The Motor Enclave Presents
Guys Night Out: Cars and Comedy
“This Is What Giving Back Looks Like in Tampa”
Big Brothers Big Sisters of Tampa Bay and The Motor Enclave have launched Guys Night Out, a new annual Enclave Signature Event that brings people together for all the right reasons: passion, purpose, and a lot of laughs. It’s part comedy show, part luxury car show, and part Tampa’s biggest guys night out, blending headline comedy, an exotic car show, a luxury goods lounge, and hands-on motorsports experiences into one unforgettable night.
Updates Each Year
2026 Guys Night Out, This Year’s Event Details
| Category | Details |
|---|---|
| Edition | 1st Annual |
| When | Friday, August 28, 2026, from 6-10 PM |
| Tickets | $1,000 per person (plus tax), limited to 300 attendees, get tickets here |
| Headliner | Adam Carolla, host of the most downloaded podcast in the world |
| Dress Code | Business casual |
| Stay | A hotel block is available at Seminole Hard Rock Hotel & Casino Tampa for guests traveling in for the event |
This Year’s Headliner
Adam Carolla
Adam Carolla is a comedian, actor, and New York Times best-selling author, and host of The Adam Carolla Show, the most downloaded podcast in the world. Known for his sharp, observational humor, he’s starred in The Man Show, Crank Yankers, and Loveline, and continues to tour nationally as a stand-up comic. His headline set anchors an evening that stands apart from any other comedy show in Tampa this year.
More Than a Party
Guys Night Out is more than a comedy show or a car show. It’s a full evening built around connection, hosted by two names synonymous with Tampa Bay hospitality and motorsports. Expect headline comedy, exotic cars under the stars, luxury goods worth millions, and a cause that turns a great night out into something that actually changes lives.
What Makes It Different, Tampa’s Luxury Car Show and Comedy Event
Hosted by Brad Oleshansky (Founder/CEO of The Motor Enclave, North America’s most exhilarating motorsports and private event venue) and Jeff Gigante (Founder of Next Level Brands Hospitality, a leading restaurateur recognized for elevating the Tampa Bay region’s food and hospitality landscape).
Headline Comedy
01
Each edition brings a nationally known comedian to headline the night, with special guest appearances throughout the evening, instantly elevating any Tampa comedy show.
Exotic Car Show Under The Stars
02
A curated lineup of exotic and luxury vehicles sets the scene, giving this Tampa car show a backdrop no typical comedy venue can match.
A Luxury Goods and Collectibles Lounge
03
Watches, wine, spirits, cigars, collectible cards, and celebrity and sports memorabilia, curated by some of the nation’s top purveyors.
Purpose-Driven Impact
04
Every ticket fuels mentorship for Tampa Bay youth through Big Brothers Big Sisters, turning a night out with the guys into a night that matters.
Event Features
- Headline comedy show with special guest appearances
- Exotic car show under the stars
- Luxury goods and collectables lounge (watches, wine, spirits, cigars, collectible cards, celebrity and sports memorabilia) curated by the nation’s top purveyors
- Bold bites and signature cocktails presented by Next Level Brands mixologists
- Enclave Race Lab advanced sim competition with a cash prize
- Autocross thrill ride competition with celebrity driving instructors
A Cause Worth Showing Up For
“Guys Night Out is about recognizing the men in our community who show up, lead, and make a difference. Through our partnership with Big Brothers Big Sisters of Tampa Bay, we have the opportunity to turn that energy into real impact by encouraging more men to step into the role of a mentor and change a child’s life.”
– Brad Oleshansky, Founder & CEO, The Motor Enclave
Enjoy a night out with the guys and join some of the Tampa Bay region’s most engaged and generous professionals to rally around a cause that helps fuel life-changing mentorship for the youth in our community. Because when we show up for our city’s kids, everyone wins.
The Start of an Annual Tradition
Guys Night Out is a new annual Enclave Signature Event, joining Cars En Coffee as one of The Motor Enclave’s flagship gatherings. This year, the night ties into the same weekend as Cars En Coffee, and future editions will continue that pairing, turning the weekend into a full Tampa events experience for car culture, comedy, and community alike.
Everything You Need to Know
Who
Tampa Bay’s most engaged and generous professionals, car enthusiasts, comedy fans, and anyone looking for a standout guys night out
What
A luxury comedy show and car show combining premium access, live headline comedy, immersive driving experiences, curated lounges, and top-tier food and cocktails
Where
The Motor Enclave, 6500 Motor Enclave Way, Tampa, FL 33610, widely regarded as Tampa’s most unique event venue and a Tampa event space unlike any other in the region
Why
Because this is what giving back looks like in Tampa: a night of car culture, comedy, and connection benefiting Big Brothers Big Sisters of Tampa Bay, now and in the years to come
Sponsorship, Sponsor Guys Night Out at The Motor Enclave
Hosted at one of the most sought-after event spaces in Tampa, Guys Night Out is quickly becoming one of the most talked about events in Tampa for brands looking to connect with an affluent, highly engaged audience across automotive, hospitality, and lifestyle categories. As a new annual Enclave Signature Event, it offers sponsors an ongoing platform alongside a cause-driven, headline-comedy, luxury car show event. Sponsorship opportunities are available at multiple levels.
Join The Experience
Tampa’s Biggest Guys Night Out
Whether you’re searching for a comedy show in Tampa, a luxury car show, or simply one of the best Tampa event venues for a night out, Guys Night Out at The Motor Enclave delivers all three in one evening, with a cause behind every ticket. Check this year’s details above and don’t wait to lock in your spot.
Still Have Questions? Contact Our Team
Have a question about tickets, sponsorship, or attending Guys Night Out? Send our team a message and we’ll get back to you.
Or reach us directly at info@themotorenclave.com or 877-8-ENCLAVE (877-836-2528)
