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.

Group of young people drinking and partying in the pool



Step right up to The Perry Hotel's Ringmaster's Pool Party, featuring carnival games, strongman photo ops, circus-themed food and drinks, music by local favorite Patrick & The Swayzees, and more. We are partnering with Florida Keys Healthy Start Coalition for this event and all proceeds from our carnival games will go to this non-profit organization. Join this one-of-a-kind spectacular for only $10 per person, and leave with an unforgettable Fantasy Fest experience. (No charge for hotel guests)

Perry Offer Thanksgiving

Thanksgiving at Matt’s

Thursday, November 22nd | 2pm–9pm

This Thanksgiving, leave the stress of cooking behind and treat your family to something truly special at Matt’s Stock Island Kitchen & Bar. We’re serving a family-style feast of hickory-smoked turkey breast, roasted brussel sprouts, pumpkin pie, and more.

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A Taste of Stock Island

Friday, December 7th | 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.

the perry hotel key west events lighted boat parade

Stock Island Lighted Boat Parade

Friday, December 7th | 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, drinks and easy viewing of the parade of watercrafts.

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“Meet the Fleet” Shrimp Boil

Saturday, January 26th | 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.

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Summer Coastal Eats

Daily Summer Menu

Hook, line, and sink your teeth into our fresh summertime flavors. Matt’s Stock Island Kitchen & Bar is offering great deals on our Summer Coastal Eats, with $10 breakfast options, $20 appetizer and lunch combos, and $30 dinners featuring an appetizer, an entree, and dessert.

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



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!

Perry Offer LiveMusic

Live Music at Matt's Stock Island Kitchen & Bar

Every Friday & Saturday from 6-8pm

Enjoy live music poolside at the Matt's Stock Island Kitchen & Bar every Friday & Saturday from 6pm to 8pm from our talented local musicians including:

  • Drew Gunning
  • Kari Daley
  • Tim Hollohan
Perry Offer HappyHour

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, including 50% off all food and premium beverages. And don't forget about our live music every Friday & Saturday.

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Matt's Bar
Daily Happy Hour

Daily 6-8pm

Enjoy daily specials on beer, wine, cocktails, and tasty even tasty tapas 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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