Key West Travel Guide: 90 miles north of Cuba, at the end of the long chain of islands known as the Florida Keys, is the island of Key West. The southernmost point in the continental United States, Key West is known for its stunning beaches, beautiful weather, laid-back island atmosphere, great food and drinks, and excellent nightlife. If you are planning to go to Key West, there are some things you should know before you go. Here is your Key West travel guide to help you plan your trip.
Background and History
Key West has been inhabited since ancient times. Prior to the 19th century, the Leys are believed to have been inhabited by tribes known as the Tequestas and Calusas, who may have arrived in the Keys as early as 800 AD. The first European to reach Key West was Spanish explorer Juan Ponce de Leon, who arrived on the island in 1521, ostensibly in search of the Fountain of Youth.
With Ponce de Leon’s arrival, Key West, along with the rest of Florida fell into Spanish hands, and remained there until it was ceded to Britain in 1763, with the conclusion of the Seven Years’ War. Twenty years later, Britain traded Florida back to Spain, and eventually Spain sold the territory to the United States, in 1821.
Between 1763 and 1821, there were few if any permanent inhabitants on Key West, or anywhere else in the Keys. The islands mainly served as temporary fishing grounds, and hideouts for smugglers and pirates. The governments of Spain and Britain exercised little control over the area during this time period. It was not until the early 1820s, after the islands had fallen into U.S. hands that the rule of law was established on Key West, and smugglers and pirates were driven out by the U.S. Navy.
Key West remained isolated until 1912, when construction of the Overseas Railroad was completed, connecting Key West to mainland Florida. The railroad was destroyed by a hurricane in 1935, and rebuilt as an auto highway in 1938. Since then, the Overseas Highway served as a scenic route for vacationers to reach Key West.
Today, the island is one of Florida’s most popular vacation destinations, attracting over 5 million visitors per year.
Key West’s climate is classified as a tropical savanna climate, much like most of the islands in the Caribbean. The island is warm year round, with average temperatures in the 70s and 80s °F, even in the winter. This makes Key West a perfect vacation destination in December, January, February, and March, when most of the rest of the United States is dealing with cold weather and snow. In fact, one of Key West’s claims to fame is that it, along with Miami Beach, are the only two places in the contiguous U.S. to never have a recorded frost or freeze.
Like most tropical islands, Key West has two main seasons, a wet season and a dry season. The driest months are November through April, which average only around 2-3 inches of rain per month. The wettest months are August and September, which average around 6-7 inches of rain.
That being said, Key West is Florida’s driest city, and with an average of 260 days of sunshine per year, you are almost guaranteed to have plenty of great weather on your trip.
One thing to note is that Key West is vulnerable to hurricanes. Like the rest of Florida, Key West is right in the path of hurricane alley. That being said, the island has been largely unaffected by major storms in recent years. Exercise precaution and avoid going to Key West if you find out that the island is at risk of being hit by a hurricane. If you are on the island when a hurricane is imminent, listen to the local authorities, and evacuate the island if instructed to.
There are two main ways to get to Key West. You can either fly in, or take a vehicle in via the Overseas Highway. It is also possible to take a boat in, although it is usually more convenient to fly or drive. Here are your options for getting into Key West:
The Key West International Airport (EYW) is the airport that serves the island. Key West International Airport receives frequent flights from Atlanta, Chicago, Dallas-Fort Worth, Newark, Philadelphia, and other major cities around the United States.
Major airlines servicing Key West International Airport are:
- Allegiant Air
- American Airlines
- American Eagle
- Delta Air Lines
- Delta Connection
- Silver Airways
- United Express
If you do choose to fly to Key West, there are car rentals available at the airport from Enterprise, Avis, Hertz, Budget, Dollar, and more, although renting a car is largely unnecessary on Key West, as it is easy to get around on foot, bicycle, and rideshare when necessary.
Taking the scenic Overseas Highway to Key West is an unforgettable way to get to the island. The 113 mile highway stretches from Miami to Key West, and offers stunning views of the ocean, coral reefs, the Keys, and the blue Florida skies along the way. The drive takes about 3.5-4 hours, and takes travelers through all of the Key’s major islands.
