In Pre-Columbian times Key West was inhabited by the Tequesta and Calusa peoples. The first European to visit was Juan Ponce de León in 1521. As Florida became a Spanish colony, a fishing and salvage village with a small garrison was established here.
The island was used by fishermen from Cuba and from the British Bahamas, who were later joined by others from the United States after the latter nation's independence. While claimed by Spain, no nation exercised de-facto control over the community there for some time. The island was considered the "Gibraltar of the West" because of its strategic location on the 90-mile (140 km)–wide deep shipping lane, the Straits of Florida, between the Atlantic Ocean and the Gulf of Mexico. On March 25, 1822, Matthew C. Perry sailed the schooner Shark to Key West and planted the U.S. flag, physically claiming the Keys as United States property.
Key West was relatively isolated until 1912, when it was connected to the Florida mainland via the Overseas Railway extension of Henry M. Flagler's Florida East Coast Railway (FEC). The Labor Day Hurricane of 1935 destroyed much of the railroad and killed hundreds of residents. The FEC could not afford to restore the railroad. The U.S. government then rebuilt the rail route as an automobile highway, completed in 1938, which became an extension of United States Highway 1. The portion of U.S. 1 through the Keys is called the Overseas Highway.
Key West claims to be the only city in the lower 48 states never to have had a frost. Because of the proximity of the Gulf Stream in the Straits of Florida, about 12 miles (19 km) south and southeast, and the tempering effects of the Gulf of Mexico to the west and north, Key West has a notably mild, semi-tropical climate. Cold snaps bring temperatures in the 40's in wintertime to the islands occasionally, due to the islands being slightly above the Tropic of Cancer, thus, not truly tropical.
Precipitation is characterized by dry and wet seasons. The period of November through April receives abundant sunshine and slightly less than 25 percent of the annual rainfall. This rainfall usually occurs in advance of cold fronts in a few heavy or light showers. May through October is normally the wet season, receiving approximately 53 percent of the yearly total in numerous showers and thunderstorms. Rain falls on most days of the wet season. Early morning is the favored time for these showers, which is different from mainland Florida, where showers and thunderstorms usually occur in the afternoon. Easterly (tropical) waves during this season occasionally bring excessive rainfall, while infrequent hurricanes may be accompanied by unusually heavy amounts. At any rate, Key West is the driest city in Florida.
Key West International Airport (IATA: EYW) (ICAO: KEYW), 3491 South Roosevelt Blvd., (305) 296-7223, . Served by several airlines, though a short runway prevents big jets from landing. Direct flights are available from Atlanta, Charlotte, most major cities in Florida, and also some flights to the Bahamas. Fares tend to be quite high. A popular route to fly in is via Miami International Airport or Fort Lauderdale International Airport.
If you plan to rent a car, be aware that both Enterprise and Alamo desks are not located at the airport. You have to call the shuttle bus and wait for 12 min to catch a ride to the Truman Av. location.
- Miami to Key West Day Tour Traveling from Miami to Key West is now possible every day. Tours depart from Miami Beach every day at 6:30AM. Travel in comfort across the Overseas Highway and 7-Mile Bridge. On this tour, you'll get to do some sightseeing in Key West and spend approximately 6 hours in Key West. You will be able to explore the island on your own pace. Complimentary Hotel pick-up is available from select hotels on Miami Beach & Downtown Miami. Tickets are available at Miami Info Tours  * (Miami Beach Tourist Information Center) and online. Ticket Link >  Reservations are required.
- Xcursions USA, ☎ 786-299-9261 (toll free: 1 888 884-6934), . a Miami based provider of Luxury motorcoach tour and sightseeing services that provides daily ground transportation Miami - Key West - Miami. edit
- Greyhound, 3535 S Roosevelt, Suite #104 (Key West Airport), ☎ 305-296-9072 (toll free: 1-800-231-2222), . Travels primarily on US-1 between Miami (3 stops) & Key West via Key Largo, Islamorada, Marathon Key and Big Pine Key. Passengers transfer to other buses in Miami and Orlando to get to other cities. Transfer to the 'Blue' or 'Green' Line bus from the airport/greyhound terminal into town. . edit
- Keys Shuttle, ☎ 305 289-9997 (toll free: 1 888 765-9997). The company provides door-to-door service between the Keys and the Miami and Ft. Lauderdale-Hollywood International Airports. edit
- MiamiToKeyWestBus.com, Mel Fisher Museum @ 200 Greene St (Wi-Fi and Restroom on Board), ☎ 305-423-9045, . Direct motorcoach transportation services to Key West from Miami. Attractions in Key West. From $29. edit
- Series of Public Buses, The Lower Keys Shuttle operated by Key West Transit provides nine trips per day between MM 0 in Key West and MM 52.5 in Marathon Key . The fare is $4 for the Lower Keys Shuttle. At Marathon,MM50, transfer to the Miami-Dade bus route 301 , Dade/Monroe Express that offers 6 trips daily between approx. 8AM and 11PM to the Florida City Wal-Mart. From the Florida city Wal-Mart, take the #38 bus (Busway Max)  to the Dadeland South (Metro Rail) Station to catch the train into Miami . The Dade/Monroe express costs $2.35 each way. Official Key West page on cross keys transit options 
Amtrak  takes you as far south as the Ft Lauderdale Airport Station. From there transfer 'Metro Rail 1x' Shuttle to the airport terminal and than to the Keys Shuttle onwards. See above. Amtrak: 1-800-USARAIL. There are NO trains to or in Key West.
