Key West Events, Tours & Nightlife 2025

Sunsets that stop time, music drifting down Duval, and turquoise water that never quits—Key West is paradise with a pulse. Use this guide to compare tickets, book must-do tours, and craft a trip you’ll talk about all year.

Top Deals in Key West

Jump to: Sunset Sails & Cruises · Snorkeling & Water Adventures · Dry Tortugas · Live Music & Nightlife · Festivals & Annual Events · Tours & Attractions · Travel Packages · By Month · FAQ

Sunset Sails & Cruises

Key West sunsets are a nightly event—catamarans, schooners, and champagne sails all race the horizon. Book early for weekends and festival dates.

Snorkeling & Water Adventures

Reef snorkeling, jet skiing, parasailing, and kayaking—choose your vibe, from mellow to adrenaline. Morning trips are calmer; afternoons pair perfectly with sunset sails.

Quick Picks

• Half-day reef snorkel (all gear included)
• Jet ski island tour (guided)
• Parasailing over the harbor
• Glass-bottom boat cruise

Dry Tortugas National Park

Home to Fort Jefferson and pristine snorkeling 70 miles west of Key West—accessed only by ferry or seaplane. Both sell out weeks in advance during peak months.

Live Music & Nightlife on Duval

From laid-back bars to all-night stages, every block of Duval hums with live music and open-air patios. Check daily lineups for your favorite acts.

Classic Spots

• Sloppy Joe’s Bar
• Hog’s Breath Saloon
• Green Parrot
• Irish Kevin’s
• Smokin’ Tuna Saloon

Festivals & Annual Events

From literary tributes to wild parades, Key West’s festival season never really ends—just changes costumes.

• Fantasy Fest (Oct): week-long costumes, parades & parties
• Hemingway Days (Jul): look-alike contest & marlin tournaments
• Key West Songwriters Festival (May): intimate shows across the island
• New Year’s Eve: multiple countdown “drops” & fireworks
• Mallory Square Sunset Celebration: daily street performers & artisans

Tours & Attractions

Explore Old Town, historic homes, and lighthouses between beach and boat days. Key West blends culture with carefree charm.

Don’t Miss

• Ernest Hemingway Home & Museum
• Harry S. Truman Little White House
• Key West Lighthouse
• Old Town Trolley or Conch Train Tour
• Key West Aquarium

Travel Packages

Bundle stays near Duval or the Historic Seaport with tours and cruises for a walk-everywhere itinerary and built-in savings.

Key West by Month

Seasons shift between ideal weather, quiet value months, and festival buzz—pick your rhythm.

• Jan–Mar: Peak weather; book sunset sails and Dry Tortugas early
• Apr–Jun: Calmer seas and clear snorkeling visibility
• Jul–Sep: Hot but great for water days; afternoon storms possible
• Oct–Dec: Fantasy Fest, holiday lights & New Year’s celebrations

Key West FAQ

What’s the best time to visit?

Winter and spring for weather; late spring and fall for smaller crowds. Summer is hot but perfect for water adventures.

Do I need to book Dry Tortugas early?

Yes—capacity is limited and dates sell out weeks in advance.

Where should I stay?

Old Town or Historic Seaport for walkability to Duval, restaurants, and marinas.

Can I do Key West without a car?

Absolutely—everything’s walkable, bikeable, or reachable via trolley and rideshare.