Florida Keys Overseas Highway – The 15 BEST TOP SONGS & PLAYLIST for Your Road Trip

Playlist with best songs - Overseas Highway Florida Keys by Mark Watson

Embark on a musical odyssey along the enchanting Florida Keys Overseas Highway with my carefully crafted playlist. As you traverse the scenic expanse of this iconic highway, connecting the tropical paradise of Key Largo to the southernmost tip of the United States in Key West, let the power of music enhance every mile of your journey. The Florida Keys, with its azure waters and breathtaking landscapes, set the stage for an unparalleled road trip experience. What are the best songs about Overseas Highways and the Florida Keys?

My curated playlist is designed to be the perfect companion, immersing you in a harmonious blend of tunes that encapsulate the essence of the Florida Keys. From laid-back beach vibes to upbeat rhythms, these songs have been handpicked to synchronize with the rhythm of the swaying palms and the gentle lapping of the waves against the shore. So, turn up the volume, roll down the windows, and let the music guide you through the sun-soaked vistas of the Florida Keys, creating a soundtrack for memories that will linger long after the road trip ends. Get ready to hit play and set the tone for an unforgettable adventure along the Florida Keys Overseas Highway!

1. The Florida Keys Song – Gerd Rube

The Florida Keys Song - Gerd Rube - playlist with song about Overseas Highway and Florida Keys

Gerd Rube, the celebrated rock singer/songwriter and guitarist from Germany, effortlessly lives the dream of a dual-season musician. Touring all over Europe in the summer and gracing the Florida Keys during winter, Gerd found his winter home in Key West, FL, enchanted by its allure. His journey began with MTV Europe featuring his “Happy Day” music video in 1993, propelling him into stardom in Germany. Now, Gerd’s original songs, including the popular “Florida Keys Song” from his latest CD “Live in Key West,” continue to captivate audiences on both sides of the Atlantic, solidifying his status as a global musical sensation.

2. Kokomo – The Beach Boys

Kokomo - The Beach Boys - get ready for your journey along the Florida Keys and Overseas Highway

“Kokomo” by the Beach Boys is undoubtedly a timeless and feel-good classic that resonates with the carefree spirit of a journey, making it a perfect soundtrack for a Florida Keys Overseas Highway adventure. This iconic song, released in 1988, captures the essence of relaxation, tropical vibes, and the allure of coastal paradises – all of which are synonymous with the beautiful stretch of islands that make up the Florida Keys.

3. Key Largo – Bertie Higgins

Key Largo - Bertie Higgins - great song for your Overseas Highway playlist

“Key Largo” by Bertie Higgins is often considered one of the best songs to play during a visit to the Florida Keys. The song’s smooth melody and lyrics evoke the laid-back and tropical atmosphere of the Keys, making it a perfect companion for a leisurely drive along the scenic Overseas Highway or a relaxing evening by the ocean. The lyrics, which tell a story of love and nostalgia, complement the picturesque surroundings, creating a memorable soundtrack for anyone exploring the beautiful landscapes and vibrant culture of the Florida Keys. “Key Largo” captures the essence of this tropical paradise and enhances the overall experience of a visit to this unique and charming destination.

4. Guitars and Tiki Bars – Kenny Chesney

What are the best songs about overseas highways and the Florida Keys?

What are the best songs about overseas highways and the Florida Keys? “Guitars and Tiki Bars” is a lively and infectious song by country music icon Kenny Chesney. Released in 2002 as a track from his album “No Shoes, No Shirt, No Problems,” the song captures the essence of Chesney’s laid-back, beach-inspired musical style. In “Guitars and Tiki Bars,” Kenny Chesney mentions the Overseas Highway, adding another layer to the song’s imagery.

5. Key Lime Pie – Kenny Chesney

Key Lime Pie - Kenny Chesney. Get ready to delve into the music paradise with a great curated playlist for Overseas Highway and the Florida Keys.

