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
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. SOLD OUT.
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.
.
April 26. 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.
Tuesday, May 5. 1:30 PM. Morgan Museum: Private Tour and Afternoon Tea
This will be a wonderful afternoon at one of our favorite museums. It will include a guided tour of the exhibits and then their fabulous afternoon tea, that includes wonderful teas, delicious sandwiches, scones, and other dessert goodies. If we have 20 people, they will give us a private tour. Cost for Tour only is $24. Cost for Tour and tea is $85.00. YOU MUST SIGN UP BY MARCH 31ST.
COMING UP
Date: TBD Tour of the Highline & Lunch
Date: TBD Dinner in the private dining room at Chez Josephine.
Date: TBD Chocolate tasting.
Past Events.
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
🎉 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
