Aspirations Winery

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>Exclusive Wine Release: Be among the first to taste our latest batch of Acai/Raspberry Pinot Grigio, which was created by mistake. Oops!</li><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></ul>
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 & Wine Tasting at Aspirations Winery in Clearwater

Pinellas County

Clearwater

Florida

Club Wine-O Social & Wine Tasting at...

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...

Club Wine-O Social & Wine Tasting at Aspirations Winery in Clearwater

This one-hour workshop is designed to teach you the art of building a beautiful and delicious board along with paired wines.
The Art of the Board: A Charcuterie &amp; Wine Pairing Workshop
Transform simple ingredients into a stunning edible centerpiece. This one-hour relaxed workshop at Aspirations Winery is designed to teach you the fine art of professional board building.
Under expert guidance, you will master essential styling techniques, from balanced flavor profiles to crafting the perfect salami rose. We provide everything you need—from high-quality, artisanal ingredients to all necessary supplies—so you can focus entirely on your creative process.
The Experience:
<ul><li>Create: Build a full-sized charcuterie board from scratch.</li><li>Learn: Master professional placement and "flow" techniques.</li><li>Sip: Enjoy the workshop in the beautiful setting of our winery.</li></ul>
After the session, we invite you to linger and enjoy your board with a glass of our locally crafted wine, or take your finished masterpiece home to share. We look forward to hosting you for an afternoon of creativity and fine flavors.
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Local Event: Charcuterie Making Class & Wine Pairing

Charcuterie Making Class & Wine Pairing

This one-hour workshop is designed to teach you the art of building a beautiful and delicious board along with paired...

The Motown and Soul Music Show is coming back to Clearwater, FL, on Friday, May 1st! 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! $38 General Admission Arrive early to save your seat and grab a bite to eat — Seating starts at 6PM and the winery opens earlier in the day. Outside Food &amp; Beverages are NOT allowed. 📞 Call the box office to reserve your tickets: 727-635-1245

Local Event: The Motown and Soul Music Show

The Motown and Soul Music Show

The Motown and Soul Music Show is coming back to Clearwater, FL, on Friday, May 1st! Relive the unforgettable sounds of Motown...

Dust off your dancing shoes—the Divas are returning to Aspirations Winery! The ultimate high-energy tribute to the queens of pop, disco, and soul returns to the intimate stage of Aspirations Winery. If you missed the last one, now is your chance to experience the show everyone is talking about! The DIVAS of the 70s &amp; 80s Show is more than just a concert; it’s a time-traveling dance party. Featuring a full live band and powerhouse vocalists, we’re bringing the legendary hits of the world's greatest female artists to life with dazzling costumes and infectious energy. Hear the Smash Hits of: • The Disco Queens: Donna Summer, Gloria Estefan, and Diana Ross. • The Pop Icons: Madonna, Cyndi Lauper, and Blondie. • The Powerhouses: Whitney Houston, Barbra Streisand, and Pattie LaBelle. • The Soul Legends: Chaka Khan, The Weather Girls, and so many more! From the disco groove of "Dancing Queen" to the soaring notes of "I Will Always Love You," this is a fast-paced, feel-good celebration of the music that defined a generation. "The one show you can’t miss... a high-energy, feel-good musical celebration!"

Local Event: The Divas are Back! The 70s and 80s Tribute Show!

The Divas are Back! The 70s and 80s Tribute Show!

Dust off your dancing shoes—the Divas are returning to Aspirations Winery! The ultimate high-energy tribute to the queens of...

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!

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

If You Know What I Mean: Improv Comedy &...

Experience a hilarious night of improv comedy & music in Tampa Bay! Inspired by "Whose Line Is It Anyway".
A Live Improv Comedy...

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

At this month’s jewelry making class you’ll create two colorful pendant necklaces using dried flowers and UV resin. A wide range of colors and flowers will be offered as well as glitters and tiny beads and pendant styles to choose from. $32 includes all materials. Bring a friend or two - or come make new friends at Aspirations! Please note: Minimum age for this class is 16 and no outside food or drink is allowed. Aspirations offers wine, beer, cocktails, food and more!
Event Details:
<ul><li>All-Inclusive: Your $32 ticket covers all materials and professional instruction.</li><li>Social Atmosphere: Perfect for a girls' night out, a unique date night, or meeting new friends in the Clearwater/Dunedin community.</li><li>Refreshments: Aspirations Winery offers an extensive menu of award-winning wines, craft beer, cocktails, and food available for purchase.</li><li>Policy: Please note that no outside food or drink is permitted.</li></ul>

Local Event: Jewelry Making Workshop | Aspirations Winery Clearwater

Jewelry Making Workshop | Aspirations Winery...

At this month’s jewelry making class you’ll create two colorful pendant necklaces using dried flowers and UV resin. A wide...

