I Love Stock Island Festival
Festival Schedule
Wednesday
June 11th
Thursday
June 12th
Friday
June 13th
Saturday
June 14th
Father’s Day
June 15th
Wednesday, June 11, 2025
I Love Stock Island Festival Kick Off!
Come take a picture in front of the 2025 I Love Stock Island Festival sign! Post your picture with the hashtag #ilovestockisland for a chance to win I Love Stock Island gear.
Where: Maloney/MacDonald Ave Grass Triangle
5690 Maloney Ave Key West, FL 33040.
When: All weekend long!
STOCK ISLAND COLLABORATIVE CLEAN UP
Join us for the Stock Island Collaborative Cleanup in partnership with the Monroe County Sheriff’s Office, Key West City Ploggers, Lazy Dog Adventures, Kayak Kings, Blue Moon Kayak, and Oceans Edge Watersport! This community-driven event aims to restore and preserve the natural beauty of Stock Island, while fostering a sense of environmental responsibility. Together, we will gather at designated locations and work hand in hand to remove litter and debris from the island’s shores, parks, and public spaces. By joining forces with the brave law enforcement officers of Monroe County Sheriff’s Office and the Ploggers of Key West for our land based clean ups, as well as Lazy Dog Adventures, Oceans Edge Watersports, and Kayak Kings of Key West, we can make a meaningful impact on the local ecosystem. Let’s come together, protect our environment, and create a cleaner, healthier Stock Island for all to enjoy.
Oceans Edge Watersports – Departing from 5950 Peninsular Ave at 1pm-3pm-Click Here to reserve your kayak or Call to reserve- 786-862-6317
Join us back at Oceans Edge Watersport Wiki Hut for the garbage to be weighed and disposes of and celebrate your hard work with a cold beverage- 7-8pm
stock Island Food Truck Tour
Embark on a delightful culinary adventure through the self guided “I Love Stock Island” Food Truck Tour. Savor the vibrant food truck scene of Stock Island at your own pace, with no tickets required.
Where: Follow the interactive map event website to Stock Island’s favorite food trucks.
When: During regular business hours. Each food truck’s hours may vary.
FYT KEY WEST FITNESS FEST
Dive into wellness with FYT Key West during the I Love Stock Island Festival! From June 11th to 15th, we’re offering complimentary daily fitness, pilates, and yoga classes to festival attendees. It’s the perfect opportunity to rejuvenate your mind and body amidst the festivities. Use code “ilovestockisland” to unlock your free class experience! This offer is limited to one-time use per person. Secure your spot today by calling 305-453-6176. Whether you’re a seasoned yogi or just beginning your fitness journey, FYT’s classes cater to all levels. Visit www.fytkeywest.com for the class schedule and explore membership options for continued wellness beyond the festival.
Where: FYT Key West- 5450 MacDonald Ave #9, Key West, FL 33040
When: Wed-Sun June 11-15, 2025- Visit www.fytkeywest.com for class descriptions and times
CAYO HUESO BREWING LOW COUNTRY SHRIMP BOIL
Join us at Cayo Hueso Brewing for a flavorful evening at our Low Country Shrimp Boil event! Indulge in a classic Shrimp Boil feast featuring mouthwatering items such as sausage, potatoes, corn, and dessert, all accompanied by a complimentary Cayo Hueso Brewing beer of your choice.
As you savor the delicious spread, take in the sights of the brew house and witness the magic of the shrimp boil as it cooks inside one of our brew kettles. Dinner will be served buffet style in a laid-back atmosphere in the Cayo Hueso Brewing courtyard.
Space is limited, so secure your spot by purchasing tickets in advance. Don’t miss out on this unique culinary experience and join us for a memorable evening of great food, refreshing drinks, fun ambiance at Cayo Hueso Brewing!
