Charming Charleston for the Holidays

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  • Charleston, SC
  • November 29 - December 4, 2022
  • 6 Days/5 Nights
  • 6 – 10 Guests


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. Join us for a trip that will showcase Charleston from in insider’s perspective. This trip is sure to hit all the senses – beautiful historic homes, meticulous private gardens, world-class cuisine, rich history, and holiday cheer at every turn.


  • Enjoy a one-of-a-kind private dinner in a lovingly restored Charleston Battery house
  • Take a holiday walking tour through Charleston’s historic district
  • Tour the Boone Hall Plantation all decked out to Christmas
  • Feel the good ‘ole southern holiday hospitality
  • Enjoy a Charleston Tea Party in the private home of a local guide
  • Take a culinary walking tour then share a meal with an award-winning local chef
  • Experience small town Holiday flair with an afternoon in beautiful historic Beaufort
  • Visit the Nathaniel Russell House for a special holiday candlelight tour
  • Dine at some of Charleston’s best restaurants including the award-winning Husk

Your Guide:

Your guide for this trip is 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.


Day 1 – Tuesday, November 29

Fly into Charleston in the morning (or the night before) and make your way to the historic Francis Marion hotel. Our hotel offers spectacular views of Charleston’s steeples, historic mansions, and famous harbor. Located downtown on Marion Square, we are ideally located within walking distance of magnificent gardens, house museums, antique shops, local boutiques, restaurants, and nightlife.

Around 6:00pm, we’ll enjoy a welcome meet and greet with a toast at the hotel bar.

Then we’ll dine at one of Charleston’s favorites, The Grocery, a short walk from our hotel.

Day 2 – Wednesday, November 30

Today, we’ll start with a guided Holiday Walking Tour of Charleston to listen to the stories and traditions of Charleston’s rich history and colorful past. Walking through America’s most charming historic district dressed up in its holiday best, the tour will highlight the vibrant neighborhoods of Charleston as well as its historic sites, architecture, and art.

After stopping for lunch at the delightful Cru Café, we’ll visit the Charleston City Market, one of the nation’s oldest public markets and cultural heart of the city. Home to more than 300 high-spirited entrepreneurs, this is always something to see, do, taste, and take home as a souvenir at the market.

We’ll then carry on, on a guided 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 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 offers an opportunity to step back in time.

This afternoon you’ll enjoy some free time as the day winds down to walk back to the hotel, shop or continue to explore before dinner.

Tonight, you’re in for a treat! We have a special privately catered dinner in one of the glorious Charleston Battery homes. Not open to the public, this grand private home has been lovingly restored and only recently been made available for small private groups. Put on your finest dinner-party attire. 

Day 3 – Thursday, December 1

After breakfast at the hotel, we’ll drive to the Boone Hall Plantation, one of America’s most photographed historical venues with true southern charm. We’ll see the world-famous Avenue of Oaks, take a tractor tour across the entire property, and attend the only remaining live Gullah presentation in the area.

After lunch, we’ll head to the hidden Lowcountry gem, Beaufort, South Carolina. Tucked into winding, historic streets framed by natural foliage and centuries-old, moss-draped live oak trees, Beaufort brings the holidays to life. While walking through the lovely, antebellum town, we’ll learn about Beaufort’s role at the center of the Secession movement. How it was suddenly occupied by thousands of soldiers had a massive wartime hospital system, and was the pathway to freedom for slaves who could get there.

After some free time to shop or wander in downtown Beaufort, we have dinner at the delightful Saltus River Grill. Then we’ll drive back to Charleston to rest up for our next day!

Day 4 – Friday, December 2

We’ll start the morning with a walking tour designed for the discerning visitor who wishes to experience Old Charleston as a guest, not a tourist. Guided by two knowledgeable and charming local guides whose families have lived in Charleston for generations, we’ll visit “their city”, visiting their friends’ private homes and gardens. We’ll then be treated to a private Charleston Tea Party with a gourmet lunch in their meticulously restored historic home decked out in its holiday best.

After such a wonderful morning and lunch, we’ll visit the nearby Charleston Museum with access to the exquisite antebellum Heyward-Washington House and the Georgian-style Joseph Manigault House. Afterwards, you appreciate some free time to either go back to the hotel, enjoy more time at the museum, or head to King Street for some holiday shopping.

For dinner, we walk over to Stella’s for a more casual evening of genuine Greek Food. 

Day 5 – Saturday, December 3

Today will begin with a walk across the street for a quick visit to the renowned Charleston Farmers’ Market during their annual Holiday Market. During December, the market is filled with many local artisans and crafters alongside local farmers. After, we’ll meet up with one of Charleston’s best chefs for a visit to another neighborhood market to observe how a Chef shops. Using the ingredients, we select at the market; the Chef will create a one-of-a-kind farm-to-table dining experience for us at a local restaurant.

This afternoon we’ll have time to spend as you please. Holiday shop on King Street, a spa treatment at the hotel or discover more of Charleston. The choice is all yours.

Our final evening, we’ll have dinner at the celebrated restaurant Husk. A favorite of locals and visitors alike, Husk transforms the essence of southern food.

Day 6 – Sunday, December 4, Departure Day

After a hearty breakfast, we’ll say our goodbyes and Happy Holiday wishes, with a promise to stay in touch with our new friends.


Trip Notes:

  • GG2P reserves the right to alter the itinerary based on weather or availability, as well as exciting opportunities that might crop up!
  • Vegetarians & Vegans - Not to worry – you will be well fed in all restaurants as well as those allergic to seafood or gluten. Options are plentiful.


Trip Cost

Trip Cost: $5,495 USD*

  • * All our trips are organized and priced based on single occupancy at all the places we stay. Everyone gets their own fabulous room! If you’re traveling with a friend/relative, or would prefer to save some money by sharing a room, we can usually organize double occupancy at a reduction in cost. Please inquire.
  • * Unless specified otherwise, all our trips are priced in the home currency of the trip’s location. However, we will invoice you in the equivalent USD calculated at the exchange rate at the time of invoice.
  • Interest-free payment plans are available. Please inquire.

What’s included?

  • All ground transportation (excluding airport transfers)
  • 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

What’s not Included?

  • Roundtrip airfare to Charleston
  • Spa Treatments
  • Airport transfers
  • Additional wine, beer, or spirits beyond what is offered at meals.
  • All personal souvenir purchases
  • Travel and Medical Insurance (required)

I’m interested, so what do I do next?

If you have questions, complete the form below. We’ll get back to you ASAP!

If you’d like to come, press the Reserve Now button above. You'll be prompted to complete a form with your pertinent details, put down a refundable $250 placeholder deposit, and schedule a time to speak with a GG2P representative. We like to speak with everyone before they embark on their first trip with Girls’ Guide to Paris & Beyond. This allows you to ask any questions or voice any concerns you may have. These are intimate, small group trips; a quick yet personal conversation allows you to get to know how our trips work and make sure it’s right for you. If it’s not, we’ll immediately refund your $250 deposit.

If it’s a Go! after your call, we’ll bill you for a non-refundable deposit, usually 35% of the trip’s cost (less the $250 place-holder deposit, if you already paid it) and your place is reserved. At this point, you’re committed to the trip, so we recommend that you purchase Travel Insurance to protect you in case your plans change unexpectedly. The balance will be due approximately 2 months before the trip.

Our cancellation policy is here.

Inquire About This Trip

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