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Events

Mark Your Calendar

From fishing strolls and harbor walks to bustling parties and live music, The Perry Hotel offers eclectic opportunities for mingling, celebrating, and simply enjoying life. Get out there and explore the many events happening right here.

girl shopping and holding up a white dress

The Green Pineapple at The Perry Turns 1!

Saturday, November 9th | 6pm–9pm

The Green Pineapple at The Perry is turning 1!   Join us as we celebrate our amazing on-site boutique with bubbles, bites, and live music.  Come early for back-to-back happy hour at Salty Oyster from 4-6pm, followed by Matt's from 6-8pm.

pop and pour

POP & POUR AT THE PERRY

Tuesday, November 12 | 6-8pm

Join us at Salty Oyster for an evening of pouring bubbles and popping some bubbly! Pop & Pour is a paint and sip class where artist Jasmine Jones will teach the newest fluid art craze: alcohol inks! In a small class setting you will learn step-by-step, all her tips and tricks for creating your very own masterpiece, ready to hang in your home.

Your spot must be reserved in advance, click here to reserve your ticket today!

platter of oysters and ceviche with decorative leaves and orchids

Thanksgiving at Matt’s

Thursday, November 28th | 1–8pm

Love our Sunday Brunch? Well get ready because we're translating that same concept into a Thanksgiving lunch/dinner you won't want to miss. Enjoy 3 buffets & a carving station with all your turkey day favorites, plus a seafood twist. Get ready to gobble till you wobble!

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TASTE OF STOCK ISLAND

Friday, December 13th | 4PM - 7PM

Get off the beaten path and eat your way across Stock Island in a matter of hours as part of the annual I Love Stock Island Festival. Taste a selection of curated plates and beverages at the locals’ favorite spots, and experience one of the Keys’ hidden gems. Plus, be some of the first to experience The Perry's new BBQ & Brews restaurant, The Barrel House! Limited tickets available, buy yours today.

the perry hotel key west events lighted boat parade

Stock Island Lighted Boat Parade

Friday, December 13th | 7PM

Kick off the holiday season and the start of the I Love Stock Island Festival at the Stock Island Marina with a procession of lighted vessels in all sizes – kayaks, dinghies, fishing boats, sailing ships, private yachts and more!  Get merry with plenty of free parking, food from Matt's Stock Island, Salty Oyster, The Barrel House, food trucks and more, along with easy viewing of the parade of watercrafts. Free, family-friendly and open to the public!

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KEY WEST HALF MARATHON SUNDAY BRUNCH

Sunday, January 19 | 10:30am-2pm

Planning to race 13.1 memorable miles in Key West? CONGRATS!! Refuel with us at the best brunch on the island - including 3 buffets (and raw bar!), unlimited small plates, and unlimited bloody marys & mimosas at the waterfront Matt's Stock Island Kitchen & Bar. Celebrate your accomplishment with great food, ease that muscle soreness with a few cocktails (guilt-free!), and most importantly, show off that medal!

RESERVE NOW

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Key West Half Marathon Farewell Party & Awards Presentation

Sunday, January 19 | 4-7pm

Join us at Salty Oyster for the official Key West Half Marathon Awards Presentation for Running Organizations & Volunteers, Free Raffles and Prizes! This dockside celebration is during our daily happy hour where guests can enjoy 50% off straight pour premium cocktails, wine, and drafts, plus daily food specials.

overhead view of a shrimp boil layout

ORIGINAL STOCK ISLAND SHRIMP BOIL

Saturday, February 1st | 12PM - 2PM

Immerse yourself in Keys culture for the annual Key West Food & Wine Festival. Sample the finest fare the Florida Straits have to offer: There’s enough Key West Pink Shrimp — and an array of wines to pair — for everyone to enjoy. Purchase your tickets today!

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SUNDAY BRUNCH AT MATT'S

Every Sunday

Sundays are fun days with brunch at Matt’s Stock Island Kitchen & Bar. Enjoy three buffets and unlimited small plates, as well as unlimited bloody marys and mimosas, every Sunday from 10:30am to 2pm. Make your reservation today!

Adults | $55
Children | $20

top level view of a grilled chicken dinner with 2 glasses of beer and fries on the side

FAMILY FRIED CHICKEN NIGHT

EVERY WEDNESDAY

Every Wednesday, Matt's Stock Island Kitchen & Bar presents a Family Fried Chicken Night with all the fixings. For just $15 per person, you and your family can indulge in cornbread mash, citrus coleslaw, roasted corn on the cob, and—of course—plenty of fried chicken!

view of a person playing the guitar with drums in the background

LIVE MUSIC AT MATT'S

September: Sunday Brunch 10:30am-2pm

Enjoy live music dockside at the Matt's Stock Island Kitchen & Bar at our weekly Sunday Brunch from 10:30am-2pm, from our talented local musicians including:

  • Drew Gunning
  • Tim Hollohan
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Salty Oyster Bar’s
Daily Happy Hour

Daily 4-6PM

Everyday from 4pm to 6pm, Salty Oyster Bar is serving up a legendary happy hour, with 50% off straight pour premium cocktails, house wine, and drafts.  Plus, daily food specials! Follow up your 1st happy hour with a 2nd just across the pool at Matt's Stock Island from 6-8pm.

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MATT'S BAR DAILY HAPPY HOUR

Daily 6-8pm

Enjoy $2 signature beers, $3 oysters, 50% off signature wine, $5 select cocktails, and even $5 tasty tapas and crudo at Matt's Stock Island Kitchen & Bar during the 6pm to 8pm happy hour. Eat, drink and be merry with us every day of the week.

Birds on the beach

Design Your Own Event

Looking to host your own fantastic gathering at The Perry? Whether you're interested in hosting a professional business meeting or a lively wedding party, allow us to help you in planning something memorable.

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