This restaurant has a fun coastal tiki vibe, great food (scratch kitchen), cold drinks, and live music out by the tiki bar. They don’t take reservations so make sure to arrive early enough to snag a good spot.
Ocala Preserve is a private gated community but these events are open and free to the public.
Join us at this free afternoon outdoor event in The Villages. Don’t worry, there is plenty of shade!
Chill vibes, classic tunes and delicious beverages under beautiful shady trees. Pets are welcome too! What more could you ask for?
Helpful Tips: Make sure to get there early and bring lawn chairs just in case, as seating is limited. If the weather isn’t being cooperative, we may move inside and seating is VERY limited there so please keep an eye on our socials for updates.
We’ll be performing several of our own main stage shows as guest entertainers with the ship’s onboard show band during this voyage. For more information about these cruises please visit Oceania’s website or contact our preferred travel agent, Tim Elrod.
If you are interested in joining us on one of our yearly private fan cruises please shoot us an email and we’ll send you more info.
We’ll be performing several of our own main stage shows as guest entertainers with the ship’s onboard show band during this voyage. For more information about these cruises please visit Regent Seven Seas or contact our preferred travel agent, Tim Elrod.
If you are interested in joining us on one of our yearly private fan cruises please shoot us an email and we’ll send you more info.
Chill vibes, classic tunes and delicious beverages under beautiful shady trees. Pets are welcome too! What more could you ask for?
Helpful Tips: Make sure to get there early and bring lawn chairs just in case, as seating is limited. If the weather isn’t being cooperative, we may move inside and seating is VERY limited there so please keep an eye on our socials for updates.
Come join us at this outdoor venue in The Villages! Tonight we are playing as a trio to give our sound that extra kick.
We will be playing inside of the Margaritaville Restaurant located on Universal’s City Walk NOT to be mistaken with the Margaritaville Resort which is in a completely different city.
Reservations are encouraged. Please ask to be seated near the entertainment.
We are back at Eden Abbey Brewery! Delicious beverages and grub plus a very chill vibe at this Mt. Dora favorite. Reservations are highly recommended as seating in the live entertainment area is very limited.
This restaurant has a fun coastal tiki vibe, great food (scratch kitchen), cold drinks, and live music out by the tiki bar. They don’t take reservations so make sure to arrive early enough to snag a good spot.
Shoot us an email if you’d like to book us for your next private event!
Chill vibes, classic tunes and delicious beverages under beautiful shady trees. Pets are welcome too! What more could you ask for?
Helpful Tips: Make sure to get there early and bring lawn chairs just in case, as seating is limited. If the weather isn’t being cooperative, we may move inside and seating is VERY limited there so please keep an eye on our socials for updates.
Shoot us an email if you’d like to book us for your next private event!
Shoot us an email if you’d like to book us for your next private event!
Shoot us an email if you’d like to book us for your next private event!
Ocala Preserve is a private gated community but these events are open and free to the public.
Chill vibes, classic tunes and delicious beverages under beautiful shady trees. Pets are welcome too! What more could you ask for?
Helpful Tips: Make sure to get there early and bring lawn chairs just in case, as seating is limited. If the weather isn’t being cooperative, we may move inside and seating is VERY limited there so please keep an eye on our socials for updates.
Please note: Council Oaks is a reservation-only, fine-dining restaurant, and the venue requires active dining and regular table turnover throughout the evening.
Guests are not permitted to “camp out” for the duration of our four-hour set, even if dining.
Thank you for understanding and for supporting us by respecting the restaurant’s policies.
Shoot us an email if you’d like to book us for your next private event!
Come join us at this outdoor venue in The Villages! Tonight we are playing as a trio to give our sound that extra kick.
We will be playing inside of the Margaritaville Restaurant located on Universal’s City Walk NOT to be mistaken with the Margaritaville Resort which is in a completely different city.
Reservations are encouraged. Please ask to be seated near the entertainment.
This restaurant has a fun coastal tiki vibe, great food (scratch kitchen), cold drinks, and live music out by the tiki bar. They don’t take reservations so make sure to arrive early enough to snag a good spot.
Shoot us an email if you’d like to book us for your next private event!
