There is perhaps no place in the United States so physically close to the mainland yet so transportingly removed from it as the Florida Keys. I’ve been visiting this 113-mile-long archipelago strung together by 42 bridges and slung off the southern tip of Florida since my college days at the University of Florida, when I first made the drive down for spring break with friends. Today, you’ll find me making pilgrimages to the Keys from my home in Tampa with my two young kids for tropical ocean adventures like snorkeling on North America’s only coral barrier reef and kayaking through the mangrove tunnels and calm lagoons around Marathon.
Whether you beeline it from Key Largo to Key West or take it slow, working your way through the islands and detouring off U.S. Highway One for surprises down sandy lanes, the joy is the journey.
“When you’re in the Florida Keys, you’re actually on a string of islands that feel more like the Caribbean than the continental U.S,” says Beth Vessels, director of marketing and communications for the Coral Restoration Foundation in Tavernier. “At certain stretches of the drive, you’re surrounded by shimmering turquoise water. It takes your breath away.”
Major 2026 Key West events to make your calendar for include the 45th anniversary of Hemingway Days in July, the 30th annual Key West Songwriters Festival at the end of April into early May, and Key West Pride in late June, celebrating 30 years of embracing the island’s vibrant LGBTQ+ community. And you’ll find smaller events and gatherings scattered throughout the year in the other islands of the Florida Keys, ranging from lionfish hunting derbies and fishing tournaments to reef cleanups and art festivals.
Each Key has its own character, Vessels says, adding “the drive from Key Largo to Key West may take several hours, but it’s one of the most memorable drives you’ll ever take.”
Over the course of a long weekend getaway, the Florida Keys promise ample opportunity to get out on the water, see interesting marine life, and soak up history and culture along with the sun. Here’s how to spend four very fun days in the Florida Keys.
An aerial shot of John Pennekamp Coral Reef State Park shows the distinct topography of the area.
Photo by Felix Mizioznikov/Shutterstock
Day 1: Dive a shipwreck, snorkel vibrant reefs, and dig into fresh seafood by a canal, all in Key Largo
About 70 miles south of downtown Miami, Key Largo is the gateway to the Florida Keys. Much of the appeal lies offshore here, says Stephen Frink, an underwater photographer and the publisher of Alert Diver magazine. “Key Largo benefits from a long history of marine conservation,” says Frink, who has lived in Key Largo since 1978, pointing to John Pennekamp Coral Reef State Park as a great place to kick off underwater explorations.
The park was established in 1960 to combat the depredations of coral scavengers, who extracted whole coral heads to display at curio shops along U.S. 1, he says. On-the-water experiences within the park’s protected waters range from glass-bottom boat tours and guided scuba-diving and snorkeling trips to renting canoes and kayaks for paddling out on self-guided tours within 50 miles of mangrove-lined wilderness.
Experienced divers don’t miss the chance to dive Key Largo’s signature wreck, the 510-foot-long USS Spiegel Grove, which was sunk upright six miles offshore in 2002 to form an artificial reef. Pelagic fish like black tip reef sharks, grouper, and barracuda are commonly seen patrolling its superstructure.
Off-duty dive instructors hang out at the canal-front Sharkey’s Sharkbite Grill, known for its daily happy hour specials and delicious mahi mahi tacos. Closer to the state park, Buzzards Roost is another fresh seafood favorite fronting the water (ask for the hogfish, a favorite Keys catch, which may not be on the menu but is often available ). REEF Ocean Exploration Center for Marine Conservation opened in June 2025 and is a great place to visit with kids, as it has interactive exhibits spotlighting coral reef health and ocean stewardship.
When it’s time to scout for the green flash—an optical phenomenon where the sun appears to flash to bright green just after sunset (or before sunrise)—on Key Largo’s bayside, Roxane Boonstra, learning ecosystems administrator at the Coral Restoration Foundation, has a suggestion for great vibes while you’re looking: “Perhaps one of my favorite local spots is Caribbean Club in Key Largo because of its relaxed atmosphere,” she says about the favorite watering hole that opened in 1938.
The bright signage at Robbie’s on Islamorada shines, and tarpon fish swim right up the dock nearby.
Photo by Danita Delimont/Shutterstock (L); photo by Iv-olga/Shutterstock (R)
Day 2: Feed enormous tarpon, eat lionfish, and celebrate sea turtles, all on Islamorada and Marathon
Continue making your way south through the Keys to Islamorada and Marathon, two islands legendary among anglers for the stream of charter boats that leave from the islands’ marinas to fish the Gulf Stream. You’ll spot some pretty impressive fish from the docks at Robbie’s Marina in Islamorada, where a few bucks gets you a small bucket of fish to lure massive tarpon, weighing up to 200 pounds, that lurk in the shallows for handouts.
Islamorada goes beyond boat drinks and Buffett tunes in its Morada Way Arts & Cultural District, a creative hub with galleries and art studios lining the street and monthly art walks that happen every third Thursday of the month. The art walks feature live music and pop-up food and craft vendors.