One issue with driving to Key West is that driving around the island can be difficult due to the narrow roads, and parking on the island can get quite expensive. If you want to experience the Overseas Highway without worrying about parking and driving around on the island, there are buses you can take from the Florida Mainland to Key West.
Buses that go to Key West include:
Miami To Key West Shuttle – $29 for a one-way trip from Miami to Key West on a double decker tour bus with wifi.
Miami to Key West Bus – One-way trip on a luxury bus with an onboard restroom from $25.
Miami Info Tours – Travel from Miami to Key West on a guided tour that goes to Key West and then leaves back to Miami 6 hours later. From $33 per person for a one-way trip.
An alternate way to get to Key West is via boat. Boats that take passengers from mainland Florida to Key West include:
Key West Express – Jet powered catamaran trips from Fort Meyer and Marco Island to Key West.
Cruises to Key West – Multiple cruise lines, including Norwegian, Virgin, and Celebrity Cruises have cruise ships that leave from Miami or Fort Lauderdale to Key West.
Key West is a small island, only about four miles long and one mile wide. Because of its small size, many of the roads on Key West are narrow with little room to maneuver. There are also many one-way streets on the island and parking is expensive and limited. For these reasons, many visitors choose not to rent a car while in Key West. Instead, popular methods of transportation on the island include bicycles, motorized scooters, golf carts, and public transportation. Another great way to get around the island is via e-bike, which is a pedal bicycle equipped with a motor to assist propulsion.
Some of the best rental places for bicycle, e-bikes, golf carts, and scooters in Key West are:
HydroThunder – Golf cart and scooter rentals. Located in downtown Key West near Mallory Square.
EZ Riders Key West – E-bike rental shop located on Truman Ave, a block away from the Hemingway House.
Eaton Bikes – Bicycle rental and repair shop that also sells cycling gear.
If you do choose to rent a car, there are Hertz, Avis, Thrifty, and Enterprise Rent-A-Car desks at the airport. However, most locals and frequent travelers to Key West will tell you to skip the rental, especially if you are staying in the Historic District, where just about everything is within walking or cycling distance.
Where to Stay
The first thing to note when deciding where to stay in Key West is that the vast majority of tourist attractions are located in the western half of the island, an area known as the Key West Historic District, Old Town, or simply the City of Key West. This is where you will find the heaviest concentration of restaurants, bars, beaches, museums, historical sites, and more. For this reason, the Historic District is where the vast majority of visitors to Key West choose to stay, and where we recommend staying.
Key West has no shortage of accommodations for travelers. From rental houses, condos, and apartments to luxury resorts, boutique hotels, and bed and breakfasts, the island has the right accommodations for any visitor.
Perhaps the best way to experience Key West is by renting a vacation home on the island. There is no way to get a more authentic Key West experience than staying in one of the historic homes on Duval Street, or any of the other streets in the Historic District. Vacationers can book a rental through various websites, including Vacation Homes of Key West and Historic Key West Vacation Rentals.
If renting a house on Key West is not for you, some of the best hotels on the island include:
Note: When considering budget hotels and motels, be aware that some have a reputation as party hotels. If you want to avoid that type of atmosphere, do some research and read reviews about the hotel before booking.
Seashell Motel – A budget motel that offers both private rooms and shared dorm-style rooms, plus free wifi, and access to the courtyard kitchen area with a gas grill.
Angelina Guesthouse – An adults-only guesthouse located in a renovated 1920s bordello. The guesthouse features nice rooms, a heated pool, breakfast, and wifi.
The Southernmost Inn – 2-star hotel located in a historic 1800s building. The inn has a pool area with two pools and a hot tub, a poolside bar, and free breakfast.
Blue Marlin Motel – A casual budget motel on the southern end of the island. Has an outdoor pool and free parking.
Eden House – One of the older guesthouses on the island, Eden House has nice rooms, a pool, and wifi.
Tropical Inn – A laid-back bed and breakfast on Duval Street, Tropical Inn Key West has a great location, nice rooms with wifi, a spa, garden, and pool. Buffet breakfasts are served every morning.
Duval Inn – Charming 3-star hotel on Duval Street with nice rooms, a complimentary breakfast and happy hour.
