36 Hours in Key West – Where to Stay, Eat, and Play

One of the most well-known islands in the Florida Keys, Key West is a uniquely positioned vacation spot that’s one of the most tropical in the U.S. A long-time favorite among those who enjoy fishing, snorkeling, and the seafood dishes on the Eastern seaboard, it’s easily accessible by both car and air and of course the sea. If you’ve only a weekend, here are the best ways to spend 36 Hours in Key West.

Where to Stay With 36 Hours in Key West

Accommodation options abound in Key West. Beachfront condos, traditional hotel rooms and suites, bed and breakfasts, and vacation rental apartments and homes are available. Amenities may include private courtyards and pools, patio bars, bicycle rentals, and on-site dining.

If you only have 36 Hours in Key West, I recommend making the most of it and staying somewhere unique.

For a traditional Florida feel, book a stay at the Margaritaville Key West Resort & Marina near Mallory Square. Enjoy panoramic views from your balcony, deck-side dining, and a soothing massage at this popular luxury resort. At DoubleTree by Hilton Hotel Grand Key Resort – Key West, guests can swim in the zero-entry pool, sip tropical drinks at the Tiki Bar, and dine at the on-site Palm Haven Restaurant. Its proximity to the airport will practically have guests lounging in luxury on arrival in Key West.

If you are looking for a budget stay without compromising on amenities, check out the NYAH Hotel.

Where to East With 36 Hours in Key West

The food in Key West is truly representative of all of the cultures that have crossed this storied island, and visitors will enjoy flavors from Latin American, Caribbean, French, Asian, and, of course, all-American dishes. Don’t miss Duetto Pizza and Gelato for some of the best pizzas in Key West. Located near Mallory Square, it serves traditional cheese pizza, pepperoni pizza, and specialty pies like Capricciosa, Con Carne, Con Pollo, Caprese, and La Margherita. Feeling adventurous? Try the white pizzas and the stuffed pizzas, too. For dessert, savour more than a dozen flavours of gelato, made fresh daily.

Latitudes Restaurant offers a more upscale dining experience with Gulf of Mexico views for that special celebration. This award-winning restaurant is known for its romantic ambiance. Dine on lobster and crab cakes, carpaccio spiced ahi tuna, and freshly prepared snapper, grouper, cobia, scallops, and lobster tail; the menu also includes steaks, pasta, and chicken dishes. Blue Heaven, another Key West staple, offers laid-back dining in a casual atmosphere. The menu features Jamaican Jerk Chicken, vegetable stir fry, plantains, Caribbean BBQ shrimp, and more, plus a full children’s menu.

Key Lime Pie

Of course, you can’t spend 36 hours in Key West without trying Key Lime Pie. Although you can find it throughout town (and in a variety of forms), the best places to enjoy it are iconic establishments like Kermit’s Key West Key Lime Shoppe, known for its classic and inventive key lime pie creations. Another must-visit is Blue Heaven, a popular eatery where you can savor their delicious version of this Floridian delicacy in a laid-back, open-air setting. For a unique twist, head to the Key West Key Lime Pie Co. located on Greene Street, offering scrumptious variations, including frozen key lime pie on a stick. These spots encapsulate the essence of Key West’s culinary scene, providing delectable interpretations of the beloved Key Lime Pie.

Things to Do With 36 Hours in Key West

Key West Snorkeling

Snorkeling is by far one of the most popular things to do in Key West. After all, the water is crystal clear, and there’s an abundance of sea life to view. Dry Tortugas National Park is a short ferry ride from Key West, and several sites there are perfect for novice and experienced snorkelers. Many visitors also book fishing charters. Hiring a local captain who knows the waters well and can provide a custom charter means visitors get to do more of the fishing they love, whether that’s a reef, wreck, deep-sea, or other fishing for snapper, grouper, tarpon, and more.

