Key West, FL Road Trips

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. In 1982, the city briefly declared symbolic independence as the "Conch Republic" in response to a United States Border Patrol blockade at the junction of U.S.

1 Ernest Hemingway House, 907 Whitehead St. 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. $14. 2 Fort Zachary Taylor, 601 Howard England Way (end of Southard Street on Truman Annex), ☏ +1 305-292-0037. 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. Before Ballast Key was deeded to the US Fish and Wildlife Service in 2019, the beach area was the southernmost point in the continental US accessible to the general public, regardless of what the famous buoy at the corner of Whitehead and South Streets says. $2-4. 3 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. $15. 4 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.

Key West is not the greatest place to bring a family. There are beaches and a few small parks 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. Because many locals get around by scooters, bikes, and/or electric cars, you may want to consider renting them at one of the many rental shops throughout the island. 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 lizards, butterflies and maybe even a snake. 1 Florida Keys Eco-Discovery Center, 35 E Quay Rd, ☏ +1-305-809-4750, [email protected]. 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. Dry Tortugas National Park, [3]. Details daily trips to Fort Jefferson. By ferry with Yankee Freedom II Sebago Watersports (Waterfront area). WReef snorkeling, sunset sails, parasailing, all-day adventures from the tame Island Ting to the active Power Adventure.

Conch Republic, 631 Greene St. 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, especially during football season. El Siboney, 900 Catherine St, ☏ +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. 1 Jimmy Buffett's Margaritaville, 500 Duval St, ☏ +1 305-292-1435. Su-Th 11AM-10PM, F Sa 11AM-11PM. Cheeseburgers. (updated May 2023) Schooner Wharf, Caroline Street. 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. A & B Lobster House, 700 Front St. The main dishes are mid-range in price, and paired with great tasting appetizers and salads. While Key West is warm and the porch may seem like a good idea, make sure you have a jacket. 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 5:30-10PM. El Meson de Pepe, 410 Wallstreet (Mallory Square), ☏ +1 305-295-2620. Authentic, delicious Cuban food and mojitos with 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.

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, ☏ +1 305-294-9354. Part of the gay-oriented Bourbon St. Complex on the 700 block of Duval. Captain Tony's Saloon, 428 Greene St. Ernest Hemingway's old stomping grounds. Pirate's Punch in a 22-oz cup. Hog's Breath Saloon, 400 Front St, ☏ +1 305-292-2032, [email protected]. Take a peek at the "hog cam" on their website. Irish Kevin's Pub, 211-C Duval St, ☏ +1 305-292-1262. Webcams here, too. Can be a lively place at times. Rick's/Durty Harry's Entertainment, 202 Duval St, [email protected]. Club with 6 venues & 10 bars. Live entertainment, VIP bar overlooking the action, juice & premium spirits bar, dance club, adult entertainment, & live rock & roll. Sloppy Joe's Bar, 201 Duval St, ☏ +1 305-294-8759. 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, bar stools, 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.

1 Angelina Guesthouse, 302 Angela St, ☏ +1 305-294-4480. Check-out: 11AM. Clean rooms, shared and private baths, pool, complimentary breakfast, wi-fi. Friendly and helpful staff knowledgeable of the city. From $77. 2 At Home In Key West, 905 Truman Ave, ☏ +1 305-296-7975, toll-free: +1-888-374-7975. Villa and condo rentals in the historic Old Town. (updated Feb 2016) 3 Atlantis House, 1401 Atlantic Blvd (1 block from the White Street Pier), ☏ +1 305-292-1532. Check-in: 2PM, check-out: 11AM. 40 yds from the Atlantic Ocean and Rest Beach. Beautiful landscaping with only 2 private Jacuzzi Suites. Complimentary Wi-Fi, off-street parking and bikes. $149-275. 4 Casablanca Bed and Breakfast (Bogarts Irish Pub), 900 - 904 Duval St, ☏ +1 305-296-0815. Family run bed and breakfast near the Old Town. Swimming pool and restaurant/bar located on the premises. Each room has its own private porch and private bathroom. Family friendly. Crowne Plaza La Concha, 430 Duval St, ☏ +1 305-296-2991. Built in 1926 and home of Key West's highest sunset celebration. Curry Mansion Inn, 511 Caroline St, toll-free: +1-800-253-3466. A small hotel with 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, toll-free: +1-888-844-0454, [email protected]. A resort-style property with a good rooftop view of the water. Book early, as the place is popular and there is limited space available.

1 Key West International Airport (EYW IATA) is the major airport on 3491 S Roosevelt Blvd (FL-A1A) serving Key West and the lower keys located 3.9 mi (6.3 km) southeast of downtown. The airport terminal is accessed from S Roosevelt Blvd along Faraldo Circle (its own access road). Major airlines serving the Key West are: Allegiant (Asheville, Cincinnati, Indianapolis, Orlando-Sanford, St Petersburg FL; Pittsburgh ) American Airlines and Envoy Airlines dba American Eagle: (Charlotte, Dallas/Fort Worth, Philadelphia; and American Eagle from Charlotte, Chicago–O'Hare, Miami, NY LaGuardia, Washington–National) Delta Airlines & ExpressJet dba Delta Connection: (Atlanta, NY LaGuardia) United & United Express operated by Republic Airlines: (Chicago–O'Hare, Houston–Intercontinental, Newark, Washington–Dulles. Additional United Flights to Tampa and Orlando are operated by Silver Airways as a codeshare partner with United). Fares tend to be higher than to and from the large metropolitan airports. A popular alternative is to fly into Miami International Airport or Fort Lauderdale International Airport, rent a vehicle and drive down the Overseas Highway (US Hwy 1) to Key West (See "By car" in the below). Likewise you may also catch a ride with Keys Shuttle from Miami International and Ft Lauderdale International Airports to your hotel or to any address in Key West and anywhere in the Keys. Call them to schedule pick-up for the return trip back to Miami or Ft Lauderdale (see "By bus" in the below).

With many narrow and one-way streets, driving Key West is difficult and parking is expensive. Many visitors choose to rent motor scooters, bicycles, golf carts, explore on foot or use public transportation. [2] 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. The tourist area in Key West is Duval Street. Key West Transit offers a fairly comprehensive bus system for local travel in and around Key West and up to MM 53 on Marathon Key in the Lower Keys. For taxi you may contact One Key West at +1 305-295-5555 to arrange for a pick-up or a ride share service such as Uber or Lyft. Taxis and ride share services are plentiful and affordable. If you plan to rent a car be aware that the 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. Renting a car is more necessary if you plan to travel extensively or point to point in different parts of the Florida Keys then if you're staying exclusively on Key West where you won't need a car at all. If your lodgings are in Old Town you can more easily walk or bike to all the attractions.