Dive Bars, Vintage Shops, And Music History – Explore Nostalgic Nashville With My 3-Day Itinerary

Whenever I find myself in the mood for good food, good music, and good times, I begin to dream about returning to Nashville, Tennessee. The iconic destination is known for country music and wild nightlife, but Nashville is so much more than a place to party. Music City has an incredibly rich history. It's a melting pot of genres from around the world, and one of the best destinations for music lovers to add to their bucket list. From dingy dive bars where you can enjoy cheap beers to upscale hotels with vintage inspired decor, the entire city is oozing with nostalgia and retro glamour, as long as you know where to look.

One of the only things I love more than great live music is shopping for vintage clothing and antique decor, and Nashville is an absolute treasure trove for both. It has a little bit of everything I love, which is probably why every few months I begin to hear Nashville calling my name again. The city somehow feels brand new each time I visit. I love returning to my favorite haunts where there's always a fresh up-and-coming band to see and new treasures waiting for me on the racks of vintage shops.

Nashville is the perfect destination for a three day trip, whether you're traveling solo, planning a girls weekend, or looking for a romantic getaway. For the entire trip, you should expect to spend anywhere from $900 to $2,000 per person for accommodations, food, shopping, and activities depending on whether or not you're feeling splurgy. Each day of my itinerary is jam-packed with shopping, historic sites, classic Americana eateries, music venues, and more. If you're someone who often feels like you were born in the wrong era, my nostalgic Nashville itinerary is for you. It will touch on where to go, what to do, and where to eat if you love immersing yourself in the vintage vibes.

9:00 a.m – 11:00 a.m: If you only have three days in Nashville, try to arrive early so that you can make the most of day one. If you're flying into Nashville International Airport, I recommend renting a car. You're going to need the trunk space for all of your shopping bags full of cool vintage stuff. Nashville makes a great addition to any picturesque southern road trip, so if you already have your own set of wheels, you'll be able to hit the ground running.

Head straight to Mel's Drive-In when you arrive. The classic American diner is located at one of Nashville's most iconic addresses on 2nd Avenue, where B.B. King's Blues Club was once located. Now it's a retro-style diner complete with neon signs, cozy booths, and an all-day brunch menu. There are classic southern comfort foods like biscuits and gravy, corned beef hash, and chicken and waffles.

11:00 a.m – 12:00 p.m: After you've enjoyed a filling breakfast at Mel's Drive-In, take a short five-minute walk to the Johnny Cash Museum so that you can start immersing yourself in music history. In 2026, it was named the best music museum in the United States by USA Today. It's full of costumes worn by the legend himself, memorabilia, and more. It's a self-guided experience and an hour gives you enough time to explore.

Noon – 3:00 p.m: Dressing up is part of the fun of visiting Nashville, and the city has some of my favorite vintage clothing stores in the entire country. You'll find a bit of everything, including vintage band t-shirts, vintage leather with plenty of fringe, silky slips, and sequined accessories. Garage Sale Vintage is a great stop around lunchtime because it is a bar, a taco joint, and a vintage store all rolled into one. There are two locations: East Nashville and Downtown. I recommend visiting visit both!

3:00 p.m – 6:00 p.m: When planning the perfect nostalgic weekend getaway, it's important that you choose accommodations that add to the experience, so consider splurging on a room at the Graduate Hotel or the Urban Cowboy. 

Urban Cowboy is a small boutique hotel located in a Victorian mansion. Each room is completely unique with glamorous decor and opulent perks like clawfoot tubs. There's a hip wine bar inside and the carriage house behind the mansion hosts a stylish pub called Public House. Graduate Nashville is also dripping in trendy vintage finery. The rooms are luxurious and comfortable, the lobby is chic, and the rooftop bar is one of my favorite spots in the city. Whichever hotel you choose, order a cocktail or mocktail from the bar, put on some music while you unpack, and relax for a bit before getting dressed for your first night out on the town.

6:00 p.m – bed time: When you're ready for dinner, head to Evelyn's in the West End neighborhood. Full of cool art and charming retro decor, Evelyn's is a super chic restaurant that highlights seasonal ingredients and describes itself as "a love letter to classic Americana." The white lily buttermilk biscuits with honey butter, the southern salad, and the steak frites are some of my favorite things on the menu. Try to save room for a sweet treat, because the dessert menu features delicacies like cherry almond bread pudding and vanilla shortcake with fruit, strawberry whipped cream, and white chocolate.

After dinner, head to Cannery Hall,  which boasts three distinct venues, for a concert. The building in which the venues are located has an interesting history. It was constructed as a flour mill in 1883 and over the years, it housed a coffee mill, a food company, a restaurant, and multiple music venues. Even if you don't recognize the bands playing during your stay, you should get tickets because one day, they will probably be famous and you'll never be able to see them play in such an intimate space again.

9:00 a.m – 10:00 a.m: After a presumably late night, you're probably going to feel ready for a comforting breakfast, so head straight to Pancake Pantry. It was one of Taylor Swift's favorite spots during her time in Nashville and it's been around since 1961.Allow a warm cup of coffee and a stack of maple bacon bourbon pancakes to wake you up. Once you're rejuvenated, head out on the town to experience some of Nashville's music history.

10:00 a.m – 2:00 p.m: Make your first stop at the National Museum of African American Music. It is the only museum in the United States that is dedicated to celebrating the many musical genres that were created by, inspired by, or influenced by African American musicians. A lot of the music we know and love today has its roots in Black gospel and the blues. The National Museum of African American Music celebrates both along with jazz, R&B, and hip-hop. If you're feeling up for it, consider signing up for the Rhythm and Whiskey tour, which combines a visit to the museum with a tasting experience at the Nearest Green Distillery. The whiskey distillery pays homage to Nathan "Nearest" Green who was the first known African American master distiller. Museum admission costs $33 per adult.