Jewelry Making Workshop | Aspirations Winery Clearwater

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 tasting 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: Browse 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></ul>
Event Details: 📅 Date: Saturday, June 20th, 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!
Calling All Local Vendors!
Aspirations Winery is gearing up for another Sip and Shop, and we want YOU to be a part of it! We're looking for talented local vendors to join us at our upcoming sip and shop on June 20th, from 11am-4pm, where our guests can enjoy your unique offerings alongside our award-winning wines. If interested, Email: Info@aspirationswinery.com or call 727-799-9463
Whether you specialize in artisanal foods, handmade crafts, holiday gifts, decor, or specialty items, we’re looking for partners who bring creativity and excitement to our gatherings. If you’re ready to share your products with a passionate crowd and grow your local presence, we'd love to hear from you!

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

Free Indoor Sip & Shop: Local Artist & Craft...

Looking for the best local shopping in Clearwater? Join us for our Summer Sip & Shop at Aspirations Winery!
Beat the Florida...

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

Design your own custom wine glass or beer mug! Choose from dozens of patterns &amp; templates. All supplies include.
Your Glass, Your Way! Forget the "everyone paints the same thing" classes. At Aspirations Winery, we believe your art should be as unique as your favorite vintage. Whether you want a beachy Florida vibe, elegant floral swirls, or a fun seasonal pattern, you will have a massive library of designs to choose from! Ticket sales ends at 6pm on June 19th. What’s Included:
The Canvas: One high-quality wine glass or beer mug.
The Designs: Access to our "Design Bar" featuring 200+ stencils, templates.
The Gear: Specialized glass paints, brushes, and aprons.
Expert Coaching: Our instructor will be floating around to help you master glass-painting techniques like dotting, swirling, and layering.
Specials: $1 off all alcodolice beverages and 10% off all food.
PLEASE: No outside food or beverage! We offer a large selection of wine, craft beer, draft sangrias, cocktails, &amp; food.

Local Event: Wine Glass/Beer Mug Painting & Personalized Sip Night

Wine Glass/Beer Mug Painting & Personalized Sip...

Design your own custom wine glass or beer mug! Choose from dozens of patterns & templates. All supplies include.
Your Glass,...

Wine Glass/Beer Mug Painting & Personalized Sip Night

BACKTRACK BLUES BAND at ASPIRATIONS WINERY - CLEARWATERGulf Coast Records artist, BACKTRACK BLUES BAND, brings its energetic, original blues music to the intimate ASPIRATIONS WINERY, 22041 U.S. Highway 19, Clearwater, Florida, on SATURDAY, June 27, at 8 pm. This is a great venue, with a large wine menu, beers, mixed drinks and food.Enjoy a night of exceptional blues guitar and harmonica, with soulful vocals and a seamless rhythm section! This band has toured the world and appeared in concert with BB King, Stevie Ray Vaughan, Buddy Guy, Johnny Winter, Kenny Wayne Shepherd, and more. Come experience exceptional live music in a friendly and comfortable setting with lots of drink and food options! We hope to see you on June 27 for a big night of original blues music, lots of wine options, beers, cocktails, foods, and FUN!!!

Local Event: An Evening with Backtrack Blues Band at Aspirations Winery

An Evening with Backtrack Blues Band at...

BACKTRACK BLUES BAND at ASPIRATIONS WINERY - CLEARWATERGulf Coast Records artist, BACKTRACK BLUES BAND, brings its energetic,...

An Evening with Backtrack Blues Band at Aspirations Winery

Join us at Emma’s Foundation for Canine Cancer, Inc Animal Rescue Fundraiser! This special Pet Portrait event lets you turn your furry friend into a masterpiece
No experience? No problem! Our artists will guide you step-by-step as you paint your pet with personalized flair. All skill levels are welcome, and you’re guaranteed to leave with a one-of-a-kind keepsake (and maybe a little paint on your nose).A portion of every ticket sold will benefit Emma’s Foundation for Canine Cancer, Inc. They focus on sparing or prolonging the life of our canine friends, by assisting with financial support.What’s Included: - Step-by-step guidance from our talented instructor - All painting supplies provided - Delicious food and drinks available for purchase from Aspirations Winery

Local Event: Emma's Foundations for Canine Cancer, Inc. Animal Rescue Fundraiser

Emma's Foundations for Canine Cancer, Inc....

Join us at Emma’s Foundation for Canine Cancer, Inc Animal Rescue Fundraiser! This special Pet Portrait event lets you turn...

