Gallery
A visual journey through the turquoise waters, historic streets, and unforgettable sunsets of Key West and the Florida Keys.
Drive across turquoise waters on the legendary Overseas Highway, toast the sunset at Mallory Square, and discover a Caribbean soul thriving at the southernmost tip of the United States. Key West is where eccentric charm, literary history, and ocean adventure collide.
Key West is not merely a destination; it is a state of mind. At Mile Marker 0, where U.S. Route 1 terminates, you will find a quirky island community that has attracted pirates, poets, and free spirits for nearly two centuries. Caribbean-blue waters, conch-style architecture, and legendary sunsets create an atmosphere unlike anywhere else in America.
The Overseas Highway is one of the most spectacular drives on Earth. Stretching 113 miles over open ocean, this engineering marvel connects the Florida Keys via 42 bridges, including the iconic Seven Mile Bridge, offering panoramas of turquoise water in every direction.
Every evening, crowds gather at Mallory Square to celebrate the sunset as if it were a nightly festival. Street performers, artists, food vendors, and musicians create a carnival atmosphere while the sky explodes in shades of orange, pink, and violet over the Gulf of Mexico.
From Hemingway's writing studio to the tales of Blackbeard, Key West is steeped in stories. The Hemingway Home preserves the author's legacy, complete with the famous six-toed cats that roam the gardens.
Key West cuisine blends fresh-caught seafood, Cuban influences, and tropical flavors into distinctive island fare. From conch fritters to authentic Key lime pie, every meal feels like a Caribbean vacation without leaving the United States.
This itinerary takes you from Miami across the Overseas Highway to the southernmost point, balancing road-trip adventure with relaxed island time.
Pick up your rental car in Miami and begin the iconic drive south on U.S. Route 1. The Overseas Highway stretches 113 miles across the Atlantic and Gulf, connecting coral islands with 42 bridges. Stop at Key Largo for a quick snorkel at John Pennekamp Coral Reef State Park, then continue through Islamorada.
The highlight is the Seven Mile Bridge, one of the longest segmental bridges in existence. The old railroad bridge runs parallel as you cruise above turquoise water with nothing but horizon. Stop at the Bahia Honda viewpoint for unforgettable photos.
Arrive in Key West and check into your conch-style inn in Old Town. Stroll down Duval Street, lined with open-air bars, galleries, and shops. Grab dinner at Sloppy Joe's Bar, Hemingway's old haunt, where bands play until midnight.
Begin at the Ernest Hemingway Home and Museum on Whitehead Street. This Spanish colonial house was Hemingway's residence from 1931 to 1939, where he wrote "For Whom the Bell Tolls." Tour the studio and meet the famous polydactyl cats, descendants of his six-toed feline. Admission is $18.
Climb the 88 steps to the top of the Key West Lighthouse for panoramic views of the island. The Keeper's Quarters Museum tells the story of the families who maintained this beacon. On a clear day, you can see all the way to the Dry Tortugas.
No Key West evening is complete without the Mallory Square Sunset Celebration. Beginning two hours before sunset, this nightly festival brings together tightrope walkers, fire jugglers, and local craftsmen. Grab a frozen coconut drink and watch the sun sink into the Gulf while musicians play reggae and calypso tunes.
Board the Yankee Freedom ferry at 7:00 AM for the 2.5-hour journey to Dry Tortugas National Park. The boat crosses 70 miles of open water, often passing dolphins and sea turtles. Breakfast is included and the crew provides narration about the park's history.
Explore Fort Jefferson, a massive 19th-century coastal fortress built with over 16 million bricks. Ranger-led tours explain the fort's Civil War history and its most famous prisoner, Dr. Samuel Mudd. After the tour, snorkel among coral reefs teeming with parrotfish and reef sharks in crystal-clear waters.
The ferry departs Dry Tortugas at 3:00 PM, arriving back in Key West by 5:30 PM. After a full day of adventure, unwind with dinner at Kermit's Key Lime Shoppe, where the legendary Key lime pie on a stick is an island institution. A regular slice costs around $6, while the chocolate-dipped version is $8.
Step into a tropical paradise at the Key West Butterfly & Nature Conservatory on Duval Street. This climate-controlled habitat houses 50 to 60 species of butterflies, along with exotic birds and flowering plants. The fluttering wings create a living rainbow around you. Admission is $15 for adults and $11 for children.
Hop aboard the Key West Conch Train, the island's original sightseeing tour since 1958. This 90-minute narrated journey covers over 100 points of interest, from the historic seaport to the Southernmost Point Buoy. Conductors share tales of shipwrecks, pirates, and President Truman's love affair with the island. Tickets cost approximately $45 per adult.
Visit the Truman Little White House, Florida's only presidential site, where Harry S. Truman spent 175 days of his presidency between 1946 and 1952. The house remains as it was during Truman's time, with original furniture and artifacts. Guided tours cost $25.
Spend the morning at Fort Zachary Taylor State Park, the best beach in Key West for snorkeling. The rocky shoreline creates natural reefs just feet from the beach, where you can spot yellowtail snapper and spiny lobsters. Admission is $7 per vehicle.
