25 Things To Do in Key West on New Year's Eve
Published April 24, 2025
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If you're fortunate to be ringing in New Year's Eve in Florida Keys island, the weather is sure to be superb.
Numerous well-known spots across the island provide distinct options for celebrating New Year's Eve in "Key West" Way.
Also, the most well-attended events here attract huge audiences, so make sure to show up early and remember to reserve your vacation ahead of time.
Here are 25 things to do in Key West on New Year's Eve!
1. First Flight Island
This trendy restaurant is wonderful to check out year-round, but their New Year’s Gatsby-themed celebration is sure to be amazing.
Arrive in your most exquisite Gatsby-themed attire to savor an open bar of four hours, champagne cheers, and a reproduction of an antique Pan US aircraft scheduled to depart at midnight.
2. Schooner America
This 3-hour boat excursion is a classic method to greet the coming year with flair.
The ticket cost covers appetizers and the open bar throughout the evening, along with lively music to elevate the atmosphere.
You will also receive a VIP pass to Schooner’s Wharf Pirate's Wench Drop that'll conclude your celebrations flawlessly.
Also, if you're visiting with kids during New Year Eve and wish to experience the city atop the water, choose a family-oriented sunset cruise.
The Sunset Sail on the Schooner is an excellent choice as it leads you through Mallory Square along with several other well-known attractions in Key West.
3. Nine One Five
Founded by proprietor Stuart Kemp, the excellent European-style restaurant has received multiple accolades for outstanding culinary achievement in NYC.
Situated in a beautifully restored Victorian home featuring a sleek and modern interior, it is an excellent spot to 'observe and be observed' in the city.
The imaginative chefs here provide a diverse selection of tapas along with an extensive menu of gourmet dishes and a premium wine variety to select from.
In fact, everything tastes wonderful here.
Feel free to choose a variety of small dishes and starters to begin with, or select a robust fresh pasta bowl to prepare you for the night.
Also, there are various dining choices available here both indoors and on the porch that faces Upper Duval Street.
Even, there's a fantastic retro-styled club room on the upper level with views of Duval St, referred to as 'Point 5', available for leasing for private occasions.
4. Tropical New Year Eve
The year won’t be officially concluded until the drag queen descends with a red high heel.
Other locations around the city also feature a maid, Cuban cigar, conch, and lime wedge.
Then, the highlight is sipping champagne at a 75-degree temperature.
5. Pirate Wench Lowering
This unique, globally renowned show welcomes New Year's Eve with a touch of pirate style.
A short time prior to midnight, exactly at the exquisite Schooner WharfBar, a 'wench' will theatrically glide down the 75-foot Schooner mast.
With a view of the historic harbor of Key West, this serves as a wonderfully enchanting maritime getaway.
6. Winter Wonderland
During December and New Year, the CoffeeButler Amphitheater at Truman Waterfront transforms into a Winter Wonderland of Key West for entire ages, a vacation experience suitable for all family members.
There are always stalls here offering food, beverages, and gifts, along with attractions and rides, illuminated exhibits, and, most importantly, a personalized skating rink suitable for both beginners and experts.
7. Afterdeck Bar & Louie’s Backyard
Two of Key West's finest spots are situated at the exact beautiful waterfront site.
Louie’s Backyard eatery is situated in a beautifully restored Greek Victorian in Key West.
Here, Chef Shook Doug presents gourmet Caribbean and international dishes, specializing in fish sourced from local waters.
Then, the Afterdeck Bar is situated in the backyard on the vast ocean deck offering a unique perspective and personal ambiance of the sea.
The dusk, lunar ascent, and celestial body viewing experiences are unmatched here, rendering it the ideal place to celebrate New Year's Eve.
8. Holiday Bazaar
This gathering occurs inside the street and on the patio outside the historical and beautiful Customs House.
Situated at exactly 281 Front Street, it showcases vendors for food and beverages as well as holiday shopping, musicians, and a festive light display that will be cast onto the Custom House's facade.
9. Red Shoe Dropping
As earlier stated, each year, thousands come together to watch a glittering high-heeled red shoe being lowered from the Bourbon Street Pub, what is undeniably the most splendid New Year Eve festivity in Key West.
Sushi, the drag queen, also called Gary Marion, recently has taken a backseat, and Randy Roberts, acclaimed drag performer, will now be in the shoe while it descends.
Anticipate a spectacular night of exciting live music, alongside abundant live entertainment and street performances in front of the Bourbon Street Pub.
10. Cocktail Tour
This New Year tour includes much more than simply cocktails and drinks.
Explore the neighborhood spots and Hemingway Daiquiri's origins, as you stroll through historic districts.
11. La Trattoria
The exquisite Italian restaurant offers delightful cuisine and a superb ambiance that it seem as though you've been taken to Italy.