Where: Cayo Hueso Brewing
5635 1st Ave. Stock Island, FL 33040
When: Wednesday June 11, 2025- 5:30pm-9pm
STOCK ISLAND MURAL ART TOUR
Embark on a vibrant artistic journey with the Stock Island Mural Art Tour, a captivating exploration of street art and creativity. This self-guided tour allows you to immerse yourself in the rich tapestry of murals that adorn the walls of Stock Island. Find one, find them all! Don’t forget to take a photo and include #ilovestockisland
Where: Guide yourself with our interactive map on the I Love Stock Island website.
When: All weekend long!
Thursday, June 12, 2025
I Love Stock Island Food Truck Tour
Embark on a delightful culinary adventure through the self guided “I Love Stock Island” Food Truck Tour. Savor the vibrant food truck scene of Stock Island at your own pace, with no tickets required.
Where: Follow the interactive map event website to Stock Island’s favorite food trucks.
When: During regular business hours. Each food truck’s hours may vary.
AN EVENING WITH WINEBOW
Join us for an exclusive Winebow Wine Tasting hosted by Oceans Edge Resort & Marina. Let Winebow entice you with its dynamic portfolio of wines. Guests will taste a variety of their carefully crafted wines and enjoy light snacks from the talented chefs at Yellowfin Bar & Kitchen. Enter the drawing for a chance to win a special prize at the end. Advanced reservations required so reserve your spot now! Space is limited.
Where: Oceans Edge Resort & Marina
5950 Peninsular Ave, Key West, FL 33040
When: Thursday June 12, 2025- 5:30pm-7:30pm.
FYT KEY WEST FITNESS FEST
Dive into wellness with FYT Key West during the I Love Stock Island Festival! From June 11th to 15th, we’re offering complimentary daily fitness, pilates, and yoga classes to festival attendees. It’s the perfect opportunity to rejuvenate your mind and body amidst the festivities. Use code “ilovestockisland” to unlock your free class experience! This offer is limited to one-time use per person. Secure your spot today by calling 305-453-6176. Whether you’re a seasoned yogi or just beginning your fitness journey, FYT’s classes cater to all levels. Visit www.fytkeywest.com for the class schedule and explore membership options for continued wellness beyond the festival.
Where: FYT Key West- 5450 MacDonald Ave #9, Key West, FL 33040
When: Wed-Sun June 11-15, 2025- Visit www.fytkeywest.com for class descriptions and times
STOCK ISLAND MURAL ART TOUR
Embark on a vibrant artistic journey with the Stock Island Mural Art Tour, a captivating exploration of street art and creativity. This self-guided tour allows you to immerse yourself in the rich tapestry of murals that adorn the walls of Stock Island. Find one, find them all! Don’t forget to take a photo and include #ilovestockisland
Where: Guide yourself with our interactive map on the I Love Stock Island website.
When: All weekend long!
Friday, June 13, 2025
5STOCK ISLAND HISTORY TOUR
Tour Stock Island in the comfort of Up The Keys’ air-conditioned tour van. In the one-hour tour, passengers learn about Stock Island’s rich history and colorful characters that have allowed for the preservation of the old Florida Keys lifestyle so that it is still present today. Limited space available. Advanced reservations required. Visit the event website to reserve your spot.
Where: The Perry Hotel & Marina, 7001 Shrimp Rd. Stock Island, FL 33040.
When: Friday June 13, 2025- 2PM, 3PM, 4PM
TASTE OF STOCK ISLAND TROLLEY TOUR & SOS FOOD DRIVE
Board the Old Town Trolley for a culinary tour of Stock Island’s favorite restaurants. At each stop you will enjoy a specially selected small plate and beverage pairing that will be explained by an expert. Each trolley small group is lead by a local tour guide. Bring a non-perishable food item to donate to the SOS Foundation Food Pantry.
Where: Meet at The Perry Hotel, 7001 Shrimp Rd. Stock Island, FL 33040.
When: Friday June 13, 2025- 4-8PM.
stock Island Food Truck Tour
Embark on a delightful culinary adventure through the self guided “I Love Stock Island” Food Truck Tour. Savor the vibrant food truck scene of Stock Island at your own pace, with no tickets required.
Where: Follow the interactive map event website to Stock Island’s favorite food trucks.
