by Melissa Puppo | March 3, 2025
Get Key-zee With These Three Guides to the Florida Keys
A quintessential guide to the Florida Keys for adventurists, Old-Florida nostalgists and solo wanderers
The Florida Keys have long promised a blend of fiery sunsets, legendary lore and mysterious habitats. When I arrived at Little Palm Island Resort & Spa, a secluded retreat off Little Torch Key, I was searching for something I couldn’t quite define. With only 30 thatched-roof bungalow suites, the resort felt worlds away from my Miami base, offering a rare calm.
As my fiance and I wandered the lush, palm-shaded grounds, the island’s quiet luxury revealed itself with every step. Later, when he returned to our bungalow to freshen up, I lingered alone, eventually settling into a hanging daybed overlooking the still, cerulean oceanfront. Seagulls skimmed the water in search of dinner, the air heavy with salt and serenity. Golden hour had cast its spell—an invitation to switch off and absorb the beauty of the moment.
Despite other guests being on the island, the scene felt suspended in time, a reminder of the simple pleasures the Florida Keys offer in abundance: tranquility, natural beauty and space to breathe. That’s the magic of this iconic chain of islands—it molds itself to every traveler’s dream. Whether you’re drawn to the charm of Old Florida, the thrill of outdoor adventure or the freedom of traveling solo, the Keys hold something special for everyone.
The following is a road map to plan your next Florida Keys adventure with everything from reimagined resorts and angling adventures to private beaches and lively Key West nights—you may find your own slice of paradise, just as I did on that swing at Little Palm Island.
For the Old-Florida Enthusiast
For those who cherish the timeless charm of the Keys—natural beauty and laid-back adventures steeped in tradition
Little Palm Island Resort & Spa
Little Torch Key
Begin your journey to the golden age at the Shore Station on Little Torch Key, where guests sip the signature Gumby Slumber cocktail before boarding a private boat, The Truman, to a four-acre tropical paradise. Thatched-roof bungalows, swaying palms and Key deer set the stage for this exclusive escape. As a Michelin Three Key Hotel for 2024, every last detail reflects the boutique resort’s commitment to excellence.
The resort’s 30 intimate suites, inspired by British West Indies design, blend vintage glamour with modern indulgences. Think: outdoor showers, four-poster canopy beds, hammered-copper tubs and private firepits lit nightly by the concierge. Panoramic ocean views and antique touches, like rattan chairs and aged brass accents, evoke Florida’s bygone era.
Unplug completely—there are no TVs, only vintage rotary phones that connect you to personalized concierge services. Whether dining with toes in the sand or cooling off by the pool, Little Palm Island invites you to “get lost,” as the resort’s motto goes.
WHAT TO DO: Take off on a seaplane trip to Dry Tortugas National Park, located about 70 miles west of Key West, with 100 square miles of open water and a tiny outcropping of islands where history and nature collide. Wander the corridors of Fort Jefferson, snorkel through coral reefs or bask on pristine beaches. Little Palm Island’s concierge can handle the details, leaving you free to soak in the adventure.
For anglers, the Florida Keys backcountry is a world-class fishing destination. Charter a trip to chase the legendary big three—tarpon, permit and bonefish—or reel in seasonal catches with the help of an expert guide. Opt for fly-fishing or spinning rods, and set out for a four-, six- or eight-hour adventure on the flats.
Closer to the resort, Looe Key feels like a postcard from Old Florida’s underwater heyday. Playful fish dart through coral, curious sea turtles glide by and the occasional eel weaves through the scenery. Book a private excursion or explore at your own pace by taking out one of the 13-foot Boston Whalers in the resort’s fleet available to guests.
These 10 Florida Keys eateries offer different versions of Key lime pie. Key lime tini, anyone?
Discover hidden sandbars or drop anchor at a secluded beach. Let the concierge elevate your experience with a custom dinner on a nearby stretch of sand or a romantic sunset cruise with your favorite wine in hand.