“Key Lime Pie” is a delightful song by country music superstar Kenny Chesney. Released in 1999 as part of his album “Everywhere We Go,” the track captures the essence of the laid-back and carefree lifestyle associated with the Florida Keys. Known for his ability to transport listeners to idyllic coastal settings through his music, Chesney does not disappoint with this sunny and upbeat tune. A great song to add to a playlist for a drive along the Florida Keys Overseas Highway!

If you would like to know more about key lime pie, check out my post about that: Top 5 Spots to Taste Key Lime Pie Along the Overseas Highway & Florida Keys

6. Conch Republic Song – Highway 1

Overseas Highway best songs

Embark on an unforgettable journey through the picturesque Florida Keys with the soulful soundtrack of the ‘Conch Republic Song – Highway 1.’ This hidden gem captures the essence of adventure as it narrates the tale of a man who discovers his haven in the sun-kissed beauty of the Florida Keys. Immerse yourself in the laid-back vibes and tropical charm of Key West, where every day is a celebration of life in this enchanting paradise. Let the rhythm of the Conch Republic Song guide you through the scenic Highway 1, turning your Florida Keys expedition into a melody of discovery and relaxation.

7. Livin’ On Key West Time – Howard Livingston & Mile Marker 24

Playlist and songs for Florida keys journey

“Livin’ On Key West Time” is a song by Howard Livingston & Mile Marker 24, capturing the laid-back and carefree lifestyle associated with Key West, Florida. The lyrics convey a sense of escaping the hustle and bustle of everyday life and embracing the slower, more relaxed pace of the tropical island. “Livin’ On Key West Time” by Howard Livingston & Mile Marker 24 is not just a celebration of the Key West lifestyle, but it also serves as a fantastic addition to any playlist dedicated to the Overseas Highway and the Florida Keys.

8. Overseas Highway – Garth Adam

Best Songs About Key West - playlist

Experience the enchanting melodies of yet another captivating song, crafted by the lesser-known artist, Adam Garth. This musical masterpiece draws inspiration from the scenic Overseas Highway, as Garth eloquently narrates the journey through this picturesque route, ultimately arriving at the place he fondly refers to as home.

9. Key West – Godiva

Key West - Godiva - Overseas Highway best songs - Florida Keys

One of the best ways to capture the essence of Key West is through the melodic lens of Key West by Godiva, a song that encapsulates the spirit of the Florida Keys and makes for an excellent companion on your journey along the Overseas Highway.

As you embark on this scenic highway that connects the keys like a string of pearls, Key West by Godiva provides a fitting soundtrack. The song, with its upbeat tempo and catchy melody, mirrors the carefree and tropical ambiance of Key West. It effortlessly transports you to a place where swaying palm trees, crystal-clear waters, and the rhythmic sounds of guitar become the backdrop of your adventure.

10. Key West Time – Jesse Rice

Key West Time - Jesse Rice - another great song about Florida Keys

Jesse Rice is a country music singer and songwriter known for his work in the genre. “Jessie Rice’s enchanting track, ‘Key West Time,‘ released in 2012 as part of the album ‘The Pirate Sessions,’ is a captivating ode to the leisurely and laid-back lifestyle of Key West. With its soothing melody and reflective lyrics, the song effortlessly captures the essence of living in this idyllic island paradise.

A perfect addition to any playlist centered around the allure of the Overseas Highway and the tranquil vibes of the Florida Keys, ‘Key West Time’ invites listeners to immerse themselves in the slow-paced rhythm of coastal living, making it a must-have for those seeking a musical escape to the sunny shores of the southernmost part of the United States

11. Duke’s On Sunday – Jimmy Buffett

Duke's On Sunday - Jimmy Buffett - best songs for your journey through the Overseas Highway

“Duke’s On Sunday” by Jimmy Buffett captures the essence of the laid-back and carefree lifestyle synonymous with the Florida Keys. Released in 1999 as part of Buffett’s album “Beach House on the Moon,” the song is a celebration of the unique atmosphere found at Duke’s Place, a fictional yet emblematic location that encapsulates the spirit of the Florida Keys.

Whether you’re cruising down the Overseas Highway or simply yearning for a taste of the Keys’ atmosphere, “Duke’s On Sunday” is a musical journey that encapsulates the soul of this idyllic tropical haven.

