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
COMING UP
Date: June 10. Strawberry Fields Central Park + lunch at Sarabeths
Date: June 30. Tour of the Highline & Lunch
Date: July 10 Theater: Celebrity Autobiography
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
Lunch at the Harmonie Club
February 5. Valentine’s Beauty and Wellness event at the luxurious Guerlain Spa at the Waldorf.
Randy Eldeman at Aman Jazz Club
March 22. Theater Event: Monte Cristo
April 19. Gotham Jazz Festival
April 26. Backstage at Radio City Music Hall
May 5. Private Tour of the Morgan Libary + Afternoon Tea
🎉 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
