United States

Charming Charleston for the Holidays

Charleston: where Christmas magic meets southern charm!

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Overview

With its captivating culture, storied history, stunning architecture, and renowned culinary scene, Charleston has earned its place as one of America’s most beloved destinations. There’s no better time to experience the charm of the Holy City than just before the holidays when the air is crisp and the festive spirit fills the streets. Join us for an unforgettable journey that offers a true insider’s view of Charleston. Enjoy a scenic carriage ride through its historic streets, explore the stunning Middleton Plantation, and take in the beauty of Wadmalaw Island. Immerse yourself in Charleston’s elegance, from private gardens and world-class dining to rich cultural heritage and the holiday magic that fills the air. This trip will delight all your senses, blending the city’s timeless allure with the season's enchantment.

Highlights

Take a holiday walking tour through Charleston’s historic district

Take a holiday walking tour through Charleston’s historic district

Learn about the historical significance of Middleton Plantation

Learn about the historical significance of Middleton Plantation

Dine at some of Charleston’s best restaurants

Dine at some of Charleston’s best restaurants

Wander the tree-covered lanes of Wadmalaw Island

Wander the tree-covered lanes of Wadmalaw Island

Explore historic downtown Charleston with an engaging guide, a beautiful horse and a comfortable carriage

Explore historic downtown Charleston with an engaging guide, a beautiful horse and a comfortable carriage

Enjoy a special evening at the historic Edmondston-Alston House

Enjoy a special evening at the historic Edmondston-Alston House

Itinerary

Here's a day-by-day itinerary of the trip. Press the "<" and ">" buttons below to scroll through each day.

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Welcome to Charleston

Day 1: Wednesday, December 2, 2026

Arrive in Charleston and take a taxi to the stylish Spectator Hotel, located at the desirable corner of the City Market and the historic French Quarter. It offers a unique boutique experience, blending Southern charm with Jazz Age flair. 

Settle in, explore the neighborhood, or simply relax and enjoy the hotel's charming atmosphere. We'll gather in the early evening for a meet-and-greet and a welcome toast in the hotel bar. 

Then, we're off to dinner at Tempest, an elegant eatery offering seasonal, locally sourced seafood delicacies and a robust wine list. 

Included

Welcome drinks

Dinner

Not Included

Airport transfer

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Charleston - History Tours

Day 2: Thursday, December 3, 2026

After breakfast, we'll start the day with a private guided tour of Charleston, where we'll discover the traditions and stories of the city’s rich history and colorful past. 

The tour will highlight vibrant neighborhoods, historic sites, architecture, and art, including Rainbow Row, White Point Garden, and some of Charleston’s most beautiful churches. We'll visit the Four Corners of Law and The Battery while viewing private neighborhoods dressed in their holiday finery.

We'll stop for some gourmet comfort food at one of Charleston's many quaint cafes. After lunch, you'll have the rest of the afternoon to discover more of Charleston on your own time. 

Before dinner, we'll take a private bus tour of historic downtown Charleston to uncover its secrets. We'll weave through cobblestone streets, past grand antebellum mansions, and under moss-draped live oaks as hidden stories come alive at every turn. Prepare for a truly memorable journey through time.

Dinner tonight will be at one of Charleston's favorite restaurants, S.N.O.B., an eclectic bistro serving up authentic lowcountry cuisine. 

Included

All meals

All activities & tours

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Historic Houses of Charleston

Day 3 : Friday, December 4, 2026

We'll start our day with a delicious breakfast and then explore Charleston's rich history with a private, behind-the-scenes tour of the Charleston Museum, where we'll discover hidden stories and secrets. 

Next, we'll journey back in time with a tour of the opulent Joseph Manigault House, marveling at its architectural grandeur and glimpsing the lives of its former inhabitants.

We'll savor a delectable lunch at 39 Rue de Jean, where we can indulge in French-inspired dishes in a charming courtyard.

Later, enjoy some free time to explore at your own pace. Wander through Charleston's quaint streets, browse unique shops, or relax and soak in the city's atmosphere.

As dusk settles, we'll experience a unique holiday event at the Edmondston-Alston House: "Christmas on the Battery." Featuring carols, candlelight, and Gullah Christmas stories, we'll be transported to a festive bygone era. 

Later, we'll sit down for a meal of fresh seafood at Amen Street Fish & Raw Bar. Treat yourself to one of their many delicious dishes featuring the bounty of the Lowcountry coast in a contemporary, lively setting.

Included

All meals

All activities & tours

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Wadmalaw Island

Day 4: Saturday, December 5, 2026

We'll start the day with a delicious breakfast at our hotel, fueling up to explore coastal gems. Our friendly guide will then whisk us to Middleton Place, a National Historic Landmark that's home to the oldest landscaped gardens in America.

Next, we'll drive to Wadmalaw Island. You'll be awestruck by the majestic Angel Oak, a centuries-old live oak draped in Spanish moss, a true symbol of the South. 

Our island journey continues to the Charleston Tea Garden, a lush, tranquil estate that's the only large-scale tea plantation in North America. We'll learn about the tea-making process and sip freshly brewed blends right where the leaves are grown.

As the sun sets, we'll return to our hotel and freshen up for a memorable evening. At the acclaimed R Kitchen, we'll dig into a five-course culinary feast.