Chill vibes, classic tunes and delicious beverages under beautiful shady trees. Pets are welcome too! What more could you ask for?
Helpful Tips: Make sure to get there early and bring lawn chairs just in case, as seating is limited. If the weather isn’t being cooperative, we may move inside and seating is VERY limited there so please keep an eye on our socials for updates.
Join us at this free afternoon outdoor event in The Villages. Don’t worry, there is plenty of shade!
We’ll be performing several of our own main stage shows as guest entertainers with the ship’s onboard show band during this voyage. For more information about these cruises please visit Regent Seven Seas or contact our preferred travel agent, Tim Elrod.
If you are interested in joining us on one of our yearly private fan cruises please shoot us an email and we’ll send you more info.
We’ll be performing several of our own main stage shows as guest entertainers with the ship’s onboard show band during this voyage. For more information about these cruises please visit Regent Seven Seas or contact our preferred travel agent, Tim Elrod.
If you are interested in joining us on one of our yearly private fan cruises please shoot us an email and we’ll send you more info.
Come join us at this outdoor venue in The Villages! Tonight we are playing as a trio to give our sound that extra kick.
Chill vibes, classic tunes and delicious beverages under beautiful shady trees. Pets are welcome too! What more could you ask for?
Helpful Tips: Make sure to get there early and bring lawn chairs just in case, as seating is limited. If the weather isn’t being cooperative, we may move inside and seating is VERY limited there so please keep an eye on our socials for updates.
Join us at the Euphoria Lounge inside the beautiful Margaritaville Resort! You don’t have to be a guest of the hotel in order to attend this gig.
We're looking forward to a fun night at the Waggon & Horses in Great Yeldham on Thursday, August 21 from 8:45-10:45pm. We're so excited that our friends The Overtures will be joining us again for a few songs during the night. If you're anywhere near Essex, we'd love to see you there for a little pub gig.
You read that right! We are playing at THE Cavern Club in Liverpool, England and if you don’t know why this is a big deal, you must not be a big Beatles fan like Charity (haha!).
Join us at the legendary Cavern Club for a 45-minute performance starting at 2:15pm on the Front Stage!
If you're in Liverpool that afternoon, we'd love to see you there. Admission to the Cavern Club is £6, and your ticket includes access to the Front Stage where we'll be performing.
This is our 4th Annual Gilly & the Girl Getaway Cruise, sailing August 2–14, 2026 aboard the luxurious Celebrity Eclipse! This incredible itinerary departs from Amsterdam and explores the stunning British Isles (England, Scotland & Northern Ireland) and Ireland, as well. As always, we’ll be performing throughout the trip and hosting exclusive events so we can spend plenty of time with our amazing fans.
This sailing is already popular with Celebrity guests, so space is becoming limited. To join our private events onboard, you must book through our travel agent, Tim Elrod at Travelmation (Tim@travelmation.net). Don’t wait! Secure your spot today and get ready for a bucket list adventure with us!
Mark your calendars for July 30th!
We’re excited to be part of a really fun night centered around good food, good wine, and live music hosted by Sandy’s Shack in Ocala, FL
This will be a 5-course dinner with wine pairings, designed to feel elevated but still relaxed and easygoing. We’ll be playing live music throughout the evening to keep things flowing and fun.
What to expect:
• 5-course dinner
• Wine pairings
• Live music by yours truly
• A laid-back night out with great people
Great for a date night, a night out with friends, or just doing something a little different.
Seating is limited and reservations are required.
For any Villagers that want to join in on this event, for $20 per person you can sign up for round trip transportation on the “Chuckle Bus” — a 20 person passenger van with karaoke and drinks! Email Sandy to book and for more info — sandy@sandysshack.com
Event Tickets Available HERE
Hosted by Sandy’s Shack
Venue - The Barn at Bellemoor
**We've had a last minute add to our schedule this month so mark your calendars if you live near or are going to be around the Lake Nona area on July 26th!
Boxi Park is a great place to hang with your friends, family and even pets! You can find a ton of different food and beverage options in this trendy neighborhood of Orlando.
Come spend the afternoon with us!