- Key West Express  This company operates daily high-speed passenger ferries from Ft. Myers Beach and Marco Island. The ferries dock at the Key West Bight Ferry Terminal in the heart of the Historic Seaport District with its many fine restaurants, bars and shops. Passengers can walk to Duval Street, the heart of old town Key West, in about 15 minutes. The ferry ride takes approximately 3.5 hours and the Ft. Myers Beach vessels has a capacity exceeding 450 passengers and amenities aboard include; out-door sundecks, flat-screen TV's, galley service and a full bar. Additionally, the Marco Island vessel features the same amenities along with a capacity of over 250 passengers.
- Private Boaters Experienced boaters can navigate to Key West along the Atlantic side of the Keys or by traveling on the Gulf of Mexico side. The first part of the trip takes you through the specially-marked Intracoastal Waterway. After Long Key, however, international markers apply. Consult the appropriate Coast Pilot and Light List manuals. Numerous marinas are waiting to entertain you, but you should make reservations ahead.
- Cruise Ships In 1969 the Port of Key West received its first regularly scheduled cruise ship. The three docking facilities -- Mallory Square Dock, Pier B (privately owned by Westin), and the Navy Mole (aka Outer Mole) -- service over half a million passengers a year. Mallory Square Dock and Pier B are right in the heart of town; Navy Mole is on military property however your ship should provide chartered trolleys to take you to Mallory Square. A schedule indicating when a particular cruise ship will be calling on Key West is available at the Port Office and online.
- Currently, there are NO international ferries to the Caribbean or the Yucatan Peninsula in Mexico. Closest thing would be the cruise ship excursions to the foreign port of cal and back. See above or contact the cruise ship company.
The Overseas Highway terminates in Key West, and links all the towns in the Keys with mainland Florida, which provides links into the US Interstate network, so driving to Key West is straightforward (3 1/2 hours or 170mi/272km from Miami along US-1), though driving around town can be difficult and long-term parking may be expensive.
From Miami International Airport: Take LeJeune Road south to 836 West. Follow the Florida Turnpike south toward Key West. The Turnpike ends at US 1 in Florida City. Follow U.S. 1 south as far as it goes and you will be in Key West.
From Ft. Lauderdale-Hollywood International Airport: Exit the airport and follow the signs for 595 West. Take 595 to the Florida Turnpike and follow the signs for the Florida Keys and Key WEST.
From the north: take the Florida Turnpike south and follow the signs for Homestead and Key West. The Florida Turnpike ends at US 1 in Florida City.Follow U.S. 1 south into the Florida Keys.
From Florida's West Coast: take I-75 Alligator Alley east to the Miami exit, and south to the Turnpike Extension.
The Key West Express leaves several time a week from Fort Myers Beach. It departs year round on all days except those indicated on calendar on the website . Trips from Marco Island departs seasonally December through April.
Driving around Key West is difficult and parking is expensive. (Although there is free parking in front of the USS Mohawk Museum, at the intersection of Southard St and Fort St.) Many visitors choose to rent motor scooters, bicycles, golf carts or explore on foot.  When renting a golf cart keep in mind that you have to find parking for this vehicle as well. Scooters and bikes can normally be parked on the sidewalk right outside your destination. However, really consider insuring anything you rent. Driving is recommended and necessary if planning to stop or stay anywhere along the Keys from Sugarloaf Key to Florida City.
The main street in Key West is Duval street.
There is a fairly comprehensive bus system with color-coded lines . Unlimited travel tickets are available for periods between 7 days and a month and are good value.
Fares: (Discounts are available for senior citizens, students etc.)
- Single Trip: $2
- 7-Day $8/Unlimited Use
- 31-Day $25
If you plan to rent a car be aware that both Enterprise and Alamo desks are not located at the airport. You have to call the shuttle bus and wait for 12 minutes to catch a ride to the Truman Ave location. Budget is the only car rental agency in Key West that does not charge additional fees (usually $10/day from anyone else) for a second driver -- so if you are traveling with a partner who drives, be advised.
One Key West Taxi Service is reached at 1-305-295-5555.
- Key West AIDS Memorial, White Street and Atlantic Boulevard on the beach. The City of Key West has lost more than a thousand of its citizens to the AIDS epidemic. Some of their names are inscribed on a memorial near the White Street Pier. The memorial is embedded in the sidewalk near the ocean, and made of flat smooth granite. The memorial was dedicated on World AIDS Day in 1997, and funded entirely through private sources. At the time of dedication, there were 730 names engraved on the memorial. There are spaces for 1,500 names, and each year more are added and dedicated in a ceremony, also on World AIDS Day in December. A group called Friends of the Key West AIDS Memorial takes care of the memorial.
- Key West City Cemetery In Key West, burial customs reflect combinations of African, Hispanic, Anglo and other mixed heritages. Due to the water table of the Keys, most burials are in above ground tombs. Grave markers with unusual inscriptions such as I told you I was sick, Devoted Fan of Julio Iglesias and At Least I know where he's sleeping tonight are not unusual. Cemetery maps are available at the front gate.
- Wildlife Rescue of the Florida Keys, Atlantic Boulevard and White Streets.
- McCoy Indigenous Park is the setting for this rescue operation in Key West that has released more than 2,000 healed animals into the wild since 1993. They take care of any animal that needs attention, from sea birds to raccoons, and at any given time you might see up to 100 creatures healing at the center. They come from all over, from the Seven Mile bridge to the Dry Tortugas. You can visit the patients any day from 9AM to 5PM, and the park is open sunup to sundown. It's free, but they like donations and volunteers.
- Southernmost Point, Corner of Whitehead and South Streets. The southernmost point in the continental USA.
- Shipwreck Museum, 1 Whitehead St., (305) 292-8990 (Fax: (305) 292-1617), . Offers a panoramic view of the island from its observation tower.
