🌴 Holiday Festivities and Why I Almost Canceled Santa

Like everyone reading this newsletter, it has been a busy season and I am tired from trying to keep it all together. You are not alone in the pressure of trying to make Christmas feel magical for our little ones. In case you have not heard it enough yet, thank you for doing the hard work of making this season memorable. Your kids will remember the moments, even if they never say it.

This weekend, I snuck away for a mommy daughter date with a close friend and our girls, and it was such a good reminder that while this stage of parenting is exhausting, there really is a light at the end of the tunnel.

This week’s newsletter is full of festive fun, including:

Enjoy! 🫶🏼🎅🏼

It has been so fun putting together local events to celebrate this magical season. I love doing fun, Christmasy things, especially when they include outdoor time and when they are free! Out last thing to do this holiday season is one of those simple, feel good traditions that makes the season extra magical! Head out to Daniel Island to stroll Park Crossing and take in some of the most impressive holiday light displays in the Lowcountry.

Homes along these streets go all out each year, transforming their yards into elaborate holiday scenes that truly stop you in your tracks. One friend even described the decorations as movie set quality, and it is hard to disagree once you see them in person. It feels like stepping into a real life Christmas story, especially for kids who are wide eyed the entire walk.

One standout home even has a mailbox for letters to Santa, so be sure your kids bring their wish lists along for the visit. It is a sweet, simple touch that turns an evening walk into a core holiday memory. Plan to make a full night of it by grabbing drive through hot chocolate on the way and enjoying a cozy family stroll before heading home. It is low effort, high magic and the perfect way to savor the final days of the season.

We recently had family photos taken by Faithy Gray Photo, and we can’t recommend her enough! She made what could’ve been a chaotic experience feel relaxed and even fun—capturing beautiful shots of our kids between the wiggles, the snacks, and the meltdowns. Faithy chose the perfect downtown Charleston backdrops that somehow captured both our family’s energy and the charm of the city. She brings a calm presence, an eye for light, and a knack for catching real connection.

Faithy is currently booking family, maternity, newborn (in-home), couples, and portrait sessions, with limited 2025 availability left and more openings in January. If you're thinking about photos in the new year, now’s the time—book before December 31 to lock in her current rates for 2026 sessions!

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This is the last weekend before Christmas and here is what you should be doing! You have almost made it and this is your chance to end the season on a high note. Head to Park Circle for the 11th Annual Holy City Holiday Market, a festive multi-day shopping event that feels like a celebration and a deep breath all at once. From December 19 through 21, Old Park Circle transforms into a holiday hub filled with local makers, food, music and family fun. All events are free, family friendly and open to the public, making it an easy yes for parents looking to soak up some holiday cheer without adding stress.

The weekend kicks off with a Preview Party on Friday, December 19 on the lawns at Holy City Brewing and Firefly Distillery. The main shopping event takes place Saturday from 11am to 5pm with more than 200 small businesses spread across Holy City Brewing, The Porter Room, Firefly Distillery and The Station Park Circle. On Sunday, the weekend wraps up with a relaxed family friendly brunch bash from 11am to 2pm on the lawns at Holy City Brewing and Firefly Distillery. Expect music, kids activities and holiday themed entertainment throughout the weekend.

While you shop, enjoy food trucks, baked goods, specialty treats and adult beverages at each venue. Families can grab a sit down meal at the Holy City Brewing taproom or relax with outdoor seating in the Firefly Distillery courtyard. One of the best parts of this market is how walkable and welcoming it feels, with each space offering something a little different while keeping kids entertained and parents happy.

Hosted by The Event Cooperative, the Holy City Holiday Market has grown from a small gathering of 16 vendors in 2015 into one of Charleston’s most beloved holiday traditions. Shoppers are encouraged to explore the Park Circle neighborhood between venues, popping into local favorites and enjoying the area. Complimentary shuttles will be running on Saturday to help with parking, or you can walk, bike or even cruise by golf cart. Mark your calendars for December 19 through 21, and make this joyful weekend part of your family’s holiday tradition.

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This is your sign to plan a proper date night downtown. The Blind Tiger Pub delivered the perfect mix of festive, fun and memorable for our recent adults only night out. Our church small group rounded up babysitters and headed downtown ready to relax, and from the moment we walked in we knew we had picked the right spot. We found garage parking just a short walk away, made reservations ahead of time and stepped into a lively, loud atmosphere filled with really special Christmas decorations that instantly set the mood for a great night out.

The Blind Tiger Pub is also steeped in Charleston history, which makes the experience even better. The term Blind Tiger dates back to the late 1800s, describing illicit drinking establishments during the temperance era. The pub opened on Broad Street in 1992 as a nod to that history and was beautifully restored in 2016. It has remained a fixture of Charleston society ever since, blending local lore with a welcoming, celebratory vibe.

The food and drinks made it an easy win for a big holiday group. We started with classic pub favorites like mozzarella sticks and poke nachos, which were perfect for sharing. For dinner, my husband enjoyed a satisfying burger and while I stuck to the steak and balsamic brussel sprouts, the kind of comfort food you want on a winter night. I ordered a winter spritz and it could not have been more perfect for a festive evening. The drink menu felt seasonal and fun, with something for everyone at the table.

The absolute showstopper, though, is the ceiling. I would normally never notice a ceiling in a restaurant, but this one is impossible to miss. It is filled with what feels like thousands of ornaments, creating a stunning and immersive holiday experience that truly sets the Blind Tiger apart. As we left, there was already a line forming outside, which confirmed we made the right choice. If you are looking for a fun, energetic and festive spot, the Blind Tiger is the perfect date night destination this season.

Every Christmas season, I reach a point where I want to cancel Santa. We made Santa a big deal in our house when our firstborn was three, and now that he is seven, being Santa feels a little overwhelming. This year it hit during Thanksgiving break when our kids made their Christmas lists. It was such a sweet moment watching our seven year old help his four year old sister by writing down her wishes, and for a second I felt confident we had done Santa right.

That confidence disappeared when I secretly opened my son’s sealed letter to Santa and saw his number one request was gold grills, yes, the kind from the song “Let me see your grills.” I stood there wondering how Santa had become responsible for ordering kid sized gold teeth off the internet.

Then came the moment that really made me question everything. I told my kids we were going to buy gifts for children who might not have money for Christmas gifts, and my four year old refused. I was very surprised because she is usually so sweet to other people (not me). She then asked why Santa doesn’t bring presents to all kids. That question stopped me cold and I laugh cried and dropped the discussion entirely.

We will still be buying gifts for kids in need, even if I have to do it by myself. This is your reminder to do the same if you’re able. Sometimes it feels better to give generously through donation boxes or Toys for Tots in Charleston than it does to chase over the top Santa gifts. And if you have thought about canceling Santa too, you are not alone!

You can find more information about toys for tots on this link. There are donation bins at most grocery stores and different drop off locations. Buy a gift, skip the wrapping and do something generous that only you will see!

Enjoy the last full week of the Christmas Season!

Love, Jenna