A dimly lit event space with red curtains, a stage with blue lighting and a drum set, and tables set for dinner.

About the Event

Celebrate the holiday season with A Sinatra Christmas at City Winery - Boston on November 30, 2026, at 7:30 PM. This special evening in Boston features Rich DiMare, delivering a captivating Frank Sinatra Tribute, accompanied by the acclaimed Ron Poster Trio. Guests will enjoy an evening filled with classic holiday tunes and timeless Sinatra hits in an intimate setting, perfectly capturing the spirit of the season. Join us for a memorable night of music at City Winery - Boston.

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A Sinatra Christmas Live in Boston

Immerse yourself in the enduring legacy of Frank Sinatra as Rich DiMare brings his acclaimed tribute performance to life. Known for his faithful renditions of Sinatra's iconic vocal style and charm, DiMare, backed by the talented Ron Poster Trio, delivers an authentic experience. Expect a sophisticated selection of holiday classics and beloved standards from the Great American Songbook, evoking the golden age of swing and seasonal cheer.

City Winery Boston Event Information

City Winery - Boston offers an intimate and refined atmosphere, combining a concert venue with a working winery and restaurant. Guests can enjoy exceptional food and wine service delivered directly to their seats, enhancing the live music experience. Prepare for your visit by noting that City Winery - Boston operates as a cashless venue for all purchases. Arrive early to find your seats and enjoy the full dining experience. Buy your tickets now.