- Key West Lighthouse, 938 Whitehead Street, . Open daily from 9:30AM-4:30PM. With a panoramic view of the island. Adults $10, Students/Seniors $9, Children $5, under 6 free.
- Key West Maps (Key West Maps), . Although the island of Key West is only 2 x 4 Miles, it is quite possible to get lost. You can find printed maps of the island and its attractions at most gas stations. If you have a smartphone try using these interactive maps of Key West. They provide the locations of just about everything on the island including various restaurants and attractions you may be looking for. Find what your looking for here: http://www.aroundkeywest.com/key-west-maps/ edit
Key West is a great place for the family. There is plenty to do during the day...for those that are awake. Enjoy an early night and prepare for the next day's adventure. However, if you are traveling with young ones, stay in a hotel off the main streets. For those who stay out all night you may not get to do these things but you should try. Be aware that the beaches in Key West are average at best. Many of the beaches are very small, made up of hard, dredged sand, and are not natural. They are not bad, per se, but if you are expecting Miami Beach caliber, you will be sorely disappointed.
- Key West Nature Preserve Two entrances on Atlantic Blvd., Ocean front property that has been turned into an accessible natural area. Enjoy seeing local Key West wildlife such as lizard butterflies and maybe even a snake.
- Astro City Atlantic Blvd. A popular stop for families on their way to and from the beach. Located directly across the street from Higgs beach.
- Florida Keys Eco-Discovery Center,  Truman Annex Waterfront. With its touch screens, stunning photos, and roomy theater showing a short high-definition film about the Keys ecosystems, this educational center has become a hit with families. It's a fun way to learn about reef and mangrove habitats before or after an excursion. The newest addition is the Living Reef exhibit, which features a 2,500-gallon reef aquarium. Free admission and parking on-site.
- Ghosts and Legends of Key West, 90 minute walking tour of Old Key West.  "Old Town Key West" Area. The most informative and historically correct versions of Key West ghost lore.
- Sebago Watersports, Waterfront Area, . Reef snorkeling, sunset sails and much more. All things water. Sebago trips are always full of fun and a wonderful crew that will take good care of you. Sunset sails, para-sailing, all day adventures from the tame Island Ting to the active Power Adventure. The para-sailing tends to be a bit brief (13 minutes), but the crew is friendly.
- Dry Tortugas National Park, . Details daily trips to Fort Jefferson. By ferry with Yankee Freedom II 
- Swim With Dolphins, for ages 5 and older.  Key Largo / Key West Area.
- Conch Tour Train, 201 Front Street, 305-294-5161, . The World Famous Conch Train sightseeing tour of Key West focuses on the historic Old Town area of the island. Highlights include the Hemingway House, Mallory Square, Duval Street and the Historic Seaport. Stops in Mallory Square and the Historic Seaport.
- Glass Bottom Boat, Snorkel, and Dolphin watch, For ages 5 and older. Key West/ Key West Area.
- Diving in Key West, . Offering Daily Dive trips to the reefs near Key West.
- Sunset Watercraft, . Key West offers a host of sightseeing opportunities, including romantic sunset cruises. At Cow Key Marina on Stock Island. Reasonable prices for the 28 mile round-the-island jet ski run (1.5 hours). The jet skis themselves are a bit beat up, but the motors hum right along at high speed. Guides are safe and knowledgeable, but give the renter plenty of rope to enjoy.
- Key West Fishing, . Offers charters, guides, and fishing information for Key West. Includes private and group fishing charters.
- Sunset Celebration, at Mallory Square in Key West (where Duval Street meets the Gulf of Mexico). This event begins every evening a few hours before sunset and is much like a street carnival, with vendors, performers, food, and fun. Also a great photo op for some of the most beautiful sunsets.
- Trails of Margaritaville Tour, Jimmy Buffett spent his "formative" years in Key West, and this tour will regale you with tales of those days. I suspect you'll hear some Semi-True Stories (believe it or not), but it's a good time for Parrotheads and non-Buffett fans alike.
- The Southernmost Scavenger Hunt Phone (305)292-9994  Since winning the prestigious "Venture Award" from the Key West Chamber of Commerce, The Southernmost Scavenger Hunt has expanded to offer a wider variety of custom designed features to their ever-popular scavenger hunts. Participants are able to enjoy all the sights and sounds that make the "Southernmost City" such an unforgettable destination.
- Fury Water Adventures, . Fury Water Adventures is a water sports company that has been in Key West for almost the past three decades. It offers snorkeling, para-sailing, jet skiing, kayaking, rock climbing, water trampoline, sunset sails and cruises, reef eco tours, and glass bottom boat tours. Fury also offers combo packages such as the Ultimate Adventure, the Rum & Reggae, and the Commotion on the Ocean.