Charity will be singing lead with Beauty & the Beats at Eastport in The Villages
Weather Permitting
Join us at the Euphoria Lounge inside the beautiful Margaritaville Resort! You don’t have to be a guest of the hotel in order to attend this gig.
🌴 New venue alert! 🌴
We're excited to be making our debut at Harry and The Natives at The Villages on Wednesday, July 15 from 5:00-8:00 PM!
If you haven't been yet, they've got a fun coastal tiki vibe, great food (scratch kitchen), cold drinks, and live music out by the tiki bar. Sounds like the perfect way to spend a Wednesday evening.
If you're nearby, we'd love to see some familiar faces helping us kick off our very first show there!
Chill vibes, classic tunes and delicious beverages under beautiful shady trees. Pets are welcome too! What more could you ask for?
Helpful Tips: Make sure to get there early and bring lawn chairs just in case, as seating is limited. If the weather isn’t being cooperative, we may move inside and seating is VERY limited there so please keep an eye on our socials for updates.
If you love beer, Korean food and a cold AC in the Summertime, you gotta come see us at this excellent family owned and run brewery in Inverness. We always have a great time here!
Come join us at this outdoor venue in The Villages! Tonight we are playing as a trio to give our sound that extra kick.
Charity will be singing lead with Beauty & the Beats at Sumter Landing Square in The Villages
Weather Permitting
Chill vibes, classic tunes and delicious beverages under beautiful shady trees. Pets are welcome too! What more could you ask for?
Helpful Tips: Make sure to get there early and bring lawn chairs just in case, as seating is limited. If the weather isn’t being cooperative, we may move inside and seating is VERY limited there so please keep an eye on our socials for updates.
Join us at the Euphoria Lounge inside the beautiful Margaritaville Resort! You don’t have to be a guest of the hotel in order to attend this gig.
Clearly, Charity wasn’t too pleased to be joining us here on Earth.
Private show at the Wynmoor Theater in Coconut Creek
Interested in booking one of our 90 minute stage shows? Please contact Steve Parry for more information.
Private show for the Valencia Grand Community in Boynton Beach
Interested in booking one of our 90 minute stage shows? Please contact Steve Parry for more information.
Private show for the Valencia Walk Community in Port St. Lucie
Interested in booking one of our 90 minute stage shows? Please contact Steve Parry for more information.
Shoot us an email if you’d like to book us for your next private event!
Chill vibes, classic tunes and delicious beverages under beautiful shady trees. Pets are welcome too! What more could you ask for?
Helpful Tips: Make sure to get there early and bring lawn chairs just in case, as seating is limited. If the weather isn’t being cooperative, we may move inside and seating is VERY limited there so please keep an eye on our socials for updates.
Ocala Preserve is a private gated community but these events are open and free to the public.
I don’t do this very often… and that’s exactly why I’m doing it.
On June 17 at Judson’s Live (Dr. Phillips Center), I’ll be stepping on stage without Mike for a very different kind of night.
This show goes back to my musical theater roots, with some adult contemporary and classic standards mixed in. Just me, a pianist, and a few special guests. Intimate table seating. Very limited tickets.
I won’t lie… doing this solo is a little scary. So I’d love to see some familiar faces out there.
https://www.drphillipscenter.org/events/tickets/2026/charity-gill/
Hope you’ll join me. 💛
Check out Charity’s band Beauty & the Beats playing at Edna’s on the Green under the big, beautiful trees. Bring your folding chairs!
Come join us at this outdoor venue in The Villages! Tonight we are playing as a trio to give our sound that extra kick.
Chill vibes, classic tunes and delicious beverages under beautiful shady trees. Pets are welcome too! What more could you ask for?
Helpful Tips: Make sure to get there early and bring lawn chairs just in case, as seating is limited. If the weather isn’t being cooperative, we may move inside and seating is VERY limited there so please keep an eye on our socials for updates.
Join us at the Euphoria Lounge inside the beautiful Margaritaville Resort! You don’t have to be a guest of the hotel in order to attend this gig.
Photography by Pratik Kshirsagar, Chris Gritti, Daniel Jordan, Michael Cairns & Kirk Marsh
Videography by Aucoin Film, Daniel Jordan, Kenji Umei & Becky Wassel