Dining with Deb™ is created by women, for women, celebrating women.

A dynamic community of professional women who gather on Martha’s Vineyard every August. Dining with Deb™ is where connection, inspiration, and empowerment take center stage.

This one-of-a-kind experience brings women together to share stories, build networks, and stand ten toes down in their power.

Dining with Deb™ — where real women make real connections.

The Experience

Deb Grant, CEO of Corporate Playbook™, brings her ultimate professional woman's experience back to Martha's Vineyard on August 12, 2025.

Conversation, community, shopping, and a sit-down luncheon with a phenomenal group of women.

ENtertainment

Appearing for the first time on Martha’s Vineyard, Dining with Deb™ presents,
The String Queens.

The String Queens (TSQ) is a dynamic trio that creates stimulating musical experiences that inspire diverse audiences to love, hope, feel, and imagine!

Marketplace

Returning in 2025…
The Dining with Deb™ Marketplace. Enjoy an on-site shopping experience featuring local and national women-led businesses and global brands.

Retail therapy is good for the soul!

Dining with Deb™ is created by women, for women, celebrating women.

Developed by Deb Grant, retired President of the GE Foundation and now President & CEO of the global consulting firm, Corporate Playbook™, Dining with Deb™ is an experience that brings together professional women, deliberately crossing racial, religious, age, and political barriers while driving meaningful connections and conversations.