Reintroducing the NYC Insiders’ Club: Where Smart, Savvy Women Celebrate Life with Style
After a pandemic pause, Cheryl Benton and Anne Akers are thrilled to relaunch the NYC Insiders’ Club — a vibrant sisterhood of women who live life with flair, curiosity, and connection. Originally launched in 2019, our club has hosted unforgettable adventures: private shopping soirées, cooking classes, tea at the Met, behind-the-scenes tours of Sotheby’s and The Players Club, and quarterly cocktail gatherings that sparked lasting friendships.
Now, the fun resumes — and it’s better than ever.
Membership Includes:
Exclusive Invitations to Insider Events
Join intimate gatherings (10–25 Tomatoes) for curated experiences that blend culture, luxury, and connection. Some events are complimentary, others ticketed — all unforgettable.
Quarterly Cocktails & Conversation
Join Cheryl & Anne at fabulous NYC spots for drinks and priceless conversation with fellow Tomatoes.
Member-Only Discounts & Giveaways
Enjoy exclusive offers on 3T events, products, and services — plus access to our coveted ticket giveaways (we always give away three!).
Connection, Camaraderie, and Community
Meet phenomenal women who share your zest for life, your love of NYC, and your passion for meaningful experiences.
Here’s a taste of what’s coming in 2026
Become a member and we’ll send you your invite.
Please note: Some of our upcoming events will be limited to smaller groups to ensure a more intimate experience. Invitations will indicate which ones are first come, first served—so be sure to RSVP early!
2026 Insider Events
More to be announced.
January (Date TBD) New Year’s Lunch at the Harmonie Club and a tour.
The Harmonie Club is a private social club founded in 1852; it is the second-oldest social club in New York. It is located at 4 East 60th Street, in a building designed by Stanford White. We will have a tour of the club and a fabulous buffet lunch.
February 5. Valentine’s Beauty and Wellness event at the luxurious Guerlain Spa at the Waldorf. Step into serenity with a guided spa tour, then unwind in our spacious relaxation lounge. Sip on a curated Valentine’s Cocktail, champagne, or sparkling water while enjoying lite bites. Treat yourself to mini facials, personalized makeup sessions, and fragrance consultations—all designed to leave you glowing inside and out.
March 22. York Theatre Musical Premiere and Lunch. MONTE CRISTO is a new world premiere musical, and we will meet the cast and theatre director. Lunch is optional.
April 19. The Gotham Jazz Festival. Judy Stewart, one of our Insider Club Members who is on the board of the jazz festival, will create a special experience with us.
Date TBD. Private Tour of Radio City Musical Hall.
Immerse yourself in its rich history and stunning art deco design. Discover art deco masterpieces such as the grand, soaring 60-foot-high Grand Foyer and step inside the Hall’s secret apartment, the Roxy Suite.
Check out the highlights of our 2025 Events.
Coming Up: December 11. Ila Luxury Spa Event at the Palace Hotel Escape to Midtown’s sanctuary of holistic wellness at the ila Only Spa — the first of its kind in the U.S. Enjoy mini treatments like Red Light Therapy, Hyperbaric Oxygen, PEMF, and world-class massage. Plus, a special presentation by Immunocologies Karen Ballou on facial yoga and Blue Zone-inspired skincare rituals. Max 25 people, Refreshments and lite bites included. Free for members.
Past Events
A Gilded Revival: Inside the Waldorf Astoria’s Spectacular Restoration
A Fun Outing Where Parisian Elegance Meets Revolutionary Grit
Backstage at the Met: Where Magic Is Made
🎉 Ready to Live Life Like a True Insider?
Join today for just $200/year and start receiving invitations to our upcoming events. The club is intimate, the perks are fabulous, and the memories are waiting to be made.
👉 Join the NYC Insiders’ Club Now.
The tomato behind The Three Tomatoes.
Cheryl Benton, aka the “head tomato” is founder and publisher of The Three Tomatoes, a digital lifestyle magazine for “women who aren’t kids”. Having lived and worked for many years in New York City, the land of size zero twenty-somethings, she was truly starting to feel like an invisible woman. She created The Three Tomatoes just for the fun of it as the antidote for invisibility and sent it to 60 friends. Today she has thousands of friends and is chief cheerleader for smart, savvy women who want to live their lives fully at every age and every stage. She is the author of the novel, "Can You See Us Now?" and co-author of a humorous books of quips, "Martini Wisdom." Because she's lived a long time, her full bio won't fit here. If you want the "blah, blah, blah", read more. www.thethreetomatoes.com/about-the-head-tomato
