Last week our family took a spontaneous 2-day, 3-night trip to Charleston, South Carolina — and it was absolutely delightful. It was our first visit and we arrived with zero planning, no strict itinerary, and a simple goal: explore the city, enjoy the sights, and eat well. Spoiler: we succeeded on all counts. It might be our favorite short trip yet (tied with New Orleans). Below are the places we visited, the activities we enjoyed, and the meals that made this weekend so memorable.
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Why We Vacationed In Charleston
After moving to Florida three years ago, our travel priorities shifted. We already have a beach and pool at home, so we now prefer walkable cities and charming towns full of shops, parks, restaurants, and architecture to explore. Charleston fit that bill perfectly. With our kids now 9 and 13, they enjoy wandering and discovering new places, so we didn’t feel the need to focus on playgrounds or children’s museums. Everything we did was kid-friendly — and dog-friendly — but some activities might be better suited to older children.
Where We Stayed In Charleston, SC
We booked a last-minute Airbnb that had a discounted window between reservations. The rental was lovely, well managed, and exactly what we hoped for: clean, well-decorated, well stocked, and welcoming to both kids and our dog. We stayed in the upstairs unit, the Poppy Suite, which had a front bedroom opening onto a balcony where we spent relaxing hours reading and enjoying the breeze. The location — in the Cannonborough/Elliotborough neighborhood — made it easy to walk to coffee shops, restaurants, and King Street.
The unit had comfortable sleeping arrangements for the kids — one in a middle bedroom and the other in a bunkroom — and the balcony became our favorite afternoon retreat. The one-bathroom setup worked fine for us, but could be a consideration for other families.
Where We Explored In Charleston, SC
With only two full days, we dedicated one day to downtown exploring and the other to the nearby beach communities. We took a relaxed, go-with-the-flow approach rather than hitting historical tours and museums. On our city day we walked from Spring Street to King Street, popping into shops, sampling food, and admiring the architecture. Charleston’s historic homes, colorful facades, and famous window boxes made the stroll endlessly enjoyable.
We loved the city’s mix of historic charm and lively color — from side porches with “hospitality doors” to the pink Huguenot church in the French Quarter. We also visited Rainbow Row and the Pineapple Fountain in the evening after a midday break at the Airbnb. Our first day included about six miles of walking, broken up by meals, shopping stops, and porch time to cool off.
Where We Shopped In Charleston, SC
Most of our shopping happened near King Street, where we wandered into stores that caught our eye. Highlights included a bright, rattan-filled Amanda Lindroth shop and Blue Bicycle Books, a wonderful independent bookstore. The kids enjoyed browsing plant and stationery shops, and we all had fun smelling soaps at the Old Whaling Company and exploring the Mitchell Hill Gallery.
Sherry also wanted to visit Sewing Down South, the pillow shop opened by a local TV personality — a fun stop even without celebrity sightings. Our two favorite shops, however, were across the bridge near the beach communities.
Exploring Charleston’s Beaches
One morning we drove out to Isle of Palms and Sullivan’s Island. We parked near The Boathouse at Breach Inlet for a beach walk — the area was welcoming to dogs — and enjoyed shells, seawater, and fresh air. Afterward we found A Maker’s Post on Sullivan’s Island, a store with art, housewares, and plants that the whole family loved. The kids each picked new books, which made it a win for all ages.
On the drive back we stopped at Plant House in Mount Pleasant, a large plant shop with DIY terrarium stations. For a modest fee, the kids assembled their own terrariums with guidance from staff, choosing plants and decorative toppings. It was hands-on, creative, and one of the most memorable stops of the trip.
Where We Ate In Charleston, SC
Our priority when traveling is tasty food and a relaxed atmosphere, and Charleston delivered. We enjoyed both casual neighborhood breakfasts and memorable lunches and dinners in town and across the bridge.
Breakfast
Both mornings we had breakfast at nearby spots. Daps Breakfast & Imbibe served strong coffee, giant egg sandwiches, and huge pancakes (the Fruity Pebble pancake was a kid favorite). Holey City Bagels offered New York–style bagels with great coffee — a satisfying local find.
Lunch & Dinner
Nearby Mexican favorites included Pink Cactus and Fuel Cantina. Pink Cactus surprised us with generous, flavorful plates despite a humble exterior; Fuel Cantina offered an excellent outdoor patio and playful atmosphere in a converted gas station. We also enjoyed a visit to the Port of Call Food Hall for variety and pineapple soft serve at The Pineapple Hut for dessert.
Our standout meal was at The Obstinate Daughter on Sullivan’s Island. We stopped for an early lunch and loved every bite: a peach flatbread pizza with balsamic drizzle, kids’ pasta and flatbread they declared “the best,” and an ahi tuna special. For dessert we shared a creative olive oil–drizzled gelato at a nearby shop — unexpectedly delicious and a perfect finish.
Was Charleston Dog Friendly?
Yes. Charleston felt very dog friendly: our Airbnb welcomed pets, many outdoor restaurants allowed dogs, and some beaches permit dogs depending on the season and location. We ate most meals outside and often had one of us wait outside with Penny while the others ordered. In shops we usually carried Penny to avoid any mishaps and asked staff if pets were welcome — every person we asked was happy to have her.
Our Trip To Charleston, SC: A Summary
For first-time visitors who like to travel without a rigid plan, Charleston is an easy win. It’s walkable, colorful, full of independent shops and great food, and welcoming to families and pets. Below is a quick recap of the places we mentioned on our trip.
- Our Airbnb: The Poppy Suite on Spring Street
- Walking down King Street
- Visiting Rainbow Row & Pineapple Fountain
- Exploring the French Quarter
- Checking out houses on Cannon Street
- Walking on the beach at Isle of Palms
Shopping
- Amanda Lindroth (home decor on King Street)
- Blue Bicycle Books (bookstore on King Street)
- Buxton Books (bookstore on King Street)
- Old Whaling Company (soap shop on King Street)
- Mitchell Hill Gallery (decor and art)
- Sewing Down South (pillow shop)
- Mildred Newberry (stationery on Broad Street)
- Wonderworks Toys (toy store in Charleston Market)
- A Maker’s Post (home goods on Sullivan’s Island)
- Plant House (plant store in Mount Pleasant)
Eating
- Daps Breakfast & Imbibe (breakfast)
- Holey City Bagels (breakfast)
- Pink Cactus (Mexican)
- Fuel Cantina (Mexican, patio dining)
- Port of Call Food Hall (variety)
- The Pineapple Hut (pineapple soft serve)
- Peace Pies (ice cream)
- The Co-Op (coffee on Sullivan’s Island)
- The Obstinate Daughter (Sullivan’s Island, pizza and seafood)
- BeardCat’s Sweet Shop (gelato)
Thanks for a fantastic trip, Charleston — we’ll be back soon!
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