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48 Hours at The Dewberry in Charleston

Jordan Rhodes

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By Jordan Rhodes

In late October I took a trip to Charleston with my little boy for his birthday. Having gone to college there I feel like somewhat of an expert on the city, but with the ongoing explosion of hotels and restaurants over the last few years, I need to get down there often in order to keep up with the pace of additions. Six visits with my kids over two years means I’ve finally figured out the best way to see the city in two days, so I decided to create a short itinerary for those looking to spend a weekend in the Lowcountry (but don’t forget we have a full city guide to Charleston on our app). And because our guides are for luxury family travel, it means they work with or without kids.

When my little boy and I landed we headed straight to The Dewberry hotel, Charleston’s newest hotspot. I had heard from so many friends how cool it is, and I was very intrigued by the design. They took a historic building from the 60s and incorporated the original elements from that era to create updated luxury, but with mid-century influences. The results are impressive, and you really feel like you have stepped into that decade. Here are a few photos, some taken by me, and some provided by the hotel:

The Living Room. Photo by the hotel

The Living Room. Photo by the hotel

The bar in the Living Room

The bar in the Living Room

Henrietta’s restaurant. Photo by the hotel.

Henrietta’s restaurant. Photo by the hotel.

The Concierge. Photo by the hotel.

The Concierge. Photo by the hotel.

Cocktails and the famous popcorn.

Cocktails and the famous popcorn.

The entrance. Photo by the hotel.

The entrance. Photo by the hotel.

Our room was beautiful, and very spacious with a four-poster bed, stunning marble bathroom, and the hotel’s own signature bath products. I could have soaked in the large, free-standing tub all day followed by cocktails in the living area, and Don Draper could have been transported to our personal bar and felt right at home on the velvet sofa. Besides hanging in our room, we also spent some time in the lobby bar area where kids are welcome, and my little boy fell in love with the popcorn.

Our personal bar.

Our personal bar.

The living area of our corner room.

The living area of our corner room.

The Dewberry bath products. I love the font they chose.

The Dewberry bath products. I love the font they chose.

The spacious bathroom.

The spacious bathroom.

This is the bread basket from room service! Perfect after a night out on the town.

This is the bread basket from room service! Perfect after a night out on the town.


The design aside, the staff is also a reason to stay here. Everyone we encountered could not have been friendlier, and it seemed like there was a balloon for my little boy every time we turned around. There’s nothing better than staying at a luxury hotel where you feel like your kids are really welcome. I also think the location is perfect, situated right in the middle of the stunning mansions down on the water, and the new foodie spots that have popped up in a renovated part of town. Plus the square right across the street is a great place for kids to run around, for older kids to ride bicycles provided by the hotel, or for the entire family to enjoy at the well-known, seasonal Farmer’s Market.

Bicycles to borrow.

Bicycles to borrow.

Garden & Gun magazine has a boutique in the lobby with amazing curated goods.

Garden & Gun magazine has a boutique in the lobby with amazing curated goods.

While we didn’t get a chance to enjoy the spa, which I hear is amazing, we did make use of the hotel’s car service which will drop you off at most of the tourist spots and restaurants on the peninsula. It was very tough for me to narrow down my picks for the perfect two-day visit, but here is what I would recommend:

Day 1

Lunch - after landing and checking in, head to Cru Cafe which is nice and quick, and not too far from your first activity. My kids devour the macaroni and cheese.

Afterwards, take a boat to Fort Sumter for a tour of this Civil War-era fort. The kids will love the boat ride, and you will enjoy the view of the historic homes and steeples. Reservations can be booked ahead of time here.

If there’s still time before dinner, pop into the aquarium next to the boat landing.

Dinner - dine at The Ordinary. While I wouldn’t recommend eating at its famous sister restaurant, FIG, with kids, they are perfectly welcome here and the seafood-based menu is incredible. I still dream about the oyster sliders.

Day 2

Breakfast - Henrietta’s at The Dewberry. My photo of the bread basket, above, says it all.

Take a walk down towards Waterfront Park where my kids are obsessed with splashing in the fountain. It is seriously all the want to do whenever we’re in town. If you’re interested in a horse-and-carriage tour they embark from the market area on the way here, but I find they are best for older kids. Afterwards keep walking towards the bottom of the peninsula where there is a great playground for kids at 70 East Bay Street. You can then wander along the water checking out the enormous historic homes if you did not take a carriage tour.

Lunch - Hop in your rented car and head to Taco Boy. You’ll love the delicious Mexican food and the boisterous ambiance is perfect for kids. I particularly love the enclosed courtyard where they can walk around.

After lunch make your way to Magnolia Plantation in your car. Kids will love the petting zoo with animals like tame deer and peacocks, and there are also train and boat rides. Adults will enjoy getting a glimpse of the antebellum south, with the moss-covered trees and house with sweeping front porch. You can also pop over to other neighboring plantations like Middleton Place and Drayton Hall. If the kids are still up for activities, Charles Towne Landing has a mini zoo and other fun activities.

Dinner - head to Leon’s Oyster Shop for insane oysters, or their famous fried chicken for those with less adventurous kids (like mine).

Day 3

Breakfast - after a long day sleep in a bit and head to Hall’s Chophouse at 10 am. The Sunday brunch with gospel choir is really special.

Next take your car out to Sullivan’s Island for some beach time. We like this beach because it is more families, less college students and surfers like at Folly Beach.

Lunch - enjoy a late lunch at nearby The Obstinate Daughter. The pizza and pasta will be enjoyed by all.

Finally, start planning your next trip to Charleston. Because we promise you will fall in love with this town full of southern charm, noteworthy restaurants, and architectural beauties.

Horse-and-carriage tours.

Horse-and-carriage tours.

Petting deer at Magnolia Plantation.

Petting deer at Magnolia Plantation.

Stunning homes.

Stunning homes.

The fountain at Waterfront Park.

The fountain at Waterfront Park.

A walk along the water.

A walk along the water.