Hosted by Carol and Laird (native of Charleston)

Charleston Chic: Ladies’ Weekend Getaway

September 25-28, 2025

Pack your bags and join Carol’s Crew for a fabulous three-day weekend in one of America’s most charming cities — Charleston, South Carolina!

This insider's trip is designed exclusively for female travelers who want to explore, connect, and create unforgettable memories. Our curated itinerary, a true local's experience, has been crafted by High Park Travel associate Laird Pelzer who grew up in Downtown Charleston.

Why Join Us?

• Make new friends in a supportive, women-only group. Perfect for solo travelers, you and a bestie, or a group of friends. 

• Experience the best of Charleston’s food, culture, and Southern hospitality.

• Perfect for both beginner and seasoned travelers.

• Safe, fun, and stress-free — just show up and enjoy some girl time in a beautiful city. 

• Plans include lots of walking activities in historic Charleston.

What’s Included:

• Hotel Accommodations in the heart of historic Charleston (3 nights)
• Breakfast at hotel

• Guided walking tour of the city’s iconic cobblestone streets and pastel antebellum houses with local guide Tommy Dew

• Forte Jazz Lounge admission

• Exclusive visit to a private garden, regularly featured on the prestigious Historic Charleston Foundation garden tour

• Meet and Greet with local craftsmen, artists, and community members involved in many facets of modern-day life in Historic Charleston

• Free time for shopping at the City Market and King Street, gallery hopping, or relaxing by the waterfront

• Evening socials with your new travel friends (drinks not included)

What's not included:

• Lunch and Dinner
• Drinks at establishments, unless otherwise noted. 
• Taxis, Ubers, Pedal Cabs, carriage rides between local activities
• Additional excursions not included in this itinerary, e.g., Carriage Ride, South Carolina Aquarium, Gibbes Art Gallery, House Museums, Fort Sumter Tour
• The Lumineers in concert (optional)

Ready to say “yes” to new adventures?

Spots are limited! Message us to reserve your place on the Charleston Chic: Ladies’ Weekend Getaway and let’s make memories together.

Itinerary:

Charleston

Sept. 25th-28th, 2025

THURSDAY, SEPTEMBER 25TH

Arrive in Charleston. Check into hotel.

5 PM Group Welcome Drinks at The Dewberry Hotel's Citrus Club ((dinner option 1, see menu on website) (*) $$
Join us to kick off the trip with a cocktail, courtesy of High Park Travel, at this exclusive venue which offers panoramic 360-degree views of the city, from the historic skyline to the waterways.

7 PM-10 PM Forte Jazz Lounge (*): Live Jazz (dinner option 2, see menu on website) $$$

Forte Jazz Lounge presents an evening of vocal jazz from the Great American Song Book. Cole Porter, Harold Arlen, George and Ira Gershwin, Duke Ellington are just a few of the composers represented in this night dedicated to The Great American Songbook.

FRIDAY, SEPTEMBER 26TH

Breakfast included at hotel

Morning walking tour through the historic district with local guide Tommy Dew.
Amongst a backdrop of stately architecture and manicured gardens, we will explore the rich, cultural heritage of one of America's most charming cities.

Optional lunch: Blind Tiger Pub (*) $$
Upscale bar food in an alehouse dating back to 1803, featuring a charming, brick-walled courtyard.

Afternoon visit to the John Rivers Museum with local artist Douglas Balentine
The John M. Rivers Communication Museum holds a wonderful collection of antique radios, televisions, phonographs, telephones, magic lanterns, motion picture projectors, and other items related to the history and entertainment of the communications and broadcasting fields.
-or-
Free time until dinner (Suggestions: The Russell House, The Old Exchange and Provost Dungeon)

Evening: Drinks on King Street at The Thoroughbred Club (*) (Live Music Daily 6PM — 9PM) $$
***Optional Lumineers Concert +$135
Elegant lounge at Charleston Place Hotel offering cocktails, small plates, desserts & live music

Dinner at Poogan’s Porch (*) $$
Located in the heart of Charleston’s historic district, Poogan’s Porch has been serving up warm hospitality and authentic Southern cuisine since 1976. Housed in a beautifully restored Victorian home, our restaurant is steeped in Lowcountry tradition.

After dinner (optional):  Henry’s for live music (*) $$
Upscale bohemian brick tavern with live jazz & a roof deck.

Optional evening activity: 7:30 PM The Lumineers Concert at Credit One Stadium, $160

SATURDAY, SEPTEMBER 27TH

Breakfast included at hotel

10 AM Marion Square Farmers' Market (open from 8am-2pm)
Held in Marion Square since 1989, this weekly outdoor market hosts local vendors with food & crafts.

Meet local craftsmen, including Capers Cauthen of Landrum Tables, at The Charleston Farmers' Market at Marion Square.

Walk with Hal Cauthen through Ansonborough to The Market.
Ansonborough is known for its stately red-brick historic homes, mostly dating to the mid-1800s, along streets lined with palmetto and oak trees.

Lunch (optional) at Tommy Condon’s Irish Pub (*) $$
Tommy Condon opened Tommy Condon’s Irish Pub & Restaurant in 1984. He has made one of Charleston’s favorite local spots serving Lowcountry specialties such as Shrimp and Grits and Fish and Chips.



Free time until dinner (Suggestions: The Market, Lower Church Street, Broad Street, Colonial Lake)

Evening: Private Garden Gathering on South Battery. This home is often featured in the Historic Charleston Foundation annual garden tour. (No photos permitted.)  As we will be welcomed personally by the homeowner, cocktail attire is suggested.

After visiting the garden, we will take a Sunset Stroll along The Battery, the perfect background for memorable group photos! Optional walk (13 minutes) along beautiful East Bay Street to dinner at Brasserie La Banque; otherwise, pedicabs, Ubers, etc. are available.



Dinner at La Banque $$$$
Lively, upscale French brasserie paying homage to traditional cuisine with updated dishes and a bar.



After dinner (optional): Walk along East Bay Street with bars and live music to the Waterfront Park and Pineapple Fountain


SUNDAY, SEPTEMBER 28TH

Breakfast included at hotel
-or-
Optional Group Breakfast/Brunch at The Marina Variety Store & Restaurant (*) $$
Southern-style breakfast, seafood-focused lunch & dinner, in a waterside diner serving since 1963.

Free time / Depart for home. 


Note: (*) indicates venue may change pending availability or weather.

Ready to say “yes” to new adventures?

Spots are limited! Message us to reserve your place on the Charleston Chic: Ladies’ Weekend Getaway and let’s make memories together.