel on a magical, water-surrounded journey.

While it's possible to hop in a car in Miami and make it to Key West (and the southernmost point in the continental United States) in less than four hours (traffic willing), that defeats the charm and richness of the Florida Keys. Every few miles there's a discovery to be had: a tiki bar, a seafood joint, a beachy resort or boutique hotel, a gorgeous nature preserve, or just a thrilling turquoise vista across the famed saltwater flats toward a blue horizon. So, make a trip of it — spend a few days in Key Largo or Islamorada near the upper end of the archipelago, dally on Marathon or Big Pine Key, then settle in for some serious quirky culture, history, and bohemia in Key West. Take time to snorkel, dive, and fish, walk the beach, and eat lots and lots of seafood (and Key lime pie). And don't worry if you don't get to everything that there is to love and explore in the Florida Keys — you'll be back.

Time Zone

Eastern Standard Time (Daylight Savings Time is observed seasonally)

Best Time to Go

Peak tourist season in the Florida Keys starts right after the holidays in late December and lasts through May. During the winter months it almost never rains, and even if clouds do push through with some showers, they're gone that day. The Keys' subtropical climate means balmy temperatures year-round (January's high temperatures are typically in the 70s), making it a superb destination when even Central Florida can be experiencing frosts. In the summer, when temperatures get into the hot range (July's average high is 86°F), the crowds disperse a bit and hotels tend to lower their prices, which makes this a great time to visit if you're looking for better deals and don't mind heat and humidity. Atlantic hurricane season runs from June 1 to Nov. 30, which means more turbulent weather and the possibility of dangerous storms (peak hurricane months for the Florida Keys are between Aug. 15 and Oct. 15). That said, some of the prettiest weather of the year — calm waters and fluffy clouds — also occur during this period.  

Festivals in the Florida Keys draw big crowds and can be a reason to go or a reason to pick another time for vacation, depending on the type of trip you're looking for. Peak festivals include Key West's Hemingway Days (including the famed Hemingway lookalike contest) in July and the Carnivalesque Fantasy Fest in October, the Original Marathon Seafood Festival in March, the 7 Mile Bridge Run (the only run surrounded by water along its entire length) in April, and the Key West Brewfest over Labor Day Weekend. (For a full list of festivals and events, check the Florida Keys Tourism Bureau's calendar, here.)

Things to Know

The Florida Keys is a 125-mile-long chain of islands that begins just south of Miami. The coral and limestone islands are linked by 42 bridges — one almost seven miles long — over the Atlantic Ocean, Florida Bay, and the Gulf of Mexico. The Keys are divided into five regions: Key Largo, Islamorada, Marathon, Big Pine and Lower Keys, and Key West. 

Key Largo is known as the Dive Capital of the World and is home to John Pennekamp Coral Reef State Park, the first underwater preserve in the U.S.

Islamorada is known as the Sport Fishing Capital of the world and is famous for its backcountry sport fishing and saltwater fly fishing.

The Seven Mile Bridge at Marathon is one of the longest segmented bridges in the world.

In the Lower Keys, Big Pine Key is home to a national refuge that protects the miniature endangered Key deer, which has made an astonishing comeback from near extinction.

Key West, famed as the beloved home of writers Ernest Hemingway and Tennessee Williams (and home to a warm and welcoming LGBTQ+ scene), is closer to Cuba (90 miles) than it is to Miami (159 miles). The island — just two by four miles in size — is home to a vibrant historic district, an international airport, and the southernmost point in the continental United States. 

The only road linking the islands — the Florida Keys Overseas Highway — is the southernmost leg of U.S. Highway 1 and is sometimes called the Highway That Goes to Sea. Its green mile marker signs begin at mile marker 113 at the Miami-Dade/Monroe County line and descend to marker 0 at the corner of Fleming and Whitehead streets in Key West (a popular photo opportunity). It's common for hotels, restaurants, and other sites to peg the locations to the closest mile marker (MM). The drive from Miami to Key West generally takes four hours.

The waters surrounding the chain, which include shallow flats, mangrove islets, and coral reefs, are protected by the Florida Keys National Marine Sanctuary. The Florida Keys Shipwreck Trail links nine historic underwater wreck and artificial reefs from Key Largo to Key West.

Over the years, residents of the Florida Keys have prospered from farming, shipwreck salvage, sponge fishing, commercial fishing (the second-largest industry in the Keys today) and tourism, the primary economic driver of the area. Tourism had its earliest booster in railroad baron Henry Flagler who completed a railroad in 1912 that linked the Keys to bring tourists south, but a hurricane in 1935 destroyed segments that were never rebuilt. The Overseas Highway, completed in 1938, became the sole way to travel among the Keys on land.

