Steph & Kiki's Charleston girls' weekend!

Hi y’all! Long time no talk on the blog, right? I always want to make a lot of time to write but it’s usually the first thing to get pushed aside when I’m busy – I’m going to work on this! Do any of you other bloggers do this? Any tips? 

Anyway, Kay & Co recently mixed it up a little bit by planning a girls’ weekend for two lovelies who were celebrating their 28th birthdays in Charleston! Stephanie & Kiki reached out to me a few weeks ago to see if I ever planned getaways for people that weren’t big groups of bachelorettes, and I was like, duh, I’d love to! It was just the two of them for the weekend and honestly, y’all, as much as I love my bachelorettes, it was so fun doing something for a smaller crew. Having only two to plan for really let me tailor the weekend to exactly what the girls wanted, not to mention it was much easier to get dinner & activity reservations at some of the best places in town when I was only scheduling two weeks out!

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Stephanie & Kiki wanted to stay really busy; their deal was that if Kiki got her fix of sight-seeing & history, she would oblige with Stephanie’s foodie wishes -- I thought this was a really cute deal and it also meant that Charleston was absolutely the perfect choice for them, right? Best food + all the history + a little bit of relaxation + = the perfect way to celebrate turning 28!

So without further ado, the itinerary I put together for the girls – they definitely stayed busy, but I made sure to schedule time every afternoon to nap & put their feet up for a bit before the evening, too. It was their birthdays -- they deserve it, right?!

Steph & Kiki's Charleston weekend itinerary:

Thursday evening

Stephanie & Kiki didn’t get into town until 11:25 pm, so I didn’t schedule anything for them that day, obviously. They had made reservations at the Andrew Pinckney Inn on their own, which is a great pick if you want to be right in the heart of downtown and have easy walking access to the whole peninsula. I stopped by the Inn earlier in the day on Thursday to drop off a gift basket for the girls to arrive to; they were greeted by rosé champagne and local sweets to enjoy after their long day of traveling, plus a few little gifts to celebrate their birthdays and remember their weekend in Charleston.

Friday morning

The girls wanted to do a lot of sight-seeing while they were in town, so they had scheduled two walking tours for themselves before they reached out to me. Um, yes, please – there’s no better way to see Charleston while also walking off some of those drinks from the night before. So Friday morning, they kicked off their weekend early with a walking tour that took them through the City Market, down towards Rainbow Row, and around the Battery, all while the tour guide provided fun facts and historic tidbits about the cutest city in the world. Beyond their walking tour, a little summary of what I gave them for the morning:

  • Breakfast at the Andrew Pinckney Inn
  • 9:45 am: guided walking tour (approximately 2 hours)
  • Explore the Battery & Rainbow Row
  • Walk through the City Market: the center of the Market is fun to walk through & has a lot of cool shops, but make sure to pay attention to the shops around the outside, too!
  • Lunch at Callie’s Hot Little Biscuit on the Market
  • Explore + shop
  • Head back to the hotel to relax + shower

Friday evening

I always like to make sure that groups staying closer to East Bay & the Market still make it to the Upper King area – it’s becoming more & more popular with tourists, but not everyone gets there if they’re staying on the other side of the Peninsula. Upper King is my absolute favorite for nightlife + amazing restaurants, so I sent the girls to Cocktail Club, this great little lounge-y spot above The Macintosh, for a craft cocktail and bacon popcorn (!) before dinner at Indaco, an Italian spot up the street.

Indaco tip: you probably won’t know what half the menu is, so just ask your server what their recommendation is, and get it. You will have no regrets, I promise. My personal favorite is the duck confit pizza!

The rest of their Friday night recommendations from me:

  • Uber to Upper King + get drinks at Cocktail Club -- their bacon popcorn is SO.  INCREDIBLY. GOOD.
  • 7:15 pm: dinner at Indaco
  • Go out on Upper King!
  • Bars I love: Stars Rooftop (one of my favorites!), 39 Rue de Jean (another favorite -- grab a seat at the bar & get one of their cocktails!), The Rarebit (amazing Moscow Mules), Prohibition, O-ku, & Juanita Greenberg’s (for a late-night snack)

Saturday morning

Friday had definitely been packed for the girls, so I slowed it down a bit on Saturday morning and sent Stephanie & Kiki to get facials at Earthling Day Spa, close to their hotel on East Bay Street. From there, I wanted them to experience one of my favorite walks around the Peninsula, so I had them uber to Cannonborough, a neighborhood that includes Upper King and some great little shops, and walk down King Street from there.

