Aspirations Winery

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

Pinellas County

Clearwater

Florida

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

Paint a custom holiday serving plate! Sip, paint, and celebrate Thanksgiving.
 Add a personal, handcrafted touch to your Thanksgiving table this year—no artistic experience required! Get your ticket by November 5th and save $5.
Gather with friends at Aspirations Winery for a cozy evening of crafting and wine. For this Wine Down &amp; Paint edition, you’ll design and paint your own festive Thanksgiving serving plate or decorative display platter.
Never painted on glass/ceramic before? No problem! Take full advantage of our "Design Bar" featuring 200+ stencils and templates—making it easy for anyone to trace and paint stunning autumn foliage, pumpkins, or seasonal lettering without having to freehand a thing.
What’s Included:
<ul><li>One food-safe/decorative plate and all paints, sealants, and supplies.</li><li>Unlimited access to our Design Bar (200+ stencils, lettering templates, and seasonal patterns).</li><li>Step-by-step guidance from our instructor.</li><li>Delicious craft wine, bites, and great company throughout the night.</li></ul>
Bring home a piece you’ll be proud to serve on or gift to your holiday host!
Grab your friends, grab a glass, and let’s make something beautiful!
Specials: 10% off all food &amp; beverages.
PLEASE: No outside food or beverage! We offer a large selection of wine, craft beer, draft sangrias, cocktails, &amp; food.

Local Event: Wine Down & Paint in Clearwater | Thanksgiving Plate or Wine Glass Painting

Wine Down & Paint in Clearwater | Thanksgiving...

Paint a custom holiday serving plate! Sip, paint, and celebrate Thanksgiving.
 Add a personal, handcrafted touch to your...

Wine Down & Paint in Clearwater | Thanksgiving Plate or Wine Glass Painting

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.
Get...

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

<img alt="🎷" src="https://static.xx.fbcdn.net/images/emoji.php/v9/ta0/1/16/1f3b7.png"> LIVE SAXOPHONE &amp; DANCING — FEATURING ALEX MOS!Join us for a special evening of live saxophone, smooth jazz, familiar favorites, and dancing at Aspirations Winery in Clearwater, FL!Enjoy 90 minutes of beautiful live music, a romantic candlelight performance, and a wonderful atmosphere. Whether you love to dance or simply relax and enjoy great music, this evening is for you!<img alt="📅" src="https://static.xx.fbcdn.net/images/emoji.php/v9/t7e/1/16/1f4c5.png"> Saturday, November 14, 2026 <img alt="🕕" src="https://static.xx.fbcdn.net/images/emoji.php/v9/t2d/1/16/1f555.png"> 6:00 PM <img alt="📍" src="https://static.xx.fbcdn.net/images/emoji.php/v9/t2d/1/16/1f4cd.png"> Aspirations Winery 22041 US Hwy 19 N, Clearwater, FL 33765<img alt="🎟️" src="https://static.xx.fbcdn.net/images/emoji.php/v9/td8/1/16/1f39f.png"> Tickets: $40 per person<img alt="✨" src="https://static.xx.fbcdn.net/images/emoji.php/v9/tf4/1/16/2728.png"> 90 minutes of live music <img alt="✨" src="https://static.xx.fbcdn.net/images/emoji.php/v9/tf4/1/16/2728.png"> Smooth jazz &amp; popular favorites <img alt="✨" src="https://static.xx.fbcdn.net/images/emoji.php/v9/tf4/1/16/2728.png"> Dancing encouraged <img alt="✨" src="https://static.xx.fbcdn.net/images/emoji.php/v9/tf4/1/16/2728.png"> Open seating — first come, first served&nbsp; food and drinks are available for optional purchase at the winery.Limited seating available! Tickets are required for admission.Invite your friends, bring someone special, and enjoy an unforgettable evening of music and dancing!We look forward to seeing you there!

Local Event: Live Saxophone and Dancing with Alex Mos

Live Saxophone and Dancing with Alex Mos

 LIVE SAXOPHONE & DANCING — FEATURING ALEX MOS!Join us for a special evening of live saxophone, smooth jazz, familiar...

