A Weekend Getaway at Key West's Casa Marina Hotel

By Audrey St. Clair
January 13, 2015

Henry Flagler opened the Casa Marina, A Waldorf Astoria Resort in 1920 on the largest expanse of beachfront in Key West. A number of renovations have since taken place, but that Roaring '20s glam is still very much alive amid the Jet Skis and parasails. Do a candelight dinner on the sand. Munch on conch ceviche at the pool bar. Get a massage on the beach. Bike up to Duval Street. It's all there — it just depends on what mood you're in.

Key West Weekend Getaway | Best Hotel in Key West | Casa Marina Hotel

Casa Marina Hotel

Opened on New Year's Eve 1920 by Henry Flagler himself, the Casa Marina hotel was originally built as a swanky spot for the patrons of the Overseas Railroad. Three days after the grand opening, President Warren Harding visited, and the hotel soon became an "it" winter destination for well-heeled sets from across the country.Courtesy Casa Marina
Key West Weekend Getaway | Best Hotel in Key West | Casa Marina Hotel | Poolside

Poolside Therapy

This adult-only pool is the perfect stopping point on the way to and from the beach. I just happened to pass by around 11 a.m. when a server greeted me with the complimentary drink of the day, a raspberry margarita. No doubt "It's 5 o'clock somewhere" is the unofficial slogan of the Conch Republic.Courtesy Casa Marina
Key West Weekend Getaway | Best Hotel in Key West | Casa Marina Hotel | Piers

Piers Aplenty

Piers in Key West are almost as common as fallen coconuts, and two of the best (and least crowded) jut from Casa Marina. From the pier, jump in the water. Watch the sunset. Board a catamaran. Or just sit, like me, dangling my feet off the edge.Courtesy Casa Marina
Key West Weekend Getaway | Best Hotel in Key West | Casa Marina Hotel | Souvenirs

Embrace the Gimmicks

Casa Marina feels like an island itself — sequestered from the tourist scene in Old Town but just a five-minute bike ride away if the party mood strikes. Which it did once or twice, as did the need for a kitschy souvenir (or three).Courtesy Casa Marina
Key West Weekend Getaway | Best Hotel in Key West | Casa Marina Hotel | Sand Sculpting

Sand Sculpting

Husband-and-wife duo Marianne van den Broek and Chris Guinto travel the world creating these jaw-dropping sand sculptures, but home base is Key West, where they've carved their way quite literally into every possible market, especially weddings. They've built everything from seahorses in the shape of hearts to a life-size sculpture of Harry Truman to intricate Halloween ghost towns. Receiving a lesson from Marianne was a highlight of the weekend. My attempt at a coconut, however, not so much.Courtesy Casa Marina
Key West Weekend Getaway | Best Hotel in Key West | Casa Marina Hotel | Private Beach

Private Beach

Casa Marina's stretch of beachfront is the largest in Key West (1,200 feet, to be exact). A lounger, my book and a mojito was all I needed on this near-cloudless afternoon.Courtesy Casa Marina
Key West Weekend Getaway | Best Hotel in Key West | Casa Marina Hotel | Southernmost Point

Southernmost Point

A stop at the iconic buoy-shaped landmark is a must for Instagram, but this isn't really the southernmost point in the U.S. (the actual one is on private property). Come for the photo and the view, and then head off. It's the only thing to see on this little corner of Whitehead Street.Audrey St. Clair
Key West Weekend Getaway | Best Hotel in Key West | Casa Marina Hotel | Hemingway House

Hemingway House

"The world breaks everyone, and afterward many are strong at the broken places," Ernest Hemingway wrote in A Farewell to Arms. He was able to capture so much with so little, a feat I aspire to in my own writing. Standing in his writing studio, imagining his fingers clicking the keys, typing perhaps those very words, I realize how many untold stories must remain between these walls.Audrey St. Clair
Key West Weekend Getaway | Best Hotel in Key West | Casa Marina Hotel | Hemingway House Cat

Hemingway House Six-Toed Cat

Snowball, the original six-toed cat, was given to Hemingway by a ship captain; there are about 50 felines roaming the grounds today. Given the small size of Key West, it's possible that many of the cats on the island are related. (Fun fact: Several of the polydactyls at the Hemingway House respond when called by name.)Audrey St. Clair
Key West Weekend Getaway | Best Hotel in Key West | Casa Marina Hotel | Hammock

Sway in the Sun

At the Casa Marina, I'm never far from a hammock — it's like the trees were put there specifically to hold them.Courtesy Casa Marina
Key West Weekend Getaway | Best Hotel in Key West | Casa Marina Hotel | Sloppy Joe's

The Bar That Started It All

This is the first location of the famed Sloppy Joe's bar that opened in 1933, which was actually modeled after the original one in Havana, Cuba. The story of the name goes like this: At this joint in Havana, owner Joe Garcia Rio sold both liquor and iced seafood — well, in the grueling Cuban heat, the ice would always melt and the patrons would tease Joe that he ran a "sloppy" place. (P.S. The bar is not to be confused with the eponymous sandwich that, of course, originated right here in the good ol' US of A.)Audrey St. Clair
Key West Weekend Getaway | Best Hotel in Key West | Casa Marina Hotel | Wedding Ceremony

Wedding Ceremony

The Casa Marina hosts nearly 100 weddings a year. With a view like that, all you really need is a simple arch (this one's made from driftwood) to frame the scene.Audrey St. Clair
Key West Weekend Getaway | Best Hotel in Key West | Casa Marina Hotel | Key Limes

Key Limes All Day

You put the (Key) lime in the coconut, and eat it all up. A homemade Key-lime tart paired with coconut ice cream is as authentic as it gets.Audrey St. Clair
Key West Weekend Getaway | Best Hotel in Key West | Casa Marina Hotel | Sunset

Saying Goodbye to the Day

Dinner on the beach at sunset as the breeze just started to pick up was the perfect way to wrap the weekend ... that and a midnight ocean swim in the moonlight.Audrey St. Clair

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