Culture / Travel

How to Spend a Perfect Weekend in Downtown Nashville — Where to Stay, Eat, Drink, and Explore

Using Bobby Hotel As Our Southern Chic Base, Music City Is a Walkable Wonderland

BY // 04.22.24

For a first-time trip to Nashville, my goal was to eat well, drink whiskey, see some live music, and learn a little about the history of the city. We achieved all of these things and more. (And by more I mean the incredible people-watching that comes with 50 or so bachelorette weekend trips taking place in downtown Nashville at the exact same time.) Using the one-of-a-kind Bobby Nashville boutique hotel as our Southern chic base, we thoroughly explored Music City in one weekend.

Bobby Hotel Lobby_1
The Bobby Nashville lobby features a cozy lounge area with a fireplace. (Courtesy)

Where to Stay in Downtown Nashville: Bobby Hotel

Adjoining the neighborhoods of Germantown and East Nashville, this 144-room boutique hotel blends Southern hospitality and urban elements. The relatively new hotel is located right off the historic Printers Alley, originally named for the thriving printing industry it housed at the turn of the 20th century. By the 1940s, the alleyway became downtown Nashville’s first nightclub district. It’s still a happening area for bars and live music spots, along with the addition of an AllSaints storefront.

Opened in 2018, Bobby Nashville was designed by New York City’s David Mexico Design Group. When you walk into the lobby, you’ll immediately see a massive chandelier constructed of car parts. Other design elements include marble columns, reclaimed artisan wood planks, copper, brass, and industrial metals. A spacious lounge area with a fireplace is available for guests to hang out or work.

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The two-bedroom suite at Bobby Nashville features a pool table and a private balcony. (Photo by Lisa Diederich Photography)

Guest rooms range from Standard King to the Bobby Two-Bedroom Suite. Eclectic decor includes Rorschach inkblot carpeting, historic world maps inspired by musicians’ lives on the road, and bedside journals for Gonzo-style literary musings. Each bathroom features glass pane walls and William Roam bath products.

A highlight of the hotel is its ninth-floor rooftop pool and bar, featuring a 1956 retrofit scenic cruiser bus where you can enjoy drinks. Soon, they’ll be adding a pickleball court to the mix.

The second-coolest space at the hotel is Bobby’s Garage, a speakeasy-style bar that’saccessible through Printer’s Alley or through the back of the hotel’s signature restaurant, Union Tavern. Bobby’s Garage features a retractable stage lit by car headlights and hosts late-night performances.

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Bobby’s Garage is a cool spot for drinks at the hotel. (Photo by Lisa Diederich Photography)

Union Tavern is also a great spot for a casual meal on property. The menu consistently changes, but focuses on locally sourced ingredients. Currently, they have everything from shrimp Wellington to baked gnocchi with short rib. The cocktail menu also features a refreshing spicy cucumber marg.

For breakfast or lunch, Café at Bobby has everything you need including coffee, beer, wine, and brunch bites. The hotel is also making their own bagels, so make sure to try one. Garage doors open up to the outdoor patio facing 4th Avenue.

Nelson's Green Brier Nashville
Check out Nelson’s Green Brier Distillery for whiskey tastings and tours. (Courtesy)

Where (Else) To Eat and Drink in Downtown Nashville

Just a three-minute walk from Bobby, Elegy Coffee is a must-visit spot for a great cappuccino. They also have locations in Germantown and East Nashville.

And why spend two hours driving to the Jack Daniel Distillery when there are so many great ones near downtown? We spent an afternoon at Nelson’s Green Brier Distillery, where you can join a tour, have lunch at the restaurant, or enjoy a whiskey tasting at the bar. (Don’t miss the frozen Cold Fashioned.)

Nashville is also home to one of the seven locations of Oak Steakhouse. The Southern restaurant concept uses Appalachian ingredients to craft dishes like the pan-seared scallops and artisanal meat & cheese board. We also enjoyed the filet mignon with a green peppercorn cream. A favorite dessert is the butter cake with bourbon caramel and bourbon burnt sugar ice cream.

Husk Nashville
The sweet potato bread is topped with a toasty peanut toffee sauce at Husk Nashville. (Photo by Megan Ziots)

You can’t go to Nashville without visiting Husk for brunch or dinner. Led by chef Ben Norton, the Southern restaurant has an outpost in Charleston as well. For Sunday brunch, we couldn’t get enough of the sweet potato bread as a starter. The menu changes frequently, but I have a feeling everything is always good here.

Another fun happy hour stop was at TailGate Brewery, an independent craft brewery in Nashville. They specialize in small-batch brews, homemade pizza, and have four taprooms in the city. We checked out the Germantown location and we’re so impressed with the pizza that I’m still thinking about it. One must get the Tie Dye Pie with mozzarella and alternating rows of marinara, pesto, and vodka sauce. It’s also topped with whipped ricotta and parmesan.

Finally, we waited to check out the three-story rooftop bar The Hampton Social until after the bachelorette party crowds dispersed on Monday afternoon. We still saw one, casual party enjoying espresso martinis, although I had a feeling they were headed back home that day. Hampton is a coastal seafood restaurant with party vibes for sure, but they also offer great food. The chilled, Maine-style lobster roll was the best I’ve ever had. Also, don’t miss the Hampton Frosé. It’s a peachy vodka and rosé mixture with edible glitter. It’s fun.

Country Music Hall of Fame
In Nashville, the Country Music Hall of Fame is a must-visit. (Courtesy of Visit Nashville)

What To Do in Downtown Nashville

When in downtown Nashville, the Country Music Hall of Fame and Museum (aka “the Smithsonian of country music”) is a must. It’s one of the world’s largest museums and research centers dedicated to the preservation and interpretation of country music history, and the experience is thorough. You’ll explore decades of music starting at the turn of the nineteenth century to current to Taylor Swift and Jelly Roll.

Bobby Nashville is located right around the corner from another historic hotspot: Skull’s Rainbow Room. The restaurant and bar is known for its live music and burlesque performances. Since 1948, the speakeasy-style basement bar has been a can’t-miss experience in Music City.

A personal venture on our Nashville trip (and the only place we couldn’t walk to) was a visit ro my favorite author Ann Patchett‘s bookstore, Parnassus Books. It’s a cool little indie bookstore with all kinds of genres available. Patchett even offers a section of her own novels (from Commonwealth to Tom Lake), all signed by her. Sadly, Ann was not at the shop that Sunday, but I’m sure if you go during the week you have a better chance of seeing her, along with her pup, Sparky.

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