Aspirations Winery

Join us at Aspirations Winery for wine, and grazing charcuterie! Members &amp; guests are welcome.
About This Event Join us at Aspirations Winery—voted one of the top wineries in Florida—for our monthly Club Wine-O Social. This isn't just a tasting; it's a community celebration! Whether you are a long-time wine club member, a local resident, or just visiting the Clearwater/Dunedin area, everyone is welcome.
What’s Included with Your Ticket:
<ul><li>Two Full Glasses: Enjoy two pours of your choice from our extensive menu of award-winning wines and fruit-infused favorites.</li><li>Grazing Charcuterie: A curated selection of meats, cheeses, and accompaniments to snack on while you socialize.</li><li>Meet the Team: Connect with our winery team and fellow wine enthusiasts in a relaxed, 2-hour open-house format.</li><li>Special Offers and Discounts for Members Only: To keep the celebration going at home, all ticket holders enjoy these exclusive event-night perks: 10% OFF any additional food or beverages ordered during the event.</li></ul>
10% OFF all to-go bottles of wine to stock your cellar.
The Ultimate Case Stacking Discount!
Yes, you can combine offers! Your event-night 10% discount stacks directly with our volume bottle savings. Mix and match any combination of your favorite wines to unlock incredible deals:
<ul><li>Save 25% Total on 6 bottles (15% standard volume discount + your 10% event bonus!)</li></ul>
<ul><li>Save 35% Total on 12 or more bottles (25% standard case discount + your 10% event bonus!)</li></ul>
Stock up on your favorites tonight and take the pairing experience home!
Event Details:
<ul><li>Vibe: Casual, social, and inclusive.</li><li>Timing: Stop in anytime during the 2-hour window!</li><li>Location: Aspirations Winery, Clearwater/Dunedin area.</li><li>Audience: Open to members, future members, and all wine lovers (21+).</li></ul>
Why Attend? Our Club Wine-O Social is the best way to experience the local flavor of Clearwater. Come for the wine, stay for the community. Space is limited, so grab your tickets early!

Local Event: Club Wine-O Social at Aspirations Winery in Clearwater

Pinellas County

Clearwater

Florida

Club Wine-O Social at Aspirations Winery in...

Join us at Aspirations Winery for wine, and grazing charcuterie! Members & guests are welcome.
About This Event Join us at...

Club Wine-O Social at Aspirations Winery in Clearwater

The Motown and Soul Music Show is coming back to Clearwater, FL, on Sunday, August 9! Relive the unforgettable sounds of Motown &amp; Soul.Grammy nominated Dre Hilton will deliver a high-energy performance honoring the greats—James Brown, Ray Charles, Stevie Wonder, The Four Tops, The Temptations, 70 Disco Era and more!$40 General Admission Arrive early to save your seat and grab a bite to eat — Seating starts at 5PM and the winery opens earlier in the day. Outside Food &amp; Beverages are NOT allowed!&nbsp;Call the box office to reserve your tickets: 727-635-1245

Local Event: Motown and Soul Music Show

Motown and Soul Music Show

The Motown and Soul Music Show is coming back to Clearwater, FL, on Sunday, August 9! Relive the unforgettable sounds of Motown...

Experience a hilarious night of improv comedy &amp; music in Tampa Bay! Inspired by "Whose Line Is It Anyway".
A Live Improv Comedy Experience in Tampa Bay Inspired by the hit TV show Whose Line is it Anyway?, If You Know What I Mean is a high-energy, fully improvised comedy show where the audience is the star. Our regular cast of elite Tampa Bay comedians and improvisers takes your suggestions and turns them into instant comedy gold.
What to Expect:
<ul><li>Audience Interaction: No two shows are the same! Every game, joke, and scene is built entirely from your engagement.</li><li>Improvised Musical Games: Get ready for full musical numbers and hilarious "serenades" created on the spot. (And yes, for the superfans, we will do a Hoedown!)</li><li>Stand-Up &amp; Warm-Ups: Your host, local comedy veteran Robin Savage, kicks things off with a stand-up set to get the crowd roaring before the improv begins.</li><li>Special Guest Spotlights: Each performance features a new guest artist from the local Tampa arts scene, ensuring every show is a unique, one-night-only event.</li></ul>
Join us for a night of surprises, music, and non-stop laughter... if you know what I mean!

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The Motown and Soul Music Show is coming back to Clearwater, FL, on Sunday, August 16th! Relive the unforgettable sounds of Motown &amp; Soul.Grammy nominated Dre Hilton will deliver a high-energy performance honoring the greats—James Brown, Ray Charles, Stevie Wonder, The Four Tops, The Temptations, 70 Disco Era and more!$40 General Admission Arrive early to save your seat and grab a bite to eat — Seating starts at 5PM and the winery opens earlier in the day. Outside Food &amp; Beverages are NOT allowed.&nbsp;Call the box office to reserve your tickets: 727-635-1245

The Motown and Soul Music Show is coming back to Clearwater, FL, on Sunday, August 16th! Relive the unforgettable sounds of...