Join us for a taste of Thanksgiving wine pairings including seasonal bites &amp; great wines.
A Taste of Thanksgiving: Wine &amp; Holiday Bites Pairing
Kick off the holiday season with our most delicious tradition of the year! Join us at Aspirations Winery in Clearwater for an intimate, Thanksgiving-themed wine pairing experience that brings the comforting flavors of the holidays right to your glass.
Skip the stress of the kitchen and jump straight to the best part: the food and the wine. Our team has carefully curated a special tasting flight of our handcrafted velvety reds and crisp whites, perfectly matched with classic, holiday-inspired bites.
What’s on the Menu:
<ul><li>The Pairings: Discover how different varietals complement and elevate classic Thanksgiving profiles, from savory roasted turkey and glazed ham to herbed stuffing and tart cranberry accents.</li><li>The Vibe: A warm, relaxed evening perfect for a pre-holiday date night, gathering with friends, or simply treating yourself to a guided tasting experience.</li><li>The Takeaway: Learn insider pairing tips to take the guesswork out of choosing the perfect bottles for your own family dinner table this year.</li></ul>
Whether you are a Thanksgiving foodie or just looking for a fantastic night of local wine, this evening promises great flavors and even better company.
Cost is $34 in advance and $39 the day of.

Local Event: Taste of Thanksgiving Wine Pairing

Taste of Thanksgiving Wine Pairing

Join us for a taste of Thanksgiving wine pairings including seasonal bites & great wines.
A Taste of Thanksgiving: Wine &...

A night of live stand-up comedy at Aspirations Winery.Lineup: Bill "Bull" Ohse (headliner) Billy Dunn Big Joe Murry Jean Bygene Benji Bell Host: Ryan ParkerLocation: Aspirations Winery, 22041 US HWY 19N, Clearwater, FL 33765Tickets: $20 plus fees at <a href="https://winerycomedy1120.eventbrite.com/?fbclid=IwZXh0bgNhZW0CMTAAcGRvZgFicmlkETEzczF4eXBMbHNQdWowS1Mxc3J0YwZhcHBfaWQQMjIyMDM5MTc4ODIwMDg5MgABH6PH3Emw-cniyhgW2jJR8edN_h7i3EE5sUZ-9wlSk8kfowcYZmqW5TwJXkCE_aem_Qil3Yji2FfzH6KwZniM5Uw" target="_blank" rel="nofollow noopener">https://winerycomedy1120.eventbrite.com</a> Winery guests use code Winery25 for 25% off.

Local Event: Live Comedy at Aspirations 

Live Comedy at Aspirations 

A night of live stand-up comedy at Aspirations Winery.Lineup: Bill "Bull" Ohse (headliner) Billy Dunn Big Joe Murry Jean Bygene...

Overview
Free open play for all players….Your ticket includes 1 drink and grazing charcuterie table and 10% off additional food &amp; beverages.
Ready for a fun day of tiles and tiles of fun? 🀄✨
Whether you’re still learning the ropes or you're a seasoned player chasing that perfect hand, come join us for a fantastic evening of Mahjong Open Play! Bring your friends, meet new players, and enjoy a lively, welcoming atmosphere. $25 for advance tickets, $30 the day of.
<h3>📋 Event Details</h3>
<ul><li>All Skill Levels Welcome: No pressure, just fun!</li><li>BYOS (Bring Your Own Set): Please bring your own Mahjong set and racks to ensure everyone gets a seat at a table.</li><li>Food &amp; Drinks: Aspirations Winery has a fantastic selection of wine, beer, cocktails, and food available for purchase to keep you fueled throughout the night. Players will recieve 1 drink and crazing charcuterie table as well as 10% off food and berverages.</li></ul>
Please note: No outside food or beverage containers are allowed in the venue.

Local Event: Mahjong Open Play Friendsgiving In Clearwater

Mahjong Open Play Friendsgiving In Clearwater

Overview
Free open play for all players….Your ticket includes 1 drink and grazing charcuterie table and 10% off additional food...

Join us for a vibrant experience creating a unique dazzling LED light. It's going to be a glowing good time! Invite your friends &amp; coworkers.
 Create your very own uniquely designed 7” LED light.
 You choose the design; an array of colorful supplies will be on hand A demonstration using resin &amp; one-on-one guidance is provided You may take your light home with you. No overnight curing needed
 Fee - $48 Per Person Advanced reservations required
 12 and above children may join, with accompanying adult. 
 No refunds or transfer to another class. You may give your ticket to another person to attend on the date of the ticket/class. Brigitte Miner – Fun-Spirationist

Local Event: Led Light Stand Class

Led Light Stand Class

Join us for a vibrant experience creating a unique dazzling LED light. It's going to be a glowing good time! Invite your...