Classic dishes of the Keys reflect the islands' exposure to Caribbean cultures, and include spicy conch chowder, Cuban classics like ropa vieja and pork marinated in mojo sauce, Key West pink shrimp, and Key lime pie. Being surrounded by fishing grounds, the Keys are a superb place to eat fresh seafood — classic catch includes yellowtail, grouper, mutton, snapper, mahi-mahi, spiny lobster, and stone crab.

How to Get Around

Shuttles from Miami International Airport (MIA): Keys Shuttle and Florida Keys Express Shuttle offer door-to-door shuttle services from Miami International Airport.

Bus Service from Miami: The Greyhound Keys Shuttle connects from the Miami Bus Station and serves the Keys all the way to Key West. Miami-Dade Transit Route 301 Dade-Monroe Express runs from Miami's West Palm Drive/3rd Avenue to Mile Marker 50 in Marathon. From there, the Key West's Lower Keys Shuttle connects Marathon to points in Key West.

Within the Keys: Some islands offer their own transportations systems. Freebee Islamorada's on-call electric vehicles take passengers among the 4 islands that comprise Islamorada. On Key West, the Duvall Loop is a free bus service with 18 stops in Old Town.

Taxis: Local cab companies generally service their island area — inquire locally for taxis. A cab stand services passengers arriving at Key West International Airport (EYW).

Ride sharing: Uber and LYFT both operate in the Florida Keys.

Bungalows Key Largo, all-inclusive Florida resort
Credit: Courtesy of Bungalows Key Largo

Best Hotels

Key Largo

Baker’s Cay Resort Key Largo, Curio Collection by Hilton

Address: 97000 Overseas Hwy., Key Largo, FL 33037
Phone: (305) 852-5553
Website

This 200-room-and-suite resort doubles down on the new charms of Key Largo, and its white-sand beachfront is a tropical playground for paddle boarding, kayaking, and sailing, to lounging along a strand shaded (and kept hidden) by a hardwood hammock forest. The resort’s fresh design features hand-carved furniture, wicker, and metalwork — a stylish fit for couples, families, and solo travelers alike.

Window view from Bungalows Key Largo
Credit: Courtesy of Bungalows Key Largo

The Bungalows Key Largo

Address: 99010 Overseas Hwy., Key Largo, FL 33037
Phone: (305) 363-2830
Website

A former trailer park on a stunning stretch of shoreline with sandy beach has been converted to a lush enclave of small cottages with big luxuries, including private verandas with plunge tubs and outdoor showers. Three restaurants on property (including a toes-in-the-sand Mexican cantina), a savvy bar with a Hemingway vibe, a top-notch spa, and a panoply of water activities including catamaran excursions make it easy to stay put. Adults only, all-inclusive, and all just 63 miles from Miami International Airport.

Cheeca Lodge & Spa

Address: 81801 Overseas Hwy., Islamorada, FL 33936
Phone: (305) 664-4651
Website

This classic upscale resort with its long dock and sportfishing vibe has emerged from a post-hurricane upgrade with a third swimming pool, second tiki bar, and 10 new casita-style villas complete with butler service. On the posh side but with lots of fun to be had in the family-friendly pools, Cheeca is a Keys icon for a reason.

Islander Resort

Address: 82100 Overseas Hwy., Islamorada, FL 33936
Phone: (305) 664-2031
Website

From its classic mid-century signage on the Overseas Highway to its rows of charmingly redone (including rooftop solar panels) oceanfront units, this family-forward resort is a nostalgic delight. There’s a 1,100-feet-long coral-sand beach for loungers, two saltwater swimming pools, a fishing pier, and new, colorful splash pads for kids. For rainy days, there’s even the Florida Keys History & Discovery Center and Aquarium right on the property.

The Moorings Village

Address: 123 Beach Rd., Islamorada, FL 33936
Phone: (305) 664-4708
Website

This former coconut plantation re-emerged in the 1960s as a small resort. Today, its aqua-shuttered estate house and sugary stretch of white sand — famously peppered with a grove of listing palms — are straight-up cinematic, and its collection of luxury cottages make for an Old Florida idyll.

Marathon

Grassy Flats Resort & Beach Club

Address: 58182 Overseas Hwy., Marathon, FL 33050
Phone: (305) 998-4590
Website

With nostalgic panache, this formerly faded property got an eye-popping redo as well as a whole new approach to sustainability. On 50 prime waterfront acres, Grassy Flats is part of the Marathon renaissance, and its classic pool scene and on-site Barrel & Bale tiki bar and beach club seals the cool deal.

