Jul
30
6:00 PM18:00

The Barn at Bellemoor (Belleview)

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

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Aug
2
to Aug 14

The 4th Annual Gilly & the Girl Getaway Cruise

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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!

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Aug
8
2:15 PM14:15

The Cavern Club (Liverpool, UK)

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.

Cavern Club

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Sep
5
4:00 PM16:00

Edna's on the Green (Wildwood)

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.

Edna’s on the Green

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Sep
20
12:00 PM12:00

Edna's on the Green (Wildwood)

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.

Edna’s on the Green

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Sep
23
to Oct 1

Oceania Riviera Cruise

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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.

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Oct
5
to Oct 19

Regent Seven Seas Explorer Cruise

  • Google Calendar ICS

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.

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Oct
24
12:00 PM12:00

Edna's on the Green (Wildwood)

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.

Edna’s on the Green

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Jan
28
to Feb 7

Regent Seven Seas Splendor Cruise

  • Google Calendar ICS

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.

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Feb
22
to Mar 1

Regent Seven Seas Prestige Cruise

  • Google Calendar ICS

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.

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Jul
26
1:00 PM13:00

Boxi Park (Orlando)

**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!

Boxi Park

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Jul
15
5:00 PM17:00

Harry & the Natives (The Villages)

🌴 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!

Harry & the Natives

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Jul
11
4:00 PM16:00

Edna's on the Green (Wildwood)

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.

Edna’s on the Green

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Jul
3
3:00 PM15:00

Edna's on the Green (Wildwood)

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.

Edna’s on the Green

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Jun
21
12:00 PM12:00

Edna's on the Green (Wildwood)

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.

Edna’s on the Green

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Jun
17
7:00 PM19:00

Charity's Solo Cabaret (Orlando)

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. 💛

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Jun
6
4:00 PM16:00

Edna's on the Green (Wildwood)

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.

Edna’s on the Green

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Jun
2
5:00 PM17:00

North Lake Presbyterian Church (Lady Lake)

We’re excited to be part of a special Dinner & Show event on Tuesday, June 2 at North Lake Presbyterian Church in Lady Lake.

Dinner begins at 5:00 PM, and we’ll be performing a 45–60 minute acoustic set starting at 6:00 PM.

We’ll be playing our usual repertoire so basically a mix of classics and crowd favorites. It’s not a religious set, just the music you’re used to hearing from us… but in a church setting :)

Dinner is optional, but admission is $10 per person either way, so you’re welcome to come just for the show.

You can purchase tickets via this LINK. Deadline for online reservations is Thursday, May 28 by 12:00 p.m

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May
17
12:00 PM12:00

Edna's on the Green (Wildwood)

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.

Edna’s on the Green

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May
15
8:00 PM20:00

Hard Rock Resort (Tampa)

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.

Council Oaks Steaks & Seafood

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