With its vibrant culture, rich history, exquisite architecture, celebrated dining scene, and friendly locals, it’s no wonder Charleston has become one of America’s best-loved travel destinations. And there is no better time to visit the Holy City than just before the holidays when temperatures are still mild. Join us for a trip that showcases Charleston from an insider’s perspective. This trip will entice all your senses, including beautiful historic homes, meticulous private gardens, world-class cuisine, rich history, and holiday cheer at every turn.
Here's a day-by-day itinerary of the schedule.
Fly into Charleston in the morning (or the night before). Make your way to the historic Francis Marion Hotel to check-in. The hotel boasts spectacular views of Charleston’s steeples, historic mansions, and famous harbor. Located downtown on Marion Square, the hotel is within walking distance of magnificent gardens, house museums, antique shops, local boutiques, restaurants, and nightlife.
We'll meet and greet with a welcome toast in the hotel bar at 6 p.m.
Then, we're off to dinner at Tempest.
We'll start the day with a private guided tour of Charleston, hearing the traditions and stories of Charleston’s rich history and colorful past. The tour will highlight vibrant neighborhoods, historic sites, architecture, and art, including Rainbow Row, The Battery, 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 will stop for some gourmet comfort food at Cru Cafe. After lunch you will have the rest of the afternoon to discover more of Charleston in your own time. With the holiday season in full swing, you'll have many options from which to choose.
Before dinner we'll explore historic downtown Charleston on a private and memorable horse-drawn carriage ride. Run by a family-owned and operated carriage company, the tour is led by a certified guide and some of the family's more than 30 horses. With Belgian and Percheron breeds from Amish working farms, these incredible horses live on a tranquil 65-acre farm and pasture sometimes called "horse heaven."
Dinner tonight will be at one of Charleston's favorite places SNOB.
After breakfast, we'll take a guided walking tour of Charleston’s enchanting alleys and hidden passages. Distinguished by their beauty, Charleston’s alleys occupy spaces that blur the line between public and private areas and offer remarkable insight into the history of the Holy City. Typically inaccessible to cars and often overlooked, walking along these cobblestone, brick, and stone pathways will give you the chance to step back in time.
Later in the afternoon we will head over to the fabulous Hotel Bennett for some Holiday afternoon tea followed by an optional tree lighting at Gabrielle Plaza.
For dinner night, we'll take a short walk to Indaco for some Italian Food and Wine.
After breakfast, we'll drive to Middleton Place, a National Historic Landmark, home to the oldest landscaped gardens in America and an enduring, vibrant, and essential part of the Charleston and American experience. We'll stop and pick up our gourmet lunch boxes from Blackbird's Market and enjoy them in Angel Oak park.
After we pick up lunch, we will drive to Wadmalaw Island to experience the Charleston Tea Garden, America's only farm-to-table tea growing & production plant. We'll do a trolley tour around the garden, and you can drink as much tea as you like.
Later in the afternoon we will head back to the hotel to freshen up for dinner. Prepare to step back in time for dinner. You're about to have a 7-course authentic 18th and 19th-century dining experience prepared by a culinary historian and chef. From the narration, you'll see that food, on its own, can tell the story of Charleston.
Today will start with a walk across the street for a quick visit to the renowned Charleston Farmers’ Market to browse the annual holiday market. The market is full of local artisans, crafters, and farmers in December. After browsing, we’ll meet one of Charleston’s best chefs for a visit to another neighborhood market to observe how a chef shops. The chef will 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.
This afternoon, the time is yours to spend as you please. Holiday shop on King Street, enjoy a spa treatment at the hotel, or discover more of Charleston. The choice is all yours.
On our final evening, we'll have dinner at Hank's Seafood. Great food and a charming ambiance can only equal an extraordinary dining experience! Hank’s Seafood Restaurant is located in a turn-of-the-century warehouse overlooking the Charleston City Market.
After a hearty breakfast, we’ll say our goodbyes and happy holiday wishes, with a promise to stay in touch with our new friends.
Named for Revolutionary War hero Francis Marion (the “Swamp Fox”), the Francis Marion Hotel became an instant Charleston landmark when it opened in 1924. Rising 12 stories above the Historic District, the hotel offers spectacular views of Charleston’s church steeples, historic mansions, and famous harbor, providing easy access to the wealth of Charleston’s attractions.
Robin Leonard, an experienced navigator who loves uncovering the unexpected in every location. After spending years in the corporate world as a consultant, Robin joined the travel industry with a goal of helping other women dream, explore and discover through travel. With a passion for all things Charleston, Robin is excited to share the magic of Charleston at the holidays with you.
The Holy City
Charleston expresses an enchanting blend of opulence and intimacy, history and hospitality, culture and cuisine, and art and architecture.
All ground transportation (excluding airport transfers)
GG2P Welcome Gift
All meals plus wine or beer at dinner
All guides, experts, and entry fees for tours, museums, and plantations on the itinerary
Your stay at the Francis Marion hotel
Roundtrip airfare to Charleston
Additional wine, beer, or spirits beyond what is offered at meals.
All personal souvenir purchases
Travel and Medical Insurance (required)
Hotel spa treatements and other incidentals
The trip officially starts on the afternoon of December 5th, so make your travel arrangements to Charleston accordingly. If your flight doesn't arrive until later in the evening, or you'd like to have time to relax in Charleston before the trip starts, just send an email to email@example.com and we'll take care of booking your room for an extra night.
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 that we love that will help you with packing and travel trips.
The weather in Charleston in December is usually lovely. You can expect day-time temperatures in the mid 60'sF (approx 17C-18C) with lows in the evening of 50°F (10°C).