Hawks Cay Resort

Address: 61 Hawks Cay Blvd., Duck Key, FL, 33050
Phone: (866) 347-2675
Website

This is pure gold for families wanting a getaway in the Middle Keys, where day trips in all directions are possible. Located a little off the main drag on charming Duck Key, Hawks Cay offers water excursions right from its marina, in addition to the charming company of local dolphins. Angler & Ale, the on-site restaurant, will cook up your catch or keep everyone happy with dishes like Florida lobster, grouper cheeks, and whole roasted snapper.

Isla Bella Beach Resort

Address: 1 Knights Key Blvd., Marathon, FL, 33050
Phone: (305) 481-9451
Website

In the aftermath of 2017’s Hurricane Irma, this new luxury resort on Marathon Key is a game-changer, with high design on a nearly one-mile stretch of private beach and surrounded by more than a thousand palms. A swimming pool and an open-air bar with a killer sunset view complete the fantasy.

Big Pine and Lower Keys

Little Palm Island
Credit: Taylor Volkens; Little Palm Island Resort & Spa

Little Palm Island

Address: Little Torch Key
Phone: (305) 684-8341
Website

The only private island resort in the United States is hidden away in the Lower Keys, and it’s a luxurious beauty made even more luxurious and beautiful with its post-hurricane renovations. Accessible only by boat and seaplane, the enclave features 30 thatched-roof bungalows with updated interiors (including new suites and feature floor-to-ceiling glass doors and outdoor copper soaking tubs), new private poolside cabanas, and the sumptuous SpaTerre spa.

Key West

Casa Marina Key West, A Waldorf Astoria Resort

Address: 1500 Reynolds St., Key West, FL 33040
Phone: (305) 296-3535
Website

Moving gracefully into its second century in 2021, this historic landmark summons the panache of the heady early days of Florida’s development at the hands of industrialist Henry M. Flagler. What remains are those glorious lines of Mediterranean Revival architecture, lovingly preserved particularly in Casa Marina’s lobby with its arched doorways and columns and timbers of Dade County pine. Modern luxuries like a pair of swimming pools, a pale sand beach, spa, and rum bar, keep this grande dame exceedingly relevant.

The Gates Hotel Key West

Address: 3824 N. Roosevelt Blvd., Key West, FL 33040
Phone: 305-320-0930
Website

Perched on the water where the Overseas Highway enters Key West, this urbane hotel with a bright, coastal sensibility feels like a getaway within a getaway (there’s free shuttles into Old Town). With a dreamy pool and top-flight rum bar, it might be tempting to never leave the property.

Kimpton Key West

Ella’s Cottages - 811 Simonton St., Key West, FL 33040
Fitch Lodge - 1030 Eaton St., Key West, FL 33040
Lighthouse Hotel - 902 Whitehead St., Key West, FL 33040
Ridley House - 601 Caroline St., Key West, FL 33040
Winslow’s Bungalows - 725 Truman Ave., Key West, FL 33040
Phone: (877) 219-4500
kimptonkeywest.com

One of the newest arrivals on the scene in Key West, this collection of five historic cottages, lodges, and inns tucked among the lush side streets of Old Town now are unified under one hotelier, and it’s a wonderful variety of boutique hotel options. Each property welcomes pets with open arms and offers complimentary bikes, hammocks, at least one pool, and continental breakfast.

Parrot Key Hotel & Villas

Address: 2801 N Roosevelt Blvd., Key West, FL 33040
Phone: (888) 665-6368
Website

This may be the ultimate Key West hideaway — hidden off a main drag and completely enveloped in lush plantings and holding three (count them!) swimming pools as well as a beachy stretch. The feel here is serene and sophisticated, but without putting on airs.

The Perry Hotel

Address: 7001 Shrimp Rd.,Key West, FL 33040
Phone: (305) 296-1717
Website

A real find tucked away on Stock Island, the Perry is a cool vision with its urbane nautical design, lively pool, adjacent marina, and great food and drink (don’t miss the excellent house restaurant — Matt’s Stock Island Kitchen & Bar — as well as the rum distillery down the walk). On-site electric vehicles can boost you into Old Town, so you won’t feel like you’re missing anything — except maybe the crowds.