Emma's Foundations for Canine Cancer, Inc. Animal Rescue Fundraiser

Bill Linville

Tiffany Razzano

Tampa Bay Area

Safety Harbor

Largo

Dunedin

Pinellas Beaches

Palm Harbor

St. Pete

East Lake

Hillsborough County

Westchase

Gulfport

Tarpon Springs

Curlew Hills Memory Gardens

Join <a href="https://www.curlewhills.com/about/about-us" target="_blank" rel="nofollow noopener">Curlew Hills</a> this Memorial Day to honor the selfless <a href="https://www.curlewhills.com/services/veterans-services" target="_blank" rel="nofollow noopener">veterans</a> from all branches of the military who bravely made the ultimate sacrifice while serving our country. The
 moving observance program will take place this Memorial Day, Monday, May 25, at 9:30 a.m. Curlew Hills Memory Gardens. The special 
event is free and the public is invited to attend. Our Memorial
Day ceremony includes inspirational speakers, an honor guard with 
presentation of colors and live musical performances of everyone’s 
favorite patriotic music. 
Guest Speaker – Mike Delancey United States Marine Corps Lance Corporal, Ret Founder of Wounded Warriors Abilities Ranch
After a sniper’s bullet in Iraq shattered his spine and left him paralyzed from the chest down, Mike DeLancey refused to let tragedy define his future. Turning pain into purpose, he co-founded Wounded Warriors Abilities Ranch and helped create an adaptive park and sports programs that serve thousands of veterans. Mike’s journey is a testament to extraordinary courage, hope and resilience.
Musical Guests: 
<ul><li> National Anthem by Jenny Dean – Reporter &amp; News Anchor with 10 Tampa Bay News</li><li> Tampa Bay Harolds of Harmony – An award-winning harmony choral group performing patriotic favorites </li></ul>
Join Curlew Hills this Memorial Day, Monday, May 25, to stand together to honor the courage and devotion of our Nation’s
 heroes. For more information about this special ceremony visit 
CurlewHills.com or call them at 727.789.2000.

Local Event: Memorial Day Ceremony

Memorial Day Ceremony

Join Curlew Hills this Memorial Day to honor the selfless veterans from all branches of the military who  bravely made the...

The Divas are returning to Aspirations Winery!
The ultimate high-energy tribute to the queens of pop, disco, and soul returns to the intimate stage of Aspirations Winery. If you missed the last one, now is your chance to experience the show everyone is talking about!
The DIVAS of the 70s &amp; 80s Show is more than just a concert; it’s a time-traveling dance party. Featuring a full live band and powerhouse vocalists, we’re bringing the legendary hits of the world's greatest female artists to life with dazzling costumes and infectious energy.
Hear the Smash Hits of:
<ul>
 <li>The Disco Queens: Donna Summer, Gloria Estefan, and Diana Ross.</li>
 <li>The Pop Icons: Madonna, Cyndi Lauper, and ABBA.</li>
 <li>The Powerhouses: Whitney Houston, Barbra Streisand, and Pattie LaBelle.</li>
 <li>The Soul Legends: Chaka Khan, The Weather Girls, and so many more!</li>
</ul>
From the disco groove of "Dancing Queen" to the soaring notes of "I Will Always Love You," this is a fast-paced, feel-good celebration of the music that defined a generation.
"The one show you can’t miss... a high-energy, feel-good musical celebration!"
Tickets are expected to move fast for this return engagement. Grab yours now

Local Event: 🎤 THE DIVAS ARE BACK! The 70s & 80s Tribute Show Returns to Clearwater

🎤 THE DIVAS ARE BACK! The 70s & 80s Tribute...

The Divas are returning to Aspirations Winery!
The ultimate high-energy tribute to the queens of pop, disco, and soul returns...

🎤 THE DIVAS ARE BACK! The 70s & 80s Tribute Show Returns to Clearwater

Spend the afternoon with us at a lovely tea party!&nbsp; We'll be serving a variety of teas, savory bites and sweets with a bit of Scottish influence!&nbsp; Music will be provided by Anthem by Music on the Violin and Cello.&nbsp; Wear a hat or fascinator!&nbsp; Bring a friend or relative.Thank you for supporting the Scottish Arts.

Local Event: An Afternoon Tea with Anthem by Music

An Afternoon Tea with Anthem by Music

Spend the afternoon with us at a lovely tea party!  We'll be serving a variety of teas, savory bites and sweets with a bit of...

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Posting Activity

Club Wine-O Social & Wine Tasting at Aspirations Winery in Clearwater

MAY

23

1:00 PM

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

Charcuterie Making Class & Wine Pairing

MAY

24

2:00 PM

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

The Motown and Soul Music Show

MAY

29

7:00 PM

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

The Divas are Back! The 70s and 80s Tribute Show!

MAY

30

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

JUN

5

7:00 PM

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

Jewelry Making Workshop | Aspirations Winery Clearwater

JUN

14

1:30 PM

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

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

JUN

20

11:00 AM

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

Wine Glass/Beer Mug Painting & Personalized Sip Night

JUN

20

1:30 PM

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

An Evening with Backtrack Blues Band at Aspirations Winery

JUN

27

8:00 PM

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

Emma's Foundations for Canine Cancer, Inc. Animal Rescue Fundraiser

JUN

28

2:00 PM

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

Memorial Day Ceremony

🎤 THE DIVAS ARE BACK! The 70s & 80s Tribute Show Returns to Clearwater

An Afternoon Tea with Anthem by Music