How you choose to ring in the New Year in Key West is entirely up to you. Since there are so many activities along Duval Street, within the historic seaport, and beyond, it’s important to know about your options and plan accordingly.

Your Key West New Year’s Eve could involve a sunset cruise, a conch shell, some Key Lime Pie, and live music on the beach, and that’s just to get started.

Start Off With A Sunset Cruise

When you’re in Key West, you should make it a point to soak up the scenery. The best way to do that is to spend a few hours on a sunset cruise. Not only is a cruise going to be less crowded, but you’ll also get better views of the Florida Keys.

Booking a sunset cruise will allow you to relax with some family or friends before you start drinking and counting down to 12. Let the breeze soothe you. Set your intentions for the New Year. Leave all of your worries of the past year on the water of Key West.

Take some amazing photos and set them as your phone background. That way, you can remember the serene feeling for the entirety of the New Year.

Indulge In Delicious Food In Key West

Diets start on January 2, which means you can spend New Year’s Eve eating some of the most delicious things that Key West has to offer for breakfast, lunch, and dinner.

Top places to try:

• Sloppy Joe’s Bar
• First Flight Island Restaurant & Brewery
• Ocean Key House

With so many places to eat in the Florida Keys, you’ll want to spend a bit of time wandering the historic seaport. Be sure to check out the various specials they’ll offer and if they’ll have a New Year’s Eve celebration. Remember, some of the higher-end restaurants will require reservations, too.

Enjoy Live Music At Top Venues

A free concert can be a great way to prepare yourself for the New Year in Key West. Many of the resorts along the beach will offer live music. You don’t have to spend a penny, though many will have bars where you can purchase a cocktail (or mocktail, if you prefer).

Some of the music you’re likely to hear as you wander the beach includes:

• Yacht rock
• Reggae
• Calypso
• Hip hop
• Country

If you wander the area long enough, you’re bound to find the music you want to listen to.

The Pirate-Themed New Year’s Eve Celebration Options

Schooner Wharf Bar offers one of the most unique Key West ways to enjoy a New Year’s Eve celebration. It’s pirate-themed, and you’ll have even more fun if you dress for the occasion.

Forget about a ball drop. Instead, Schooner Wharf Bar drops a pirate wench from the top of the mast of their ship. There are also cannon blasts to help celebrate the clock striking midnight.

The lowering of the pirate wench is a lot of fun, and the celebration has been going on for years.

Schooner Wharf Bar is located in Key West Bight, and you’ll find hats, party favors, and more. There will also be live music and holiday drink specials.

Here’s the best part of all of it: You won’t need reservations to see the pirate wench drop. Even if you’re not at that location, you’ll still be able to get a fairly decent view if you’re around the historic seaport.

Midnight Activities

While the ball drop is the quintessential activity of New Year’s Eve throughout most of the country, things are a bit different for Key West New Year’s Eve. Knowing about the many midnight activities around Duval Street and beyond will allow you to decide where you want to be.

Whether you want to spend the evening with drag queens and a drag queen Sushi (otherwise known as Gary Marion), a key lime wedge, a conch shell, or you want to drink until your heart’s content on Duval Street, there are options for you.

Conch Shell Drop

At Sloppy Joe’s Bar, you’ll find a gigantic manmade conch shell that is dropped as a huge clock counts down to midnight. One thing to know is that all of the tables are on a first-come, first-serve basis.

If you plan on visiting Sloppy Joe’s Bar, arrive early. The event includes live music and will go on until two in the morning. Oh, and a conch shell souvenir is a must.

Red Shoe Drop

At the New Orleans House on Duval Street, you’ll find a giant red high heel that drops at midnight. Drag queen Sushi is the host of the event and will actually climb into the shoe as it’s lowered into the crowd. You’ll get the best view with VIP balcony tickets.

Pirate Wench Drop

The island’s colorful seafaring heritage is on display with the pirate wench drop at Schooner’s.

Key Lime Drop

Over on the Sunset Pier, you’ll find a key lime wedge that drops. This is a ticketed event that gives you access to a private tent with butler-passed appetizers as well as an open bar.

Tips On Where To Stay

Where you stay is up to you. There are plenty of options across Key West, so you’ll want to decide a few things about your New Year’s Eve plans first.

Ideally, you shouldn’t have to walk too far for the festivities. The reason is to ensure you can drink your champagne or anything else without having to worry about how to get back to your room.

Southernmost Beach Resort

One of the top places to stay because the views of the Florida Keys are stunning. The resort sits on white sand beaches and offers three heated pools (because it can be chilly in Key West in December).

For New Year’s Eve, you’ll find a free concert or two at the resort, and when you’re a guest, you’ll have the best seats in the house. It’s common for the Sand Bar at the resort to also offer a silent disco for NYE.

Ocean Key Resort & Spa

The Ocean Key Resort & Spa also offers you a prime location that is close to Sloppy Joe’s Bar and Duval Street and offers some incredible sunset views. Plus, you can make an entire weekend out of your New Year’s Eve, complete with romantic vacation packages, couples massages, and more.

Tips On Booking Your Key West New Year’s Eve

As you can imagine, New Year’s Eve in Key West is a top destination. You won’t want to leave your New Year’s Eve plans to chance, regardless of how many people you’re traveling with.

Here are a few tips to ensure you make the most of your trip to Key West:

Book Your Hotel Early

Hotels book quickly, so as soon as you know you’re going to Key West, book your hotel. More importantly, book on the beach or within the historic seaport area so that you’re close to all of your New Year’s Eve celebration activities.

Decide Where You Want To Be At Midnight

While barhopping is common on New Year’s Eve in Key West, decide where you’ll want to be when the clock strikes midnight. This will allow you to sip your champagne and ring in the New Year on your terms. Many places will be selling VIP tickets, so plan ahead.

Determine What Kind Of Live Entertainment You Want To Embrace

Drag queens, live music, pirate themes, and more exist. Book the tickets to the party you want to go to before they all sell out.

Plan On Walking Old Town

While Key West offers plenty of ways to get around the island, you probably won’t want to rely on driving yourself anywhere, especially once the sun sets. Instead, choose to walk around Old Town and Duval Street. It’s safer, and you’ll get to your destinations faster than being stuck in Uber and taxi traffic, which is so common on New Year’s Eve.

Start Your Key West New Year’s Eve With Us!

A Key West New Year’s Eve can be memorable since there is so much to do on the island. Why not start with a sunset sail so that you can truly enjoy the last sunset of the year? At Key West Boat Trips, we create a relaxing and fun tour for your small group. You’ll be able to watch the sunset on a private boat rather than being on the crowded sunset pier. After all, you deserve to set your intentions for the New Year in peace, right?

The time on the cruise is yours, so you’ll have the opportunity to dip your toes in the water, splash around a sandbar, and even enjoy some of the finest food that Key West is known for. All you have to do is book your sunset cruise for New Year’s Eve. We’ll take care of the details so you can ring in the New Year in the most exciting way possible.