Key West’s Best Travel Tips

A vacation in Key West is the best…. This 2 x 4 mile island is a tropical heaven at Florida’s Mile 0, packed with history, colorful Bahamian architecture, sunshine, a vibrant bar scene, and friendly funny locals. Key West is more authentic than Miami’s South Beach, less fancy than Fort Lauderdale, Naples or Palm Beach.

The island “Key” is beautiful, with lush palm and mahogany trees, surrounding turquoise seas and white sand. Roosters run wild among the lively streets lined with fragrant flowers, al fresco bars and eateries. Key West is wide open and welcoming. Sure, cruise ships tend to crush the down town by day (for now – locals would like to ban them), but ships are long gone by sunset- a highlight of the day here. And Key West’s beaches are soft sand perfection. You can always find a remote, romantic secluded spot by bike or boat charter.

72 Hours at Mile 0, What to do for the Best of Key West!

Start with a stroll down Duval Street, the core of Key West. Grab a drink at any of Key West’s world-famous watering holes to kick off your Key West Mile 0 mood. You can even carry your cocktail from one bar to the next in a “to go” cup.

Hop aboard the Conch Tour Train for a 90-minute orientation and tour of Key West’s top spots by trolley. The Conch (term for a native in KW) guides are great at cramming 500 years of history, and humor, (ok, facts mixed with some fiction), into an entertaining easy-breezy open-air ride from Front Street, by Mallory Square, to the Southernmost Point of the island and back. The Conch Tour Train is a Key West tradition since 1958.

Rent a Bike to get around the island, $10 well spent as you can swiftly ride around the island, ring your bicycle bell and carry things in your basket. Be sure to lock your bike at each stop, bike racks are plentiful.

Snap a selfie at the Southernmost Point beacon marking Mile 0, as low as you can go, south on Whitehead. Here you are at the end of the US, just 90 miles to Havana Cuba, 160 to Miami. Nearby on South Street is the 1896 Southernmost Mansion. This turn-of-the-century manse is also the most photographed for its grand gingerbread style. The Mansion was designed with just one bedroom, the wealthy wife didn’t want guests.

Climb the 88 steps up the Key West Lighthouse, for a grand view of the island. This 1847 Light was constructed inland from the sea, 14’ above sea level, a year after the original wooden tower on the Point was destroyed by hurricane.

Ernest Hemingway’s 1928 Home is next to the Lighthouse. The famed American author, of four wives and a six-toed cat, lived in Key West for a decade, wrote the Sun Also Rises in this inspirational vacation location. He also frequented Sloppy Joe’s Bar daily on Duval Street. Hemingway’s prolific tragic tale is well preserved here, and at Santiago’s – a local tapas joint honoring “The Old Man and The Sea.”

Truman’s Little White House is a fantastic tour, where President Harry Truman escaped D.C. and what he called the “great white jail” to improve his health, but also to host serious political summits from 1945 to ‘53. You will be “just wild about Harry” upon learning more about our 34th President, and the six following Commanders in Chief to visit this charming Key West property that dates back to 1890.

Bike to Fort Zachary Taylor Park, Florida’s southernmost State Park to explore the 87 acres, the sand beach, nature trails and the 1845 military fort named for our 12th President Taylor (1849-1850). The beach and fort offer stunning views of Key West Harbor.

Stroll Key West’s beautiful palm tree-lined streets like Simonton to witness the island’s unique architecture, Bahamian style cottages, New England revivals, Bermudan, so many handsome brightly-painted well-kept homes with their southern wrap-around porches. Key West has over 3,000 historic wood homes, many in the Old Town are on the national register of historic places.

Key West’s wildlife, and we are not talking night life …yet, is bountiful – with butterflies flitting about, heron and egret, even free-range chickens and roosters roaming the town. Chickens are a protected species on Key West, cock fighting was outlawed decades ago, and now roosters rule the roost, with no natural predators- not even BBQ as it’s a $500 fine to foul with the fowl.

Get on a boat, charter a private boat from Fury Adventures or board their catamaran for an excursion to the outlying mangrove islands to see the brilliant shallow turquoise waters, fish, snorkel around the Florida Keys Reef that has claimed so many ships, and made many a wrecker success (wrecker is a Key West term for pirates and looters that reigned these tricky waters for centuries –there was very lucrative salvaging with two ship wrecks a week on average loaded with trade and treasures).