When: During regular business hours. Each food truck’s hours may vary.
FYT KEY WEST FITNESS FEST
Dive into wellness with FYT Key West during the I Love Stock Island Festival! From June 11th to 15th, we’re offering complimentary daily fitness, pilates, and yoga classes to festival attendees. It’s the perfect opportunity to rejuvenate your mind and body amidst the festivities. Use code “ilovestockisland” to unlock your free class experience! This offer is limited to one-time use per person. Secure your spot today by calling 305-453-6176. Whether you’re a seasoned yogi or just beginning your fitness journey, FYT’s classes cater to all levels. Visit www.fytkeywest.com for the class schedule and explore membership options for continued wellness beyond the festival.
Where: FYT Key West- 5450 MacDonald Ave #9, Key West, FL 33040
When: Wed-Sun June 11-15, 2025- Visit www.fytkeywest.com for class descriptions and times
STOCK ISLAND MURAL ART TOUR
Embark on a vibrant artistic journey with the Stock Island Mural Art Tour, a captivating exploration of street art and creativity. This self-guided tour allows you to immerse yourself in the rich tapestry of murals that adorn the walls of Stock Island. Find one, find them all! Don’t forget to take a photo and include #ilovestockisland
Where: Guide yourself with our interactive map on the I Love Stock Island website.
When: All weekend long!
Saturday, June 14, 2025
FYT KEY WEST FITNESS FEST
Dive into wellness with FYT Key West during the I Love Stock Island Festival! From June 11th to 15th, we’re offering complimentary daily fitness, pilates, and yoga classes to festival attendees. It’s the perfect opportunity to rejuvenate your mind and body amidst the festivities. Use code “ilovestockisland” to unlock your free class experience! This offer is limited to one-time use per person. Secure your spot today by calling 305-453-6176. Whether you’re a seasoned yogi or just beginning your fitness journey, FYT’s classes cater to all levels. Visit www.fytkeywest.com for the class schedule and explore membership options for continued wellness beyond the festival.
Where: FYT Key West- 5450 MacDonald Ave #9, Key West, FL 33040
When: Wed-Sun June 11-15, 2025- Visit www.fytkeywest.com for class descriptions and times
FATHER SON HAIR CUTS
Visit Beards and Brews Barbershop & Bar for Father-Son Haircuts. Get Dad ready to look and feel his best on Father’s Day with an amazing hair cut and barber service from the amazing staff at Beards and Brews! Pay for Dad’s haircut and get your son’s haircut for free! And don’t forget to come a little early and enjoy a beverage at the bar while you wait! This is sure to be great Father-Son bonding time during the I Love Stock Island Festival
Where: 5450 MacDonald Ave Unit 6. Key West, FL 33040
When: Saturday June 14, 2025- Call ahead to schedule your appointment. (305) 292-1460
I love Stock Island Food Truck Tour
Embark on a delightful culinary adventure through the self guided “I Love Stock Island” Food Truck Tour. Savor the vibrant food truck scene of Stock Island at your own pace, with no tickets required.
Where: Follow the interactive map event website to Stock Island’s favorite food trucks.
When: During regular business hours. Each food truck’s hours may vary.
FATHER’S DAY BRUNCH
Celebrate Father’s Day weekend in style with brunch at Matt’s Stock Island Kitchen at the Perry Hotel and Marina! Join us on Saturday and Sunday from 8:30 am to 1:30 pm for a culinary experience that Dad won’t forget.
Indulge in a delectable brunch spread crafted by our talented chefs, featuring Dad’s favorites. From savory classics like Shrimp and Grits to sweet treats, there’s something for everyone to enjoy.
With stunning waterfront views and a relaxed atmosphere, Matt’s Stock Island Kitchen provides the perfect setting for a memorable family gathering.
Reservations are recommended to secure your table. Book your spot now through the link below and treat Dad to a brunch experience he’ll cherish forever!