For those who prefer unwinding on land and in luxury, the resort’s serene pool offers the perfect setting to dive into a good book or recharge with poolside pampering by the attentive staff. Just steps away, SpaTerre provides a sanctuary of relaxation, blending the natural healing power of the sea with luxurious treatments like the Madrugada in-ocean sunrise massage or the organic nourishing seaweed leaf wrap.
WHERE TO DINE: At Little Palm Island, the culinary approach is no less indulgent than the rest of the resort. The acclaimed Dining Room offers exceptional seafood, Caribbean flavors and French techniques, with panoramic water views for breakfast, lunch and dinner. For a more intimate experience, tables set on the sand invite guests to savor lobster-studded pasta and rum-spiked desserts beneath the stars, beachside.
Casa Marina
Key West
For a stay steeped in history, Casa Marina offers a timeless escape in Old Key West. Built in the 1920s as part of Henry Flagler’s legacy, this iconic property blends historic charm with modern luxury after a $79 million renovation. Guests enjoy easy access to Duval Street and Old Town while indulging in vibrant island-inspired rooms and suites.
Casa Marina features myriad unique dining options, including breakfast in Flagler’s Ballroom and Papa’s Pilar rum flights at The Canary Room. The hotel’s crowning jewel is Key West’s largest private beach—1,100 feet of pristine coastline. Spend days snorkeling, jet skiing or taking dolphin tours, and try your hand at sand sculpting with award-winning resident sculptor Marianne van den Broek. Guests also enjoy access to The Reach Key West, Casa Marina’s nearby sister property.
WHAT TO DO: If you’re a foodie at heart, grab a spot with Key West Food Tours. The group offers options like The Hemingway Experience, where you’ll explore the island Papa-style, and the Historic Seaport Food & Cultural Walking Tour, featuring fresh catch straight from local waters.
WHERE TO DINE: Book a reservation at the resort’s recently opened restaurant, Dorada, with gorgeous oceanfront views and an eclectic island-style menu underscored by Baja-Mediterranean fare. Or opt for a romantic dinner on the beach with your toes in the sand.
Nearby Blue Heaven, a culinary staple, is most known for its signature meringue-style Key lime pie and loitering feral chickens, and is an excellent spot to enjoy brunch, where the star is the lobster Benedict topped with a Key lime hollandaise sauce.
Marquesa Hotel
Key West
Amid the hustle and bustle of Key West lies Old-Florida charm at the Marquesa Hotel. You can’t miss the property, with its iconic beachy blue facade and prime corner spot in the historic district, just two blocks from Duval Street. Formerly a clothing store, corner grocery store and boarding house, it’s now the perfect perch to soak in the city’s charm, savor the flavors of the hotel’s iconic Café Marquesa and start dreaming about your return trip to the Keys.
WHAT TO DO: No visit to Key West is complete without a stop at the Ernest Hemingway Home and Museum. Wind your way through the storied residence where the Nobel Prize-winning author penned classics like “To Have and Have Not,” and don’t be afraid to pet the famous polydactyl cats who live there. For a deeper dive into Hemingway’s life and literary legacy, opt for a guided tour.
Spend your afternoons cozying up with a book on a gingerbread-trim porch or catching some rays by one of the three pools. Café Marquesa is ideal for quaint morning breakfasts or a romantic dinner for two. The best part? You’re just steps away from the area’s best activities and nightlife if you decide to venture out and about.
Rum enthusiasts shouldn’t miss Key West First Legal Rum Distillery, where free tours reveal the craft behind their award-winning spirits. Sample their signature blends—like the smooth Bad Bitch Rum Spanish Marie—and grab a bottle to savor or purchase one of the many gift selections.
For a one-of-a-kind experience, book the “Flamingle” encounter at the Key West Butterfly and Nature Conservatory. Meet resident flamingos Rhett and Scarlett up close, then wander the lush conservatory filled with vibrant butterflies in a
tropical haven.
