Last year, my brother hatched a plan to propose to his girlfriend Kassie on her birthday in Nashville. As soon as he told me, I was thrilled and immediately started putting together an itinerary that would make their engagement trip truly unforgettable. We covered all the bases during our stay – from brunch to bars, shopping to sightseeing, we did it all in style. And speaking of style, I also had a ball planning out all of my outfits for the trip. So if you’re looking for some inspiration for your next visit to Nashville, read on because I’m excited to share our full itinerary and all of the looks that LITERALLY made it happen.
Day 1 – We arrived in town and set up for Kassie’s engagement party. After the party, we hopped into a White Limozeen (on the rooftop of the Graduate Hotel) for drinks and pictures before heading to Jeff Ruby’s for a celebratory dinner. Afterwards, we explored downtown Nashville, hitting up honky-tonks like Aldeans, Ol Red, Luke Bryan’s, and Redneck Rivera.
Day 2 – We started the day with brunch at Hampton Social, where we toasted the newly engaged couple with guitar shots. Next up was a 2-hour party bus tour of downtown Nashville, where we visited iconic Nashville hotspots like Tootsies, Casa Rosa, and Pushing Daisies. Afterward, we headed home to change, before making our way to Twelve Thirty Club for apps and dinner before exploring more bars on Broadway.
Day 3 – We started the day with delicious donuts from 5 Daughters Bakery before hitting up some of the city’s best shopping, like Stoney Clover, Love Shack Fancy, and Finnleys. For an early lunch, we enjoyed tacos at Bartaco before exploring The Gulch and stopping at Rustler Hat Co. Later that evening, we enjoyed happy hour at LA Jackson with stunning rooftop views and then headed to Bourbon Steak for dinner. We ended the night at the Russel Dickerson concert, which was a blast… he’s such a fun performer.
Day 4 – We started the day with breakfast at Milk & Honey before treating ourselves to a Lip Lab experience. Next, we explored some of Nashville’s most famous landmarks before stopping for lunch at Stateside Kitchen. We took a tour of the Ryman and celebrity homes before enjoying dinner at Casa Rosa and hitting up more bars on Broadway.
Day 5 – On our final day, we had breakfast at Monell’s before doing some last-minute shopping at Vici and Blush Boutique. We enjoyed a late lunch at Roberts Western World before heading to the airport for our return flight.
This trip was jammed packed with iconic Nashville experiences, and our itinerary was the perfect mix of sightseeing, shopping, and celebrating. I loved exploring all the hotspots in Nashville and trying amazing food at local restaurants. As for my favorite outfit, it’s hard to choose just one. I already can’t wait to go back!