Like Running or Walking? Love Wine? This race is for you!Join us on Saturday, December 19, 2026 at 9:00am and 11:00am (you will select your start time during registration) for an exciting Christmas themed event that features the scenic views of Aspirations Winery! Located in sunny Clearwater Florida, we hand-craft over 30 wines every year, right here at our veteran and family owned &amp; operated craft winery. Although we specialize in making some of the tastiest award winning, fruit-infused wines around, we also produce your favorite dry reds, whites as well as some dessert wines. So, whether you are looking to run, walk or just enjoy the wine this race is a sure thing for a great time and an incredible experience! This race is timed and scored by J3 Timing. Results will be posted at <a href="https://www.j3timing.com/?fbclid=IwZXh0bgNhZW0CMTAAcGRvZgFicmlkETFtRlltSm44OFYxZWNITVVZc3J0YwZhcHBfaWQQMjIyMDM5MTc4ODIwMDg5MgABHj9KweJCatR_48q-qmPlCgDv_M4aSUZIUIH2xJ0CNC-ZKp99hQvAQmWEyDwI_aem_JU3KXSMAOpqNQPvgxNEA4Q" target="_blank" rel="nofollow noopener">www.J3Timing.com.</a>

Local Event: Aspirations Winery Christmas Wine run 5k

Aspirations Winery Christmas Wine run 5k

Like Running or Walking? Love Wine? This race is for you!Join us on Saturday, December 19, 2026 at 9:00am and 11:00am (you will...

Gather your friends or family and form teams of six, four or two to compete to see who can finish a jigsaw puzzle the fastest! (6-person teams will have a 1,000-piece, 4-person teams will have a 500-piece, and 2-person teams will have a 300-piece). One team in each division will win a prize package, including trophies for all team members. All teams get to take their puzzle home, too! Wine, beer, non-alcoholic beverages and food 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

Whispering Souls Puzzle Championship

Gather your friends or family and form teams of six, four or two to compete to see who can finish a jigsaw puzzle the fastest!...

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

Coachman Park

Escape to a tropical celebration featuring live trop rock, steel drums, and over 60 coastal and boutique vendors. This family-friendly festival offers free admission, food trucks, and craft cocktails by Caribbean Moonshine, with exclusive VIP tickets available for a premium experience including a treasure hunt and artisan nosh.

Local Event: Pirates, Parrots & Paradise

Pirates, Parrots & Paradise

Escape to a tropical celebration featuring live trop rock, steel drums, and over 60 coastal and boutique vendors. This...

Peace Memorial Presbyterian Church

&nbsp; 



 
CELEBRATING BURT BACHARACH: Come enjoy a jazzy popular music program of tunes from the Great American Songbook and especially celebrating favorites composed by Burt Bacharach. Among many great selections, you will hear Raindrops Keep Falling on My Head, This Girl’s In Love with You, What the World Needs Now is Love Sweet Love and Close to You. Seating is first- come, first served. Doors open at 2:30.
&nbsp;THE ARENAS, LASKY &amp; NASH TRIO is a terrific new jazz group performing in the Tampa Bay Area.We all know Alejandro Arenas, bassist from the popular La Lucha Jazz Combo.Here he is joined with renowned jazz pianist Simon Lasky and wonderful vocalist Allison Nash to create an easy, breezy sound you will love.
Peace Memorial Presb. Church (the pink church downtown) 110 S. Ft. Harrison Ave., Clwr. (corner of Pierce and Ft. Harrison). Doors open at 2:30.
<img src="file:///C:/Users/Jordan/AppData/Local/Temp/msohtmlclip1/01/clip_image002.png">
PARKING: east across Ft. Harrison in County lot (enter off Pierce); north of the church hall at County Utility Bldg; and one full block east in the lot reserved for Peace at NE corner of Pierce and Garden. Also, with construction going on downtown, please use this link to find a helpful and regularly updated city parking map. 
INFO:For more info, see <a href="https://peacememorialpresbyterian.org/" rel="nofollow noopener" target="_blank">https://peacememorialpresbyterian.org/</a>
or call (800) 479-8846. 
SAVE THE DATES This season we celebrate 20 years of fine music programs in downtown Clearwater. Calendar these dates for the regular 2026-27 Peace Music Series:
Nov. 8; Dec. 13, 2026 and Jan. 10; Feb. 14; and March 14, 2027- all programs at 3 PM. 
Plus “ A Charlie Brown Christmas” with live jazz trio on Mon. Dec. 21.- shows at 6 and 8 PM.

Local Event: Jazz Concert Celebrating Burt Bacharach

Jazz Concert Celebrating Burt Bacharach


 
  



 
CELEBRATING BURT BACHARACH: Come enjoy a jazzy popular music program of tunes from the Great American Songbook and...