A trip to Music City isn't complete without sampling some Nashville hot chicken and when you're done exploring the National Museum of African American Music, you'll be right around the corner from Hattie B's Hot Chicken. It's super popular, and there's a reason why. The chicken is juicy and flavorful.

Afterwards, walk about five minutes to the Country Music Hall of Fame. It's been called the "Smithsonian of country music," and there are exhibits dedicated to the ever evolving genre and musical artists who have impacted the country music scene over the years. (Make sure to check out our guide to make the most out of your trip to the Country Music Hall of Fame.) Admission costs $32 per adult.

2:00 p.m – 5:00 p.m: To cool off and rest your feet, head straight to the rooftop masterpiece inspired by the Queen of Country herself, Dolly Parton. The White Limousine, located on the rooftop of the Graduate Hotel, is a retro dream come true. Plan on spending the rest of the afternoon here soaking up the sun and swimming in the pristine pool. This is the perfect place to snap cute photos because everything is pink, white, and fabulous. The White Limousine is extremely popular, so you're going to want to make reservations well in advance, especially if you plan on swimming. A day pass to the pool costs $40 and it's worth every penny. You can also reserve a daybed or a cabana for $100 – $200. Butter buns, deviled eggs, crispy haricot verts, and croquettes with goat cheese and smoked onion jam are a few of the mouthwatering snack highlights. When you're ready for dinner, opt for fresh seafood, salads, or French onion dumplings.

7:00 p.m – 3:00 a.m: Get dolled up in your finest attire and hit the town for a night at the historic Ryman Auditorium. It was built over 130 years ago and now, it's the perfect spot to catch internationally recognized musical acts. Some of the greats like Elvis, B.B. King, and Johnny Cash have all performed there over the years. The theater is stunning, and attending a show there is an experience that everyone should have at least once.

After the show, check out the Nashville strip. It's located on Lower Broadway and is also known as the Honky Tonk Highway. It's a wild party and at times, it will feel like a tourist trap, but you need to visit at least once. The bars have live music, even on weekdays, and most of them don't charge a cover. It's a lot of cover songs and drunk people singing along at the top of their lungs, but every now and then, you'll stumble on talented artists that you can immediately tell will be famous one day. Stay out as late as you want: the bars in Nashville don't close until 3:00 a.m.

10:00 a.m – 11:00 a.m: Allow yourself the luxury of sleeping in on your final full day of vacation and enjoy breakfast in bed at your hotel, but then get ready to hit the ground running because there is still a lot to see and even more to do.

11:00 a.m – Noon: Start your morning off slow with a tour of the historic Belmont Mansion. Construction on the antebellum estate began in 1850 and it took around a decade to complete. Over the years, it served as a private residence and a school for women. It's located about 15 minutes from downtown, but it's worth the drive time if you're interested in history and architecture. A self-guided tour costs $18 per person and you can explore the mansion in about 45 minutes. For a more in-depth experience, consider booking one of the guided tours. The standard guided tour costs $22 and takes about an hour and 15 minutes. Learning about the enslaved African-Americans who built the house and were forced to work there provides some much-needed perspective about the challenges that Black Americans endured.

Noon – 4:00 p.m: Before your trip comes to an end, carve out some more time to hunt for vintage treasures. I'm a big fan of leaving some room for spontaneity in your travel itinerary, so plan on grabbing lunch whenever your stomach starts to grumble. Nashville has so many amazing options to choose from, so pick whatever sounds good to you in the moment. If you need some recommendations, check out our food lover's guide to Nashville's best eats. 

High Class Hillbilly is a great first shopping stop and my favorite vintage shop in Nashville. The collection is curated by Nikki Lane, a singer, songwriter, and style icon who personally sources all of her vintage. This is the perfect place to pick up a pair of colorful leather cowboy boots, a unique hat, and a snazzy leather jacket to wear to a concert. If you're willing to splurge, there is also some incredible vintage sterling silver jewelry. If you're shopping for furniture, art, and home decor, head to Gaslamp Antiques and Decorating Mall. Starland Vintage and Unusual is a good final stop of the day but just make sure you have at least an hour to browse. 

6:00 p.m – midnight: I recommend taking it easy on your final night in Nashville, but opting for a more laid-back experience doesn't mean it has to feel boring. Head to Char for dinner. It's a classy, contemporary restaurant that blends modern design elements with vintage touches. The Southern-style steakhouse has options like classic rib-eyes and cornbread dusted red fish. Make sure to save some room for a slice of pecan pie. While you eat, you can enjoy the sound of live piano music drifting from the lounge. Performances by the Nashville Jazz Workshop are offered nightly.

After dinner, it's a six minute walk to The Bluebird Cafe, which is another one of Nashville's most iconic music venues. The Bluebird Cafe only has 90 seats, so it's incredibly intimate and a wonderful place to see up-and-coming artists. The venue focuses on celebrating songwriters and usually there are multiple musicians performing each night. Tickets can be purchased online in advance. In addition to the ticket fee, which is usually around $30, all guests are required to spend a minimum of $15 per person on food and drinks.

After the music ends at The Bluebird Cafe, head back to your hotel and spend the final hours of your vacation relaxing. If you're anything like me, you'll already be mentally planning your next trip to Nashville.