Experience the music of Billy Joel up close! "Florida's Billy Joel" delivers an intimate, hit-filled solo piano concert.
Get ready for a New York State of Mind right here in Florida!
Join us for an unforgettable, intimate evening celebrating the music of one of the greatest singer-songwriters of all time. "Piano Man" is a spectacular solo tribute show that captures the raw passion, complex musicianship, and soaring vocals of Billy Joel in an up-close-and-personal setting.
Just Mark and his keys—delivering the massive energy of a full concert with the personal connection of a classic piano bar. Whether you want to sway to the classics, sing at the top of your lungs, or just relive the soundtrack of a generation, this performance promises standing ovations.
<h3>Meet the Artist: Mark, "Florida's Billy Joel"</h3>
The journey began in 1989 at Yankee Stadium, where Mark witnessed Billy Joel’s iconic Storm Front Tour. Inspired by that legendary performance, Mark set out on a lifelong mission to bring that same raw passion and drive to the stage.
Before relocating to the sunshine state, Mark spent years performing full-time across the competitive New York and New Jersey music scenes. Over his career as a premier front-man and keyboardist, he has shared stages and jammed with rock royalty, including Bruce Springsteen, Cheap Trick, Elvis Costello, and Gregg Allman.
In 2008, after moving to Florida, Mark's ultimate dream came to life with the launch of his "Piano Man" Tribute Show. Tackling Billy Joel's intricate piano compositions and distinct vocal range entirely on your own is a challenge few musicians can master—but for over 11 years, Mark has done just that. Performing in major venues and theaters across the U.S. and abroad, he has earned the well-deserved title of "Florida's Billy Joel."
<h3>What to Expect:</h3>
In this masterfully executed solo performance, Mark commands the room, delivering decades of timeless hits exactly the way you remember them. Prepare to sing along to all your favorites, including:
<ul><li>Piano Man</li><li>Uptown Girl</li><li>We Didn't Start the Fire</li><li>Only the Good Die Young</li><li>New York State of Mind ...and many more!</li></ul>
Spaces for this exclusive, intimate engagement are limited and tickets sell out fast. Secure your seats today and join us for a killer show! NO OUTSIDE FOOD OR BEVERAGES ARE ALLOWED! Aspirations Winery has wine, beer, cocktails, food and more!

Local Event: "Piano Man" – An Intimate Solo Tribute to Billy Joel Live!

"Piano Man" – An Intimate Solo Tribute to Billy...

Experience the music of Billy Joel up close! "Florida's Billy Joel" delivers an intimate, hit-filled solo piano concert.
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"Piano Man" – An Intimate Solo Tribute to Billy Joel Live!

Looking for the best local shopping in Clearwater? Join us for our Summer Sip &amp; Shop at Aspirations Winery!
Beat the Florida heat and shop in comfort inside our spacious event room. We are bringing together the most talented local craft vendors, fine artists, and makers from across the Tampa Bay area for a one-day-only boutique market experience.
What to expect:
<ul><li>🍷 Sip: Enjoy over 40 award-winning wines, craft beers, and seasonal cocktails available at the bar.</li><li>🛍️ Shop: vendors offering unique handcrafted jewelry, home decor, local art, and so much more!</li><li>🎨 Support Local: Meet the artists and makers behind your favorite local Clearwater brands.</li><li>🍕 Eat: Delicious flatbreads and snacks available for purchase to keep you fueled while you shop.</li><li>Live Music: Live music from 12-3 From Matt Frick</li><li>Door Prize Drawings: Every hour with purchase of beer or wine</li></ul>
Event Details: 📅 Date: Saturday, August 22nd, 2026 🕚 Time: 11:00 AM – 4:00 PM 📍 Location: Aspirations Winery | 22041 US Hwy 19 N, Clearwater, FL 33765 🎟️ Admission: FREE (Please RSVP via Eventbrite to receive an entry reminder!)
Parking is free and plentiful. This is a family-friendly, indoor event!

Local Event: Free Indoor Sip & Shop: Local Artist & Craft Market at Aspirations Winery

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Looking for the best local shopping in Clearwater? Join us for our Summer Sip & Shop at Aspirations Winery!
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Gather your friends or family and form teams of four or six to compete to see who can finish a 1,000-piece jigsaw puzzle the fastest! One team in each division will win a prize package. Your entry fee includes puzzling fun, meat/cheese/crackers and you get to take the puzzle home! Wine, beer and non-alcoholic beverages available for purchase from our host, Aspirations Winery! Sponsorship packages available, too. LIMITED number of teams, so don't delay in registering! All proceeds benefit the Whispering Souls African-American Cemetery Restoration Project, as we welcome our new irrigation system and have water bills to pay now!

Local Event: Whispering Souls Puzzle Championship

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Gather your friends or family and form teams of four or six to compete to see who can finish a 1,000-piece jigsaw puzzle the...

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Club Wine-O Social at Aspirations Winery in Clearwater

JUL

24

6:00 PM

Aspirations Winery, 22041 US Hwy 19 N, Clearwater, FL

Motown and Soul Music Show

AUG

9

7:00 PM

Aspirations Winery, 22041 US Hwy 19 N, Clearwater, FL

If You Know What I Mean: Improv Comedy & Musical Show in Tampa Bay

AUG

14

7:00 PM

Aspirations Winery, 22041 US Hwy 19 N, Clearwater, FL

Motown and Soul Music Show

AUG

16

7:00 PM

Aspirations Winery, 22041 US Hwy 19 N, Clearwater, FL

"Piano Man" – An Intimate Solo Tribute to Billy Joel Live!

AUG

21

7:00 PM

Aspirations Winery, 22041 US Hwy 19 N, Clearwater, FL

Free Indoor Sip & Shop: Local Artist & Craft Market at Aspirations Winery

AUG

22

11:00 AM

Aspirations Winery, 22041 US Hwy 19 N, Clearwater, FL

Whispering Souls Puzzle Championship

AUG

30

1:00 PM

Aspirations Winery, 22041 US Hwy 19 N, Clearwater, FL