Exploring Key West’s Warm Weather Delights: A Guide to the Top 10 Activities in May

Exploring Key West’s Warm Weather Delights: A Guide to the Top 10 Activities in May

Top 10 Things To Do in Key West in May

With its laidback island vibe, beautiful beaches, and Caribbean-influenced culture, Key West is a delightful place to visit any time of year. But in May, this southernmost city in the continental United States truly comes alive. The weather is warm but not yet sweltering, the ocean breezes keep things comfortable, and there are lots of fun events happening. From new exhibits at museums and attractions, here are the top 10 things to do in Key West in May.

  1. Relax at Key West Beaches

May is one of the best months to enjoy Key West’s world-renowned beaches before the summer crowds arrive. Grab a beach chair at the famous Smathers Beach, with its nearly two miles of soft white sand. Here you can swim, jet ski, parasail or simply soak up the sun while taking in scenic views of the blue-green water. Nearby, the more secluded Andrew Jackson State Park offers nature trails through mangrove trees in addition to sandy stretches. For an only-in-Key-West beach experience, head to Higgs Beach, which mixes warm Gulf Stream waters with a melting pot of locals and visitors. Be sure to stop by the nearby Key West African Cemetery to honor this important part of local history. And no trip is complete without visiting the iconic Southernmost Point marker, where you can pose for a photo just 90 miles from Cuba.

  1. Take in the Key West Culture

Key West has a funky, free-spirited local culture that’s palpable as you walk down the streets. The island has attracted eccentrics, artists and outliers since the 1800s, when it was a strategic naval port and a nexus of wreckers and salvagers. That diverse heritage is on display at the Key West Shipwreck Museum, which brings local maritime history to life through artifacts and oral histories. For literary history, visit the home of Key West’s most famous resident, Ernest Hemingway, where he wrote some of his greatest works in the 1930s. Of course, no discussion of Key West culture is complete without mentioning the drag and cabaret scene. Head to nightlife hot spots like 801 Cabaret or Aqua Nightclub for hilarious, jaw-dropping drag queen shows. And be sure to people-watch at classic haunts like Sloppy Joe’s Bar, where Hemingway was a regular.

  1. Tour Key West Art Galleries and Exhibits

In keeping with its artistic spirit, Key West boasts a thriving gallery and museum scene. May features new exhibit openings, guest artists, and chances to meet creators. One highlight is The Studios of Key West, showcasing the island’s best contemporary art across a range of mediums. Stop by the Key West Art & Historical Society to take in masterpieces portraying local scenes, including the famed Key West Prize art competition. For provocative, socially-conscious works, check out galleries where resident artists create political art. And nature lovers will appreciate the Key West Botanical Garden and Tropical Forest, which hosts creative exhibits amidst its collection of orchids, bromeliads, and tropical plants. Keep an eye out for special events, like meet-the-artist nights, that add extra flair to the regular exhibits.

  1. Go Fishing

Anglers are drawn to Key West for its access to the Gulf of Mexico and Atlantic Ocean, which offer outstanding saltwater fishing year-round. Come May, popular catches include snapper, grouper, mahi-mahi, and even marlin. For beginners, easiest places to drop a line include the Historic Seaport Harborwalk, Higgs Beach Pier, and off bridges like White Street Pier. Those seeking a full Charter experience can book a half day or full day fishing expedition with one of the many experienced local guides, who provide top-quality rods, bait, and equipment. The knowledge local Captains have of the best spots to catch different types of fish is invaluable. Many excursions include an opportunity to cook and enjoy your fresh catch right on board. If spearfishing, lobstering, or catching stone crab interests you, most Charters offer a variety of fishing activities beyond pole fishing. Back on land, you can have your catch cooked any way you like it at one of Key West’s waterfront seafood restaurants.

  1. Dine at Key West Restaurants

Speaking of restaurants, Key West is a paradise for foodies who love fresh seafood, Caribbean flavors, Cuban cuisine, and of course Key Lime pie. For fine dining, make reservations at Latitudes or Azur that blend local ingredients with global techniques and flavors. Alternatively, kick back with live music and drinks at classic haunts like Schooner Wharf Bar & Grill or Two Friends Patio Restaurant. Sample conch fritters, fish tacos, or cracked conch at casual spots like Conch Republic Seafood Company. Experience the fresh catch of the day grilled, blackened, fried or stewed at Harpoon Harry’s. Savor Cuban sandwiches loaded with ham, roast pork, Swiss cheese and pickles at one of the many Cuban bodegas. Try authentic paella and sangria at Spanish-infused restaurants like Santiago’s. And save room for dessert at Blue Heaven, where the decadent Key lime pie comes topped with billowy meringue. From food trucks and waterside shacks to upscale candlelit dining rooms, Key West’s culinary scene offers delicious ways to soak up local flavors.