WHERE TO DINE: Secure your reservation well in advance to ensure a table at Latitudes, which is an essential destination for beachfront dining. A private ferry whisks you to the restaurant, tucked away at Sunset Key Cottages. Here, you can enjoy some of Key West’s best seafood and sunset views.
For the Adventurist
Designed for thrill-seekers and explorers who crave the untamed side of the Keys—dive deeper, paddle further and embrace every wild adventure
Baker’s Cay Resort
Key Largo
Baker’s Cay Resort is truly a haven for outdoor enthusiasts, thanks to its expansive shorelines and unmatched access to open-water adventures. Situated on 15 waterfront acres in Key Largo, Baker’s Cay Resort offers 200 rooms and suites and a seamless blend of adventure and relaxation. Its proximity to John Pennekamp Coral Reef State Park, home to the iconic Christ of the Abyss statue, makes it a prime spot for exploring Key Largo’s underwater treasures. Guests can dive, snorkel, paddleboard, kayak, parasail, go deep-sea fishing and more.
On land, ride a beach cruiser along scenic trails or unwind in beach chairs by the bay. Dining options include Calusa, with panoramic views of Florida Bay that pair perfectly with tropical-inspired American cuisine. For a low-key affair, tuck into the hideaway cove bar Dry Rocks for Mexican cuisine and live music on the weekends. Here, savor signature Baker’s Cay Patrón reposado and anejo under the guidance of the hotel’s certified tequila connoisseurs. By day’s end, your final adventure can always culminate with a ritual sunset Champagne toast.
WHAT TO DO: Wade into the heart of real Florida with a trip to Everglades National Park, just an hour away. Drive the nearly 40-mile Main Park Road to Flamingo, the southernmost district of the park, for private backcountry fishing excursions (Deep South Fishing Charters is a favorite), kayaking, biking, bay tours and more. Find sustenance, a marina and a place to stay the night in the heart of the Glades at the Flamingo Lodge.
Score a few fish on your charter? Back in Key Largo, the Baker’s Cay culinary team is happy to prepare your fresh catch for dinner as part of their Dock to Dish program.
John Pennekamp Coral Reef State Park offers opportunities to snorkel or dive in the country’s first underwater park. Prefer to stay dry? Glide over vibrant marine life on a glass-bottom boat tou
For a more chill adventure, with adult beverages involved, take a two-hour sunset water tiki cruise through Florida Bay’s uninhabited mangrove islands. With a captain at the helm, sip a cocktail, soak in breezy tunes and enjoy the scenic journey back to Baker’s Cay.
WHERE TO DINE: Key Largo Fisheries, near mile marker 100, has been a local institution since 1972, famed for its fresh seafood and stone crabs. Watch as fishing boats unload their catch—lobster, shrimp and mahi-mahi—straight into ice-filled market displays. Then, savor your meal al fresco, overlooking the marina.
For a taste of local charm, head to the family-owned Key Largo Conch House, a bungalow-style eatery renowned for its golden, crispy conch fritters. Pair them with a No Wake Zone Coconut Keylime Ale for the ultimate Keys combo.
Cheeca Lodge & Spa
Islamorada
This 27-acre luxury resort is a paradise for anglers, steeped in a rich fishing tradition that has drawn adventurers for generations. At its heart is a 525-foot fishing pier—one of the longest in the Florida Keys—so it’s no surprise that Cheeca Lodge & Spa hosts thrilling fishing charters and yearly tournaments, like the All American Backcountry Fishing Tournament held in November. With world-class amenities, it’s a premier destination for anglers chasing their next big catch.
Wander miles of private white sand beaches, soak in the sunshine at one of three pools and enjoy award-winning on-site dining options, like Atlantic’s Edge, Cheeca’s flagship restaurant known for its tropically inspired menu.
