The Key West Songwriters Festival returns May 4-8 for its 21st annual celebration. With 200 artists performing 50 concerts over five days, the festival has continued to get bigger and better every year. It draws serious music fans together to celebrate the unsung heroes of music making: the songwriters. You may know many of their chart topping and Grammy Award winning songs, but you might not know their faces and names. The songs they write are oftentimes recorded by legendary artists like Garth Brooks, Rascal Flatts and Lonestar, while their persona remains largely behind the scenes. This all changes every May when the songwriters get their moment in the Key West sun. It’s a collaborative and experimental atmosphere, much like you’d experience at a listening room in Nashville. The acts range from emerging talents to longtime hit makers. There’s also a nice blend of country, rock and other genres.

Fury Water Adventures has been a longtime supporter of this unique local event, offering our annual Key West Songwriters Festival sunset sail to those who enjoy music and the water. Here is your ultimate guide to Key West’s top music venues, things to do during the festival and the best hotels for your stay.

Key West’s Top Live Music Venues

Enjoy the sights and sounds of the Songwriters Festival from one of Key West’s many famed establishments. Whether you want to party in the heart of the excitement or prefer a mellower atmosphere, there’s a live music venue singing your name.

Smokin’ Tuna Saloon
This is the official bar of the Key West Songwriters Festival. With a spacious outdoor patio, stellar sound system and slightly off the beaten path locale, it’s a no-brainer for good music and good times. Many of the festival’s top concerts are staged here.

What’s more Key West than Jimmy Buffet’s Margaritaville? As a huge part of Key West’s musical legacy, this tropical oasis will host a handful of concerts. Swing by for your cheeseburger in paradise!

Blue Heaven
You can’t go wrong with an evening at Blue Heaven, especially when they host a Songwriters concert. This beloved open-air bar and restaurant located in Bahama Village has all the chill vibes and Key West charm you’re looking for.

San Carlos Institute
For a more formal concert experience, the San Carlos Institute on Duval Street always hosts some of the most desirable concerts of the festival inside their historic theater.

Green Parrot Bar in Key West

Green Parrot
While the Green Parrot isn’t on the official Songwriters Festival line-up, it’s easily Key West’s most beloved local bar and one of the best live music venues on the island. Swing by, order a round of root beer barrels and dig into some free popcorn while you groove to the music.

The Best Acoustics Are Found on the Ocean

For years, Fury’s sunset sail has been one of the hottest tickets at the festival. Who wouldn’t want to sail into the sunset aboard a 65-foot catamaran while listening to an intimate concert featuring some of the best singer-songwriters in the industry? We’ll be serving up delicious appetizers and all you can drink margaritas, beer and wine. In year’s past, we’ve been honored to host Bo Bice, James Slater and our own Cory Heydon Band. This year, talented performers will entertain our guests on May 6 and May 7. It promises to be another stellar party! Buy Tickets For The Fury Songwriters Sunset Sail

Where to Stay for the Weekend

Even the island’s hotels like to get into the action of the Songwriters Festival with poolside concerts, parties and more. Here are a few of our top picks for where to stay while in town for the weekend. Each of the hotels listed below will be participating in official Songwriters Festival events.

Casa Marina
This gorgeous and historic hotel built by Henry Flagler in the 1920s is a luxurious, oceanfront haven and the perfect venue for an outdoor concert.

The Marker
As the first newly build hotel on the island in 20 years, The Marker is a hot spot in an even hotter location right in the heart of the Historic Seaport. Swing by for some poolside tunes in the courtyard during the festival.

Pier House
The Pier House is a classic Key West harborfront resort. The sprawling property features waterfront swimming pools, fine dining and, surprisingly, one of Key West’s best dive bars.

Ocean Key Resort & Spa
The Ocean Key Resort & Spa is perhaps Key West’s most luxurious hotel. Home to Sunset Pier bar and Hot Tin Roof restaurant, it’ll be a great place to get the party started and to get a good night’s sleep.

A Look Back at Our Previous Sunset Sails

We were extremely honored to host singer-songwriter duo Joey + Rory in 2012. That same year, James Slater, Howard Livingston and Chase and Jesse Rice also joined us.

In 2011, we welcomed a stellar lineup including American Idol finalist Bo Bice, Adam James, Tyler Farr, Ray Scott, Steve Bogard, Dean Alexander, Billy Yates, Kristy Lee Cook, Marty Dodson, Laura Warshauer, Dillon Dixon and Karla Davis.

During the 15th annual festival in 2010, James Slater & Friends, Ross Copperman, Kip Moore, Steven Lee Olsen, Marty Dodson, Tebey Ottoh, Bridgette Tatum joined us aboard our sunset sail. We were also proud to have Key West local Cory Heydon and Massacoustics on board.

Last Updated 08/08/2022