A Very Sinatra Christmas Special at Hotel Commonwealth
Sunday, December 14th
6pm & 8:30pm
Hotel Commonweatlh
Get ready, Boston. One of the city’s most charming holiday traditions is back and it is already becoming one of the most searched winter events in town. A Very Sinatra Christmas Special at Hotel Commonwealth is turning the Fenway Ballroom into a sparkling holiday hideaway, complete with panoramic views of Fenway Park, classic cocktails, and a set list worthy of Ol’ Blue Eyes himself.
If you love festive nights out like the ones we feature in our best December events roundup or want something as cozy and romantic as our Boston date night ideas list, this show belongs at the top of your holiday calendar.
And yes, tickets will absolutely sell out. Boston has spoken. Sinatra is Christmas.
Why This Holiday Concert Is a Must in Boston
Picture this: you arrive at the Hotel Commonwealth’s Fenway Ballroom and step into a warm glow of twinkle lights, soft jazz, and cocktails that make those “little town blues” melt away. The moment the first notes of “Fly Me To The Moon” fill the room, you will know you made the right choice.
This special evening is produced by Concerts Under the Stars and features one of Boston’s top jazz vocalists performing timeless holiday classics like White Christmas, Have Yourself a Merry Little Christmas, and New York New York. You get the nostalgia, the atmosphere, and the pure joy of a holiday concert right in the heart of the city.
If seasonal magic is your thing, this belongs on your list right next to our Boston Christmas lights and holiday displays guide.
Event Highlights That Make It Unforgettable
🌆 Stunning Fenway Park views before and after the concert
🎁 A complete Sinatra holiday set list
🍸 Classic cocktails under the stars
🍽️ Lite bites for purchase
🎄 All the cozy festive vibes you want in December
The concert runs 65 minutes, with shows at 6 p.m. and 8:30 p.m. Doors open one hour early so you can take photos, sip something classic, and settle into the moment.
The event is indoors, fully accessible, and for guests 18+. Hotel Commonwealth has a one drink minimum.
The Tentative Program
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 holiday gems
Verdict: This Is Boston’s Most Elegant Holiday Moment
If you are searching for a holiday night out that feels elevated, intimate, and full of warmth, A Very Sinatra Christmas Special is the one. It is perfect for date nights, friend outings, and anyone who wants a break from the usual holiday chaos.
🎟️ Do not wait. Tickets will move fast. Grab your spot now and step into a Sinatra inspired winter night at Hotel Commonwealth.
