Key West Activities & Attractions
Key West rewards the curious. Turn a corner and find a hidden garden, get out on the ocean, follow the music into a neighborhood bar, or spend an afternoon gallery-hopping through Old Town, just another day in paradise.
Water Activities & Sports
Snorkel, sail, kayak, or spot dolphins. Ocean Key puts you in the center of Key West’s best water adventures, from easygoing cruises to full-throttle fun.
Key West Beaches
Find your way to Key West’s best beaches, from activity-filled shores to quieter stretches, all within easy reach when Ocean Key sets your home base.
Wildlife & Eco-Activities
Explore Key West’s diverse ecosystem, from dolphin encounters and butterfly conservatories to the National Key Deer Refuge and vibrant coral reefs within the Florida Keys.
Shopping
Explore Key West shopping with Ocean Key’s guide to Duval Street boutiques, famous handmade sandals, artisanal Key lime treats, local art and unique island souvenirs.
Museums
Discover Key West’s rich heritage through Ocean Key’s guide to iconic museums, featuring Hemingway’s home, maritime shipwrecks, presidential history and vibrant local art.
Art Galleries
Immerse in Key West’s creative scene, from nature-inspired fine art and photography to contemporary international collections, tribal rugs and unique locally crafted sculptures.
Key West Dining
Explore a curated selection of Key West dining, featuring casual seafood shacks, vibrant sunset piers and upscale waterfront restaurants offering diverse Caribbean and international flavors.
Key West Nightlife
Experience Key West’s electric nightlife, featuring legendary Duval Street dive bars, world-class drag shows, upscale wine galleries and vibrant dance clubs.
Mallory Square
A historic Key West hub since the 1800s, Mallory Square delights locals and tourists with iconic sunsets, unique shops, dining, museums and culture.
Key West Sunset Pier
Sunset Pier is Key West’s most iconic outdoor venue. Visit for breathtaking views, tropical flavors and live music every day with, the best seat in town for sunset celebrations.
Key West Bar Crawl
Ocean Key’s bars serve up tropical cocktails, live music and harborfront views, from lively Duval Street icons to sunset-perfect spots right over the water.
Shows & Festivals
Fantasy Fest
South Florida’s premier 10-day costume festival featuring over 60 parties, glamorous balls and a spectacular, must-see grand parade.
Phil Peterson Poker Run
Ride from Miami to Key West in South Florida’s biggest motorcycle party, featuring poker challenges and legendary Duval Street celebrations.
Race World Offshore Championships
Experience the thrilling Key West World Championship from our legendary Sunset Pier, the city’s premier vantage point for offshore racing.
Key West Half Marathon
Experience a fast, flat and scenic race through historic Key West, celebrated by Runner’s World as a top winter half-marathon.
Mile 0 Fest
Experience the “friendliest festival” in paradise, featuring the best Red Dirt and Americana music at island venues, including Sunset Pier.
The Key West Songwriters Festival
Discover the stories behind the songs at the world’s largest songwriters festival, featuring five days of live music at Sunset Pier.
Just a Few Friends Fest
Experience five days of trop rock music and island community at this unique Labor Day festival.
Events Calendar
Good times and good vibes are always on deck. Check out our activities and the local music scene at Ocean Key Resort and Sunset Pier.
Jun05Snorkel Experience
Dive into the 3rd largest coral barrier reef in the world and the only barrier reef in the continental United States.
Date: May 8 - June 26, 2026
Time: Friday's, varies by tour operator
Location: Off-Site (Catamaran / Key West waters)
Jun06Sunset Sails
There is nothing quite like a Key West sunset, and the second-best place to view one (after the Sunset Pier, of course) is out on the water.
Date: May 9, 2026 - June 27, 2026
Time: Saturday's, Varies (sunset)
Location: Off-Site (Key West waters)
Jun07World Class Fishing
The Florida Keys are known for amazing fishing. From the flats and shallows, sight fishing for permit, tarpon or bonefish or in the deeper waters of the backcountry, on the hunt for snapper, grouper or tuna.
Date: May 10, 2026 - June 28, 2026
Time: Sunday's, Varies by charter
Location: Off-Site (Florida Keys waters)
Jun09Double Dip Snorkel Trip
Explore the turquoise waters of the 3rd largest coral barrier reef, teeming with fish, coral, sea turtles and more.
Date: May 12, 2026 - June 30, 2026
Time: Tuesday's, 2:00 pm – 5:00 pm
Location: Off-Site (Catamaran / Key West reef)
Jun10Zero Duval Scavenger Hunt
Experience a one-of-a-kind, interactive scavenger hunt in the downtown area of Old Town, starting at Zero Duval.
Date: May 13, 2026 - June 24, 2026
Time: Wednesday's, 10:00 am – 12:00 pm
Location: Old Town Key West (starts at Zero Duval)
Jun11Haunted Tours
Explore the SPOOKY side of Key West with a haunted historical tour.
Date: May 14, 2026 - June 25, 2026
Time: Thursday evenings (varies by operator)
Location: Off-Site (Key West – walking or trolley tour)
Jun11Ocean Key Lime Bike Tour
Sightseeing the Key West way with a leisurely island bike tour that can be done in flip flops!
Date: May 14, 2026 - June 25, 2026
Time: Thursday's, 10:00 am – 12:00 pm
Location: Key West (guided bike tour)
Jun11Key West Farmers Market
Visit the Key West Farmers Market every Thursday at the Truman Waterfront.
Date: May 14, 2026 - June 25, 2026
Time: Thursday's, 2:00 pm – 7:00 pm
Location: Truman Waterfront
Jul23Hemingway Days
Fans of Ernest Hemingway’s literary greatness and vigorous life – including scores of bearded Hemingway look-alikes
Date: July 23 - 27, 2026
Time: Varies by event
Location: Key West (Sloppy Joe's Bar, 201 Duval St., and other venues)
Oct16Fantasy Fest
Fantasy Fest turns Key West into a spectacle of masked processions, parties, contests and dances attended by tens of thousands.
Date: October 16 -25, 2026
Time: Varies by event
Location: Key West (multiple venues)
