All Events

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Winter Haven Happy Hour Walking Tour

Winter Haven Happy Hour Pub Crawl - August 21, 2026

New
No Reviews
August 21, 2026, 4:30 pm
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7:30 pm
Price: $157
Experience Winter Haven’s local nightlife on a guided happy-hour pub crawl featuring drinks, food, and entertaining local stories. Schedule: Wednesdays and Fridays, 4:30–7:30 p.m. Exact meeting and parking instructions are provided with your booking. Guests must meet the tour’s age requirements. View full tour details and book now. Read more...
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The Cocktail Classic Winter Haven

New
No Reviews
August 21, 2026, 5:00 pm
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August 29, 2026, 11:30 pm
Main Street Winter Haven’s Cocktail Classic is a week-long tasting experience showcasing Downtown Winter Haven’s cocktail and dining offerings. Participating venues will feature specialty cocktails and mocktails, creative appetizers, and mixology experiences. Guests can sample the offerings and vote for Best Cocktail Bar and Best Cocktail. Official details: https://www.mainstreetwh.com/tag/downtown-winter-haven/ Read more...
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Winter Haven Brunch Tour - August 22, 2026

New
No Reviews
August 22, 2026, 10:30 am
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1:30 pm
Price: $117
Enjoy a delicious guided brunch experience featuring local Winter Haven restaurants, flavors, and stories. Schedule: Saturdays, 10:30 a.m.–1:30 p.m. All featured tastings are included. Exact meeting and parking instructions are provided with your booking. View full tour details and book now. Read more...
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Flavors of Winter Haven Food Tour - August 22, 2026

New
No Reviews
August 22, 2026, 2:00 pm
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5:00 pm
Price: $124
Discover the flavors, history, and locally owned restaurants of downtown Winter Haven on this guided culinary walking tour. Schedule: Tuesdays, Thursdays, and Saturdays, 2:00–5:00 p.m. All featured tastings are included. Exact meeting and parking instructions are provided with your booking. View full tour details and book now. Read more...
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Winter Haven Chef’s Table Experience - August 22, 2026

New
No Reviews
August 22, 2026, 5:00 pm
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8:00 pm
Price: $250
Enjoy an elevated guided dining experience showcasing Winter Haven chefs, restaurants, and thoughtfully prepared courses. Schedule: Thursdays and Saturdays, 5:00–8:00 p.m. Exact meeting and parking instructions are provided with your booking. Minimum guest requirements may apply. View full tour details and book now. Read more...
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Winter Haven Coffee, Tea, and Dessert Tour - August 24, 2026

New
No Reviews
August 24, 2026, 10:00 am
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3:00 pm
Price: $125
Join us on a sweet and savory journey through Winter Haven’s local coffee shops and dessert destinations. Enjoy coffee, tea, pastries, desserts, local stories, and a guided walking experience. Schedule: Mondays, Wednesdays, and Fridays, 10:00 a.m.–3:00 p.m. All tastings are included. Exact meeting and parking instructions are provided with your booking. View full tour details and book now. Read more...
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Flavors of Winter Haven Food Tour - August 25, 2026

New
No Reviews
August 25, 2026, 2:00 pm
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5:00 pm
Price: $124
Discover the flavors, history, and locally owned restaurants of downtown Winter Haven on this guided culinary walking tour. Schedule: Tuesdays, Thursdays, and Saturdays, 2:00–5:00 p.m. All featured tastings are included. Exact meeting and parking instructions are provided with your booking. View full tour details and book now. Read more...
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Winter Haven Coffee, Tea, and Dessert Tour - August 26, 2026

New
No Reviews
August 26, 2026, 10:00 am
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3:00 pm
Price: $125
Join us on a sweet and savory journey through Winter Haven’s local coffee shops and dessert destinations. Enjoy coffee, tea, pastries, desserts, local stories, and a guided walking experience. Schedule: Mondays, Wednesdays, and Fridays, 10:00 a.m.–3:00 p.m. All tastings are included. Exact meeting and parking instructions are provided with your booking. View full tour details and book now. Read more...
Winter Haven Happy Hour Walking Tour

Winter Haven Happy Hour Pub Crawl - August 26, 2026

New
No Reviews
August 26, 2026, 4:30 pm
-
7:30 pm
Price: $157
Experience Winter Haven’s local nightlife on a guided happy-hour pub crawl featuring drinks, food, and entertaining local stories. Schedule: Wednesdays and Fridays, 4:30–7:30 p.m. Exact meeting and parking instructions are provided with your booking. Guests must meet the tour’s age requirements. View full tour details and book now. Read more...
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The Jam with No Name at Jessie’s Lounge - August 26, 2026

New
No Reviews
August 26, 2026, 7:00 pm
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11:59 pm
Every Wednesday at 7 PM, The Jam with No Name—hosted by Frankie—welcomes musicians of all skill levels to perform at Jessie’s Lounge in Downtown Winter Haven. Bring an instrument, share your talent, or come enjoy live music and drinks. Official event details: https://jessieslive.com/events Read more...