Join Grammy-nominated music journalist Bill DeMain on the Nashville Music City Legends Tour and discover the inside story of how Nashville became the iconic Music City. Explore decades of musical history and hear fascinating anecdotes from interviews with legendary artists like Dolly Parton, Willie Nelson, and David Bowie.
Join Grammy-nominated music journalist Bill DeMain on the Nashville Music City Legends Tour and discover the inside story of how Nashville became the iconic Music City. Explore decades of musical history and hear fascinating anecdotes from interviews with legendary artists like Dolly Parton, Willie Nelson, and David Bowie.
- The Hermitage Hotel - Tennessee’s exclusive 5-star hotel, established in 1910. Notable guests have included Charlie Chaplin, Enrico Caruso, JFK, Paul McCartney, and Dolly Parton.
- Woolworth Theatre - Originally F.W. Woolworth’s, opened in 1913, this was the historic site of Nashville’s sit-ins, led by the esteemed freedom rider and advocate of…
- The Hermitage Hotel - Tennessee’s exclusive 5-star hotel, established in 1910. Notable guests have included Charlie Chaplin, Enrico Caruso, JFK, Paul McCartney, and Dolly Parton.
- Woolworth Theatre - Originally F.W. Woolworth’s, opened in 1913, this was the historic site of Nashville’s sit-ins, led by the esteemed freedom rider and advocate of “good trouble,” John Lewis.
- The Arcade - Known as “Nashville’s oldest shopping mall,” constructed in 1902. The visit includes The Peanut Shop, which began in 1927.
- The Peanut Shop - Initially opened in 1927 as Planter’s Peanuts, it remains one of the oldest businesses in downtown Nashville. It’s a nostalgic experience with friendly service and complimentary samples!
- Printer’s Alley - Formerly the hub of Nashville’s red light district, it was a central spot for music performances and backstage negotiations. Legends like Jimi Hendrix, Johnny Cash, and Tim McGraw have performed here.
- Millennium Maxwell House Hotel Nashville - Previously the location of Nashville’s most magnificent hotel and the first to serve the famous coffee. Discover the true story behind “Good to the last drop.”
- Ryman Auditorium - The gem of downtown Nashville. Originally built as the Union Gospel Tabernacle in 1892, it hosted the Grand Ole Opry from 1943-74. It holds stories of icons like Hank Williams, Johnny Cash, and Elvis Presley.
- Tootsies Orchid Lounge - Nashville’s renowned honky tonk, once a hub for songwriters, managed by the vibrant Tootsie Bess. Her jukebox featured demos of hits like “Hello Walls,” “Crazy,” “A-11,” and “Sunday Morning Coming Down.”
- Country Music Hall of Fame and Museum - The premier music-related museum in Nashville, offering a fantastic permanent collection and dynamic exhibits.
- Skull’s Rainbow Room - A legendary nightclub that has welcomed artists such as Willie Nelson, Roger Miller, Dolly Parton, and Andy Griffith. Paul McCartney even composed a song here.

- All Fees and Taxes
- All Fees and Taxes
- Lunch
- Lunch
This tour is perfect for music enthusiasts eager to discover the story behind Nashville’s transformation into Music City.
Your knowledgeable guide is Grammy-nominated music journalist Bill DeMain, who boasts over thirty years of experience writing for esteemed publications like MOJO and Rolling Stone. He also serves as a Nashville correspondent for the…
This tour is perfect for music enthusiasts eager to discover the story behind Nashville’s transformation into Music City.
Your knowledgeable guide is Grammy-nominated music journalist Bill DeMain, who boasts over thirty years of experience writing for esteemed publications like MOJO and Rolling Stone. He also serves as a Nashville correspondent for the BBC.
DeMain has conducted interviews with a wide range of pop and country music legends, including Dolly Parton, Merle Haggard, Paul Simon, Billy Joel, Loretta Lynn, Willie Nelson, David Bowie, and Stevie Nicks.
As a celebrated songwriter, DeMain’s compositions have been performed by artists such as Marshall Crenshaw, Kim Richey, and Curtis Stigers. He is also part of the renowned pop duo Swan Dive, with his music featured in TV series like Sons of Anarchy and Private Practice.
A long-time resident of Nashville, DeMain will guide you through the city’s rich musical history, spanning from country to rock, ensuring your visit to Nashville is truly memorable.
For a full refund, cancel at least 24 hours before the scheduled departure time.
For a full refund, cancel at least 24 hours before the scheduled departure time.