- Ernest Hemingway House, 907 Whitehead Street, . 9AM-5PM daily. Hemingway lived and wrote here for a decade. He also raised cats, the descendants of which still roam the grounds and have extra toes. $12. edit
- Restless Native Charters, (Key West bight marina at historic waterfront seaport), ☎ 305-394-0600, . Luxury sailing catamaran for sail/dive, sunset sails, private partys, weddings/proposals. Upscale food and drink and a great adventure on the water. edit
- Dolphin Tours (Wild About Dolphins), 6000 Peninsular Ave, Stock Island FL (Key West Harbour Yacht Club), ☎ 305-294-5026, . An absolutely wonderful private boat tour to snorkel and dolphins sightings. Capt. Sherry is the best! edit
- Harry S. Truman Little White House, 111 Front St., . A historic retreat used by President Harry S. Truman. Guided tours are available, as well as a gift shop. It's still used as a retreat and place of business by US government officials today. edit
- Honest Works Island Pottery co, 929 Truman Ave (mile marker 1), ☎ 4193089221, . 9 - 6. Honest Works Island Pottery Co. is a vibrant art gallery and active studio space in Old town Key West. Stop on by and watch the pottery in the making or make it yourself. Honest Works offers pottery classes, as well as, paint your own pottery for locals and tourist alike. In this dynamic studio space artists, Adam Russell and Kelly Lever, create and display their own colorful island pottery. Come on in and fell the artist energy flowing! edit
- Fort Zachary Taylor, 601 Howard England Way (end of Southard Street on Truman Annex), ☎ 3052920037, . 8AM - sundown. The perfect romantic place to cuddle up with someone special, unwind, and watch the sun set as sailboats glide by...all without the crazy circus of Mallory Square. It doesn't get any more romantic in this crowded city. Nature trails, 1866 fort with a real moat, beaches, snack stand. $6-8. edit
- Key West Pub Crawl (Duval Crawl), 218 Whitehead Street #2 (Corner of Whitehead & Greene), ☎ 305-294-7170, . 8pm. Key West is famous for its bars- day or night the pubs are always rocking. Are you looking for the ultimate Key West tradition? Come along and do the “Duval Crawl,” a 2.5 hour guided tour offered Tuesday and Friday nights at 8PM. 5 cocktails and a souvenir t-shirt are included. price listed is for those who book online. regular price is $35.00 a person. $29.95. edit
- Southernmost Bike Tour, 218 Whitehead Street, ☎ 305-849-2706, . 8am - 8pm. Join your knowledgeable local guide for a leisurely ride through Historic Key West. Your two hour adventure includes the use of a comfortable beach cruiser bicycle, safety helmet and a complimentary bottle of water. On the tour you will visit numerous points of interest such as Truman Annex, the Southernmost Point, White Street Pier and the Key West Cemetery. Your route will take you down picturesque Old Town streets lined with tropical foliage, past famous homes and stunning gardens. Don’t forget your camera, sunglasses and comfortable shoes! $34.95. edit
- Ocean Vue Adventure (Key West Snorkel, Glassbottom Boat and Dolphin Encounter), 201 William St., ☎ (305) 851-5788, . 9 - 5. Ocean Vue Adventures is the local 3-in-1 tour, where guests can enjoy a glassbottom boat ride and see all the sea creatures on the way out to the coral reef for a great snorkel, then venture out to see the dolphins play in their natural habitat. edit
- Fantasy Fest, . Annual event. Will next be held October 17 - 26, 2014.
- Gay Spring Break.  Annual event held in February, March, and April targeting college-age LGBT students.
- Womenfest, . Annual event Will next be held September 4 - 9, 2012. One of the largest lesbian-oriented parties on earth!
- Tropical Heat, . Adult-themed event for gay men held every year. Will next be held August 16 - 19, 2012.
- Lobsterfest Held every year around the first week in August. This year: August 10 - 12, 2012.
Key West is not like Miami. There are very few high end shops or big name brands. While there are a few, Key West is not the place for this type of shopping. Fly into or out of the Miami airport and spend a day in South Beach if this is what you are looking for. There are a lot of shops in Key West, especially along Duval Street. You can find something to wear at night which in Key West isn't much (price or material). Lose your sunglasses...they have them. Need suntan lotion..check. Want a tattoo? You could get probably get 20 or so if you went to every tattoo place in Key West. This is not a good idea if you have been drinking. You may regret it the next sober morning when you realize you have one or more.
- Blue, 718 Caroline St, . A boutique specializing in women's clothing. Everything from fun tees, to comfy linen pants they have everything for a casual day of drinking.
- Fairvilla Megastore, 520 Front Street, across from the Pier House, Phone: +1 305 292-0448, . Intimate apparel, exotic fashions, sensual accessories, romantic gifts, playful novelties, passionate books and tantalizing movies! M-Sa 9AM-2AM, Su 10AM-2AM.
- Key Lime-N-More, 424 Greene Street, Next door to Captain Tony's Saloon, Phone: +1 305 296-9515, . All things Key Lime. The only home made Key Lime pie on the island. Friendly shopkeepers that treat you as more than just another tourist. Hours vary.
- Conch Republic Gifts  A gift store offering Conch Republic-related items including flags, shirts, magnets and more.
- Paradise Tattoo, 627 Duval St., ☎ 305-292-9110, . 10AM-10PM, 7 Days. What better way to remember your trip to Key West than with a permanent souvenir? Paradise Tattoo is Key West's Largest, Cleanest & Oldest Studio. So come on get stuck in Paradise. edit
- Bare Bones Beach Shop, inc., 2770 N. Roosevelt Blvd. (Overseas Market next to Winn-Dixie), ☎ 305-296-5970, . 9am-6pm Mon-Sat. Bare Bones Beach Shop has swimwear and beach products for men, women and children, in addition to stylish dog clothing and accessories. mid. edit
- 7 Artists & Friends (nearly 100% Local Art), 122 Duval Street (Just 2 blocks from cruise ship dock), ☎ 305.294.8444, . 10am-10pm. 7 Artists & Friends represents many of Key West’s favorite artists. Come in and check out the fresh caught local art. Photo realism, sculpture, jewelry, abstract, watercolor, photography, whimsy and glass; this gallery has it all. edit
- Conch Republic, 631 Greene Street. Enjoy their spacious waterfront setting where the atmosphere is like a trip back in time to the way Key West used to be. Enjoy fresh fish and a raw bar. Feel like you are dining outside with the large windows that remain open during the day. A great place for a drink & some snacks specially during football season.