The Reach Key West, Curio Collection by Hilton

Address: 1435 Simonton St., Key West
Phone: (305) 296-5000
Website

The Reach is fun-loving and relaxed — the perfect place to plop down near all the fun of Old Town, but with a sweet bit of beach, a romantic pier to stroll, and a beautiful restaurant and bar with a broad terrace for taking the breeze (and views). Perfect for girlfriends, engagements, and millennial getaways.

Lorelei Restaurant & Cabana Bar
Credit: Courtesy of Lorelei Restaurant & Cabana Bar

Best Restaurants

Key Largo

Alabama Jack’s

Address: 58000 Card Sound Rd., Key Largo, FL 33037
Phone: (305) 248- 8741
Website

The low-key vibe at this open-air bar on two barges is like a welcome to the world of the Florida Keys (even though you have to jog a little off the Overseas Highway and cross a toll bridge to get there). But it’s a rite of passage: Don’t miss the conch fritters and the house band — they’ve been playing there forever.

The Fish House Restaurant & Seafood Market

Address: 102401 Overseas Hwy., Key Largo, FL 33037
Phone: (305) 451-4665
Website

A Key Largo tradition for nearly 40 years, this bright blue shack has been the place for big plates of fresh catch and Key lime pie (another claim as the best in the Keys). Look for smoked fish and smoked fish dip here, both Florida specialties.

Tuna Avocado nachos at Key Largo Conch House
Credit: Courtesy of Key Largo Conch House

Key Largo Conch House

Address: 100211 Overseas Hwy., Key Largo, FL 33037
Phone: (305) 453-4844
Website

Let this family-owned institution be your introduction to the conch fritter, a Florida Keys specialty. And if you’re in a breakfast mood, tuck into a stack of Key lime pancakes.

Mrs. Mac's Kitchen

Address: 99336 Overseas Hwy., Key Largo, FL 33037
Phone: (305) 451-3722
Website

Named for founder Jeff MacFarland’s mother in 1976, this brightly colored diner has been a local landmark as well as a tourist destination, and for every good reason. Whether it’s fresh fish and grits for breakfast or the house tomatoey “konk” chowder and fried fish baskets for lunch, Mrs. Mac’s is an Upper Keys must.

Islamorada

Lorelei Restaurant & Cabana Bar
Credit: Courtesy of Lorelei Restaurant & Cabana Bar

Lorelei Restaurant & Cabana Bar

Address: 96 Madeira Rd., Islamorada, FL 33036
Phone: (305) 664-2692

It’s all about catching the sunset and some live music at this toes-in-the-sand favorite, reveling in local favorites like the house-smoked fish dip and Key lime peppercorn snapper. The “Frozen” Key Lime Pie on the dessert menu is renowned.

Pierre's Lounge & Restaurant at Morada Bay

Address: 81600 Overseas Hwy., Islamorada, FL 33036
Phone: (305) 664-3225
Website

It can’t all be salty seafood dives in the Keys, so look to Pierre's for Old Florida elegance: a picturesque plantation-style manor house, a palm lined beach, and elevated takes on fresh catch. Part of the compound, the Beach Cafe is waterfront dining by torchlight.

Marathon

Castaway Waterfront Restaurant & Sushi Bar

Address: 1406 Ocean View Ave., Marathon, FL 33050
Phone: (305) 743-6247
Website

This sprawling, classic seafood dive has a progressive streak, as owner John Mirabella has joined in the movement to catch the invasive lionfish species that has made an assault on the Keys’ underwater ecosystem. The result is lionfish on the menu in the aptly named “King of the Jungle” sushi roll (check out the videos on the screens above the bar showing Mirabella diving for the wild-looking fish).

Keys Fisheries

Address: 3502 Gulfview Ave., Marathon, FL 33050
Phone: (866) 743-4353
Website

There’s nothing better than a seafood dive next door to one of the coast’s largest fish exporters, and this salty classic is pure Keys fun (get the stone crabs when they’re in season). The Lobster Reuben and Key lime pie are famous (and rightly so), so bring your appetite.

Big Pine and Lower Keys

South of the Seven's Gumbo
Credit: Courtesy of South of the Seven

South of the Seven

Address: 17075 Overseas Hwy., Sugarloaf Key, FL 33042
Phone: (305) 741-7115
Website

If you’re wondering, the name means you’re south of the Seven Mile Bridge that marks the Lower Keys. Feel like an insider? Now it’s time to celebrate with big picture window views of the water and the Mediterranean inspired menu in this recent redo inside the landmark Sugarloaf Lodge.