Where: Matt’s Stock Island Kitchen
7011 Shrimp Rd. Stock Island, FL 33040
When: Saturday June 14, 2025- 8:30am-1:30pm
I LOVE STOCK ISLAND FESTIVAL FOR THE FAMILY
Mark your calendars for the MAIN EVENT! The 2nd annual I Love Stock Island Festival for the Family! This lively celebration will be filled with fun and excitement for everyone. An artisan market, delicious food and drinks, activities for kids, fun games, entertainment, and a silent auction just to name a few. This community event is free of charge but come prepared buy raffle tickets and to place a bid for some exciting silent auction prizes, where proceeds will be benefiting the SOS Foundation and Food Pantry right here on Stock Island. You won’t want to miss out!
Where: Bernstein Park- 6751 5th Street, Stock Island, FL 33040
When: Saturday June 14, 2025- 4pm-8pm
BOURBON, BEEF AND BBQ DINNER
Join us for a weekend celebration honoring the special dads in our lives at Matt’s Stock Island Kitchen, nestled within the scenic beauty of The Perry Hotel & Marina. Treat your dad to an unforgettable culinary experience featuring mouthwatering BBQ delights infused with the richness of bourbon flavors. Indulge in a delectable array of menu items carefully crafted to satisfy every palate, including BBQ Ribs St. Louis Style, Surf ‘n Turf, and Grilled Ribeye. Reservations recommended
Where: Matt’s Stock Island Kitchen at the Perry Hotel- 7001 Shrimp Road, Stock Island, FL
When: Saturday & Sunday June 14 and 15, 2025- 5:30pm-9pm
STOCK ISLAND MURAL ART TOUR
Embark on a vibrant artistic journey with the Stock Island Mural Art Tour, a captivating exploration of street art and creativity. This self-guided tour allows you to immerse yourself in the rich tapestry of murals that adorn the walls of Stock Island. Find one, find them all! Don’t forget to take a photo and include #ilovestockisland
Where: Guide yourself with our interactive map on the I Love Stock Island website.
When: All weekend long!
Sunday, June 15, 2025
FYT KEY WEST FITNESS FEST
Dive into wellness with FYT Key West during the I Love Stock Island Festival! From June 11th to 15th, we’re offering complimentary daily fitness, pilates, and yoga classes to festival attendees. It’s the perfect opportunity to rejuvenate your mind and body amidst the festivities. Use code “ilovestockisland” to unlock your free class experience! This offer is limited to one-time use per person. Secure your spot today by calling 305-453-6176. Whether you’re a seasoned yogi or just beginning your fitness journey, FYT’s classes cater to all levels. Visit www.fytkeywest.com for the class schedule and explore membership options for continued wellness beyond the festival.
Where: FYT Key West- 5450 MacDonald Ave #9, Key West, FL 33040
When: Wed-Sun June 11-15, 2025- Visit www.fytkeywest.com for class descriptions and times
STOCK ISLAND HISTORY TOUR
Tour Stock Island in the comfort of Up The Keys’ air-conditioned tour van. In the one-hour tour, passengers learn about Stock Island’s rich history and colorful characters that have allowed for the preservation of the old Florida Keys lifestyle so that it is still present today. Limited space available. Advanced reservations required. Visit the event website to reserve your spot.
Where: The Perry Hotel & Marina, 7001 Shrimp Rd. Stock Island, FL 33040.
When: Saturday June 15, 2025- 10AM, 11AM, 1PM
FATHER’S DAY BRUNCH
Celebrate Father’s Day weekend in style with brunch at Matt’s Stock Island Kitchen at the Perry Hotel and Marina! Join us on Saturday and Sunday from 8:30 am to 1:30 pm for a culinary experience that Dad won’t forget.
Indulge in a delectable brunch spread crafted by our talented chefs, featuring Dad’s favorites. From savory classics like Shrimp and Grits to sweet treats, there’s something for everyone to enjoy.
With stunning waterfront views and a relaxed atmosphere, Matt’s Stock Island Kitchen provides the perfect setting for a memorable family gathering.
Reservations are recommended to secure your table. Book your spot now through the link below and treat Dad to a brunch experience he’ll cherish forever!
