A Very Sinatra Christmas Special at Hotel Commonwealth

This December, Boston’s holiday magic gets a whole lot smoother. Hotel Commonwealth will host A Very Sinatra Christmas Special — an unforgettable evening filled with timeless charm, cocktails, and the music of the one and only Frank Sinatra.

Frank Sinatra Tribute Concerts Under the Stars – Boston Holiday Event

This December, Boston’s holiday magic gets a whole lot smoother. Hotel Commonwealth will host A Very Sinatra Christmas Special — an unforgettable evening filled with timeless charm, cocktails, and the music of the one and only Frank Sinatra.

Get Tickets Here!

Produced by Concerts Under the Stars, this elegant holiday event celebrates the golden age of jazz and the spirit of the season. Gather your friends, raise a glass, and let the voice of one of Boston’s top jazz vocalists transport you back to the era of “Old Blue Eyes.”

🌆 Breathtaking views of Fenway Park from the Fenway Ballroom & Terrace

🎁 A Sinatra Christmas Special featuring Sinatra’s holiday classics

🍸 Sip classic cocktails under the stars and “melt away those little town blues”

🍽️ Lite bites available for purchase

🎶 Tentative Setlist

Expect to hear your favorite Sinatra standards and holiday favorites, including:

Fly Me To The Moon

White Christmas

I’ll Be Home For Christmas

What a Wonderful World

Have Yourself a Merry Little Christmas

I’ve Got the World on a String

Let It Snow

The Christmas Song

Mele Kalikimaka

New York, New York

…and more timeless tunes that will leave you swooning.

Date: Sunday, December 14

Showtimes: 6:00 p.m. & 8:30 p.m.

Duration: 65 minutes (doors open 60 minutes early)

Location: The Fenway Ballroom & Terrace, Hotel Commonwealth, Downtown Boston

Age Requirement: 18+ with valid ID

Accessibility: Fully accessible venue

Weather: Indoor concert — no need to worry about the chill!

Please note: Hotel Commonwealth enforces a one-drink minimum policy.

🎟️ Don’t Miss Boston’s Most Stylish Holiday Concert

Join us for A Very Sinatra Christmas Special and relive the golden holiday sound of Frank Sinatra in a glamorous setting overlooking Fenway Park. This is more than just a concert — it’s a night of elegance, nostalgia, and pure holiday joy.

Tickets are selling fast for both showtimes.

👉 Reserve your seats now for A Very Sinatra Christmas Special at Hotel Commonwealth

Michelle McCormack

Michelle McCormack

Michelle is founder of Secret Boston. She is a media strategist and creative director. Fun fact: she was once chased by a lion in Africa while on a photo shoot for Town & Country Mag. (It’s been all uphill since then!) Her work spans media, politics, and emerging tech, from early crypto and NFTs to AI today. She’s lived in four countries and five cities, but deep down she’s always from JP.

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