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Stories, Songs & Sunshine: Inside the 2025 Key West Songwriters Festival

April 29, 2025 by Dominique Barrera Leave a Comment

🎶 Dive into the 29th Annual Key West Songwriters Festival – April 30–May 4, 2025 🎶

Get ready for five unforgettable days of music, storytelling, and island vibes at the 2025 Key West Songwriters Festival! From April 30 through May 4, the island transforms into a songwriter’s paradise, hosting over 150 acclaimed and emerging artists across more than 50 shows. Presented by BMI and Rams Head Presents, this festival is the largest of its kind in the world and has been a launching pad for stars like Kacey Musgraves, Maren Morris, and Florida Georgia Line. ​

🌟 Festival Highlights

  • Opening Night – April 30: Kick things off at the iconic Sunset Pier Kick-Off Party at Ocean Key Resort & Spa, featuring performances by Dylan Altman, Robert Randolph, and Guthrie Trapp. ​

  • Headliner – May 1: Country sensation Nate Smith takes the stage at the Coffee Butler Amphitheater, with support from Chase Matthew.

  • Duval Street Block Party – May 3: Enjoy a free, high-energy street concert in the heart of Old Town.​

  • Sunday Songs & Mimosas – May 4: Wrap up the weekend with intimate acoustic sets at Williams Hall, La Te Da, and the Key West Woman’s Club. ​

  • 🎤 FEATURED ARTISTS

    This year’s lineup boasts a mix of legendary songwriters and rising stars:​

    • Veterans: Chuck Cannon, Bob DiPiero, Rebecca Lynn Howard, Raul Malo, Liz Rose, Jeffrey Steele, and Bridgette Tatum.​

    • Newcomers: Matt Castillo, Bre Kennedy, Jackson Nance, DJ Smoke, and The Kentucky Gentlemen. ​

      📍 Venues Across the Island

      Experience performances in a variety of unique settings:​

      • Historic Theaters: Key West Theater, San Carlos Institute.​

      • Beachfront Bars & Resorts: Southernmost Beach Resort, Dante’s Pool Bar, Blue Heaven.​

      • New Additions: Marquesa Hotel, The Alamo, Island Dogs.​

      • Festival HQ: Rams Head Southernmost Bar & Restaurant. ​

      🎟️ Tickets & Access

      While many shows are free, select performances require tickets. For the full schedule and ticket information, download the official festival app or visit the Key West Songwriters Festival website. ​

      ☀️ Weather Outlook

      Expect classic Key West sunshine throughout the festival:​

      • May 1: Partly sunny with a couple of showers, high of 83°F.​

      • May 2–4: Mostly sunny and pleasant, highs ranging from 84°F to 86°F.​


      💡 Insider Tips

      • Arrive Early: Popular venues fill up quickly; early arrival ensures a good spot.​

      • Stay Hydrated: Keep cool with plenty of water and sunscreen.​

      • Explore the Island: Take breaks between sets to enjoy Key West’s beaches, shops, and historic sites.​

      • Whether you’re a die-hard music fan or just looking for a unique island experience, the Key West Songwriters Festival offers an unparalleled blend of talent, ambiance, and community spirit. Don’t miss out on this celebration of song and story in one of the world’s most picturesque settings!

      • THANK YOU FOR STOPPING BY!

Filed Under: Uncategorized Tagged With: Acoustic Music, Country Music Events, Florida Keys Music Festival, Island Festivals, Key West Events, Key West Songwriters Festival, Key West Travel, Live Music Key West, Songwriters Festival 2025, Things to Do in Key West

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