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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.

YOGA ON THE LAWN

YOGA & MIMOSAS ON THE LAWN

SATURDAY, DECEMBER 7th | 8–8:50AM

Join us for Yoga & Mimosas on our first official event on our new event lawn! Led by Rebecca Schwab-Talpas of Salute to the Sol, find your zen waterfront with a cool island breeze. Price is $20 per person and includes a complimentary mimosa at our new VIP Terrace at The Barrel House!

RSVP ON FACEBOOK

plate with eggs Benedict and glass of orange juice

PRESENTS IN PARADISE BRUNCH

December 8th | 10:30am–2pm

This holiday season, Matt's Stock Island is giving back with a special Presents in Paradise Brunch. A portion of the proceeds for three buffets, endless small plates, cocktails, and more, will go to Presents in Paradise, a homegrown nonprofit that delivers gifts and holiday spirit to families that might otherwise miss out on Christmas. Reserve your table today!

Adults | $55
Children | $20

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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!

Green Pineapple gift shop store

Sip & Shop at The Green Pineapple

Friday, December 13th | 5:30–8:30pm

Join us at our onsite boutique for an evening of bubbles, light bites, music and shopping fun as part of the I Love Stock Island Festival and Lighted Boat Parade! Complete your holiday shopping list with luxury style and beautiful artistry featuring:

  • Fresha London Clothing
  • Theresa Kalvaitis Fine Art Photography & Scarfs
  • Whimsy Key West Art – Barb Sage’s vibrant expression of Keys living comes to life on colorful art & creative décor.
  • Zen by Karen Moore – Karen Moore’s handcrafted gemstone & ocean element jewelry, positive energy you can not only wear, but feel!

perry hotel event lawn

DISCOVER STOCK ISLAND

Saturday, December 14th, 10am-4pm

Get ready to 'Discover Stock Island!'  This FREE and public event takes place on Saturday, December 14 between the hours of 10 am – 4 pm as part of the I Love Stock Island Festival.  The Perry and Stock Island Marina Village are your home base for concessions, holiday marketplace, kid's play area, adult beverages, live music, new pool (open for all guests!), and more!

LEARN MORE

buffet brunch setup

I LOVE STOCK ISLAND BRUNCH & POOL PARTY

December 15th | Brunch from 10:30am–2pm

After a weekend of fun at the I Love Stock Island Festival (Dec. 13-15, 2019), spend your Sunday in true Stock Island style at our special Brunch Pool Party. Indulge in three separate buffets, unlimited small plates, endless mimosas, and more. Then spend your afternoon poolside at our new waterfront pool at the Barrel House! Reserve your table for brunch today.

Adults | $55
Children | $20

girl holding a hair dryer over a painting

POP & POUR - HOLIDAY ORNAMENTS

Thursday, December 19th | 7-9pm

Join us at Salty Oyster with artist Jasmine Jones for our version of 'paint & sip' - Pop & Pour! In true island style, we will be painting under the palm trees, but with a holiday twist!  This class will feature ornament painting, perfect for decorating your own home or for gift-giving. Great for all-ages, and 21+ get a complimentary drink ticket with class purchase!

LEARN MORE

spread of food on a table

CHRISTMAS EVE AT MATT'S

Tuesday, December 24 | 6-10pm

Celebrate the Eve of the holidays with us at Matt’s!  Enjoy award-winning American Coastal Comfort cuisine featuring local favorites like the Black Grouper with Cornbread Gnudi, Char Grilled Skirt Steak on a bed of Risotto, Seafood Tower served in a vintage tacklebox, and holiday specials – plus craft cocktails, signature beers, and an unbeatable wine selection.  Eat, drink, and be Merry with us!

RESERVE NOW

wooden chair and table overlooking marina

CHRISTMAS DAY BRUNCH AT MATT'S

December 25th, 2019 | 11am-4pm | $65 per person

What’s Christmas day without a memorable holiday meal? Fill your belly and your spirit with our Christmas brunch, featuring all of the essentials from 3 buffets with holiday inspired favorites like wild mushroom ravioli, orange and vanilla scented sweet potatoes, carving station with pineapple & mangrove honey glazed ham, smoked Wagyu tri-tip, and more.  Don't forget about the bottomless bloody marys and mimosas! 

RESERVE NOW

event lawn at The Perry

108 SUN SALUTATIONS WITH HEALTH & FITNESS FAIR

Tuesday, December 31 | 8:00am–12pm

Join us on the new event lawn for 108 Sun Salutations to end 2019!  This donation based event is open to the public with proceeds going to the Florida Keys SPCA. Celebrate your practice with a mimosa toast, then shop health & fitness booths including FYT Key West, Amber Air Essentials, and more. Booths open at 9:30 following yoga - please BYOM (bring your own mat).

RSVP through Facebook

two glasses of champagne being cheersed

NEW YEAR'S DAY BRUNCH

January 1st, 2020 | 11am–4pm

This New Year’s Day, we’re celebrating with your favorite Matt’s Stock Island brunch holiday essentials. We're kicking up our 3 buffets a notch and including seasonal favorites like goat cheese & roasted vegetable quiche, grilled & chilled asparagus with lemon & tarragon, cheddar biscuits, and a carving station with pineapple & honey glazed ham, hot smoked salmon, smoked Wagyu tri-tip, and more. Make your reservation today!

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KEY WEST HALF MARATHON SUNDAY BRUNCH

Sunday, January 19th | 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

salty

Key West Half Marathon Farewell Party & Awards Presentation

Sunday, January 19th | 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.

girl shopping and holding up a white dress

SIP & SHOP AT THE GREEN PINEAPPLE

Friday, January 31st | 5:30pm–8:30pm

Join us at our onsite boutique for an evening of bubbles, light bites, music and shopping fun in conjunction with Matt's Stock Island and Salty Oyster's happy hours (4-8pm). This event features different local artists each month for the perfect night out on the waterfront!

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.

Start Planning

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