For a meal you can feel good about, find Castaway Waterfront Restaurant & Sushi Bar in Marathon, a classic Keys haunt hugging another canal where dishes made with invasive lionfish are almost always on the menu and manatees can often be seen frolicking within feet of the outdoor tables.
Continuing the conservation theme, rescued and rehabbed turtles are the lure at Marathon’s Turtle Hospital, a nonprofit organization that works to release endangered sea turtles and offers guided tours throughout the day.
Seven Mile Bridge lives up to its name from up on high; No Name Pub is so famous it doesn’t need a name.
Photo by Zoshua Colah/Unsplash (L); photo by William Silver/Shutterstock (R)
Day 3: More snorkeling, tiny deer, and a great beach for camping, all in The Lower Keys
Just south of Big Pine Key in the Lower Keys, Looe Key Sanctuary Preservation Area is one of the best places for snorkeling in the entire region, thanks to its shallow reefs and abundant marine life. “Within the MPAs (marine protected areas) the fish act differently. They have learned to not be alarmed by the presence of divers, not associating them with spearfishing,” says Frink. Captain Hook’s offers daily snorkeling and diving trips.
While the Florida Keys aren’t known for abundant beaches, there are some pleasant sandy stretches at Bahia Honda State Park, known for its waterfront camping sites and the derelict Bahia Honda Railroad Bridge that’s a favorite sunset photo subject. Calusa Beach, right next to the bridge, is lapped by clear waters that are particularly pleasant for swimming.
Big Pine Key is famous for a diminutive land species, the key deer, which can be observed all over the 10-square-mile island, including along the roadside and on trails within the National Key Deer Refuge. The refuge was founded in 1957 to protect the endangered subspecies of white tail deer that lives only on a few of the Lower Keys.
When you’re ready to try what many locals claim is the best pizza in the Florida Keys, head to No Name Pub, festooned with thousands of dollar bills inside and tucked away down a quiet lane on Big Pine Key. I can confirm that the pub also has one mighty fine key lime pie.
The trolleys of Key West are a useful way to get a lay of the land.
Photo by digidreamgrafix/Shutterstock
Day 4: Bahama Village, Cuban sandwiches, and a sunset sail, all in Key West
U.S. Highway One ends in Key West, the most populous island in the Florida Keys; it’s also where you’ll find the biggest party scene, along its main drag, Duval Street. The thoroughfare is lined ith souvenir shop after restaurant after bar, on repeat.
It may sound like a touristy tip, but Arunas Dulskis, concierge at La Concha Key West along Duval Street, always suggests that first-time visitors to Key West ride the hop-on, hop-off Old Town Trolley to get an overview of the four-mile-long island and its layered history. Stops include the Southernmost Point, Ernest Hemingway Home, Key West Aquarium, and others. “It takes about 90 minutes to do the whole loop, and you’ll get a lot of great information about the island and have a better idea of where you want to spend your time,” says Dulskis, who is originally from Lithuania but has called Key West home for 18 years.
To explore on your own on foot or by bike, he suggests Key West’s Bahama Village neighborhood as a place you can get to know Key West’s immigrant and Black history. One example: Bahamians came here for maritime jobs, settling in Key West in the 1800s. Right nearby, at Fort Zachary Taylor Historic State Park, visit a Civil War–era fort that’s a National Historic Landmark before snorkeling or swimming in cool, deep waters fronting Key West’s best beach.
If you crave a picnic to accompany your beach stint, bring Cuban sandwiches from Sandy’s Cafe, a long-standing island favorite, where they’re sold from a walk-up window astride a laundromat.
Dulskis suggests finishing the day with a sunset cruise on the water with Danger Charters. The Wind & Wine Sunset Sail features a local musician, full cocktail bar, and hors d’oeuvres that might include smoked fish dip or shrimp cocktail, he says, adding, “Anytime I have a date, that’s where I bring them.”
Playa Largo Resort & Spa is full of palms and water and blue sky.
Courtesy of Playa Largo Resort & Spa
Where to stay in the Florida Keys
New Key Largo Marriott property Playa Largo Resort & Spa, Autograph Collection has its own beach and a waterfront pool overlooking Florida Bay, a prime spot for sunsets. Baker’s Cay Resort is a romantic property along Florida Bay in Key Largo, surrounded by tropical foliage on the site of a former pineapple plantation.
On Islamorada, the Islands of Islamorada has 22 waterfront villas for a stay on a private beach, as well as an on-site marina and pickleball courts. Marathon’s Isla Bella Beach Resort & Spa is tucked off the Overseas Highway near Seven Mile Bridge with its own beachfront, a lively beach bar, five oceanfront pools, and a marina.
La Concha Key West, Autograph Collection is a historic property along Duval Street with a lovely rooftop bar overlooking Old Town. If you want quieter Key West beaches removed from the action, try Sunset Key Cottages, which has a top-notch oceanfront restaurant and a decadent spa a short private ferry ride from docks near Mallory Square.