Homes of Famous Key West Residents

In addition to its sun-soaked beaches and vibrant outdoor activities, Key West unfolds a rich tapestry of American literature and history that beckons exploration. Dive into the cultural fabric with visits to iconic landmarks associated with literary legends and historical figures. The former residence of the iconic writer Ernest Hemingway stands as a testament to his legacy, now doubled as a museum and home to the famed six-toed cats that roam the premises. Walking through the rooms where Hemingway penned some of his most famous works offers a unique glimpse into the mind of this literary giant.

For theater enthusiasts, the home of renowned playwright Tennessee Williams opens its doors to the public. Step into the world where Williams found inspiration for his timeless plays and immerse yourself in the ambiance that shaped his creative spirit. Additionally, a journey through history unfolds at the Harry S. Truman Little White House, once a retreat for the 33rd American President. The preserved residence provides insight into Truman’s life and the significant decisions made during his visits to Key West.

These literary and historical treasures add depth to the vibrant island experience, offering a well-rounded itinerary for those seeking a cultural infusion during their 36 hours in Key West. Each site echoes the whispers of the past, inviting visitors to connect with the profound stories that have shaped Key West’s unique identity.

Take a Guided Bike Tour of Key West

Taking a guided bike tour during your fleeting 36 hours in Key West allows you to explore iconic landmarks and hidden gems easily. Pedal through the charming streets to witness the architectural beauty of landmarks like the Ernest Hemingway Home (home to the famous six-toed cats), the former residences of playwright Tennessee Williams, and the Little White House, once inhabited by President Harry S. Truman. As you navigate the quaint neighborhoods, you’ll also have the chance to admire the picturesque Southernmost Point, revel in the vibrant Mallory Square, and cruise along the historic Old Town. The guided bike tour covers the must-see attractions and unveils lesser-known sites, adding depth and richness to your brief yet immersive encounter with Key West’s history and culture.

Discover the Life of Jimmy Buffett

Key West holds a special place in the heart of legendary musician Jimmy Buffett, and exploring his ties to the island adds a unique dimension to your Key West visit. Renowned for his Margaritaville empire, Buffett’s life in Key West is a captivating tale of inspiration, music, and the laid-back island lifestyle. You can delve into this intriguing story by taking a dedicated Jimmy Buffett tour that unravels the chapters of Buffett’s life on the island. Visit significant locations such as Sloppy Joe’s Bar, where Buffett often performed, and gain insights into the anecdotes and experiences that influenced his music. This tour offers a glimpse into the fascinating life of a music icon and allows you to relish the Key West atmosphere that has inspired countless songs.

Is 36 Hours in Key West Enough?

As the sun sets on my whirlwind adventure in Key West, I can’t help but reflect on the charm and allure of this vibrant island paradise. A mere 36 hours felt like a fleeting taste of the laid-back atmosphere, yet it left an indelible mark on my travel memories. From strolling through the historic streets lined with pastel-hued cottages to indulging in culinary delights at unique eateries, each moment seemed to transport me to a world where time slows down.

The tropical breeze, warm sunshine, and inviting turquoise waters created a backdrop that beckoned exploration. Whether snorkeling amidst vibrant coral reefs or casting a line into the abundant fishing grounds, Key West revealed itself as a haven for outdoor enthusiasts. And let’s not forget the world-class dining experiences – each restaurant is a culinary gem offering a fusion of flavors that delight the palate.

While my brief sojourn in Key West has left me yearning for more, it’s evident that this island paradise is more than just a destination; it’s a retreat for the soul. The allure of returning to uncover hidden gems, experience the unique culture, and soak in the sun-soaked ambiance is strong. So, is 36 hours in Key West enough? It’s a tempting taste, but I’m already plotting my return to dive deeper into the richness this charming slice of paradise has to offer. Until next time, Key West, your enchanting spirit lingers.

Author: Floyd Davis is a fishing Captain and a longtime Key West, Florida resident. He fishes for key-west-fishing when he is not too busy drinking.

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Cover image credit – www.ivisitanguilla.com