How Does Key West Ring in the New Year? Your 2026–2027 Local Guide
Ring in 2027 in Key West with famous New Year’s Eve celebrations, the final sunsets of 2026, and the first ones of the new year. Enjoy jet skiing, snorkeling, parasailing, and other watersports throughout the holiday week, along with special events and festivities around the island.
Quick Answers
Key West rings in the New Year by:
-
Celebrating the final sunsets of 2026 and first ones of 2027. Key West is famous for its sunset celebrations, and sunset sails, dinner cruises and combination excursions offer memorable ways to close out the year and welcome the next.
-
Welcoming 2027 with famous midnight drops. Key West’s unique New Year’s Eve traditions include the Red Shoe Drop, Conch Shell Drop, Pirate Wench Drop and other celebrations around the island.
-
Making the most of New Year’s Week. Jet skiing, parasailing, snorkeling, dolphin trips, sandbar adventures and local events offer plenty to enjoy throughout the holiday week and to kick off the new year.
Celebrate the Final Sunsets of 2026 and First Ones of 2027
Make sunset excursions part of your New Year’s plans. Choose from sunset sails, dinner cruises and combination excursions featuring snorkeling and dolphin encounters before a sunset cruise back to Key West.
Sunset Sip & Sail: Enjoy unlimited drinks, appetizers and live music as you sail into the sunset.
Sunset Dinner Cruise: Enjoy a tropical dinner buffet, open bar and live music aboard the Party Cat.
Two-Reef Snorkel & Sunset Cruise: Snorkel two reef locations, then enjoy unlimited beer, wine and champagne during the sunset cruise back to Key West.
Dolphin Watch, Snorkel & Sunset Cruise: Look for dolphins in their natural habitat, snorkel, then enjoy unlimited drinks and the sunset while returning to the dock.
New Year’s Eve Celebrations in Key West
Key West has its own unforgettable ways of welcoming the new year. Instead of a traditional ball drop, crowds gather for quirky midnight countdowns, live entertainment and local traditions, including one that has been shared with audiences around the world.
Red Shoe Drop: A giant red high heel descends from above Bourbon Street Pub on Duval Street, with this year’s featured drag performer, Jada Pinkett Fox of Dallas, Texas, aboard to welcome 2027. Event organizers have confirmed CNN will once again cover this famous Key West tradition.
Conch Shell Drop: Sloppy Joe’s welcomes 2027 with its famous giant conch shell lowered at midnight on Duval Street.
Pirate Wench Drop: Schooner Wharf Bar celebrates in the Historic Seaport as a pirate wench is lowered from the mast of a tall ship at midnight.
Other Key West traditions include the Flight Attendant Drop at First Flight Island Restaurant & Brewery and the Key Lime Wedge Drop at Sunset Pier. Bars, restaurants and entertainment venues throughout the island also host parties, live music and festivities.
New Year’s Week on the Water
Get ready to welcome 2027 with some Key West adventures on the water! The days between Christmas and New Year’s Eve are a great time to enjoy everything the island has to offer. Here are a few ways to make the most of your holiday week:
Rise & Reef Morning Snorkel: Start your morning with a light breakfast aboard the Sandie Cat before exploring Key West’s coral reef. Enjoy unlimited mimosas and draft beer after snorkeling.
Jet Ski Tours: Circle Key West on a guided 28-mile adventure with stops at points of interest and a local sandbar. A second rider rides free.
Parasailing: Soar above the turquoise waters for spectacular views of Key West and the surrounding islands. Choose from convenient departure locations around the island.
Do It All Watersport Adventure: Enjoy 10 watersports activities, including jet skiing, snorkeling and a private inflatable waterpark, with an option to parasail. Grilled lunch, soft drinks and unlimited beer, wine and champagne after activities are included.
Sandbar & Kayak Adventure: Explore winding mangrove waterways by kayak, try paddleboarding and relax at a secluded sandbar. Lunch and unlimited mimosas, draft beer and wine are included.
Dolphin Watch & Snorkel: Look for wild dolphins in their natural habitat, then explore Key West’s underwater world. Enjoy unlimited draft beer, wine, champagne and soft drinks after snorkeling.
And that’s just a sample of the amazing adventures available during New Year’s week! Explore all Sunset Watersports activities and book your favorites in advance during one of Key West’s most popular times to be on the island.
New Year’s Around the Island
Key West is known for throwing great parties, and there’s plenty happening across the island between Christmas and New Year’s Day! Discover festive waterfront displays, seasonal attractions, historic home tours, special dining experiences and live entertainment throughout the week.
Harbor Walk of Lights: Stroll through the illuminated Historic Seaport, with waterfront restaurants, shops and bars along the way.
Waterfront Winter Wonderland: Head to Truman Waterfront Park for amusement rides, ice skating, seasonal displays and family activities.
67th Annual Key West Home Tours: Step inside four privately owned historic homes and the Oldest House Museum on December 29–30, from 1–4 p.m.
New Year’s Day Hangover Brunch at Four Marlins: Celebrate the first day of 2027 with an elegant oceanfront brunch at The Reach, featuring bottomless mimosas and live music.
First Fridays on Fleming: Browse galleries, boutiques and artisan pop-ups along Fleming Street on January 1, from 6–9 p.m., with music and tastings.
The Restless Natives: Allman Brothers Tribute: Catch a live tribute to the Allman Brothers Band at the Key West Theater on January 1 at 8 p.m.
For additional events and newly announced festivities, check the Florida Keys Events Calendar and Key West Attractions Association Calendar.
Key West New Year’s FAQs
What is the weather like in Key West for New Year’s?
-
Expect warm days and mild evenings, with average highs around 76–78°F and lows around 66–68°F. Pack lightweight clothing, sunscreen and a light jacket for breezy evenings and boat excursions.
Can you swim and snorkel in Key West during New Year’s week?
-
Yes! Swimming and snorkeling are available year-round. Average ocean temperatures are around 75°F in December and 73°F in January. Cold fronts and windy conditions can affect water activities, so check the forecast before your trip.
How busy is Key West between Christmas and New Year’s?
-
The week between Christmas and New Year’s Day is one of Key West’s busiest times of year, with visitors arriving to celebrate the holidays and enjoy the island’s festivities. Plan ahead and reserve accommodations, restaurants and watersports excursions early to secure your preferred dates and times.
Are Key West’s New Year’s Eve celebrations free?
-
Many of the famous midnight drops, including the Red Shoe Drop, offer free public viewing. VIP parties, special dining experiences and other ticketed celebrations may require reservations.
Are restaurants, attractions and watersports open on New Year’s Day in Key West?
-
Many businesses and excursions operate on January 1, although some have adjusted schedules or limited availability. Confirm holiday hours and departure times directly with each operator.
Planning some beach time during your Key West getaway? Here’s a helpful guide to the best beaches on the island.