Unwind after a day of adventures at the signature Spa at Cheeca Lodge, hidden among the lush foliage and bougainvilleas. Treatments like the indulgent caviar facial or 100-minute therapeutic deep-tissue massage beckon. For extra pampering, add on a CBD scalp massage, gemstone collagen mask or dry brushing exfoliation.
WHAT TO DO: During regular lobster season (August–March), grab your mask, snorkel, gloves and a trusty tickle stick, and swim along sandy bottoms and rocky crevices in search of spiny lobsters—the region’s tastiest treasures. For those new to the crustacean hunt, local outfitters like Forever Young Charter Company offer expert guides to share tips on luring these rock lobsters into your net.
Dive into the thrill of Islamorada Dive Center’s shark encounters, where you’ll get up close to local, friendly sharks. As you descend into their underwater world, you’ll witness these proficient predators glide effortlessly through coral reefs. For an extra adventure, enroll in a PADI Aware shark conservation specialty course and help protect these incredible creatures.
The Keys are a kiteboarding paradise, where shallow waters and steady winds cater to all skill levels. Curious first-timers to the sport can find lessons at Otherside Boardsports.
WHERE TO DINE: Start your day at Mangrove Mike’s, a local favorite now run by Mike’s niece. Dig into hearty classics like the seafood Benedict and cinnamon roll French toast served in a cozy, laid-back setting.
While casual eats reign supreme in the Keys, the fine-dining outpost Chef Michael’s serves up fresh catches, like petite lionfish “Creole” and snowy grouper, along with signature dishes such as roast duck and grilled prime New York strip steak.
Three Waters Resort & Marina
Islamorada
Adventure seekers heading to the sportfishing capital of the world will find the perfect match at the reimagined Three Waters Resort & Marina. This expansive property merges the former Postcard Inn Beach Resort & Marina with Pelican Cove Resort & Marina, offering a vibrant mix of activities. The full-service marina runs daily offshore and backcountry charters, while nine dining spots cater to every craving.
Novice anglers can try their hand at fly casting or lobstering with expert guidance. Explore hidden coves on a guided Jet Ski tour. Even the resort’s complimentary Rum Runner water taxi feels like part of the adventure, connecting you to its sister properties—Amara Cay Resort and La Siesta Resort & Villas. After a busy day of surf and sand, reprieve in your island-inspired room with some suites opening directly onto the sandy beach.
WHAT TO DO: Robbie’s of Islamorada is a quintessential Keys experience. Watch the world-famous tarpon feeding from the docks or grab a bucket of fish to feed them yourself. Beyond the docks, hop aboard the Captain Michael party fishing boat for a group trip to reel in snapper, grouper or mackerel. Afterward, browse the open-air market or dine at the Hungry Tarpon restaurant, where the kitchen staff will cook the fish caught aboard the Captain Michael.
Head to Windley Key Fossil Reef Geological State Park to explore 8-foot quarry walls of fossilized coral and Key Largo limestone. Hike five short trails and soak in the island’s
natural beauty.
WHERE TO DINE: Islamorada Pizza Co. at the resort offers seven hearty pies, including the Carnivore and mushroom-topped Nonna. In spring 2025, Kindler is expected to debut with a crackling hearth for searing, grilling and charring, featuring shellfish towers and fresh fish, with the option to cook your own catch.
Off-property, the tiki-inspired Islamorada Fish Company serves its classic fish dip alongside sweeping views of Florida Bay or visit Islamorada Brewery & Distillery, the Keys’s only brewery-distillery, for craft beers and small-batch spirits.
For the Solo Traveler
Whether you’re seeking solitude or eager to connect with fellow adventurers, the Florida Keys offers the perfect escape for the independent explorer.
Isla Bella Beach Resort
Marathon
Looking for a getaway where the only distractions are the sound of the ocean lapping up on the beach or the attentive staff catering to your every need? Isla Bella Beach Resort offers just that. Wander a private, mile-long coastline, discover quiet spots to read or unwind by one of five oceanfront pools.
