Are you ready to explore a picturesque city and make lasting memories?

Join us for our Charleston Holly Days Trip!
December 6th - 9th, 2025

Step into the magic of the holiday season with Charleston Holly Days, the ultimate Wandering Women getaway!

Immerse yourself in the charm of Charleston as we explore its twinkling historic streets, indulge in festive flavors, and soak in the warm Southern hospitality. This trip is your chance to celebrate, connect, and unwind with like-minded women while experiencing the beauty of the low country during its most enchanting time of year. Join us for a journey filled with laughter, adventure, and a little holiday sparkle— because the best gifts are unforgettable experiences!

Spend 4 days and 3 nights with our Wandering Women group on a getaway where everything is planned especially for you. We’ve included a walking food tour, horse and carriage ride, plantation tour and delicious meals.

RESERVE YOUR SPOT NOW!

"I loved the women in the group. I knew only one of them before the trip, and by the end I had created special friendships with each of them. That was beyond my expectations.”

-LEAH GOERKE

Save the date:

Saturday, December 6th - Tuesday, December 9th

Join Us

Why travel with Wandering Women?

1. We provide you with the community and connections you are longing for but can’t easily create on your own.

2. You’ll have fun and feel safe as a single traveler with opportunities to explore new places and adventures.

3. Your lodging, meals and itineraries are planned for you with our curated travel experiences.

4. You’ll save time and money as all the research and reservations are taken care of for you.

5. You will have peace of mind because we provide on-site management to make any real time changes needed and to work out any issues.

Our Dates

Our women's adventure kicks off at the Dewberry Hotel for 4 days and 3 nights from December 6th through 9th.

Our Resort

We’re staying at the iconic Dewberry Hotel. It’s a mid-century landmark celebrating Charleston’s quintessential style.

Experience America’s favorite city through the lens of John Dewberry. At The Dewberry, sincerity outshines obligation and every element is specifically designed to deliver luxury, warmth and a nod to old Charleston.

Our Activities

We’ll gather the first evening for a Welcome Reception to meet and greet each other. Each morning we will meet for a full breakfast to get the day started off in the best way possible. We will be enjoy a walking food tour, a horse and carriage ride, a plantation tour and all of Charleston’s splendor during the holiday season.

Our Leader

Diane Tamango is our trip leader. By day, Diane collaborates with organizations to achieve their marketing strategies. Outside the office, she is passionate about helping make a difference within her community. As a Wish Granter and Volunteer Captain with Make-A-Wish Massachusetts and Rhode Island, she helps spread hope and joy to critically ill children and their families. Diane is a well-traveled adventurer whose journeys span both personal exploration and professional endeavors. Her adventurous spirit has fueled trips spanning the U.S., Caribbean, and European destinations. She's enjoyed several past Wandering Women adventures. As a Wandering Women trip ambassador, Diane is excited to help facilitate connections, friendship, memorable experiences, exploration and fun!