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 no plans—just a desire to wander, enjoy the sights, and eat well (spoiler: we did all three). It may rank as one of our favorite weekend getaways, tied with New Orleans. Below are the places we visited, the meals we loved, and the activities that made this short trip so memorable.
Why We Vacationed in Charleston
Since moving to Florida three years ago, our travel style has shifted. We no longer chase poolside or beachfront hotels—because we have both at home—and now prefer walkable cities and small towns full of shops, parks, architecture, and good food. Charleston fit that bill perfectly. With our kids now 9 and 13, we wanted a trip focused on exploring and enjoying the city rather than playgrounds and children’s museums. Everything we did was kid- and dog-friendly, though families with much younger children may prefer a different itinerary.
Where We Stayed in Charleston, SC
We booked a last-minute Airbnb—the upstairs unit called “The Poppy Suite”—after it appeared with a short vacancy. It was beautifully decorated, spotlessly clean, well-stocked, and welcoming to both kids and dogs. The rental is in Cannonborough/Elliotborough, a highly walkable neighborhood minutes from restaurants and coffee shops, which made it the perfect base. The suite has one bathroom, which worked fine for our family, and a front bedroom that opens to a shaded balcony we used to rest and read between outings.
Where We Explored in Charleston, SC
With just two full days, we dedicated one day to exploring Charleston’s historic districts and another to visiting nearby beach communities. We took a relaxed approach rather than a strict itinerary: walking from our rental to King Street, popping into shops, enjoying the architecture, and sampling local food. Charleston’s historic homes, side porches with “hospitality doors,” and abundant window boxes made for endlessly charming strolls.
We also visited Rainbow Row and the Pineapple Fountain and ended up walking roughly six miles the first day, broken up with lunch, a midday rest at the rental, and plenty of stops in shops. Guided walking tours looked fascinating too—something to consider for a longer return visit.
Where We Shopped in Charleston, SC
King Street offered a variety of independent shops and boutiques. We wandered into a beautiful home-decor-filled Amanda Lindroth store and always try to visit a local bookstore—Blue Bicycle Books quickly became a favorite. Other notable stops included a soap shop, a gallery-style decor store, and a charming stationery shop where our kids indulged their love of pens and markers.
Exploring Charleston’s Beaches
On our second day we drove to Isle of Palms and Sullivan’s Island. We enjoyed a morning beach walk at Breach Inlet, where the kids hunted shells and our dog, Penny, delighted in sniffing around. Afterward we found A Maker’s Post on Sullivan’s Island—a standout shop mixing art, housewares, and plants that everyone in the family enjoyed. On the return trip we stopped at Plant House in Mount Pleasant, an expansive plant shop where the kids built terrariums at a DIY station—a hands-on activity they still talk about.
Where We Ate in Charleston, SC
Food was a highlight. We’re casual diners who look for tasty, well-priced meals with a good vibe—and Charleston delivered.
Breakfast
Both mornings we ate locally. Daps Breakfast & Imbibe served excellent coffee and oversized egg sandwiches and pancakes (the Fruity Pebble pancake was a hit with our daughter). On another morning we enjoyed New York–style bagels at Holey City Bagels, paired with a relaxed coffee shop atmosphere.
Lunch & Dinner
Nearby Mexican restaurants Pink Cactus and Fuel Cantina both impressed—generous portions and lively patios. Fuel Cantina’s back patio, set in a repurposed gas station, offered string lights, big fans, and yard games that kept the kids entertained. We also enjoyed the Port of Call Food Hall for variety and tried pineapple soft serve at The Pineapple Hut for dessert.
Our standout meal was an early lunch at The Obstinate Daughter on Sullivan’s Island. Casual family-friendly service and exceptional food—my peach flatbread pizza with balsamic was unforgettable, and every plate at our table was finished clean.
Was Charleston Dog Friendly?
Yes—Charleston was very dog friendly. Our Airbnb welcomed Penny, and many outdoor restaurants and beaches allowed dogs during our visit. We typically carried Penny into shops to keep her safe around displays and other animals, and we always asked staff when in doubt. The Isle of Palms allowed dogs during our visit in May, but rules vary by season and location, so it’s wise to check local regulations before you go.
Trip Summary: Highlights and Recommendations
For a first-time, lightly planned 2-day, 3-night trip, Charleston exceeded our expectations. It’s a walkable, colorful city with excellent food, charming shops, historic architecture, and easy beach access nearby. Below is a quick list of the places and experiences we enjoyed, organized for convenience.
- Airbnb base: The Poppy Suite on Spring Street
- Stroll King Street and browse local boutiques
- Visit Rainbow Row and the Pineapple Fountain
- Explore the French Quarter and historic Cannon Street homes
- Walk the beach at Isle of Palms
Shopping
- Amanda Lindroth (home decor)
- Blue Bicycle Books (bookstore)
- Buxton Books (bookstore)
- Old Whaling Company (soap and gifts)
- Mitchell Hill Gallery (decor and art)
- Sewing Down South (pillows and textiles)
- Mildred Newberry (stationery)
- Wonderworks Toys (market toy shop)
- A Maker’s Post (Sullivan’s Island home goods)
- Plant House (Mount Pleasant plant shop and terrarium station)
Eating
- Daps Breakfast & Imbibe (breakfast)
- Holey City Bagels (breakfast)
- Pink Cactus (Mexican)
- Fuel Cantina (Mexican, outdoor patio)
- Port of Call Food Hall (variety)
- The Pineapple Hut (pineapple soft serve)
- The Co-Op (Sullivan’s Island coffee)
- The Obstinate Daughter (Sullivan’s Island—pizza and seafood)
- BeardCat’s Sweet Shop (gelato)
Thanks for a great trip, Charleston—we’ll be back soon.
Other Family Trips We’ve Taken
If you’re planning family-friendly travel, you may also enjoy our write-ups of other destinations, including New Orleans, Palm Springs, St. Petersburg (FL), Mexico, Costa Rica, and more—each with tips on activities, shops, and kid-friendly dining.