Safety Harbor Resort and Spa

Silent Slayer Ghost Tours is marking the last Friday the 13th until August 2027 with a four-hour, after-dark bus tour of real Tampa Bay locations tied to documented crimes, misfortune, and local haunted legends.
The Friday the 13th Horror Bus departs from Safety Harbor Resort &amp; Spa at 7:00 PM and makes four stops across Tampa Bay, sharing the history behind each location along the way. The evening includes a spirit box session at a cemetery, giving guests a hands-on look at a tool commonly used by paranormal investigators.
The tour is limited to 22 guests on a luxury mini-bus. Guests must be 21 or older, and the bus is BYOB.
“Friday the 13th has carried a reputation for bad luck for generations,” said Cynthia Dominick, founder of Silent Slayer Ghost Tours. “This tour focuses on real history and real stories, with no actors or theatrics. It’s a chance to see a side of Tampa Bay most people drive past every day.”
About Silent Slayer Ghost Tours: 
Founded in 2021 and based in Safety Harbor, Silent Slayer Ghost Tours offers ghost walking tours in Safety Harbor and Tarpon Springs, paranormal investigations at historic sites across Florida, and themed Horror Bus experiences. Founder Cynthia Dominick was named the Safety Harbor Chamber of Commerce 2026 Tourism Person of the Year and received a Besties Award from Visit St. Pete-Clearwater.

Local Event: Friday the 13th Horror Bus Tour in Tampa Bay

Friday the 13th Horror Bus Tour in Tampa Bay

Silent Slayer Ghost Tours is marking the last Friday the 13th until August 2027 with a four-hour, after-dark bus tour of real...

First Presbyterian Church

This Friday, Nov. 20 event is designed for people who value live music in a beautiful setting. Featuring The Paradies String Quartet, the concert will feature popular music from the 1960s through today surrounded by candlelight at the historic First Presbyterian Church of Dunedin. 
Add-on or book a ticket for Saturday, Nov. 21 rooftop event at The Fenway Hotel overlooking St. Joseph Sound. Meet the quartet, enjoy a continental breakfast with live cello music by Liz Glushko.

Local Event: Candlelight & Strings

Candlelight & Strings

This Friday, Nov. 20 event is designed for people who value live music in a beautiful setting. Featuring The Paradies String...

Thursday, December 3, 2026 from 1pm – 4pm


 Join us as we celebrate one year of serving the Clearwatercommunity with a Customer Appreciation and Hearing Health Event. Learn more about hearing health and come meet our team!


 ■ Complimentary Hearing Screenings†
 
 ■ Free demonstration of the latest technology 
 
 ■ Enjoy complimentary refreshments 


 1541 S. Highland Avenue, Clearwater, FL 33756 
 727.748.1908 • hearinglife.com 
 Lisa Williams, Hearing Instrument Specialist Lic. #AS5922
RSVP by Wednesday, December 2, 2026 

 †See office for details. *30% discount is off standard list prices. One offer per purchase. Offer cannot be combined with any other offer or discount, including the HearingLife ValuePlan (HLVP). Not valid on prior purchases. Offer not available to any consumer who has private or federal health insurance coverage. Private pay purchases only. The CROS system andEssential products do not qualify for this offer. Hearing aids must be purchased by 11/25/26. Exclusions apply. See office for details. Offer valid from 12/3/26 thru 12/10/26.

Local Event: Celebrating one year of helping people hear better at HearingLife in Clearwater. 

Celebrating one year of helping people hear...


    Thursday, December 3, 2026 from 1pm – 4pm


    Join us as we celebrate one year of serving the Clearwatercommunity with a...

Nearby Communities

State Edition

National Edition

Posting Activity

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

NOV

6

7:00 PM

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

Wine Down & Paint in Clearwater | Thanksgiving Plate or Wine Glass Painting

NOV

7

2:00 PM

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

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

NOV

13

7:00 PM

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

Live Saxophone and Dancing with Alex Mos

NOV

14

6:00 PM

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

Taste of Thanksgiving Wine Pairing

NOV

19

7:00 PM

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

Live Comedy at Aspirations

NOV

20

7:30 PM

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

Mahjong Open Play Friendsgiving In Clearwater

NOV

21

12:00 PM

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

Led Light Stand Class

DEC

12

6:00 PM

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

Aspirations Winery Christmas Wine run 5k

DEC

19

9:00 AM

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

Whispering Souls Puzzle Championship

FEB

7

1:00 PM

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

Pirates, Parrots & Paradise

Jazz Concert Celebrating Burt Bacharach

Friday the 13th Horror Bus Tour in Tampa Bay

Candlelight & Strings

Celebrating one year of helping people hear better at HearingLife in Clearwater.