The Cabana Inn – 3-star, adult-only hotel with big rooms, an outdoor pool, and gardens.
Margaritaville Beach House Key West – A casual 3-star hotel with an island-inspired theme. Located right across the street from Smathers Beach.
Opal Key Resort & Marina – Upscale resort with roomy suites with ocean views. Great dining, a pool, and a marina on site.
Hyatt Centric Key West Resort & Spa – 4-star boutique hotel located just off Duval Street. Features great seafood dining, a spa, outdoor pool, and private dock.
Ocean Key Resort & Spa – Located at Zero Duval Street, the Ocean Key Resort & Spa features luxury suites with whirlpool tubs, a restaurant, spa, and poolside lounge.
Southernmost Beach Resort – A sophisticated resort on the southern end of the island. Renovated in 2021, the Southernmost Beach Resort offers lavish suites, three pools, and a private pier and beach.
What to See
Key West’s rich history and modern popularity mean it has no shortage of must-see sites. Here are the places you should visit on your trip to Key West.
Located at 907 Whitehead St.
Open 9AM-5PM daily.
The Hemingway House is one of the most popular tourist attractions in Key West. Hemingway lived in the historic house for eight years between 1931 and 1939. It was in this house that Hemingway wrote some of his most famous short stories, including “The Snows of Kilimanjaro” and “The Short Happy Life of Francis Macomber.”
Hemingway also famously raised polydactyl cats in and around the house, and the descendants of those cats still live on the property today.
Today the house features a museum dedicated to Hemingway’s life and works. The house still has much of the same furniture and possessions that were there when Hemingway occupied the house.
The Truman Annex is a historic neighborhood in Key West that features the “Little White House,” a historic house where President Harry S. Truman once lived and worked. The Truman Annex is one of the island’s most upscale neighborhoods, with park-like, manicured grounds, and beautiful historic houses, many of which are available to rent.
The main attraction in the Truman annex is, of course, the Harry S. Truman Little White House.
Located at 111 Front St, Naval Air Station.
Open 9AM-5PM daily. Guided tours available.
The Little White House is where Truman frequently vacationed in the winter while in office. Beginning in November 1946, Truman made a total of 11 visits to Key West, staying in the same house each time. Truman conducted official White House business from the house, meeting with Cabinet members and foreign officials, and issuing documents that read “The White House, US Naval Station, Key West, Florida.”
Today, the Little White House has been converted into a museum, and is open daily for tours.
Fort Zachary Taylor State Park
Located at 601 Howard England Way.
Open 8AM – Sundown daily.
Fort Zachary Taylor State Park is a historic park centered around a Civil War-era fort. The fort is adjacent to the beach, and provides a tranquil, laid-back environment to picnic, explore, watch the sunset, and unwind as you watch the boats go by. Fort Zachary Taylor State Park is the real southernmost point on the island, aside from a section of the island that is U.S. Navy property, and inaccessible to the public.
Fort Zachary Taylor State Park is the most peaceful area on the island, offering a respite from the hustle and bustle of Duval Street and Mallory Square. The park also features hiking trails, a snack stand, and a moat, and it sometimes features Civil War battle reenactments.
One of the most famous sites in Key West is the Southernmost Point Buoy. Marking one of the southernmost points on the island, the buoy famously reads “90 miles to Cuba.” Probably the most visited landmark on the island, the Southernmost Point has been marked since 1970, when it featured an original wooden sign reading “The Southernmost Point of the Southernmost City.”
Although the point does not actually represent the southernmost part of the island, it is an interesting attraction to visit, and a great place to take photos.
Key West Lighthouse
Located at 938 Whitehead Street.
Open 10AM – 5PM
A 65-foot high lighthouse that was completed in 1825, the Key West Lighthouse is one of the island’s must-see attractions. 88 steps to the top, the lighthouse offers an incredible panoramic view of the island.
Decommissioned in 1969, the lighthouse is no longer in use, but serves as a museum dedicated to Key West’s maritime heritage. The museum’s collection includes art and photographs depicting the lighthouse’s history, and artifacts from Key West’s past.