- El Siboney, 900 Catherine Street, +1 305 296 4184. This Cuban restaurant, tucked into a quiet residential intersection, flies well below the tourist radar. Delicious food at very reasonable prices. To sum it up, this is where the locals go for Cuban.
- Jimmy Buffett's Margaritaville, 500 Duval Street, +1 305 292-1435. Key West is pretty close to paradise, so you might as well have a cheeseburger while you're there. Prices are not overly high. Less than 4 bucks for a Cheeseburger in Paradise.
- Schooner Wharf, Caroline Street, a surprising choice for breakfast, this rough and ready landmark has a three-egg seafood omelette that, coupled with a Bloody Mary or two, will shock you back to life from a throw down night on Duval.
- Mam's Best Food, 405 Petronia Street (between Duval and Whitehead), (305) 896-0923. Key West's only Glatt Kosher eatery (closed Friday afternoon and all day Saturday). Authentic home-cooked Israeli food. Hebrew spoken. The falafel and mezze are popular with local "Goyim" as well as visiting Jews.
- BO's Fish Wagon, 801 Caroline St Key West, FL 33040, (305) 294-9272. This is an open air shack that sells food, beer/wine, and has music on Friday nights. Check it out when you are headed towards Turtle Krawls from Duval Street. As seen via Bobby Flay on The Food Network. You will see license plates from previous customers adorning the spaces.
- A & B Lobster House 700 Front St, The main dishes are mid-range in price paired with great tasting and priced appetizers and salads it will be hard to forget your meal here. While Key West is warm and the porch may seem like a good idea make sure the ladies have jackets. It is right on the water and with the fans on high blast it can get a little chilly.
- Mangia-Mangia Pasta, 900 Southard St, +1 305 294-2469, . Every day 5:30PM-10PM.
- El Meson de Pepe, 410 Wallstreet, Mallory Square, +1 305 295-2620, . If you want authentic, delicious Cuban food look nor further. I have been visiting this place for about the last 5 years when I drive down to Key West. Be ready for a special treat on the days that Pepe himself takes over the kitchen and creates his delectable masterpieces. The prices are very reasonable and their Mojitos have a kick. Every night at Sunset, they have a band playing and enough space for dancing and having a couple of drinks at the bar.
- Roof Top Cafe Exactly what the names suggest, this is a restaurant situated on the roof top of a building. Overlooking Mallory square this place is perfect for dining during sunset or under the stars. As well as dinner they also serve Breakfast and lunch. Nothing is too expensive and the food is of good quality.
- The Half Shell Raw Bar Phone: (305)294-7496 231 Margaret St. A Taste of Old Key West! Traditional Key West Raw Bar & great Key West seafood restaurant! Oysters, clams, shrimp, more! A low key restaurant for casual lunch or dinner. Settle down to an informal atmosphere, local characters, great bar and waterfront dining. It's a little piece of Old Key West on the historic Key West Bight. Drop in! Enjoy a frosty drink and the freshest seafood this side of the reef!
- Nine One Five, 915 Duval Street. Dinner served from 6PM-11PM. With weather so nice you want to spend as much time outside as possible. So why not take your dining outside...or as close as possible? Join others on the porch of this dignified Victorian home. Similar to tapas dining, everything is intended to be shared and mixed and matched.
- Seven Fish, 632 Olivia St., +1 305 296-2777, . This very small restaurant tucked away on Olivia St, is a true delight. The staff is intelligent and polite, the fish dishes are always fresh and innovative. Reservations a must.
- Square One, 1075 Duval St # C12, +1 305 296-4300, . They serve breakfast lunch dinner and even Sunday brunch. The menu is very similar to many other restaurants. A lot of fish and seafood. A lot of "tropical' flavors and many fruits are included in the ingredients of their dishes.
- Louie's Backyard, 700 Waddell Avenue. One of Key West's finest restaurants with gourmet preparations, including their signature dish of shrimp and grits. Large oceanfront deck is popular with locals and visitors during sunset.
There are a large number of drinking establishments of various types. The main tourist strip on Duval Street has numerous watering holes.
- Bourbon Street Pub, 724 Duval St, +1 305294-9354, . Part of the gay-oriented Bourbon St. Complex on the 700 block of Duval.
- Captain Tony's Saloon, 428 Greene Street, . Ernest Hemingway's old stomping grounds. Pirate's Punch in a 22 oz cup.
- Fat Tuesdays, 305 Duval St., +1 305296-9373, . So you're not in New Orleans...who says that means you can't have Mardi Gras! Featured on MTV's Real World Key West here it is Mardi Gras everyday.
- Hog's Breath Saloon, 400 Front Street, +1 305292-2032 (email: firstname.lastname@example.org), . Take a peek at the "hog cam" on their website.
- Irish Kevin's Pub, 211-C Duval Street, +1 305292-1262, . Webcams here, too. Can be a lively place at times.
- The Lazy Gecko Bar 203 Duval St, . Next door to Sloppy Joe's bar. This place offers air conditioning if you can't take the heat. Also cool off with one of their 12 daiquiris. Hungry? Grab a slice of pizza or a fresh sandwich. Starting early...join The Lazy gecko for happy hour from 5-8. Like your friends a lot? Rent the whole place!
- Rick's/Durty Harry's Entertainment, 202 Duval St., email@example.com. Complex offers it all! Key West's #1 Club w/ 6 different venues & 10 bars. Best live entertainment, VIP bar overlooking the action, famous juice & premium spirits bar, hottest dance club, premier adult entertainment, & best live Rock & Roll!