Key West Sunset is the crescendo of the day. Go to Mallory Square to see the mayhem as daylight fades. Locals and visitors flock to Key West’s western promenade for a circus atmosphere of entertainment leading up to the sunset. Jugglers, singers, dancers and palm readers perform, as people gather in anticipation of the coveted green flash as the sun disappear into the sea.

Evenings, strolling Duval Street is a must, drink in hand. Music and revelers pour out onto the sidewalks from Sloppy Joe’s, Captain Tony’s, Senor Frogs, Kevin’s, Hogs Breath, Bull & Whistle, Hard Rock Café, Aqua, Vinos, … the list of Key West bars goes on and on, so does the party till the wee hours. Duval Street is particularly fun during Key West Fests, when Duval is closed to vehicle traffic and becomes a pedestrian party zone – like Fantasy Fest over Halloween annually and Key West Pride in June! Key West has an open liberated vibe, LGBTQ are welcome here, like Ptown on Cape Cod – you can let your freedom flag fly. Drag Queens dominate the entertainment scene, Doms do too – lol!

Green Parrot on Whitehead is where the locals head at night for beers, bingo, live music, karaoke, you name it… this old bar is Key West casual and cool.

Mornings in Key West are conversely very quiet, peaceful, poetic. Early is a great time to wake up, grab a delicious brewed Cuban coffee and walk or bike to explore the charm of this southernmost island enclave of 27,000 residents – aka Conchs.

Key West Best Travel Tips:

The Best place to rest is H20 Suites, this luxury hotel debuted in December 2016, and its posh, with perfect service and a great location. H20 Suites is on the southern part of the island, the quieter side, just a block from Duval Street, and two to the beach, the Southernmost Point, and the Key West Lighthouse. This all-suite hotel is more South Beach Miami art deco than old world Florida, it is sophisticated with top concierge service to complement the chic decor. Our suite was swank, with modern lighting, a beautiful bathroom, our own pool, luxurious bedding and two big screen TVs. The highlight of H20 Hotel is the rooftop pool, where you are served complimentary Mimosa and Bloody Mary’s late morning, wine and snacks in the afternoon. We could walk to the sandy beach  – where chairs and towels are provided to H20 guests, and we could stroll to dozens of great dining spots, yet our serene room was so private at night.

Artist House Key West is more charming and historic. This pretty purple B&B on Eaton Street is in the heart of Old Town with an artsy antique feel. Our spacious room had a romantic four-poster bed and fireplace (which you won’t need). The House kitchen offers snacks and drinks always, and a wonderful complimentary Breakfast from Cuban Coffee Lady. You can dine in the pretty garden patio out back by the plunge pool hot tub. Happy Hour is also served here daily with gratis wine, a nice chance to relax and chat with fellow guests. Bikes are available to rent from the friendly team at Artist House.

Fly into Key West airport (EYW), the approach by plane is super scenic, and the airport is small and easily managed, overdue for its upgrade “coming 2024.” And there are two bars in the Key West Airport too… the upstairs bar before security is the better choice if you have time to spare

Take a Key Lime Taxi  for the 3 mile ride to town along the waterfront past several beaches.

Don’t rent a car in Key West – you can walk to most everything, ride a bike, Uber or hire a pedi-cab. Parking is tight in this tiny Old Town.

Dress in Key West is super casual, beachy, not fancy … most restaurants and bars have outdoor seating – which is delightful in the 70-degree balmy weather. Some locals barely wear clothes! Key West temperatures bottom and top out at 49-99, with typically a light breeze!

Dine on local seafood, grouper, snapper, cobia, lobster tail, shrimp, Gulf Oysters, crab, capped off with Cuban coffee and Key Lime Pie… see our Top Key West Dining Spots reviewed

Find a pool bar –  Blue Mojoito at the Hyatt, or Dante’s, fun on a hot day to quench your thirst, and enjoy the “scene”.

Beware the pushy shop keepers on Duval Street. Aggressive salespeople promising miracle creams and quality jewelry really take away from the otherwise relaxed vibe of the Conch Republic. Yes Key West was declared a Conch Republic in 1982 following the opening of the Seven Mile Bridge in Marathon.

See our Tips on The Best Dining and Drinking in Key West

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