All the meals here taste fantastic and there's also an excellent wine selection, rendering it an ideal venue for a memorable New Year Eve celebration.
Also, their outdoor bar and dining area with a fantastic Duval Street view are perfect for providing you with a prime spot for New Year's Eve.
Moreover, it is located at the rear on the Appelrouth Lane next to Virgilio’s bar, a beloved music spot in the area that you shouldn't overlook for its exceptional chocolate martini cocktails.
12. Historical Inns Tour
Although located far from North Pole, the Inns of Key West in New Year and December are adorned as though it is anticipating Santa's visit.
So, delight in that festive mood and the distinctive heritage and architecture of Key West through the Holiday Historical Inn Tours.
These tours highlight four celebratory island accommodations every night along with features such as a visit to Key West's Butterfly and Nature Conservatory and Hemingway Rum Co Distillery.
The tour remains self-directed, allowing guests to begin at any asset, and trolleys additionally offer transit between stations.
Also, innkeepers are available to provide information about the area and its past, and they will invite you in for drinks and small bites.
13. Tennessee Williams's Fine Arts Centre
Ensure you purchase tickets in advance for the tropical rendition of Nutcracker ballet by Key West at this arts center.
Shown every year, the story of Clara's enchanting journey to the Sugarplum Fairy's realm is changed into a marine and island fantasy.
The performance features a professional team consisting of 15 members along with over 50 Keys kids and various local entertainers.
Then, following this performance, the theater welcomes a range of December events such as musical honors and classic television specials from Hollywood.
Even, the center additionally houses the SouthFlorida Symphony, and their schedule features a variety of live shows, ranging from performances featuring renowned artists such as Kristin Chenoweth to Broadway productions like Jersey Boys.
Note that there is a high demand for The Nutcracker tickets, so purchase in advance if you wish to view this vibrant display.
14. Sloppy Joes Bar
In the performance at this bar, a massive shell is dropped slowly from the roof (similar to Times Square's ball drop, though with a Florida twist).
Customers within the spot can observe this conch shell falling on the screens, although the prime viewing location is at the corner of Duval and Greene Street.
15. Little White House
This place is a historic museum which has been flawlessly renovated and remains a stunning sight to see during New Year.
It's adorned precisely as it stood during WWII, including its Christmas holiday lights and the assortment of 1950s and 1940s decorations.
In December and New Year, it provides unique VIP tours that include champagne, hot cocoa, snacks, and additional items.
Also, Presidential Christmas Greeting Cards are displayed here and as an extra, you can collect gifts in their gift store.
Even, their Collector ornaments provide an excellent filler for stockings.
Also, you probably didn't know that Key West before has functioned as a presidential getaway since 1880 at the time Ulysses Grant traveled to Key West.
Harry Truman too was said to hated residing in Washington DC and saw this White House as his refuge.
He was here for 175 days during his presidency between 1946 and 1952.
Then, if you are searching for an ideal present for any history enthusiast, choose one of their custom-designed White House's Collector ornaments to commemorate your visit to this heritage site.
16. Boat Parade
As festive parades march down Main St in quaint towns throughout America, residents of Key West hang lights and garlands everywhere, from small boats to large yachts, and bring their celebrations onto the water.
In Key West's yearly Lighted Boat Parade inside the stunning Historic Seaport, you will be amazed by their inventiveness.
Jumping dolphins, twirling candy canes, toy soldiers, doves of peace, and naturally, Santa's sleigh shimmers throughout the water while they glide along.
The boats are outfitted to dazzle with intricate embellishments interlaced within the riggings and masts resembling a rotating holiday decoration of 20 feet or an Art Decor angel of 30 feet.
Although excellent scenic views are available at various restaurants, bars, and resorts in the harbor zones and Historic Seaport, the prime spot is at Schooner Wharf, the place where boats make a turnaround for judging stations.
Then, if you prefer to take part in the boat parade rather than merely being a spectator, many charter boats offer ticket sales.
Indeed, this yearly boat parade, beloved by locals, is perfect for families.
Observe tall ships, rowing boats, yachts, and all there is as you glide through the seaport adorned in festive cheer.
17. Bike Parade
This Holiday Village and Be Lighted Bike Ride organized by Wesley House Family Services is a top family-oriented New Year Eve's event in Key West.
The excitement starts at exactly 4 pm in Truman Water front Park at Coffee Butler's Amphitheater, located in Key West.
This Holiday Village operates between 4 and 8 pm, while the Bike Ride departs at exactly 8 pm from the beautiful Amphitheater and takes the same path as the FantasyFest parade, down Duval Roadways and up Whitehead.
It serves as the family-oriented pre-event for the delightful bike ride, showcasing more than 18 community booths and providing activities, treats, crafts, DJ, food vendors, and pictures with Santa for the children.