Key West City Cemetery
A historic 19-acre cemetery in the heart of Key West’s Old Town, the Key West City Cemetery was established in 1847, and is estimated to hold as many as 100,000 graves. The cemetery features a number of different sections, including a Catholic section, a Jewish section, an area dedicated to casualties from the U.S.S. Maine, and Los Martires de Cuba, which is a memorial dedicated to Cuba casualties from the Ten Years War, Cuba’s war of independence from Spain.
Key West also features another historic cemetery known as the African Cemetery at Higgs Beach, where 294 of 1,342 Africans were buried in 1860, in the months after being rescued from a slave ship.
Key West Garden Club
Located at 1100 Atlantic Blvd
Open daily, 9:30am – 5pm.
A tropical garden in the western part of the island on the site of a former Civil War fort, the Key West Garden Club is one of the most beautiful places on the island. The oceanside gardens feature thousands of plants, and many fountains and paths leading through the ruins of the historic fort. The gardens’ Martello Tower offers some of the best views on the island, and the gazebos, courtyard, and water lily pond are the perfect places for quiet relaxation.
What to Do
One of the most popular things to do on Key West is go to the island’s beautiful beaches. If you are interested in relaxing on the beach or swimming in the refreshing ocean waters, here are the beaches in Key West that you should be sure to visit.
Key West’s most popular beach, Smathers Beach is a long, laid-back beach, with calm waters that are great for swimmers. The beach is also great for kicking back and relaxing and sunbathing. There is no entrance fee to get on Smathers Beach, which is convenient, but also can lead to the beach getting crowded. Despite the relaxed atmosphere, there are jet skis, kayaks, and snorkeling equipment available for rent right on the beach.
A tiny beach just off of Mallory Square, Simonton Beach is convenient to access, and right next to some great bars and restaurants where you can grab a drink or a meal to enjoy right on the beach. The small size of the beach means it can get crowded.
Fort Zachary Taylor Beach
A beautiful beach with calm, clear waters that are perfect for swimming and snorkeling. Plenty of picnic tables, and nearby cafes to grab lunch or a drink. There are also umbrellas and chairs available to rent on the beach.
One of Key West’s smallest beaches, South Beach is a 200-foot long beach at the end of Duval Street. The beach is said to have been a favorite of Tennessee Williams during his time on Key West. Today, it is a great spot for swimming or sunbathing, but has no public restrooms, so it is not great for travelers with young children.
Watersports, including jet skiing, boating, parasailing, kayaking, glass bottom boat tours, scuba diving, and more are all very popular on Key West. Some of the best watersport companies on the island include:
Fury Water Adventures Key West – Fury Water Adventures’ offerings run the gamut from reef snorkeling tours to catamaran charters, dolphin watch cruises, glass bottom boat tours, jet ski rentals, parasailing trips, and sunset sailboat cruises. There is truly something available for any traveler, from high octane adrenaline junkies to families with small children.
Key West Scuba Diving – Explore Key West’s stunning reefs and shipwrecks up close with a scuba diving package from Key West Scuba Diving. The company offers courses and adventures geared toward everyone from novices to experienced divers.
Key West Sunset Cruise – Go for an unforgettable sunset sail around Key West or charter a yacht to take out with a group.
Sebago Watersports – Parasailing, reef snorkeling, all-day jet ski rentals, and much more make Sebago Watersports one of the best options on the island for watersports of any kind.
Most visitors to Key West have no idea that the island is actually home to multiple undeveloped, natural areas. Aside from the coral reefs and marine wildlife that exist off Key West’s shores, the island also has:
Key West Nature Preserve – A quarter mile path just off Atlantic Blvd leads to a rare area of undeveloped beach and mangrove forest, where you can see a variety of wildlife, including birds, lizards, and snakes.
Dry Tortugas National Park – While not actually on Key West, Dry Tortugas National Park is located about 70 miles west of the island, and is a popular day trip destination. Home of the massive 19th-century fortress, Fort Jefferson, the park is accessible by a daily ferry from Key West, as well as private boats and chartered seaplanes.
Key West is home to numerous popular festivals that attract visitors from around the world. The most famous of Key West’s festivals include:
Fantasy Fest – A 10-day long adult festival featuring costumes, parades, music, and drinking, centered on Duval Street.
