Key West Travel Guide: Beaches, Bars & Island Life
Escape to Key West for tropical beaches, lively bars, waterfront sunsets and laid-back island life in the heart of the Florida Keys.
Key West, Florida Keys
Key West is a tropical island at the end of the Florida Keys where roosters roam free, flip flops are worn as dress shoes and beach vibes rule above all else. The key is home to many restaurants, bars, boutique hotels, historic sights, colorful wooden houses and waters dotted with sailboats.
The Overseas Highway
The Overseas Highway is a scenic stretch of road crossing the ocean and connecting the Florida Keys with mainland Florida. We made a day trip of our drive on the highway, stopping at multiple keys along the way.
Tiki Bar at Postcard Inn. A hotel bar on Islamorada credited with inventing the Rum Runner cocktail. We stopped for a drink to find the restaurant under renovation.
Robbie’s. We ordered a Rum Runner here and stopped to hand feed the tarpon swimming around the restaurant’s dock. For $5, we bought a bucket of fish and dangled them over the edge of the dock. Soon after, a tarpon jumped from the water snatching the fish directly from our hands.
Keys Fisheries. A restaurant on Islamorada with all manner of fresh caught seafood. We stopped here for their famous lobster ruebens.
Sea Turtle Hospital. A sanctuary to rehabilitate rescued sea turtles on Marathon Key. Tour the facility and its tanks of sea turtles. I visited here on a trip to the keys years ago.
7 Mile Bridge. A stretch of the overseas highway crossing 7 miles of open ocean. Stop at the 7 Mile Bridge Vista to walk onto the pedestrian bridge and overlook and the blue tropical seas. We spotted manatees swimming here.
Bahia Honda State Park. We stopped here for some afternoon sun and beach time. We lounged in the shallow waters of Loggerhead and Sandspur beaches.
Big Pine Key. One of the last keys before reaching Key West. We kept an eye out for the Key Deer, an endangered species of tiny deer native to the island.
The Conch Republic
Key West, also called The Conch Republic, is truly an island paradise! While here, eat fried conch fritters and conch ceviche from one of the island’s many restaurants, buy a conch shell from a souvenir shop and spot Conch Republic flags flying from locals’ homes.
See the Sights
Duval Street. A famed and historic street stretching a mile across the key with seafood restaurants, cocktail bars, Cuban cafes, art galleries and souvenir shops. The north end is the most touristy while the south end is quieter and more local.
The Old Town. A historic area with colorful wooden houses located at the north end of Duval street.
Southernmost Point Buoy. A striped concrete buoy and monument marking the southernmost point in the continental US only 90 miles from Cuba.
Bahamas Village. A neighborhood on the south side of the key settled by immigrants from the Bahamas. Come to see the colorful houses and tropical gardens.
The Hemingway Museum. The former residence of American writer Ernest Hemingway. Tour his home and writing studio where he wrote many of his iconic novels and short stories. Walk through the grounds’ lush gardens and pet Hemingway’s cats.
Key West Lighthouse. A short white lighthouse with a spiral staircase leading to the crown with panoramic views of the key. The light house keeper’s house is a small museum dedicated to the history of Key West.
Fort Zachary Taylor Beach. A park with a coral beach, short nature trails and a civil war era fort. Come here to swim and sunbathe, walk the nature trails and explore the cannon lined red brick and black cement fortress. The beach has a snack & beverage hut renting umbrellas & lounges. Wear beach shoes to avoid the jagged coral lining the beach. Along the shore is a shaded park with picnic tables and grills.
Higgs Beach. A small but sandy beach between two piers for snorkeling, swimming and sunbathing.
Mallory Square. No night in Key West would be complete without joining hundreds of people and watching the sunset from Mallory Square during the daily sunset festival. Arrive early with a drink in hand as the day ends and the night begins.
Truman Waterfront Farmers Market. A Thursday afternoon market with vendors selling boozy popsicles, empanadas, samosas, honey, breads, cheeses, vegetables and tropical fruits like dragon fruit, pineapple, papaya, star fruit and lychee.
Places to Eat and Drink
Key West is where “it’s 5 o’clock somewhere” and “island time” meet. There are many restaurants with laid back vibes and bars serving tropical cocktails.
Tiki Bar. A cocktail bar with classic tiki drinks like the Mai Tai, Jungle Bird, Zombie and Hurricane. There is live music nightly, a shop selling tiki mugs and a hidden tiki bar in the back.