- Sloppy Joe's Bar, 201 Duval St, +1 305 294-8759. Website blocked by spam filter, but it's (not surprisingly), sloppyjoes dot com. Ernest Hemingway's "new" stomping grounds. Sloppy Joe's used to sit at the current location of Captain Tony's, but the landlord raised the rent on the owner back in 1937. Legend has it that upon hearing the news, the bar owner and his customers (including Hemingway) moved the bar, barstools, alcohol, etc. across Duval Street to a former restaurant - its current location.
There are also plenty of places to wet your whistle that aren't necessarily right on Duval Street.
- Green Parrot Bar, 601 Whitehead St, +1 305 294-6133, . The last (or first, depending on your direction of travel) bar on US 1. Not your typical trop-rock bar, the Green Parrot leans more toward blues. Great bands, and an unbelievable selection of blues on the jukebox. Just remember, no snivelers.
- Rum Barrel Tavern, 528 Front St, +1 305 292-7862, . Pat Croce's place features the largest selection of rums in the world. Not a rum drinker? Plenty of other libations to be had. Several big-screen TVs (you'll never miss an event involving a Philadelphia team) and a deck overlooking Old Town.
- Schooner Wharf Bar, 202 William St, +1 305 294-3302, . A last little piece of Old Key West, Schooner Wharf is an open air bar that sits on the Key West Bight. Grab a brew and watch the yachts.
- Finnegans Wake 320 Grinnell St Celebrate life in true Irish Style.
- Bogarts Irish Pub, 900 - 904 Duval Street, Key West, ☎ 305-296-0815, . An Irish pub and restaurant attached to a bed and breakfast located right on Duval Street. Daily happy hour specials offered as well as great Irish food. Come in and say hi and enjoy a nice cold pint. edit
- Kokomo Joe's Off Duval Bar Crawl, 422 Fleming St (crawl starts at Agave 308 on Front St), ☎ (305)731-9630 tix 800 979-3370, . 3. Pub Crawl off the beaten tourist path. "Zoo Keepers" take you the "Very Important Party Animals" on a drinking safari through Key West. Great fun way to get to know your way around the Key West bar scene. Drink like a local, many say it's the best pub crawl in Key West. You get 5 drinks and a t-shirt with our slogan "A Blind Chimp Could Find a Bar on Duval" $35. edit
- Angelina Guesthouse, 302 Angela St, ☎ (305) 294-4480, . checkout: 11. Clean rooms, shared and private baths, pool, complimentary breakfast, wi-fi. Friendly and helpful staff knowledgeable of the city. $94+. edit
- Atlantis House, 1401 Atlantic Blvd (1 block from the White Street Pier), ☎ 305-292-1532, . checkin: 2PM; checkout: 11AM. 40yds from the Atlantic Ocean and Rest Beach. Beautiful landscaping with only 2 private Jacuzzi Suites. Perfect for Honeymooners and special occasions. Complimentary Wi-Fi, off-street parking and bikes. $149-$275. edit
- Old Town Manor, 511 Eaton Street, ☎ 305-292-2170, . checkin: 3 PM; checkout: 12 PM. Pet friendly luxury inn located a half block from the excitement of Duval Street. Eco-friendly bed and breakfast with 14 rooms and continental breakfast served daily in our garden courtyard. $115-$375. edit
- Casablanca Bed and Breakfast (Bogarts Irish Pub), 900 - 904 Duval Street, ☎ 305-296-0815, . Family run bed and breakfast located right on Duval Street just steps away from Old Town. Swimming pool and restaurant/bar located on the premises. Each room has its own private porch and private bathroom. Family friendly. edit
- La Concha Hotel, 430 Duval St, ☎ 305-296-2991, . Built in 1926 and home of Top Spa on Duval. edit
- Curry Mansion Inn, 511 Caroline Street, +1 800-253-3466, . A small hotel just steps from Duval on Caroline, plenty of free parking, open bar cocktail party with piano player every afternoon, breakfast buffet with cooked to order eggs.
- Doubletree Grand Key Resort, 3990 South Roosevelt Blvd., ☎ 1-888-844-0454 (firstname.lastname@example.org), . The newest resort-style property among luxury Key West hotels. This place has a good roof top view of the water. For those of you traveling to Key West for poker run and boat races this is a very popular place. However, book early there is limited space available. edit
- Douglas House, 419 Amelia Street, ☎ +1 305 294-5269 (email@example.com). This hotel offers the perfect pool-side setting with swimming pool and heated jacuzzi all surrounded by lush tropical gardens. edit
- Eden House, 1015 Fleming St. (In Old Town), ☎ +1 305-296-6868, . Key West's original guest house. Fully renovated, lush grounds. edit
- Garden House Inn, 329 Elizabeth Street (parking across st. at church for $10/day), ☎ +1-800-695-6453, . checkin: 3PM; checkout: 11AM. A fun and relaxed B&B, with 10 rooms, all with private baths. Amenities include a heated lagoon style pool with spa jets and a cascading waterfall, surrounded by tropical gardens that weave throughout the Inn grounds. Along with a nightly happy hour, a continental breakfast is available each morning. $149 - 299. (24.559026,-81.801218) edit
- Grand Guesthouse Bed and Breakfast, 1116 Grinnell St., ☎ +1 888-947-2630 or +1 305-294-0590, . In Old Town just a five-block walk from Duval Street and the beach. edit
- Heron House Bed & Breakfast, 512 Simonton Street, +1 305 294-9227, +1 888 861-9066. . In the heart of the historic district, 23 room bed and breakfast. Complimentary breakfast is served in the mornings and a wine and cheese tasting each night.