  1. Take a Day Trip to Dry Tortugas National Park

For a fascinating day trip, take the high-speed ferry 70 miles west of Key West to Dry Tortugas National Park. This remote paradise is made up of seven small islands, most uninhabited. Tour Fort Jefferson, a massive 19th century coastal fortress that takes up one island. Snorkel and scuba dive the turquoise waters to discover coral reefs and sunken shipwrecks. Keep an eye out for birds like sooty terns, brown noddies and other species that call Dry Tortugas home. Kayak, paddleboard and swim off secluded beaches to take in the pristine natural beauty. Pack a lunch to enjoy on the ferry ride out as no outside food is allowed on the island. Bring plenty of water, sunscreen and a hat, as there are few shaded areas or buildings once you arrive. Guided tours provide insight into the natural features and history of this unique park, accessible only by boat or seaplane. While a day trip is sufficient to take in the highlights of Dry Tortugas, you can also camp overnight on Garden Key to extend your stay in this isolated tropical paradise.

  1. Ride Around in Style on a Key West Trolley Tour

One of the best ways to get oriented in Key West and learn about the history and highlights of the area is by trolley tour. Local guides drive visitors to all the top attractions and lesser-known spots, providing narration and answering questions along the way. Some trolleys are enclosed, while others are open-air, allowing you to feel the warm ocean breeze as you ride. Stops often include the Hemingway House, Southernmost Point, Truman Little White House, Duval Street, Mallory Square and other iconic landmarks. You’ll learn about the colonial era to modern day as you wind past historic homes, neighborhoods, and architectural gems. Specialty tours range from ghost and haunted history to art and culture, magic, and old town architecture. Sunset tours end with a viewing of the famous Mallory Square sunset celebration. Multi-day pass options are available if you want to use the trolley as transportation between lodging, dining, and attractions. Trolley tours are perfect for families with kids, seniors, those with mobility issues, and anyone wanting a low-key overview to simply soak up the atmosphere of Key West.

  1. Celebrate Key West Culture at Local Hot Spots

While Key West hosts various annual festivals, you can experience authentic local culture any time by heading to classic hot spots where locals gather. Start your morning with coffee and breakfast at Cuban Coffee Queen, a colorful cafe with pressed sandwiches and strong cafe con leche. At night, join the laidback party at Schooner Wharf Bar, where you can eat, drink, people watch and listen to live music right on the waterfront. The Green Parrot Bar is a historic hangout dating back to the 1890s, with a lively mix of locals, sailors, bikers and out-of-towners rubbing shoulders. Their motto, “Come as you are,” sums up the accepting vibe. Enjoy sunset atop the iconic Sunset Pier, where you can sip mojitos and watch the sky light up in a fiery display of color. And be sure to catch a drag show at 801 Cabaret, where fabulously dressed performers lip sync and dance up a storm on stage. From low-key tiki bars to bustling open air restaurants, Key West offers plenty of ways to soak up the spirited culture.

  1. Relax at a Key West Spa

Of course, lots of visitors head to Key West simply to relax and rejuvenate. The island offers a variety of pampering spas where you can get a massage, facial, body treatment, or salon service while soaking up the tranquil atmosphere. For a full resort spa experience, treatments at Hyatt Centric Key West Resort include lipid hydrating facials, cooling aloe massages, and rejuvenating body scrubs using ingredients like coconut and sea salt. The iconic Pier House Resort and Spa offers sea-inspired treatments like the Liquid Glow, incorporating Marine Serum to heal skin damaged by sun and saltwater. For a more intimate, personal touch, book a service at a local spa like The Clay Studio Key West. Their expert estheticians and massage therapists incorporate local botanicals like coconut, key lime, sea lavender, and hibiscus into treatments in their peaceful space in Old Town. Whether it’s a quick manicure or an all-out spa day, Key West’s spas offer relaxation for your body and mind.


With island music, artistic culture, delicious food, natural beauty, and historical attractions, Key West offers the perfect island escape in May. You can soak up the sunshine and warm ocean breezes on beautiful beaches by day, then feast on fresh seafood and enjoy drag cabaret shows at night. New museum exhibits showcase emerging Keys artists, while tours and trolley rides reveal the rich history. Outdoor activities range from world-class fishing to snorkeling vibrant reefs to biking tropical trails. And the island provides plenty of spots to sip a mojito, read a Hemingway novel, or simply do nothing but relax and recharge. Whether you’re visiting for a long weekend or an extended stay, Key West in May has something delightful to offer every type of traveler. With comfortable temperatures and fewer crowds than summer, it’s an ideal time to experience this one-of-a-kind sunny escape. You’ll find a blend of adventure, indulgence, natural wonders, history and culture that you won’t find anywhere else. When you’re seeking that perfect mix of tropical charm, lively entertainment, and island vibes, Key West in May is the ultimate destination.

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