Square Grouper Bar and Grill

Address: 22658 Overseas Hwy., Cudjoe Key, FL 33042
Phone: (305) 745-8880

Before hitting the hurly burly of Key West, this Lower Keys standout is the perfect post-up with its great cocktails and smart seafood dishes like flash-fried conch with wasabi drizzle. Don’t miss the seafood stew.

Key West

5 Brothers Grocery and Sandwich Shop

Address: 930 Southard St., Key West, FL 33040
Phone: (305) 296-5205
Website

Line up with the locals at this historic corner grocer to grab a superb Cuban sandwich or another local classic, the Cuban mix (ham, pork, salami, Swiss cheese, lettuce, tomato, and pickles). Did we mention they also sell cigars?

Blue Heaven Restaurant Entrance in Key West, Florida
Credit: Getty Images

Blue Heaven

Address: 729 Thomas St., Key West, FL 33040
Phone: (305) 296-8666
Website

With its dense foliage and quirky décor, this Key West landmark is the bohemian hangout of choice, whether hitting the little stand-up bar for happy hour or taking a table for a whole blissful brunch, lunch, or dinner. Yes, the rooms upstairs were once a bordello, and yes, Hemingway refereed boxing matches here, and yes, the Key lime pie is the tallest (and most delicious) you’ve ever seen.

Captain Tony's Saloon

Address: 428 Greene St., Key West, FL 33040
Phone: (305) 294-1838
Website

At the original location of Hemingway's main bar, Sloppy Joe's, check out decades of dollar bills (and stuff) tacked to the ceiling. And tell your friends that you drank where Hemingway went to drink his scotch-and-sodas.

Cuban Coffee Queen

Address: 284 Margaret St., Key West, FL 33040
Phone: (305) 292-4747

This is the original location of Key West’s tasty spot for a café con leche (Cuban espresso with steamed milk), cortadito (double Cuban espresso with cane sugar topped with steamed milk), smoothies, breakfast sandwiches, and Cuban favorites like rice & beans. The bags of coffee make great souvenirs.

Little Pearl

Address: 632 Olivia St., Key West, FL 33040
Phone: (305) 204-4762

Aptly named, this beautiful, fashion-forward restaurant with its sweeping marine blue banquettes is a true find in Key West. The chef’s tasting menu puts local catch and thoughtful, tropical-inspired preparation at the center. Reservations required.

Pepe’s Café & Steak House

Address: 809 Caroline St., Key West, FL 33040
Phone: (305) 294-7192
Website

A Key West must, a historic treasure, and worth waiting in line for (because you will). Opened by a Cuban fisherman in 1909, Pepe’s serves up tasty fare all day, but it’s those ample breakfasts with eye-opening mimosas and greyhound cocktails made with fresh juice that define a perfect Key West morning.

Green Parrot Bar

Address: 601 Whitehead St., Key West, FL 33040
Phone: (305) 294-6133
Website

Key West is a bar town, and even if doing a crawl down Duval Street isn’t your thing, you’ll want to pay homage to this famed live music joint with its broad porches and stay for a round and a set (or two). As the sign says, it’s a sunny place for shady people.

nine one five

Address: 915 Duvall St., Key West, FL 33040
Phone: (305) 296-0669
Website

With its double French Caribbean porches and street level bar, this tucked away gem on upper Duval is a lovely perch for an evening watching the world swirl by while tucking into house-made pastas with seafood. (Reservations recommended)

Southern Most Point - 90 Miles to Cuba marker in Key West, FL
Credit: Getty Images

Things to Do

Coral Restoration Foundation
Credit: Tim Grollimund/Florida Keys News Bureau

Coral Restoration Foundation

Address: 5 Seagate Blvd., Key Largo, FL 33037
Phone: (305) 453-7030
Website

Whether you just drop in for an eye-opening explanation of the peril faced by Florida’s coral reefs or you book ahead and join the volunteer coral planting program, this is truly a great way to connect to the reef ecosystem that’s so crucial in Florida (and elsewhere). It’s also a great way to tap into Key Largo’s diving scene.

A green sea turtle swims amid the Florida Keys coral reef tract near John Pennekamp Coral Reef State Park in Key Largo
Credit: Frazier Nivens/Florida Keys News Bureau

John Pennekamp Coral Reef State Park

Address: 102601 Overseas Highway, Key Largo, FL 33037
Phone: (305) 451-6300

This is a must-see for snorkelers and divers alike (and if you don’t swim, there’s always the glass-bottom boat tours). These 70 nautical square miles form the first undersea park in the U.S. and while the upland areas sport mangrove swamps and tropical hammocks, it’s the coral reefs that are worth suiting up for (and don’t forget, the waters of the Keys are always warm, even in the depths of winter). Join a snorkeling or scuba tour or rent kayaks, paddle boards, or canoes.