Eaton Street Seafood Market. A seafood market and restaurant serving the day’s fresh catch. We came for conch ceviche, stone crab claws and beers from Islamorada Brewing.
Schooner Wharf Bar. Come here for the shrimp! They source their shrimp from Key West’s last shrimping boat docked in front of the restaurant. We devoured the coconut shrimp and drunken shrimp, a peel and eat shrimp boiled in beer and spices!
Speakeasy Inn and Rum Bar. An inn with several rooms and a rum bar with one of the largest collections of rum in the US. Sip rum neat at the bar while chatting with locals and other vacationers or sit on their porch overlooking Duval Street while enjoying a Painkiller.
Hemingway Social Club. A cocktail bar attached to the Hemingway Rum Distillery. Come here for cocktails like a Hemingway Daiquiri made with their house rum while listening to the live music.
Cafelito. A cafe with a walk up window selling iced Cuban coffees and Cuban pastries like the guava and cheese turnover.
Sally Frog’s. A bar near Malloy Square with cocktails and local beers like the Crazy Lady Honey Blonde Ale brewed at The Waterfront Brewery.
Cuban Coffee Queen. A small coffee shack by the harbor selling cups of Cuban coffee.
Cocomelon. A juice bar and cafe selling ice cold fresh coconuts. Come here to sip coconut water from the tropical fruit while relaxing in their patio.
Kermit’s Key Lime Shop. Come for the key lime pie! They sell it by the slice, whole and frozen on a stick.
Dry Tortugas National Park
Sixty miles from Key West are the Dry Tortugas, a national park with several low lying islands, protected marine and avian reserves, a massive civil war fortress, a lighthouse and a campground.
Fort Jefferson. A hexagonal three level civil war fort rising from the sea. The historic red brick fort is surrounded by a moat with a large interior courtyard and the ruins of many military structures.
We spent time exploring the 3 levels of the fort. The ground level houses many of the fort’s supportive facilities like a bakery, cistern and the barracks. The second level was dedicated to the prisoners’ cells and the hospital. The third level is overgrown with trails leading along the wall past cannons and to the fort’s lighthouse.
Outside of the fort is a moat and wall designed to protect the main fort from the sea. Walk along it to admire its historic outer walls, look out towards the sea and spot tropical fish.
Beaches. Outside of the fort, there are two coral beaches to swim at with warm and shallow water. The South Beach was the calmest and clearest for swimming and snorkeling. There is some sea grass and fragments of broken coral throughout the bay. The North Beach was a little choppier with less visibility for snorkeling.
Snorkeling. Along the wall of the South Beach, we spotted smaller tropical fish, some living coral, sea anemones, pink jellyfish and the carcass of a giant spiny lobster.
Land Bridge. Walk the tidal land bridge towards the avian reserve of Long Key. The shallow stretch of sand is covered in conch shells, sand dollars and broken coral. Come here to spot pelicans and sandpipers.
Loggerhead Lighthouse. A black and white lighthouse visible on the horizon from Fort Jefferson on Loggerhead Key, nearly two miles away.
Camping. There’s something special about camping on a desert island in the middle of the sea! Camp overnight in a protected grove of trees and bushes.
Yankee Freedom. The main company ferrying between Key West and the Dry Tortugas. The ticket includes transit, a tour of the fort, snorkel equipment, breakfast, lunch and cocktails for purchase.
Getting Here. It takes 2 hours 30 min to reach the Dry Tortugas from Key West with 4 hours on the island. Book in August and September for $50 off an order of 2 tickets. Book here.
Where to Stay
We stayed at the Speakeasy Inn & Rum Bar. The boutique inn on the south end of Duval Street has two floors of newly renovated rooms and is stumbling distance away from their rum bar. Our stay included free parking, a welcome cocktail and discounted drinks!
Getting Around
Key West is very walkable, especially along the mile long stretch of Duval Street. Even so, there are many rentals offering bikes, scooters and golf carts.
Bikes $10 / day
Scooters $35 / day
Golf carts $100 / day
The Conch Train. A multi-car trolley that rides around the city passing most of the sights with a narrated guide.
Location Specifics
Locals leave during the month of September to vacation elsewhere. As a result, some restaurants and bars are closed. However, as this is the slow season, many hotels offer deals making the island more affordable to visit.
For Next Time…
We loved our time visiting Key West! We hope to return for more rum cocktails, sunset views and the tropical atmosphere. Outside of Key West, we would love to spend a few nights exploring the other keys more.