Side note: if you’re planning a trip to Charleston, I highly recommend taking a morning to walk through Cannonborough/Elliotborough –  lots of locals (including yours truly) call it home, as do Insta-worthy stores like Sugar Bakeshop, Mac & Murphy, and Cannonborough Collective.

For Stephanie & Kiki, I made the Cannonborough walk happen by including a stop at Brown’s Court Bakery after their facials; Brown’s Court is in the heart of Cannonborough and is a great start to the walk down Cannon Street to Upper King. I won’t bore you with every turn & stop along this quintessential Charleston walk – but if you’re interested in learning more about where to see & how to take this walk, send me a message!

After a leisurely walk down the Peninsula, Cru Café was a perfect stop for lunch for the girls – serving up amazing food in a historic Charleston home, it’s also located right next to the Market. Make a reservation, they don’t have a ton of tables and they book up fast.

Quick stop back at the hotel to relax for a bit and the girls were on their way again – this time, heading to a Sunset Cruise around the Charleston Harbor and then back downtown for dinner and a Haunted Jail Tour. Stephanie & Kiki were here in November, so their Sunset Cruise was earlier, but spring and summer tours would board later in the evening than five pm, of course. From there, the girls wanted to check out Fig on East Bay before a Haunted Jail Tour – both of which I recommend, followed by a stop at The Gin Joint, The Bar at Husk, or SNOB for a nightcap before heading back to the hotel to sleep after a packed day.

Stephanie & Kiki’s Saturday itinerary:

  • Light breakfast at the hotel
  • 9 am: facials at Earthling Day Spa
  • Uber to Upper King + get coffee at Brown’s Court Bakery (try a croissant!)
  • Shop + sight-see on King Street
  • From Brown’s Court, turn right out the door, stop into Cannonborough Collective, then head towards King Street & turn right – wander & shop! The Farmer’s Market in Marion Square goes until 2 pm – definitely stop to check it out!
  • 2:30 pm: lunch at Cru Café
  • Relax + nap

Saturday evening

  • 5:00 pm: Sunset Cocktail Cruise (don’t forget drinks & snacks!)
  • 7:30 pm: dinner at Fig
  • 10 pm: Haunted Jail tour

Sunday morning

Sunday was a more relaxed day for the girls – they’d seen so much yesterday that I wanted to give them a chance to take it a bit slower and have time to revisit anywhere that they particularly loved on Saturday. Brunch was a definite must, so I made reservations at Poogan’s Porch, one of my favorite places to send groups because of their phenomenal classic Southern brunch and perfect setting in a historic home on Queen Street. After brunch, Sunday Funday is always my go-to – I recommended a variety of rooftop bars, casual restaurants with great mimosa deals, and a few stores to pop into for Stephanie & Kiki to take it easy.  

You’ll notice I included an alternative Sunday option: the girls hadn’t left the Charleston Peninsula yet, so I also mentioned taking an uber to Folly Beach to grab drinks, walk the beach, and experience Folly’s adorable little downtown and great local vibe.

  • 11 am: Poogan’s Porch brunch
  • Post-brunch drinks at the Rooftop at Vendue
  • Shop + Sunday Funday
  • Favorite Sunday drinking spots: Vendue, Taco Boy (downtown or on Folly), Home Team BBQ (downtown or on Sullivan’s), Stars Rooftop, Juanita Greenberg’s, Republic
  • Light dinner at The Watch Rooftop + Spirits
  • Other dinner options: Leon’s (try the frosé!), Taco Boy, Workshop (kind of like a cafeteria of food trucks, plus a brewery), Home Team BBQ

Alternative Sunday afternoon: after a drink at Vendue, grab an Uber to Folly Beach – spend the day bar-hopping, walking the Pier, and grab dinner at Taco Boy!

Monday morning

The girls were leaving Monday afternoon, so I kept Monday morning light – they wanted to see a plantation, so I sent them out to Boone Hall, an easy Uber from downtown and a great place to spend a few hours exploring. From there, lunch at Butcher & Bee, a unique spot with a great vibe, or Workshop, which is a cool outdoor spot where a few food trucks have set up a type of “cafeteria.” Then back to the hotel and on to the airport!

  • Breakfast at Kudu or the hotel
  • Grab an Uber + explore Boone Hall Plantation: the house tour is fun & not too long, and the Slave Quarters + Cotton Dock are also pretty!
  • Uber back downtown + get lunch at Butcher & Bee or Workshop
  • Grab bags from hotel + head to the airport!

I loved how Stephanie & Kiki made the most of their time in Charleston – I had so much fun creating an itinerary for them & recommending all my favorite spots to make sure they didn’t miss a thing. I’d love to make this happen for you, too – if you’re planning a trip to Charleston, send us a note & we’ll plan something amazing!