Romantic Events & Date Night in Boston

Spring Experience 2026

Wed, 6 May 2026

Citizens Opera House

Theater

Boston Ballet presents Spring Experience 2026 at the Citizens Bank Opera House, a program of contemporary and classical ballet. This formal, artsy evening delivers precise technique and expressive storytelling with high-energy choreography in a historic Boston venue.

An Evening With Vanessa Carlton: Veils Tour

Tue, 12 May 2026 at 3:30 PM

City Winery Boston — Main Stage

Music

Vanessa Carlton headlines City Winery Boston's Main Stage for the Veils Tour, delivering intimate piano-driven pop with her signature storytelling. Expect lush melodies, refined arrangements, and a classy evening at this renowned venue on May 12, 2026.

The Sleeping Beauty

Wed, 27 May 2026

Citizens Opera House

Theater

Experience Boston Ballet's The Sleeping Beauty at the historic Citizens Bank Opera House in downtown Boston, May 28–June 7, 2026. This lush, classical production features dazzling dancing, ornate sets, and Tchaikovsky's iconic score that enchants audiences of all ages.

An Evening with Chelsea Berry

Sat, 30 May 2026 at 3:30 PM

Haymarket Lounge at City Winery Boston

Music

City Winery Boston presents Chelsea Berry for an intimate evening at the Haymarket Lounge. Enjoy a songwriter-rich folk set with soulful vocals in a warm, up-close venue—perfect for fans of heartfelt originals and storytelling.

Flowers + Opera

Sat, 6 Jun 2026 at 10:00 AM

Brookline Arts Center

Theater

Experience a unique fusion of flowers and live opera at the Brookline Arts Center. An intimate, gallery-style evening where lush floral designs accompany operatic pieces, creating a sensory blend of scent, color, and song in a welcoming community venue.

Frankie & Johnny in the Clair de Lune

Thu, 18 Jun 2026 at 3:30 PM

BCA Black Box Theatre, 539 Tremont St.

Theater

Frankie and Johnny in the Clair de Lune at BCA Black Box Theatre in Boston is a sharp romantic comedy about a late-night couple navigating love, vulnerability, and stubborn pride. Intimate, word-forward staging in a compact Black Box space promises witty banter, real stakes, and a night of candid theatre.

Sarah McLachlan - Better Broken Tour

Fri, 10 Jul 2026 at 3:30 PM

Leader Bank Pavilion

Music

Sarah McLachlan headlines the Better Broken Tour at Boston's outdoor Leader Bank Pavilion. The show is July 10, 2026, with doors at 6:30 pm and the concert at 7:30 pm; rain or shine. All support acts subject to change. An intimate, melodic evening from a renowned singer-songwriter in an iconic venue.

Air Supply - A Matter of Time Tour

Thu, 5 Nov 2026 at 3:00 PM

The Chevalier Theatre

Music

Air Supply brings its Matter of Time Tour to Chevalier Theatre in Medford for a night of timeless soft-rock and romantic ballads. Expect signature hits like All Out of Love delivered in a warmly intimate venue with polished harmonies and crowd sing-alongs.

Joshua Radin

Thu, 19 Nov 2026 at 3:30 PM

City Winery Boston — Main Stage

Music

Singer-songwriter Joshua Radin brings his intimate, melodic folk-pop to the Main Stage at City Winery Boston. Expect heartfelt tunes from his acclaimed catalog delivered in a warm, wine-bar setting that makes for a personal listening experience.

Maybe Happy Ending

Tue, 2 Feb 2027 at 2:00 PM

Citizens Opera House

Theater

Maybe Happy Ending at Citizens Opera House in Boston is a contemporary theater piece staged in an intimate opera-hall atmosphere. Expect a lush blend of drama and musical storytelling, served by live musicians and expressive performances that fuse narrative depth with operatic sensibilities. A refined, adult-oriented evening of performance.

Coppélia

Wed, 10 Mar 2027

Citizens Opera House

Theater

George Balanchine’s Coppélia, a sparkling classical ballet by Boston Ballet, returns to the Citizens Bank Opera House in Boston for a run March 11–21, 2027. In this playful village tale, charm and mischief collide with precision dancing, making it a vivid, entertaining night of dance.

Cinderella

Wed, 28 Apr 2027

Citizens Opera House

Theater

Frederick Ashton’s Cinderella graces the Citizens Bank Opera House in Boston from April 29 to May 9, 2027. A radiant ballet that blends fairy-tale storytelling with lush orchestration, it showcases luminous dancing, elegant stagecraft, and magical production values that enchant audiences of all ages.

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