Flappers to Rappers (1925–2025)Opening Reception in the Raleigh Room & Great Lawn Loggia

January 20, 2026 — 6:00 p.m. — 8:30 p.m.

Kick off SYTA Summit with a warm welcome at the historic Cavalier Hotel! Enjoy a reception in the Raleigh Room and Great Lawn Loggia, elegant spaces that have hosted guests since 1927. The evening will feature a local oyster tasting and culinary delights by the Cavalier Hotel’s master chef. Connect with colleagues, savor coastal flavors, and experience the charm of this iconic hotel!

 

Casual Dinner and Spirit Tastings

 January 21, 2026 — 6:30 p.m. — 9:00 p.m.

The Hunt Room at The Cavalier Hotel and Tarnished Truth Distillery.

Join us in front of the fireplace in the Hunt Room at the Cavalier Hotel for an intimate evening of great food, spirit tastings and connection. Steeped in tradition, the Hunt Room evokes the spirit of classic American taverns with its warm fireside ambiance and rustic charm. Guests will enjoy a curated selection of spirits, paired with stories of their craft, in a setting that reflects the rich heritage of Virginia Beach’s historic Cavalier. Throughout the evening, attendees may experience a tour and tasting in the Tarnished Truth Distillery.
The whiskey distillery sits where the original laundry facility for the hotel once was. All of their equipment was hand made in America by Vendome Copper and Brass works.

 

Closing Celebration: Flappers to Rappers (1925–2025)

Wednesday, January 21, 2026 — 6:30 p.m. — 9:00 p.m.

The Crystal Ballroom, The Cavalier Hotel

Join us for a spectacular closing night celebration that bridges the glamour of the Roaring ’20s with the excitement of the modern era! This Flappers to Rappers event celebrates a century of style, music, and dance, blending the jazzy big band vibes of the past with the bold rhythms and trends of today.

Channel your inner flapper with fringe, feathers, and pearls—or embrace your contemporary chic with your sneakers, chains, and street style. Sip on classic cocktails, enjoy high-energy music spanning the decades, and dance the night away as we celebrate the best of both eras.
For those who want to join the fun without going all out, SYTA will provide “1920s and 2025” props to help you get into the spirit. This unforgettable evening promises a lively mix of nostalgia and now—highlighting the charm of the past and the energy of today as we close our time together in style.