Lignumvitae Key Botanical State Park

Address: 77200 Overseas Hwy., Islamorada, FL 33036
Phone: (305) 664-2540
Website

Well off the beaten path, this 300-acre castaway island is home to the Lignum vitae, a small and spectacular tree that grows in the tropics and blooms in glorious blossoms (its wood is among the densest and heaviest on earth). You’ll need a boat or kayak to get here; check out rentals and outfitters here.

Turtle Hospital

Address: 2396 Overseas Hwy., Marathon, FL 33050
Phone: (305) 743-2552
Website

Leave the old-school petting aquariums behind and fall in love with the residents in rehabilitation here at the first state-licensed veterinary hospital devoted solely to the treatment of endangered sea turtles in the world. The tours are excellent and well worth booking in advance.

Bahia Honda State Park
Credit: Getty Images

Bahia Honda State Park

Address: 36850 Overseas Hwy., Big Pine Key, FL 33043
Phone: (305) 872-2353
Website

A longtime favorite, this 524-acre state park is getting a $2.96 million restoration of its north side in 2021, including a redo of 24 campsites. Meanwhile, the entire park is a magnet for beachgoing, swimming, and snorkeling: a perfect day-trip visit.

A Key deer searches for food in the National Key Deer Refuge on Big Pine Key
Credit: Andy Newman/Florida Keys News Bureau

National Key Deer Refuge

Address: 30587 Overseas Hwy., Big Pine Key, FL 33043
Phone: (305) 872-0774
Website

They’re tiny, adorable, and unique to the Florida Keys. And now these miniature Key deer are protected, having been saved from the brink of extinction. Start at the Visitor and Nature Center for more on the Key deer, including where to see it and how to explore the refuge’s 9,200 acres of preserved forest, tropical hardwood hammocks, freshwater and salt marsh wetlands, and mangrove forests.

Audubon House & Tropical Gardens

Address: 205 Whitehead St., Key West, FL 33040
Phone: (305) 294-2116
Website

No, Audubon didn’t sleep here (or live here). But this grand 1840s house museum with its lush courtyards is named for the famed naturalist whose paintings of Florida birds are truly iconic. Join daily tours to get a glimpse into historic Key West life as well as Audubon’s famed birds — or just enjoy a few quiet and cooling moments in the shady courtyard. (Insider intel: Audubon did spend crucial time in scouting birds in Key West in 1832 but lived aboard a sailboat.)

Ernest Hemingway Home & Museum in Key West
Credit: Laurence Norah/Florida Keys News Bureau

Ernest Hemingway Home & Museum

Address: 907 Whitehead St., Key West, FL 33040
Phone: (305) 294-1136
Website

There is no better pilgrimage in the Keys than to the home of its most famous literary citizen. Enjoy the lounging cats that are offspring of Papa’s original gang, get the story behind the swimming pool, and walk the tiny catwalk to his writing studio.

Harry S. Truman Little White House

Address: 111 Front St., Key West, FL 33040
Phone: (305) 671-9199
Website

Harry Truman gave ‘em hell, and then he donned a tropical shirt and had buddies over to fish and play cards at this circa-1890 naval site, which, as Truman set up shop there for 175 days of his presidency from 1946 through 1952, became known as the Little White House. Join a tour at Florida’s only presidential site to get a personal feel for the man behind the office and make time to stroll the leafy lanes of its neighborhood.

Hemingway Rum Company

Address: 201 Simonton St., Key West, FL 33040
Phone: 305-414-8754
Website

Located right in the bustling docks area of Old Town, this new distillery is the perfect jump into the cool shade for a tour, tasting, and a bit of shopping. The star of the show here is Papa’s Pilar, a premium rum in a captivating bottle produced with the Hemingway family’s blessing.

Honest Eco Sustainable Nature Tours

Address: 231 Margaret St., Key West, FL 33040
Phone: 305-294-6306
Website

Key West is full of cruise charters, but this progressive tour company is head and shoulders above the rest for its commitment to sustainability and environmental education. Owned and operated by biologist Billy Litmer, Honest Eco operates out of the Historic Seaport and features SQUID, Key West’s first electric power charter boat. Schedule a Dolphin Watch and Snorkel or an All the Above Trip, which adds kayaking and organic vegetarian lunch.