- Hyatt Key West Resort and Spa, 601 Front Street (One block from Duval Street), . Newly renovated. Intimate resort with casually elegant Floridian touches, combined with sumptuous, rich fabrics and stunning ocean views. Private marina to fish, scuba, snorkel, parasail, waverunners, or sail on the “Floridays,” the resort's 60-foot Irwin sailboat which offers daily sunset cruises and private charter trips. Exercise studio, private beach, pool with oversized whirlpool. Indoor and outdoor dining is available at two restaurants, where guests can watch the sunset. edit
- Island City House Hotel, 411 William Street, +1 305 294-5702, . Charming and historical hotel offering 24 suites for lodging near Old Town.
- Key West Bed and Breakfast, 415 William Street, +1 800-438-6155,  Classic Caribbean Casual. This three story Victorian in the heart of old town is full of color and art.
- Pier House Resort and Caribbean Spa, One Duval Street (On the corner of Duval and the Gulf of Mexico), ☎ 800-327-8340 305-296-4600, . checkin: 12:00; checkout: 11:00. Pier House completed an 11 million dollar renovation in 2008. Elegant accommodations, lush gardens, a private beach, a selection of restaurants and bars, a full-service spa. edit
- Reach Resort, 1435 Simonton Street (in Old Town), ☎ +1 305 296-5000, Spa: +1 305 296-3535, Reservations: +1 888-318-4316, . checkin: 4:00 PM; checkout: 11:00 AM. With the only natural beach on the island as a backyard, this hotel is just a block away from Duval Street. edit
- Rose Lane Villas, 511 Eaton Street, ☎ 305-292-2170, . Pet and family friendly 1,2 & 3 bedroom villas on a quiet street only steps to the heart of Old Town Key West. Swimming pool, parking, fully equipped kitchens and more. $229-$959. edit
- Southern Cross Hotel, 326 Duval Street, 1-888-364-3200, . A no-frills hotel with a great location. Located right on Duval Street between Eaton and Caroline. Just steps from everything that Key West has to offer.
- Southernmost Hotel, 1319 Duval St, ☎ (305) 296-6577, . Across the street from the southernmost beach. edit
- Casa Marina Resort, 1500 Reynolds Street, ☎ +1 305 296-3535 Reservations: 888-303-5717, . checkin: 4:00 PM; checkout: 11:00 AM. A sophisticated Key West resort featuring top-notch dining and pristine private beach. edit
- The Inn at Key West, 3420 N. Roosevelt Blvd. (US 1), . Luxury rooms and world-class amenities, accommodations feature a king or double queen size beds some with oversized bathrooms. Freshwater pool, tiki bar and poolside restaurant. Located on the east end of the island, about 3 miles from Duval Street, so it's very quiet and good for families, but you'll need your own car to get to where most of the action is.
- Tropical Inn Key West  Historic Key West bed and breakfast with Bahamian-style Conch houses. Located on Duval Street.
- Historic Key West Inns, 725 Truman Avenue, ☎ 305.294.5229, . Visitors to Key West, FL will find beauty, warmth and comfort in any of the six hotels that comprise the Historic Key West Inns. All hotels are centrally located in Old Town and provide easy access to the culture and vibe that is Key West. Online reservations available. edit
- Cypress House (Historic Key West Inns), 601 Caroline Street (US 1 to Old Town to Simonton St. Turn right and proceed 8 blocks), ☎ 305.294.6969, . Designed for adult couples, guests will find well-appointed, unique and modern rooms in this historical Key West landmark. Start each day with a complimentary, poolside breakfast and then return from the day's revelry to an afternoon mix-n-mingle. Reserve a room at this lush, tropical, gated paradise online today. edit
- Key Lime Inn (Historic Key West Inns), ☎ 305.294.5229, . Settle into the fully updated guestrooms spread out across an acre of grounds and experience the property's tranquil, spacious feel. Then step out and walk or pedal to the restaurants and nightlife that is Duval Street. Modern amenities await your arrival. Reserve one of the 37 guestrooms online now. edit
- Albury Court (Historic Key West Inns), 1030 Eaton Street, . Couples looking for romance or planning a Key West honeymoon will delight in the modern amenities, comforts and privacy of this historic hotel. Located in a residential neighborhood, guests can walk to all the area's major attractions. Or perhaps you'll decide to while away the days at our courtyard pool complete with 6 foot waterfall. Check availability and book online. edit
- Chelsea House (Historic Key West Inns), 709 Truman Avenue, ☎ 305.296.2211, . Couples with 4 legged family members will enjoy knowing there are a few guestrooms that are pet friendly. Regardless, our guests will enjoy plenty of space to lounge, enjoy the pool and the tropical Victorian architecture. Choose the room with amenities to fit your needs and reserve online today. edit
- Lighthouse Court (Historic Key West Inns), 902 Whitehead Street, ☎ 305.294.9588, . Located near museums, Duval Street and many area favorites, guests will enjoy a wide range of guestrooms and suites. Forty guestrooms throughout ten buildings ensure you'll find the amenities you're looking for from the budget conscious to those seeking luxurious accommodations. Reservations are available online. edit
- Merlin Guesthouse (Historic Key West Inns), 811 Simonton Street, ☎ 305.296.3336, . Families will find rustic modern lodging in a classic guesthouse providing access to all the best of Duval Street and the area beaches. Five buildings in a gated compound surround a private courtyard and pool. A variety of rates helps guests on any budget determine the best style of accommoadations. Book online today. edit
- Historic Key West Inns (Albury Court Hotel), 1030 Eaton Street (At the corner of Frances and Eaton Streets. US 1 bear right at Key West and continue to Old Town about 3 miles), ☎ 305.294.5229, . One of six Historic Key West Hotels on the island of Key West, Fla. Uniquely styled in the heart of Old Town. Guestrooms offer casual elegance in a historic building. Check availability and reserve online today. edit