12. Drunk On Mallory Square – Dani Hoy

When you find yourself in Key West, be sure to set the mood with the enchanting tunes of 'Drunk On Mallory Square' by Dani Hoy.

Mallory Square is a vibrant and iconic destination located in Key West, Florida. Renowned for its stunning sunset views over the Gulf of Mexico, Mallory Square has become a popular gathering spot for locals and tourists alike. Song Drunk on Mallory Square by Dani Hoy reflects the vibrant and chill time on Key West, where on Mallory Square, people celebrate every sunset. They party and have fun together, enjoying the time and place.

13. Florida Keys – Mads Krul

Florida Keys - Mads Krul - perfect playlist about Overseas Highway and Florida Keys

Florida Keys” by Mads Krul is a hidden gem, often overlooked in the vast landscape of music. This enchanting song invites listeners to immerse themselves in the laid-back atmosphere of the Florida Keys, a tranquil paradise where the pace of life slows down to a soothing rhythm. Mads Krul skillfully weaves a narrative through his lyrics, capturing the essence of the slow and easy living that characterizes this tropical haven.

14. Key West Address – James T. Slater

Key West playlist - Key West Address - James T. Slater

James Thomas Slater, a highly accomplished singer/songwriter based in Nashville, has left an indelible mark on the music industry with his exceptional talent. As a two-time Grammy-nominated artist, Slater has become renowned for his ability to craft poignant and resonant songs that capture the essence of American popular music.

One of his notable compositions that stands out is the song “Key West Address.” This piece is a testament to Slater’s ability to weave narratives that transport listeners to specific places and evoke a deep sense of emotion. “Key West Address” is particularly notable for its connection to the vibrant and eclectic atmosphere of Key West and the Florida Keys. Through his lyrics and melodies, Slater paints a musical portrait that reflects the unique charm, laid-back lifestyle, and tropical beauty of this iconic region.

15. Sand in Her Shoes – Thom Shepherd

Sand in Her Shoes - Thom Shepherd - Playlist with perfect songs for your travel - Overseas Highway and Florida Keys

“Sand in Her Shoes” is a popular country song written by Thom Shepherd, a talented singer-songwriter known for his contributions to the country music scene. The song is a catchy and feel-good anthem that captures the essence of a carefree, beachside lifestyle.

Released in 2014, “Sand in Her Shoes” quickly gained popularity for its infectious melody and relatable lyrics. The song paints a vivid picture of a woman who’s not afraid to embrace the simple joys of life. With sandy shores beneath her feet and the sun on her face, she revels in the freedom of the beach lifestyle. The lyrics convey a sense of escape from the daily grind, allowing listeners to imagine themselves in the same idyllic setting. This is definitely another great song to add to your playlist for the Overseas Highway and Florida Keys adventure.

Overseas Highway Florida Keys Playlist

101 best stops - Overseas Highway Florida Keys by Mark Watson

πŸ‘ Find out more:

Overseas Highway Florida Keys Travel Guide - 101 best stops by Mark Watson

Explore the finest attractions along the Overseas Highway and Florida Keys with my travel guide, ‘Florida Keys Overseas Highway Travel Guide – 101 Best Stops,’ now available on Amazon. This comprehensive guide is your ultimate companion for those seeking adventure and wonder along THE OVERSEAS HIGHWAY & FLORIDA KEYS! Discover 101 amazing places with convenient ‘Scan QR and go’ functionality for easy navigation.


Pacific Coast - Mark Watson

Mark Watson is a California-based member of a Los Angeles motorcycle club and an avid traveler. He has completed seven full journeys along the iconic Pacific Coast Highway on his Harley-Davidson and is passionate about promoting this historic drive to others. Mark has also explored the Alaska Highway and Route 66, and has authored four bestselling travel guides on Amazon: “Route 66 Travel Guide – 202 Amazing Places,” “Alaska Highway Travel Guide – 202 Best Stops,”, “Pacific Coast Highway Travel Guide – 202 Best Stops”, and “Florida Keys Overseas Highway Travel Guide – 101 Best Stops.”

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