Key West Butterfly and Nature Conservatory

Address: 1316 Duvall St., Key West, FL 33040
Phone: (305) 296-2988
Website

Come for the 50 to 60 types of butterflies, stay for the pair of flamingos who stroll the glass conservatory and enchant every visitor. The Learning Center — which focuses on the Monarch butterfly — is terrific for naturalists of all ages.

Key West Pro Guides

Address: 5130 US-1, Key West, FL 33040
Phone: (866) 259-4205
Website

Ready to live that sportfishing dream? The guides here can help even a fishing novice get the Hemingway experience on the water, and they're ready to help experts land that trophy fish.

Mallory Square

Address: 400 Wall St., Key West, FL 33040
Website

Yes, it’s touristy. And yes, you can’t not go for at least one sunset to join the throngs of revelers who ogle the buskers, sip daiquiris, and do their best to spot Key West’s famed Green Flash right at sunset. Do not miss the cat acrobatics (seriously).

Old Town Literary Walking Tour

Website: 77 Love Lane, Key West, FL 33040
Phone: (305) 293-9291
Website

This 90-minute guided walk offers an inside look at the landmarks and sites that mark the city’s literary legacy, including the houses and favorite haunts of Tennessee Williams, Shel Silverstein, Elizabeth Bishop, and Robert Frost, among other luminaries. For the full Ernest Hemingway, make sure to make time to visit the Ernest Hemingway Home & Museum, above.

Southern Most Point - 90 Miles to Cuba marker in Key West, FL
Credit: Getty Images

Southernmost Point

Address: Whitehead and South sts., Key West, FL 33040
Phone: (305) 809-3700
Website

Can you resist a photo opp at the big, brightly-painted buoy that marks the continent U.S.’s southernmost point? If not, get up early and head over to this picturesque corner and snap your shot before the line starts forming (because it does).

Kermit's Key Lime Shoppe in Key West
Credit: Courtesy of Kermit’s Original Key West Key Lime Shoppe

Best Shopping

Shell World

Address: 97600 Overseas Hwy., Key Largo, FL 33037
Phone: (305) 852-8245
Website

Kitschy and over the top, this is a classic Florida Keys tourist stop, but it’s truly worth it. Take in the splendor, pick up a souvenir, and know that you’re part of a great tradition of roadside attractions.

Florida Keys Outfitters

Address: 81219 Overseas Hwy., Islamorada, FL 33036
Phone: (305) 664-5423
Website

You’re in the sportfishing capital, so let’s get to it: This excellent shop will get you outfitted for your saltwater flyfishing adventure, pair you with a guided excursion once you’re inspired (you will be). Also, a great selection of sun protection gear, which is vital down here.

Ocean Gardens & Gifts

Address: 82237 Overseas Hwy., Islamorada, FL, 33036
Phone: (305) 664-2793
Website

If your home isn’t nautically themed, it will be after an hour (or more) at this emporium of all décor maritime, from antiques to artisan takes (there’s shells and jewelry, too). From anchors to oysters, it’s a marvelous place to linger.

Portside Studio and Gallery

Address: 81888 Overseas Hwy., Islamorada, FL, 33036
Phone: (617) 756-9919
Website

Bright and airy, this hip gallery in the heart of the Keys not only showcases the work of owner Valerie Perreault, but it also rotates shows of emerging artists and plays home to classes, film festivals, lectures, performances, and installations.

Rain Barrel Village

Address: 86700 Overseas Hwy., Islamorada, FL, 33036
Phone: (305) 521-2043
Website

There’s no resisting Betsy, the 40-foot-long spiny lobster beckoning to you from the side of the road. A nod to the old-Florida tourism of days gone by, this collection of brightly colored cottages amid gardens with all manner of arts, crafts, and clothing is pure fun.

Village Square at the Trading Post

Address: 81868 Overseas Hwy., Islamorada, FL, 33036
Phone: (305) 440 – 3951
Website

A charming collection of pastel cottages is home to an equally charming collection of shopping and snacking: You’ll find some beachy boho fashion, home décor, plants and other botanicals, art, burritos, and coffee.

90 Miles to Cuba

Address: 616 Greene St., Key West, FL, 33040
Website

In a colorful corner of the Historic Seaport District, artist Linda Reike curates vintage finds including rare books, nautical antiques, jewelry, and 1930s postcards from Key West and Cuba.

Bésame Mucho

Address: 315 Petronia St., Key West, FL, 33040
Phone: (305) 294-1928
Website

Chic and eclectic, this romantic boutique in colorful Bahama Village never fails to come up with the must-have, from a Kiehl’s beauty update or perfume to gorgeous jewelry or a cunning small antique.