Where: Matt’s Stock Island Kitchen
7011 Shrimp Rd. Stock Island, FL 33040
When: Saturday June 14, 2025- 8:30am-1:30pm
THE PERRY MARINA & BAD BOY TAQUERIA & TEQUILA FESTIVAL CLOSEOUT BASH & POOL PARTY
Join us for an unforgettable finale to the “I Love Stock Island Festival” the Perry Marina & Bad Boy Taqueria and Tequila’s Festival Closeout Bash!
Bring your friends and family and let’s close out the I Love Stock Island Festival in Style with great food, drinks, music and community spirit! Don’t forget your swimming gear to enjoy a plunge in the Perry Marina’s pool next to Bad Boy’s restaurant. Enter the raffle for a chance to win some great prizes and proceeds from the raffle will benefit the SOS Foundation Food Pantry right here on Stock Island!
When: Sunday June 15, 2025- 2pm-6pm
Where: The Perry Marina & Bad Boy Taqueria & Tequila- 7011 Shrimp Road, Stock Island, FL 33040
13TH ANNUAL VFW FISHING TOURNAMENT AWARDS DINNER
Join us in celebrating our top anglers at the Awards Dinner featuring excellent cuisine and beverages. Chance to win door prizes, too. Nobody leaves emptyhanded.
Where: American Legion Post 28, 5610 College Road, Key West
When: Sunday June 15, 2025- 6:30 p.m.
YOGA ON THE LAWN AT THE PERRY HOTEL
Join us for a rejuvenating yoga class where serenity meets nature. This gentle hatha flow class offers a balanced approach to effort and ease, core strengthening, and deep relaxation. Move to your breath, stretch mindfully and rest completely. All levels and ages are welcome. Please arrive 10 min early.
Where: The Event Lawn @ The Perry Hotel & Marina
7011 Shrimp Rd. Key West, FL 33040
When: Sunday June 15, 2025, 8am-9am
BOURBON, BEEF AND BBQ DINNER
Join us for a weekend celebration honoring the special dads in our lives at Matt’s Stock Island Kitchen, nestled within the scenic beauty of The Perry Hotel & Marina. Treat your dad to an unforgettable culinary experience featuring mouthwatering BBQ delights infused with the richness of bourbon flavors. Indulge in a delectable array of menu items carefully crafted to satisfy every palate, including BBQ Ribs St. Louis Style, Surf ‘n Turf, and Grilled Ribeye. Reservations recommended
Where: Matt’s Stock Island Kitchen at the Perry Hotel- 7001 Shrimp Road, Stock Island, FL
When: Saturday & Sunday June 14 and 15, 2025- 5:30pm-9pm
I love Stock Island Food Truck Tour
Embark on a delightful culinary adventure through the self guided “I Love Stock Island” Food Truck Tour. Savor the vibrant food truck scene of Stock Island at your own pace, with no tickets required.
Where: Follow the interactive map event website to Stock Island’s favorite food trucks.
When: During regular business hours. Each food truck’s hours may vary.
13TH ANNUAL VFW FISHING TOURNAMENT
Spend Father’s Day out on the water with Dad and join the 13th Annual VFW Fishing Tournament. This tournament is known up and down the Florida Keys as being a great family event! This is a two-day fishing event, but anglers have a choice of fishing on Saturday June 14, OR Sunday June 15. Whether you are a returning angler, or new to our tournament, this is one event that you do not want to miss. All proceeds benefit needy and disabled veterans in Monroe County. Contact the VFW Southernmost Post 3911 at vfw39110@yahoo.com for more detail to register!
STOCK ISLAND MURAL ART TOUR
Embark on a vibrant artistic journey with the Stock Island Mural Art Tour, a captivating exploration of street art and creativity. This self-guided tour allows you to immerse yourself in the rich tapestry of murals that adorn the walls of Stock Island. Find one, find them all! Don’t forget to take a photo and include #ilovestockisland
Where: Guide yourself with our interactive map on the I Love Stock Island website.
When: All weekend long!