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Key West
The Conch Republic
The Southernmost Point of the United States, 90 miles to Cuba
Why
The Why, When & How to visit...
Key West is a great getaway for that quintessential laid back island life vibe within the US. It's a combination of New Orleans, Charleston, and the Caribbean with historic southern colonial homes, beautiful flora & fauna, and island vibes. Located where the Atlantic Ocean meets the Gulf of Mexico, Key West has great weather for a Spring Break getaway. It's also a short drive from the airport to get your vacation started right away.
When
How
The Key West Airport (EYW) is a short ~10-15 minute drive to the center of town. There are direct flights from major US cities from the east coast to Texas. EYW is a super small airport where you actually deplane on the runway, which is a fun way to arrive.
November - May are ideal months to visit Key West with highs in the mid to high 70s to low 80s F and limited rain of 3-4 days on average each month. If you're interested in visiting during one of the main events that take place, check out the events calendar here.
Alternatively, Miami's airport (MIA) is 160 miles away, which is typically a 3-4 hour drive, but can take (much) longer with traffic, so flying into Key West is best. Cabs and Uber are accessible from the airport and around town. The town is mostly walkable, but also fun to rent a bike, scooter or golf cart to get around.
Where
to stay...
1) The Reach Key West - The Reach is a 4-star beachfront hotel, part of Hilton's Curio Collection, with a private beach, outdoor pool, and pier on the south-end of Key West. It re-opened at the end of 2019 following a multi-million dollar renovation. It has a well-done nautical, coastal theme highlighted in the rooms, restaurant and lobby decor.
Each room has a balcony for private outdoor space. The restaurant & bar is a modern tribute to tropical fishing lodges of the 1930's with outdoor oceanfront dining. It also has a weekend brunch with live music. For more information and the ability to book, click here.
2) The Marker Key West Harbor Resort - The Marker is located on the north-end in the heart of Key West on the harbor close to many restaurants, bars & attractions. The hotel has an airy, island chic decor throughout with spacious rooms each with a balcony. It also has 3 outdoor pools and an adjacent outdoor restaurant & bar. More details on the hotel, along with the ability to book is accessible here.
3) Kimpton Key West - There are a few Kimpton properties centrally located around Duval Street, ranging in size, each with the same trendy island decor. I stayed at the Kimpton Winslow Bungalows last time I went, which is an amalgamation of old homes and bungalows. It has twists & turns with 3 pools and a pool bar surrounded by beautiful flora & fauna.
The Kimpton Lighthouse Hotel is the other one I'd recommend, which is a little more centrally located across from Ernest Hemingway's House. It also comprises a collection of mid-1800 buildings, including a lighthouse with an outdoor pool and bar. More details on the Winslow's Bungalows, along with the ability to book is accessible here and the Lighthouse Hotel here.
What
to...
Do
1) Explore the Town - Key West is known for Duval Street, which is a strip of bars and restaurants many with live music. Some of my favorite spots are listed below under Eat & Drink. Mallory Square is also a main tourist spot with an aquarium, museums and a popular spot to watch the sunset.
Seeing and taking pictures in front of the Southernmost Point Buoy is kind of a must. Go in the early morning to try to avoid a line. To enjoy some time at the beach, head to the Fort Zachary Taylor State Park. This is where you'll find the famous Key West Direction Sign and a small, nice beachfront space.
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One of my favorite areas of town was the Truman Annex on Emma Street with the Truman Little White House where President Truman spent winters. The Truman Annex is a mini Pleasantville and nice place to stroll or drive through. There's also a Farmer's Market nearby every Thursday 2-7 pm to go for a snack.
Touring Ernest Hemingway's home complete with its 6-toed cats is also a common tourist activity. Alternatively, this 65 minute nighttime tour, takes you to places he lived, worked and played while sharing stories of the history of Hemingway and Key West.
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2) Take a Sunset Sail - Key West is famous for its sunsets. The best place to watch the sunset is on the water. This catamaran option provides appetizers, including peel-and-eat shrimp and has a full bar equipped with champagne, wine, sangria, beer, liquor, and soft drinks all included. So you can enjoy drinks and food, while listening to the sounds of live music, and taking in the sunset. If you prefer a private boat ride, this option can take up to 6 passengers on a 2 hour sail.
If a tiki boat is more your style, check out this option for a 2 hour group BYOB sunset sail limited to 6 passengers. The boat is equipped with a bathroom, bluetooth TV and stereo, and padded bar stools. The boats can also be rented for private reservations for 2 hours here and 4 hours here.
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3) Enjoy some Water Activities - Key West offers a variety of water activities to keep you entertained. This 6 hour catamaran excursion starting at 10 am offers a range of water activities, including snorkeling, kayaking, parasailing and jet skiing. It includes breakfast and lunch to keep you fueled throughout the day.
Alternatively, there's a shorter 4.5 hour option with both morning and afternoon departure times that offers some of the same water activities with food & drinks too on more of a large pontoon boat to check out here. If fishing is your preferred water sport, there's fishing on a 64' catamaran boat available here.
Eat
When in Key West, eat Key Lime Pie. Preferably covered in chocolate on a stick. Oysters on the rooftop of the Schooner Wharf Bar and Gator Bites at White Tarpon were also highlights. Schooner also has Key West Conch Fritters served with Key Lime mustard to try. One of my favorite places for a casual, good lunch on the water is the Sunset Pier. For a more upscale experience, book an advanced, outdoor reservation at Latitudes on Sunset Key. There's a water taxi that takes guests to and from Sunset Key.
Drink
Key Lime drink like a Key Lime Martini from White Tarpon or Key Lime Beer or local beer from First Flight located in the first Pan Am office. Also, at classic dive bars, like Green Parrot and Captain Tony's Saloon. Another fun spot is Shots & Giggles with an order window. Being 90 miles from Cuba, there are a few Cuban cafes with Cuban coffee & food to get too. *If of legal drinking age to drink responsibly
To try the Key West food highlights in one swoop, take this 2.5 hour walking Secret Food Tour available in a small group or private option.
Wear
Pastels & Tropical Prints
Watch
Looking for ideas...
Listen
"Livin' on Key West Time"
by Howard Livingston
& Mile Marker 24