- Vacation Homes of Key West (VHKW), 507 Whitehead St Key West (Across from court house on Whitehead St.), ☎ (305) 294-7358, . checkin: 4:00pm; checkout: 11:00am. Vacation Homes of Key West ~ key west rentals offered by an established locally operated rental agency representing authentic Old Town villas, cottages, estates, and penthouses for rent in Key West. Daily, weekly, & monthly rentals available in 1-12 bedroom rental properties. $110-450. edit
- Eden House, 1015 Fleming Street (Florida A1A Key West, FL 33040 Take N Roosevelt Blvd to Palm Avenue Causeway 2.9 mi / 7 min Follow Palm Avenue Causeway, Palm Ave and Eaton St to Fleming St 1.1 mi / 3 min Turn right onto Palm Avenue Causeway 0.4 mi Continue onto Palm Ave 0.3 mi Slight left onto Eaton St 0.2 mi Take the 3rd left onto Grinnell St 390 ft Take the 2nd left onto Fleming St Destination will be on the left), ☎ 1-800-533-5397, . checkin: 3:00 PM; checkout: 11:00 AM. A tranquil, peaceful setting with all the amenities and none of the attitude. In historic old town Key West, just a short walk from Duval Street. Eden House hotel offers affordable rates, a heated pool, Jacuzzi, elevated sundeck, waterfalls, hammocks, swings, garden cafe, wi-fi internet service and friendly service - all in a lush, tropical setting. The Eden House is Key West, Florida's original hotel. Built back in 1924, the hotel has been owned and operated since 1975 by Mike Eden. Now fully renovated and a Green, Eco-Friendly Lodging, the original art deco hotel building is joined by several renovated conch houses, making for a lovely property with a full range of accommodations - from apartment suites to semi-private rooms, and everything in between. edit
- The Marker Resort Key West, 200 William Street, ☎ 855-969-3206, . A luxury waterfront resort on the Historic Seaport of Key West offering spacious accommodations, complimentary Wi-Fi, complimentary parking, three tropical tree-lined pools and more. edit
There is no longer any camping in Key West, but you can still find some just outside the City limits on Stock Island. Within Key West itself, parking is very limited and RV's are generally discouraged, so your best shot is to stay somewhere outside the city and drive a smaller vehicle into town.
- Boyds Key West Campground, 6401 Maloney Ave., +1 305 294-1465 . Boyd's is a family owned and operated campground and RV park that opened in 1963. Only 5 miles from Duval Street and downtown (3 miles to Smathers Beach) and has city bus and taxi service to all of Key West. Oceanfront and able to accommodate the largest RVs as well as tent camping with marina space for your boat. It has a pool, laundry, gameroom, boutique, 4 bathhouses and nighttime security.
- El Mar RV Resort, 6700 Maloney Ave., +1 305 294-0857 .
- Leo's Campground & RV Park , 5236 Suncrest Rd., +1 305 296-5260, .
There are a few more a little ways up the Keys that cater to RVs. The number of campsites are limited, so do not be shocked by the price. Make your reservations well in advance six months to a year so you are sure to get your spot. You will notice the use of "MM" or "Mile Marker" in the addresses. This is how US 1 is marked. MM 0 is in Old town Key West and the beginning of US 1. The numbers go up, so you can tell just how far an address is from Key West.
- Bluewater Key - Clark's RV Lot Rentals, Mile Marker 14.3, Sugarloaf, +1 305 744-0999 .
- Bluewater Key RV Resort, MM 14.3 U.S. 1 Sugarloaf Key, +1 305 745-2494, .
- Geiger Key Marina and RV Park, 5 Geiger Road, Big Coppitt Key, +1 305 296-3553, .
- Sugarloaf Key Resort KOA Kampground, MM 20 Summerland Key, +1 305 745-3549 (800) 562-7731, .
Key West is well known as a gay tourism mecca, so if homosexuality offends you or you don't want to have to spend half your day answering questions from your kids about why those 2 men are holding hands or those 2 women are kissing on the park bench, consider giving Key West a miss. Having said that, however, the LGBT community (both tourist and resident) adds a great deal of fun, colour and livelihood to Key West and if you have an open mind then it becomes an important and enriching part of the Key West experience.
Violent crime is extremely rare, but vehicle break-ins and pick-pocketing are not uncommon. Key West is home to a large homeless population. Most are harmless, but many suffer from drug and/or alcohol addiction and resort to aggressive panhandling and petty crime to finance their addictions. Use the same level of common sense you would use elsewhere in the USA...keep valuables out of plain view, park your vehicle in a well-lit, heavy traffic area and if you get lost try not to make it too obvious.
Pay attention to the weather. The Keys are a narrow band of islands that offer little protection from tropical storms. In the past storms have generated waves with enough strength to demolish bridges and topple freight trains and engines sitting on tracks. The locals seem immune to these dangers: rely on National Weather reports, rather than the opinion of locals. If it is suggested you go back to the mainland, do so immediately. There is only one highway out and it can become clogged quickly. The Overseas Highway can and will be closed for a period should a car or truck accident occur. Always allow extra time if traveling back to the mainland to meet a flight or cruise.
Key West is well known as a popular tourism location for the LGBT community. The LGBT community (both tourist and resident) in Key West is open and vibrant and adds a great deal of fun, color and livelihood to Key West.
The only way out by land is back toward Miami. On the way up the road you can visit Big Pine Key, Marathon, Islamorada, and Key Largo. There are numerous local islands accessible only by boat to visit as well.
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