Guests seeking a tropical escape without leaving the country need look no further than Key West. This island city in the Florida Keys, just 90 miles north of Cuba, checks all the boxes: year-round warm weather, crystal-clear water, white sand beaches, lively nightlife, and a bohemian vibe. But when is the best time to visit Key West?
Every month is filled with music and food festivals, or quirky events that define this laid-back destination known as the Conch Republic, so the best time of year to visit Key West really depends on the kind of experience you want to have.
Culturally and geographically distanced from the mainland, Key West has long held a seductive allure for creative spirits and eccentric personalities, from Ernest Hemingway to Jimmy Buffet. You’ll find a thriving contemporary arts scene with high-end galleries, literary festivals, concerts, and theatre productions. Tropical gardens and a picturesque mélange of architectural styles give Key West an irresistible visual charm. Walk down palm-lined streets and you’ll see Queen Anne-style historic homes, ornate Victorians, a sprinkling of Spanish Colonial, restored cigar-makers’ cottages, and pastel-colored tropical houses, none taller than 40 feet. The low skyline is a result of zoning regulations that preserve Key West Historic District’s visual character.
Add in sidewalk cafes, open-air bars, restaurants, and nightclubs, and this southernmost point in the U.S. packs a lot of fun into six square miles. Best of all, it’s easily accessible with Tradewind Aviation.
Tradewind operates on-demand private charter flights in their Pilatus PC-12 fleet, providing the opportunity to fly directly into Key West International Airport with no connections and no crowds. Onboard, sip champagne and relax with comfortable seating for eight guests, ample luggage space, and seamless service. It’s the most elegant and efficient way to transition from the tarmac to a toes-in-the-sand getaway. With a hub near Palm Beach, and a trusted network of partners for longer distances, Tradewind offers the best availability in the industry for private flights to Key West.
Here’s a season-by-season guide to the best time to visit Key West, Florida so you can plan your perfect getaway.
Peak Season: December – April
Key West is the quintessential winter escape. During festive season, the island buzzes with holiday and cultural events. This is the best time to visit if you want sunny, dry weather. Skies are clear, gentle breezes float in from the Gulf, and temperature highs hover in the 70s. March brings the most crowds to the island, along with the highest prices, as snowbirds overlap with spring breakers.
Take advantage of the perfect weather by playing beach volleyball at Key West’s largest public beach, Smathers Beach. Snorkel or dive along the reef, take a private sailing charter or sunset cruise, walk down the charming streets of Old Town to admire the architecture, and explore art galleries. Head to Mallory Square before sunset to sip cocktails amidst jugglers, clowns, and magicians in a nightly sunset celebration, followed by an alfresco dinner on the waterfront.
Annual events during festive season include the Key West Holiday Fest, the Schooner Wharf Bar Lighted Boat Parade, and the Harbour Walk of Lights. From late November to early January, the seaport sparkles with 60,000 twinkling lights strung around palm trees, street lights, and boats whose owners go all out to “deck the hulls.”
Unique celebrations on New Year’s Eve include dancing in Duval Street where thousands gather to watch a giant, illuminated conch shell drop at Sloppy Joe’s Bar. Alternatively, there’s a giant red stiletto drop with a drag queen suspended inside at the Bourbon St. Pub complex.
January is packed with more events like the Key West Food & Wine Festival, a culinary and wine extravaganza with celebrity chefs. Mile 0 Fest, a five-night festival of Red Dirt and Americana music, features established and rising artists who perform in outdoor venues. Writers will be interested in the Key West Literary Seminar, a conference and festival with readings, panel discussions, and workshops.
February is the Key West Art and Craft Festival, an outdoor art show exhibiting work from artists across America and Canada. In March you can witness, or participate in, the Queen Conch Shell Blowing Contest, a celebrated local tradition which heralds April’s big event, the Conch Republic Independence Celebration. This 10-day-long event of parades, boat races, and parties was established in 1982 as a tongue-in-cheek response to a U.S. border patrol blockade of the Florida Keys.
Spring Shoulder Season: Late April – Early June
Savvy travelers visit the Keys after the spring break crowds have left, but before the summer heat arrives. Fewer tourists make it easier to score a reservation at favorite restaurants like Latitudes, a romantic choice for dinner on a private island accessed by a scenic boat ride. Visit popular sites like the Southernmost Point for a photo (go before 8am to beat the cruise ships,) and charter a boat for sandbar hopping. For those eager to snorkel North America’s only coral barrier reef or dive shipwrecks along the Florida Keys Shipwreck Trail, spring is the best time for warm waters and an abundance of marine life.
The Key West Songwriters Festival happens annually in late April/early May. Billed as the largest festival of its kind, it’s five days and nights filled with live music and storytelling from veteran and up-and-coming songwriters.
Summer: June – August
The island is more tranquil during the summer as crowds thin out further. Beaches are quieter and the pace slows down as the days heat up. It’s humid, and a good time to cool off in the water. Spend a quiet morning kayaking or paddleboarding through the mangrove tunnels, take a jet ski tour, go deep-sea fishing, or try your hand at lobstering. Summer thunderstorms appear but pass quickly–this is the beginning of hurricane season.
Annual summer events include Key West Pride Week (June), the Key Lime Festival (July), and Hemingway Days (July). The latter is a week-long birthday bash honoring Papa, who lived and wrote on the island in the 1930s. Events include a look-alike contest, a marlin fishing tournament, the Lorian Hemingway Short Story Competition, and more. Topping off the summer is Lobsterfest in late July/early August, a street festival honoring Florida’s spiny lobster with live music and delicious lobster dishes.
Fall: September – November
Fall is ideal for those seeking a more private, low-key retreat, though the weather is not dependable as September is peak hurricane season. Fortunately, up-to-the-minute tropical weather forecasting provides ample time to prepare in case of a storm.
Spend fall days sailing the backcountry with a local captain who will show you gin-clear creeks and shallow water flats where baby nurse sharks live. Snorkel to explore the sandbars and to see soft corals and starfish. Take time to explore historic sites like the Truman Little White House and Hemingway’s home, garden and the resident six-toed cats. Lounge by the water with an icy cold mojito.
Though quiet compared to high season, there are two high-octane fall festivals that have become legendary. Fantasy Fest in late October is a decadent, Mardi Gras-style costume carnival. In November, Jimmy Buffet fans convene for the Parrot Heads Festival with live music, parties, and themed activities.
No matter the time of year, explore Lunara Bay, a collection of 26 waterfront estates just minutes from downtown Key West, that offers discounts to Tradewind guests when paired with a private flight. Each home has a private boat dock, pool, and chef’s kitchen. A dedicated guest experience manager arranges excursions, in-home dining, and access to the island’s most coveted events.
Key West is beautifully different in every season. Their official motto, “one human family” encapsulates the island’s welcoming ambiance and the city’s commitment to embracing diversity and inclusivity. And getting there is effortless when you fly personal with Tradewind. Choose your favorite season, book your charter flight, and make this tropical getaway more than just a dream.
To learn more about booking a private charter flight with Tradewind, please visit our website. To receive a quote, please submit an inquiry here or contact our specialists at sales@flytradewind.com or 1-203-267-3305 option 2.
Featured Photo by Sean Pavone / Envato / CC B