Key West, the southernmost city in the United States is the capital of the self-proclaimed “Conch Republic”. This place is like no other in the United States and thus unlike any place in the world!
The singer and songwriter Jimmy Buffet perfected his song, “Wasting Away in Margaritaville” while living in Key West. It has a reputation as a bastion of free thought and has been the home of such different celebrities like Ernest Hemingway, Harry S Truman, Tennessee Williams and Calvin Klein as well as Jimmy Buffet.
When the Spanish were first exploring the New World, Key West was passed over for habitation because of its small size. So it was first a haven for pirates. However, its strategic location jutting out into the Straits of Florida eventually attracted the interest of the various European and New World military powers. The USA gained control of Key West in 1821 when the former Governor of South Carolina, John Simonton, bought the island in a disputed transaction that cost him $2000.
Simonton developed the island as a haven for the rich and by 1830, Key West was the richest town in the USA per capita. Frequently devasted by hurricanes and rebuilding meant that the distinctive local construction was designed to be easily repaired.
During the early 1960s, however, Key West became the site of Naval Air Station Key West because of its proximity to the Communist regime in Cuba. Today, Key West is considered to be a fun, crazy and exciting place to relax.
You may fly into Key West International Airport because it has many flights arriving from nearby Miami but large jets cannot land due to the short runway. Many visitors drive from south Florida on US Route 1 across the overseas highway that connects the Florida Keys and ends at Key West. I’d advise the drive because you pass through cool places like Key Largo before arriving in the Conch Republic (pronounced ‘Conk’).
Travelling around the island is fun because it’s popular to rent golf carts or motor scooters. There’s also a tram that gives tours of most sites on the island. If your hotel is central around Duval Street, you can walk or bicycle everywhere.
There’s so much to do in this tropical paradise! Here are my top tips on what you should not miss:
- Ernest Hemingway Home and Museum – This beautiful colonial-style mansion was built in 1851. Ernest Hemingway moved in in 1931 and the site is now dedicated to a museum of his life. You can see his personal effects, European antiques from his collection and his studio where he wrote many of his books.
The house is also a haven for polydactyl cats (cats with at least one extra toe on each paw) which are mostly descendants of his beloved original Polly.
- Mallory Square – This is the best spot in Key West to watch the sunset. This plaza is a bustling hive of activity with arts and crafts exhibits, street food vendors, performers and related revelry.
- Harry S. Truman’s Little Whitehouse – In 1946, the home became President Harry S. Truman’s “Winter Whitehouse” and later presidents used it as a place to rest and unwind; even to this day!
It’s open as a museum with information on the cold war era and naval history.
Local residents often fly in!
- Butterfly and Nature Conservatory – Among the hustle and bustle of the busy main street you’ll find an oasis with an incredible collection of sixty species including exotic butterflies. It’s the perfect way to spend the afternoon with butterflies fluttering around you, surrounded by lush greenery.
Noon at the OK Coral!
- Dry Tortugas National Park – This impressive 19th-century fort is on an island surrounded by crystal-clear waters and is accessible by boat, ferry or seaplane. The guided tour will give you an insight into the history, sea life, reefs and you can even snorkel and swim.
While travelling in the seaplane, your pilot will point out interesting shipwrecks along the route.
- Scuba diving – The Vandenberg is an artificial coral reef built from a retired US Navy missile tracking ship that was intentionally scuttled. It’s in 150 metres of water and you can pre-book scuba diving tours to explore this beautiful underwater world.
- Beaches – A trip to Key West would not be complete without visiting the scenic white sand beaches, these are my two favourites:
- – Smathers Beach is located on the south side of the island. It’s a two-mile stretch of beautiful sandy shores lined with palm trees and calm waters for swimming.
- – Fort Zachary Taylor Beach is less crowded than other beaches on the island. Its crystal-clear waters make for the perfect snorkelling spot.
- Papa’s Pillar Rum Distillery – A rum distillery and brand dedicated to Ernest Hemingway.
If you’re looking for something unique to do on the island, then take this tour and enjoy the tasting at the end.
- Sunset cruise – Explore the hidden coves of the Key West on a delightful late afternoon. You’ll have a memorable time.
Here’s a Pro-tip: Want to try something completely unique? Ride a floating Tikki bar around Key West as you enjoy music, frozen cocktails and wonderful views. It’s great fun!
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Being on an island you can expect lots of fresh seafood, fresh fish shacks and fruity cocktails. Here are my top dining spots:
- A&B Lobster House – This fine-dining establishment has been serving succulent and delicious dishes since 1957. The beautiful wraparound balcony is the perfect spot to enjoy classic Caribbean lobster as you watch the sunset over the marina.
I seafood and I want to eat it!
- Glazed Donuts – The owners of this excellent bakery are culinary geniuses. They develop sophisticated recipes in the form of delicious glazed doughnuts. Have you ever seen a doughnut topped with torched meringue?
- Latitudes – Located on the private island of Sunset Key, this restaurant is perfect for special occasions. You take a short scenic boat trip to reach the restaurant. It’s right on the beach and the fine dining menu is wonderful. I especially enjoy the wagyu steak.
- La Te Da – This historic hotel is the perfect late-night spot for entertainment and cocktails. The establishment has multiple bars including a piano bar and an adults-only cabaret show.
- Rick’s Bar – This is the ultimate entertainment complex with eight bars in one place. Late-night karaoke, live rock music, rooftop cocktails and dancing into the early hours are all available to enjoy with old and new friends.
- Sunset Pier at Ocean Key Resort & Spa – This fits the quintessential island vibe you expect of the Key West with rainbow-coloured tables and chairs on a beautiful dock strung with fairy lights. The 360-degree views are romantic.
Key West is used to catering to a rich and relaxed crowd. These are the best hotel options on the island:
Pink skies at night sailor’s delight?!
- Parrot Key Hotel & Villas – This beautiful and historic property features four swimming pools and many rooms have panoramic views over the Gulf of Mexico. The hotel is decorated in Key West chic and offers little touches like L’Occitane products complimentary in your room.
- The Mermaid & The Alligator – This intimate bed and breakfast is housed in a beautiful 1904 Victorian Home. Their beautiful garden is surrounded by tropical plants where you can enjoy a dip in the plunge pool before relaxing in your beautifully decorated room.
- The Capitana Key West – This nautical and modern looking boutique hotel is the perfect spot for luxury. With its immense swimming pool overlooking the sea, it’s the best place to enjoy the full ‘Key West Experience’. This hotel is pet-friendly; your puppies or kitties will be indulged as much as you.
Key West is the perfect paradise island because it offers all of the tropical relaxation with glamour and convenience. You’ll really enjoy visiting the Conch Republic!