Books & Books

Address: 533 Eaton St., Key West, FL, 33040
Phone: (305) 320-0208
Website

This lovely indie bookstore — and non-profit and community center for readers and writers — was founded by beloved author (and Key West resident) Judy Blume and is ground zero for Key West's literary scene.

Collections Key West

Address: 6810 Front St., Key West, FL, 33040
Phone: (305) 923-4778
Website

On funky Stock Island (a neighborhood of Key West), this eclectic gallery owned by longtime resident Karen Wray features works ranging from paintings, sculpture, and glass, to antiques and collectibles. It’s pure Key West. 

Gallery on Greene

Address: 606 Green St., Key West, FL, 33040
Phone: (305) 294-1669
Website

For collectors and oglers, Nance Frank’s gallery with a deep bench of Key West artists (including a stellar roster of Cuban artists) is a must visit.

The Green Pineapple

Address: 1130 Duval St., Key West, FL, 33040
Phone: (305) 509-7378
Website

Putting breezy tropical style in perfect harmony with eco-mindedness, these chic little boutiques are the best destination for tunics, shade hats, local artisan jewelry, and an overall sense of wellbeing. There’s a second location in Bahama Village (310 Petronia St.) and a third in the Perry Hotel (see Best Hotels, above).

Kermit's Key Lime Shoppe in Key West
Credit: Courtesy of Kermit’s Original Key West Key Lime Shoppe

Kermit’s Original Key West Key Lime Shoppe

Address: 200 Elizabeth St., Key West, FL, 33040
Phone: (305) 906-0325
Website

Don’t think you’re being too touristy falling prey to Kermit’s charming presence outside, inviting you to try a little sample and come on inside. It’s totally worth it. This institution is the spot to grab all manner of sweets that have the words “Key” and “lime” in them.

Kino Sandals

Address: 107 Fitzpatrick St., Key West, FL, 33040
Phone: (305) 294-5044
Website

It’s rare that a souvenir is truly a local favorite as well, but you won’t find a Conch (Key Wester) who doesn’t have a perfectly broken-in pair of these leather sandals. Hit the landmark shop founded by Cuban immigrant Roberto “Kino” Lopez in 1966 and gape at the 17 designs and myriad shades (you can also watch them being made).

Lilly Pulitzer Key West

Address: 600 Front St., Key West, FL, 33040
Phone: (305) 295-0995
Website

Because you know you need that inimitable shift dress for sunset cocktails, and if you haven’t dipped into the tropical preppy splendor that is Lilly Pulitzer, then now’s the perfect time.

Rodriguez Cigar Factory

Address: 113 Fitzpatrick St., Key West, FL, 33040
Phone: (305) 296-0167
Website

The oldest cigar company in the Florida Keys is a fragrant place to spend some time, even if you’re not sure you’re a cigar smoker (but the perfect place to bring back a souvenir for the one in your life). Tours include demonstrations, a cigar, and Cuban espresso (book online in advance).

Weather

The climate in the Florida Keys is subtropical, and the proximity to the Gulf Stream and Gulf of Mexico means that the average summer and winter temperatures rarely differ more than 10 degrees. Which means year-round paradise (except for hurricane season). Here's how the seasons break down:

Winter: What's not to love about a season where it hardly ever rains, and the temperatures hover between 75 and 80 degrees? January's high is 74.8° F and the low is 64.9°, and February is about one degree warmer. The average rainfall for both months hovers below two inches.

Spring: Early spring is still pretty dry, but with May comes more precipitation (3.5 inches of rain) as hurricane season looms officially on June 1. In terms of average temperature, March opens with an average high of 78.6° F and by May that high is up to 85.1°.

Summer: Even at the peak of summer, the average high is 89° F, and the lack of highways and urban sprawl means that the heat doesn't bake quite like it does elsewhere. And all the water surrounding the Keys has a cooling ocean effect. But it's rainy season, with June and August topping out at just over five inches per month.

Fall: This season includes some of the feistiest months of hurricane season, so this can mean threatening storms. It can also mean beautiful, calm days with billowy clouds. The high temps of August start to decline, down to 88° F in September, 84.4°in October, and a balmy 80° in November.

Apps to Download

Florida Keys & Key West Travel: Planning, booking, and exploring.
iOs | Google Play

Key West Tour Guide: Audio tours from Key Largo to Key West.
Google Play

Miami Key West GyPSy Guide: Guided commentary from Miami to Key West.
iOs | Google Play