18. Conch Train Tour
This tour is among the simplest methods to experience the intricate decorations adorning the historic houses and lodgings in Key West.
The yellow vivid trains have started meandering through Old Town's cool streets since 1958.
Typically, the tour provides the local views's clear rundown and a vibrant island heritage, and in December and New Year, the train runs double responsibility for the Lights Tour.
Gliding through the warm evening, this ride lasting an hour often results in caroling—possibly motivated by the cookies and cider offered before the ride.
If you are going on a trip with a team, reserve a personal charter and allow the carols to resonate.
19. Martin's
You should visit Martin's for an exquisite Sunday gourmet brunch.
Their selection of eggs gourmet benedict is really remarkable.
They are also renowned for their nice Bellini cocktail drinks, and they even serve fantastic French toast and tasty German dishes.
Indeed, Martin’s boasts a stylish island-cosmopolitan vibe both indoors and outdoors, featuring a Duval St view along with cozy garden dining at the rear.
20. Eaton Bikes Tour
Riding a bike through Old Town is among the finest ways to experience the playful New Year's Eve festive ornaments.
Classic architectural features are altered here and gingerbread carpentry is adorned with sparkling lights and frozen spikes.
Also, massive stars and garlands hang from curved terraces, as green garlands and red ribbons decorate the columns.
People are motivated by this annual contest, incorporating reindeer, candy canes, and snowmen alongside the frangipani, bougainvillea, and hibiscus throughout their yards.
Moreover, Eaton Bikes offers road bikes, mountain bikes, seaside cruisers, trikes, and additional options.
Rentals come with a complimentary bike collection and delivery anywhere inside Key West.
If it has been some time since you last rode a bike, consider taking it for a test before you take it to the streets.
21. Triathlon Race
Key West's Triathlon draws competitors from various locations to race in a tropical setting.
With 1000 participants, it’s a “large competition on a small island”.
Also, the swimming segment in the water here is significantly warmer than other competitions worldwide this month.
22. Sebago's Schooner
This is a classic sailing ship constructed by Harvey Gamage Ship yard located in Maine's South Bristol.
With it, you will not just view the intricately adorned boats closely but also appreciate a celebration gathering by the water.
Also, savor a flute of sparkling, artisanal wine, beer, sangria, or other celebratory drinks complemented by handcrafted cheeses and fresh fruit.
In fact, you won't discover a more exceptional holiday experience in Key West.
So, prepare to grin for the camera as you drift by the judges' area at the Schooner Wharf.
Note that tickets begin for adults at the cost of $49.95.
23. Reggae Lou
For a relaxing conclusion to New Year's Eve, at exactly 5 pm, head to the Sunset Pier to experience an easygoing live reggae melody while the sun sinks for the last time in the year.
This occasion guarantees to be enjoyable and entertaining and is ideally suited to kick off your merrymaking before the New Year festivities truly start.
24. America 2.0
You won't find superior seats for double of the Key West's top festivities - New Year Eve at Schooner and the Lighted Fun Boat Parade - more than on America 2.0.
The stylish schooner is almost a replication of the first vessel to triumph in 1851 in the America Cup, and it is crafted from mahogany trims and teak decks.
The festive cruise voyage experience lasts for three hours beneath the shimmering moonlight and breathtaking ornaments.
As other boats go by, you will savor warm cider, conch soup, and cookies paired with beer, vino, and Champagne.
Then, at their exclusive New Year's Eve party for adults, enjoy all the excitement up close with exclusive dockside entry to Schooner's.
The renowned "Lowering ofthe Pirate Wench" occurs from the top rig just above you.
Note that visitors are recommended to pack their own picnics for this Boat Parade.
25. Key West's Bight
Key West's festive season begins with "Bight" ahead of Christmas and New Year's Eve celebrations at the lovely Historic Seaport.
Nautical Harbor Walkof Lights showcases Fishing Buoy's Christmas Tree, an authentic Nautical pine Christmas Tree, together with Lobster Trap's Christmas Tree celebrating Key West's nautical heritage.
They depart with great celebration at Greene & Elizabeth Street, then the Celebrations extend all the way along the sea wall--beyond Greene Street, Margaret Street, and William St to the KW Ferry Terminal.
Then, enjoy an evening walk after having dinner at a waterfront restaurant and engage in festive shopping right at the charming boutiques near the route.
The Bight also welcomes an array of activities such as pet picture sessions with Santa, festive music shows, a charity violin event, a vintage car exhibition, and the Boat Parade.
Conclusion
These are the top Key West activities to celebrate New Year's Eve.
From lively parties to elegant dinners, you’re guaranteed to enjoy a fantastic celebration inside Key West.