Rent a kayak and paddle through the mangrove tunnels of the Key West National Wildlife Refuge. These waters are home to manatees, stingrays, and countless birds. Guided eco-tours depart from Higgs Beach and cost around $65 per person.
Indulge in fresh-caught seafood at a waterfront restaurant along the Historic Seaport. Try the yellowtail snapper, a Keys specialty, or the famous conch fritters with Key lime mustard sauce. Order Key lime pie for dessert, made with genuine Key lime juice.
Drive 37 miles north to Bahia Honda State Park, consistently ranked among the best beaches in the United States. The park features a historic railroad bridge, pristine sand beaches, and excellent snorkeling. The calm waters on the Gulf side are ideal for families, while the Atlantic side offers deeper water and better coral.
Continue to Big Pine Key, home to the endangered Key deer, the smallest subspecies of white-tailed deer. These tiny deer roam freely through the National Key Deer Refuge. Drive slowly at dawn or dusk for the best chance of spotting them. Stop at the No Name Pub, covered in thousands of dollar bills.
Head back to Key West for a night on the town. Start with a cocktail at the Sunset Pier, then explore Duval Street. For live music, check out the Green Parrot, a favorite since 1890.
Wake up early to beat the crowds and snap your photo at the Southernmost Point Buoy, the brightly painted marker that declares you are just 90 miles from Cuba. The line can stretch over an hour by mid-morning, so arriving before 8:00 AM is essential. The nearby Southernmost House Historic Inn is worth a quick look.
Browse the boutiques and art galleries along Duval Street and Old Town side streets for unique souvenirs. Local artists sell vibrant paintings, while conch shell jewelry and handmade cigars make perfect gifts. Stop by Cuban Coffee Queen for a cafecito and Cuban toast before you hit the road.
If you are flying, Key West International Airport is just ten minutes from Old Town. If driving, stop at Robbie's of Islamorada to feed the tarpon from the dock. As you cross the Seven Mile Bridge one last time, you will already be planning your return.
The ideal time to visit Key West is from November through May, when temperatures hover between 75 and 82 degrees and humidity is low. To avoid cruise ship crowds, check the Port of Key West schedule online and plan Duval Street and Mallory Square visits on days when no ships are docked. Cruise ships typically arrive Tuesday through Thursday, making weekends pleasantly quieter. Hurricane season runs June through November.
A mid-range 7-day Key West trip costs approximately $1,800 to $4,200 per person. Accommodation in Old Town averages $250 to $450 per night, while guesthouses outside the district run $150 to $250. Dining ranges from $15 at fish shacks to $80 at upscale restaurants. The Dry Tortugas ferry costs $200 per adult, and rental cars start around $50 per day.
Old Town Key West is highly walkable, and most major attractions sit within a one-mile radius. The Duval Loop and Old Town Loop free shuttles connect the historic district with Smathers Beach and the cruise ship terminal. Bicycles and scooters are popular rentals. If you plan day trips, a rental car is necessary, though parking in Old Town averages $25 to $35 per day. Rideshare services operate on the island but can be slow during peak hours.
Key West is a major cruise port, with ships carrying up to 4,000 passengers arriving several times per week. When multiple ships dock simultaneously, Duval Street and Mallory Square can become uncomfortably crowded between 10:00 AM and 4:00 PM. Visit popular attractions before 9:00 AM on cruise days for a more relaxed experience. Many local restaurants offer early-bird happy hour specials for the same reason.
A visual journey through the turquoise waters, historic streets, and unforgettable sunsets of Key West and the Florida Keys.
Read reviews from travelers who have experienced the magic of the southernmost paradise.
"The Overseas Highway drive alone was worth the trip. Crossing the Seven Mile Bridge with blue water in every direction gave me chills. Key West felt like a Caribbean island."
"Dry Tortugas was the highlight of our Florida vacation. The fort was fascinating and the snorkeling was better than anything in the Caribbean. Bring plenty of sunscreen because there is almost no shade."
"Visiting Hemingway's home was a pilgrimage. The six-toed cats were adorable, and the guide shared stories about his writing routine. Sloppy Joe's was touristy but fun."
"Mallory Square at sunset is pure magic. Performers and musicians create an incredible atmosphere under a sky turning every shade of orange and pink. Kermit's Key lime pie on a stick is the perfect snack."
"We checked the cruise ship schedule and planned our Duval Street walks on non-cruise days. The island felt relaxed and local without the midday crowds."
"Fort Zachary Taylor had the best snorkeling without a boat. We saw lobsters, parrotfish, and even a nurse shark. Entry is only $7 per car, the best bargain on the island."
"The Conch Train was surprisingly informative. Bahia Honda State Park was gorgeous, but pack bug spray."
"Key West exceeded every expectation. The yellowtail snapper and conch fritters were incredible. We stayed in a conch-style guesthouse and walked everywhere. The island has a unique energy that is completely unforgettable."
Key West awaits with turquoise waters, legendary sunsets, and the kind of laid-back charm that stays with you long after you leave. Let us help you plan your perfect Florida Keys adventure.