Included

All meals

All activities & tours

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Charleston - Holiday Market & Chef Experience

Day 5: Sunday, December 6, 2026

After breakfast at the hotel, we'll head out for a morning stroll to Marion Square. Then, we'll visit the renowned Charleston Farmers’ Market to browse their annual holiday market. The market is full of local artisans, crafters, and farmers, even in December. 

After browsing, we’ll meet with one of Charleston’s best chefs for a visit to another neighborhood market to observe how a chef shops. We'll sit back and relax as they create a one-of-a-kind farm-to-table dining experience for us at a local restaurant using the ingredients we selected at the market.

You can spend this afternoon as you please. Shop for holiday gifts on King Street, enjoy a spa treatment at the hotel, or discover more of Charleston. The choice is yours.

Before dinner, we'll experience historic downtown Charleston on a private and memorable horse-drawn carriage ride. The tour is led by a certified guide and is run by a family-owned and operated carriage company. Belgian and Percheron breeds from Amish working farms pull the carriages. These horses live on a tranquil 65-acre farm and pasture, sometimes referred to as "horse heaven."

On our final evening, we'll enjoy a delightful dinner at Magnolias. Savor Southern cuisine classics with a modern twist in this elegant setting, the perfect blend of tradition and innovation.

Included

All meals

All activities & tours

Not Included

Spa treatment

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Departure Day

Day 6: Monday, December 7, 2026

After a hearty breakfast, we’ll say our goodbyes and send happy holiday wishes, promising to stay in touch with our new friends. Your guide will be available to help arrange a taxi to the airport based on your flight time.

May the spirit and joy of the holidays linger with you wherever you're headed next.

Included

Breakfast

Not Included

Airport transfer

You'll Be Staying Here

The Spectator Hotel

The Spectator Hotel

Steeped in history and southern charm, the Spectator Hotel offers a unique stay in the heart of Charleston's Historic District. Offering the best address in Charleston’s bustling historic district, this hotel evokes the exuberance of the Jazz Age and the genteel glamour of the Old South. Step inside the sophisticated boutique jewel and discover why, year after year, they are recognized among Charleston’s top hotels. 

Hosts

Stacia Whitney

Stacia Whitney

Stacia is a dedicated trip leader with a knack for creating seamless and memorable travel experiences. A self-proclaimed foodie, she finds joy in exploring local markets and discovering how food connects to a destination’s culture. Her passion for travel goes beyond places—she thrives on building connections with the people she meets along the way. 


With a solid foundation of experience, Stacia is known for her warmth, organization, and ability to make every traveler feel welcome. By the end of each journey, she’s not just a guide but a friend, ensuring every trip is as meaningful as it is enjoyable. 

Price

Private Room

Private Room

Everyone gets their own fabulous room!

$7,995

Shared Room

Shared Room

Share a room with a friend or family member

$6,895

The Holy City

Charming Charleston

Charleston offers a captivating mix of luxury, warmth, history, and friendly hospitality, made even better by its rich Lowcountry culture and delicious cuisine. During the holiday season, the city's beautiful architecture is adorned with the joyous spirit of Christmas, making it even more magical and inviting.

Charming Charleston

What's Included

What's Included

All meals (except where indicated), including beer & wine with dinner

Christmas on the Battery carols at the Edmondston Alston House

All in city transport when needed, except during free time

Farm-to-table dining experience at a local restaurant

Private horse and carriage ride through Charleston

Private tour of the Joseph Manigault House

All entrance fees included in the itinerary

Private tour of the Charleston Museum

Private walking tour of Charleston

Accommodation at a 5-star hotel

Expert Guides and Trip Leaders

Private bus tour of Charleston

Visit to Wadmalaw Island

Visit to Charleston Tea Garden

Visit to Middleton Place

Additional wine, beer, or spirits beyond what is offered at meals.

Travel and Medical Insurance (required)

Roundtrip airfare to Charleston

All personal souvenir purchases

Spa treatments

Airport transfers

FAQs

The trip officially starts on the afternoon of December 2nd, so make your travel arrangements to Charleston accordingly. If you'd like time to relax in Charleston before the trip starts, book your room for an extra night on the Add-on section of our website. 


Otherwise, plan to be settled into the hotel and ready to meet the group by 4 pm.

We will have a Zoom call about 8-10 weeks before the trip starts to discuss all that information and give you a packing list. Here is a great website we love that will help you with packing and travel trips.

The weather in Charleston in December is usually lovely. You can expect daytime temperatures in the mid-60°Fs (approx 17°C-18°C) with lows in the evening of 50°F (10°C). 

We require that everyone traveling with Girls' Guide be able to comfortably walk 3–5 miles per day unassisted, and without difficulty, can navigate stairs, uneven streets or paths, and occasional steep terrain. Most of our trips require this level of physical mobility and fitness, especially when visiting historic towns and landmarks where vehicle access is limited and walking often offers the best experience. 


Additionally, some of the 4 and 5-star boutique or historic hotels we stay in do not have elevators and may require climbing stairs to get to your room or access other facilities in the hotel. 

Inquire about this trip

Charming Charleston for the Holidays

United States· Departs on December 2, 2026 · 6 Days

$7,995/pp