A Speakeasy, a Tea Party, and a Rooftop Toast: Fenway Hotel Sets the Mood for Valentine’s Day

WHO: 

The historic Fenway Hotel in Dunedin, Florida

WHAT:

This Valentine’s season, Fenway Hotel leans into romance with a playful twist, pairing Prohibition-era intrigue, elegant dining, and rooftop revelry across a curated lineup of February experiences. From a limited-run speakeasy pop-up to refined tea service and celebratory brunch, Fenway offers multiple ways to mark the occasion, whether guests are planning a classic date night, a Galentine’s gathering, or something in between. Highlights include:

• Room 27 Valentine’s Speakeasy – Fenway’s hidden speakeasy transforms for Valentine’s season with an intimate, Roaring Twenties-inspired cocktail experience offered on select February evenings. Guests are welcomed into Room 27 for a reservation-only night of handcrafted cocktails and vintage ambiance. Reservations are $10 per seating ($20 on Fridays) and available online.
• Valentine’s Tea Party at HEW Parlor & Chophouse – An elegant afternoon tea brings a romantic lens to Fenway’s signature dining room, featuring a curated selection of sweet and savory bites created for the season. Designed for couples, friends, and families alike, the Valentine’s Tea Party is $70 per person with reservations available online.
• Valentine’s Day Dinner at HEW Parlor & Chophouse – On Valentine’s Day, HEW complements its regular dinner menu with chef-driven specials crafted for the occasion, offering guests a refined, relaxed alternative to prix-fixe dining. Reservations are available via OpenTable.
• Galentine’s Brunch at Hi-Fi Rooftop Bar – Friendship takes center stage at this rooftop brunch overlooking St. Joseph Sound. Guests can enjoy bottomless mimosas and Bloody Marys alongside shareable brunch bites in a bright, celebratory setting. Tickets are $65 and reservations are available online. 

WHEN:

Mark your calendar:

• Room 27 Valentine’s Speakeasy – Feb. 2, 3, 6, 9, 10 & 13. Two seatings nightly: 6:30–8:30 p.m. and 9–11 p.m.
• Valentine’s Tea Party – Sunday, Feb. 8, 2:30–4:30 p.m.
• Valentine’s Day Dinner at HEW Parlor & Chophouse – Saturday, Feb. 14, 5–10 p.m.
• Galentine’s Brunch at Hi-Fi Rooftop Bar – Sunday, Feb. 15, 10 a.m.–Noon 

WHERE:

Fenway Hotel – 453 Edgewater Drive, Dunedin

Complimentary valet parking available 

HOW:   

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