Barefoot in Margaritaville is the ultimate acoustic Jimmy Buffett tribute, blending timeless hits with lesser-known gems that true Parrotheads will love. This talented duo, with engaging storytelling, shares fascinating anecdotes about Jimmy Buffett's life and the inspiration behind his songs, making every show a memorable journey to paradise.
Whether you're planning a tropical-themed party, a laid-back gathering, or a vibrant event at a bar or brewery, they deliver an unforgettable experience. Perfect for private events, corporate functions, and small concert venues, this tribute act will have you singing along, sipping something tropical, and dreaming of sunny shores.
1 review
Nicole L.
August 30, 2026We had the absolute pleasure of having Barefoot in Margaritaville perform at our assisted living community, and they were fantastic! 🌴🎶
From the moment they arrived, they brought such a fun, upbeat energy that our residents, families, and team members thoroughly enjoyed. Their music was engaging, entertaining, and had everyone smiling, singing along, and enjoying the moment.
What really stood out was how wonderful they were with our residents. They created an atmosphere that was inclusive and welcoming, and they truly understood how to make the performance enjoyable for everyone.
We are so grateful to Barefoot in Margaritaville for helping us create such a memorable event. They were professional, personable, and incredibly talented. We would absolutely recommend them and would love to have them back again!
Thank you for bringing a little bit of Margaritaville to our community! 🍹🌺🎵
Hired as: Jimmy Buffett Tribute
Barefoot in Margaritaville
Thank you so much! We had a great time and everyone was so fun!
Price range: Starts at $750
Gig length: 30 - 240 minutes
Kick off your flip-flops and sail away with us! Barefoot in Margaritaville isn’t just a concert — it’s an escape to paradise.
This award-winning tribute show celebrates the songs and stories of Jimmy Buffett with rich harmonies, warm acoustic vibes, and plenty of Parrot Head spirit. We blend the biggest hits with the hidden gems that only true Buffett fans know, creating a laid-back, singalong experience that feels like a beach vacation in every show.
🎶 What makes us different?
A true acoustic tribute — intimate, energetic, and island-inspired.
Storytelling woven between songs, sharing the life and adventures of Jimmy Buffett.
A journey through the classics and the deep cuts that Parrot Heads love.
From bars and breweries to private parties and concert stages, Barefoot in Margaritaville transforms any venue into an island getaway. Whether you’re sipping a margarita, dancing barefoot, or belting out your favorite chorus, you’ll leave with sunshine in your heart and sand in your soul.
👉 Book the award-winning Barefoot in Margaritaville today — and let’s turn any night into a trip to paradise.
Pineapple Cowboy is a seasoned musician, storyteller, and performer with over 30 years of experience captivating audiences with his unique blend of laid-back charm and musical talent. A skilled guitarist, vocalist, and ukulele player, he brings the spirit of the tropics to every stage, whether leading a full band or performing intimate acoustic sets.
With musical influences ranging from Elvis and The Beach Boys to Weezer and Jimmy Buffett, the Pineapple Cowboy combines nostalgia with fresh energy. His performances are a tribute to the stories behind the songs, weaving humor, heartfelt moments, and anecdotes about life, love, and the beach.
As one-half of Princess Pupule and the Pineapple Cowboy, he delivers a diverse setlist that spans tropical beach tunes, rock, pop, country, and classic oldies. When performing as part of Barefoot in Margaritaville: An Acoustic Jimmy Buffett Tribute, the Pineapple Cowboy dives deep into Buffett’s world, sharing beloved hits and hidden gems while regaling audiences with tales of the man who inspired generations to chase the island dream.
Outside of music, the Pineapple Cowboy’s creativity extends into recording original works, including his singles Meet Me On a Beach and Retirement Plan, as well as his recently released album Flip-Flop Tan Lines. He played the start role of Tully Mares in Escape to Margaritaville put on by The Gateway Players of Southbridge. He also has a knack for engaging audiences beyond the music, with a flair for storytelling and humor that turns every performance into an unforgettable experience.
Princess Pupule brings vibrant energy and years of artistic expertise to every performance. With over 30 years of experience as a musician and dancer, she has captivated audiences with her unique blend of talent, charisma, and storytelling.
As a musician, Princess Pupule is a versatile performer known for her powerful vocals and mastery of the random instruments. Her repertoire spans a wide range of genres, from the laid-back vibes of tropical and beach music to rock, country, and pop favorites. She is also skilled in percussion, adding rhythmic flair to her performances. Her influences include Blink-182, The Eagles, Queen, Britney Spears, and the iconic sounds of 90s and 2000s alternative music, which shine through in her dynamic performances.
As one-half of Princess Pupule and the Pineapple Cowboy, she engages audiences with her storytelling, seamlessly blending humor, heart, and history. Whether performing a full acoustic Jimmy Buffett tribute with Barefoot in Margaritaville or leading a crowd in an upbeat mix of songs, Princess Pupule knows how to create unforgettable moments for her audience.
When she’s not performing, Princess Pupule is a passionate advocate for the arts, sharing her love of music and dance with others and encouraging everyone to embrace the joy of creativity.
We only need a power connection. We provide our own sound - able to range from intimate backyards to 3000 seat venues. Basic lighting will be provided if needed as well. We are flexible with space and can generally make any area work.
Thursday
Recurring Performance
5:30pm - 8:00pm
•
Milford, MA
Acoustic Band