Lobsterfest – Held in early August every year, Lobsterfest features great food and drinks from vendors from around the island and beyond.
Goombay Festival – An annual African and West Caribbean heritage festival featuring live entertainment and parades.
Key West is famous for its fresh seafood dishes, its Caribbean and southern-US style cooking, and its key lime pie. Some of the most popular restaurants on Key West are:
El Siboney – A family-friendly Cuban restaurant that is popular among the locals and often overlooked by vacationers. Quiet with great food at prices that are hard to beat.
Schooner Wharf – A dockside bar and grill open since 1984, Schooner Wharf has live entertainment, and great breakfast, lunch, and dinner options.
Ocean Grill & Bar – Great local seafood in a casual atmosphere. Serves brunch and dinner.
El Meson de Pepe – Cuban food and drinks in a great restaurant right on Mallory Square.
Nine One Five – Great contemporary American cuisine in a converted Victorian-era house right on Duval Street.
Tavern N Town – Bi-level dining room with great seafood and steakhouse favorites.
Seven Fish – Modern seafood restaurant with fresh fish dishes and an aquarium.
It is no secret that one of Key West’s biggest attractions is its nightlife. When the sun goes down, the party is just getting started in Key West, particularly on Duval Street and Mallory Square. Some of Key West’s best bars include:
The Green Parrot – Located in a building built in 1890, the Green Parrot has been a Key West mainstain for generations. Featuring frequent live music and a lively atmosphere, The Green Parrot is a great place to go to get a few drinks.
The Roost – A popular craft cocktail bar that also serves local beer and fine wine. Stop in for creative and amazing craft cocktails with an island twist.
Shots and Giggles – A relaxed, casual bar located right off of Greene Street, Shots and Giggles to grab a drink and watch the game.
Tiki House – Tiki bar with great island-themed drinks made with real fruit and plenty of rum.
General Horseplay – A lively bar with great house cocktails, wine, and beer. Friendly staff and great bartenders who know how to make some of the best drinks on the island.
22&Co – Fresh cocktails in a fun, lively environment. 22&Co’s cocktail menu features some of the most unique and creative drinks in Key West. The Peanut Butter Martini is a must-try.
Mary Ellen’s Bar & Restaurant – A friendly neighborhood bar with a casual, laid-back atmosphere. Great selection of drinks and food.
The first thing to note about shops in Key West, is that Key West is not Miami Beach. The upscale, luxury shopping centers that you’ll find in major metros like Miami do not exist in Key West. The shops in Key West are, for the most part, smaller and much more low key.
Most of the shops in Key West are concentrated on Duval Street. There are plenty of great places to buy souvenirs from your trip, or to grab something you forgot to pack–sunblock, sunglasses, an outfit for a night out, etc. Here are some good shops in Key West:
The Coast Outpost – A clothing shop that sells high-quality, custom made hats, shirts, sweatshirts, and more. One of the best clothing shops on the island.
Conch Republic Gifts – A good souvenir and gift shop. Stop in to pick up a Conch Republic flag, driver’s license, hat, magnet, or another souvenir.
Besame Mucho – High quality gift shop with custom-made products at reasonable prices.
What to Avoid
Like any major tourist destination, Key West has its share of tourist traps. Here are some things on the island you should avoid.
Chain Restaurants – Key West has a number of chain restaurants within its limits, including a couple of well-known and upscale ones. You are better off avoiding these restaurants and getting the true Key West experience by going to the locally owned ones.
Shady T-Shirt Shops – Key West has historically had a problem with unscrupulous merchants fleecing customers with expensive, low quality, custom iron-on t-shirts that have last minute charges added. Key West has since passed ordinances to prevent this kind of behavior, but there are still scammers on the island. If you are looking for high quality custom-made goods, The Coast Outpost is a good option.
Jewelry Stores – Some jewelry stores on Key West have a reputation for trying to pass off fake gems as authentic. Avoid buying any expensive jewelry on your trip.
Only going to Duval Street and Mallory Square – Although Duval Street and Mallory Square have a reputation for having the best bars, restaurants, and shops on the island, there are plenty of great establishments all throughout Key West. Try to avoid limiting yourself to just Duval Street and Mallory Square, and branch out to visit bars and eateries in other areas.