Wake up to stunning sunrises from your balcony, then retreat to a bright, airy room with thoughtful touches like rainfall showers. Start your day at The Marketplace, where you can grab freshly brewed coffee, shop curated gifts or sign up for daily adventures.
Whether you’re relaxing on the pier in Adirondack chairs, sipping drinks at the beach bar or dining at Sushi Cabana, Isla Bella offers the perfect balance of peace and indulgence. Be sure to book a coconut milk and honey body treatment at The Spa for the ultimate unwind.
WHAT TO DO: Join other Isla Bella guests and the Conch Republic Marine Army for a complimentary outing to restore mangrove habitats, and have fun spotting manatees from aboard the cleanup boat while you’re at it.
Take the Pigeon Key Express train to the “tiny island under the Old 7 Mile Bridge,” where you can explore the original bridge’s construction and feed sharks in the saltwater pool.
For a closer look at wildlife, head to the National Key Deer Refuge on Big Pine Key. Early mornings or late afternoons offer the best chance to spot the elusive Key deer. Don’t miss the Blue Hole trail, where you might see a resident alligator—one of the most reliable places in the Keys to spot them.
WHERE TO DINE: Guests rave about booking a sunset dinner at Mahina, the Polynesian-inspired restaurant at Isla Bella. Savor mahi-mahi and ahi poke, then head to the sand for a stunning photo with a gorgeous backdrop.
Off-property, Keys Fisheries, known for its lobster Reubens, offers fresh seafood in a no-frills atmosphere along the water. Order by naming your favorite superhero or answering other fun prompts from the staff—part of the quirky charm.
Ocean Key Resort & Spa
Key West
Solo travel doesn’t have to mean time alone. Ocean Key Resort places you at the center of Key West’s action with its prime location at 0 Duval Street. Nestled between Key West Harbor and Mallory Square, the property is perfectly positioned for spectacular sunsets—best enjoyed from your balcony or the Liquid Pool Bar & Lounge.
The resort’s colorful, hand-painted furnishings and tropical details embody the vibrant spirit of the Keys. Every room and suite feature stunning views of the Gulf, harbor or Old Town Key West, with some outfitted with oversized Jacuzzis for an added element of fun.
Need to unwind? Head to SpaTerre for the tropical essence massage, which includes a brown sugar and Tahitian shell body polish and organic coconut melt.
WHAT TO DO: Snap a photo at the Southernmost Point Buoy, one of Key West’s most recognizable spots, marking the island’s southern tip just 90 miles from Cuba.
Bike your way through historic downtown with stops at the Key West Garden Club, Smathers Beach or the Historic Key West City Cemetery.
In the mood for a classic rum runner or Hemingway daiquiri? Belly up to the hotel bar for a chat with friendly staff and locals who know where to find the best pours in town. Aside from the obvious mainstays like Sloppy Joe’s and Hog’s Breath Saloon, favorite watering holes include Tipsy Rooster Liquor Store and Bar, The Rum Bar and Hemingway Rum Company.
WHERE TO DINE: Ocean Key’s iconic Sunset Pier, with its colorful umbrellas and stools, is a must-visit. Enjoy classic Keys fare like peel-and-eat Key West pink shrimp and seafood tacos, all while soaking in daily live music.
For some of the city’s best sunset views and prime people-watching, head to Hot Tin Roof, the hotel’s signature restaurant led by Chef Scott Maurer, who celebrates 10 years at the restaurant this year. Named after Tennessee Williams’s play “Cat on a Hot Tin Roof,” its menu is inspired by the flavors of the Keys, Cuba and the Caribbean.
The beauty of the Florida Keys lies in its ability to offer something unique for every traveler. For me, it was the unforgettable moment on that hanging daybed at Little Palm Island Resort, watching golden hour transform the sky. For you, it might be the solitude of solo travel, reeling in a big catch on a charter or uncovering a hidden piece of Old-Florida history. Now, close your eyes and picture the
possibilities—then start planning your Florida Keys escape.
