Fenway Hotel Hits Holiday High Notes with December Full of Flavor and Fun

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Fenway Hotel Hits Holiday High Notes with December Full of Flavor and Fun

Posted by Sara Tirrell, December 1, 2025

Fenway Hotel is rolling out a high-energy lineup of holiday programming designed to stand out in a crowded season of merrymaking. Highlights include immersive speakeasy nights, family-friendly traditions and a festive dining experience:

  • Room 27 Winter Wonderland – The hotel’s secretive speakeasy transforms into a snow-dusted hideaway offering handcrafted, holiday-themed cocktails and a curated, two-hour experience. Reservations are $10 ($20 on Fridays) for select nights and can be made
  • National Ugly Christmas Sweater Day – Whether they sparkle, jingle, light up or clash, all festively-dressed guests will receive 10% off their check at Hi-Fi Rooftop Bar or HEW’s Parlor Bar during this quirky holiday celebration. More information online.
  • Photos with Santa – All kids naughty and nice are welcome to stop by Fenway Hotel for a visit and a photo with Santa and Mrs. Claus. Bring a camera and enjoy a classic holiday tradition in a historic setting. Details available online.
  • Christmas Day Feast at HEW Parlor & Chophouse – A multi-course, family-style holiday meal served throughout Christmas Day. Reservations available on OpenTable.

WHEN:               

  • Room 27 Winter Wonderland – Two seatings (6:30-8:30 p.m. and 9-11 p.m.) every Monday, Tuesday, and Friday in December starting Dec. 5 (except Dec. 12), plus Thursday, Dec. 11.
  • National Ugly Christmas Sweater Day – Friday, Dec. 19, 4 p.m. – Midnight
  • Photos with Santa – Sunday, Dec. 21, 5-7 p.m.
  • Christmas Day Feast – Thursday, Dec. 25, 11 a.m.-7 p.m.

WHERE:             

Fenway Hotel – 453 Edgewater Drive, Dunedin
(Complimentary valet parking available for HEW Parlor & Chophouse and Hi-Fi Rooftop Bar patrons.)

For more information and reservations, visit the Fenway Hotel events page or Fenway Hotel.com.

 

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