New Year’s Vegas Night on the Beach, Rat Pack & Comedy by Jim Florentine

Step out of the Keys and straight onto the Strip.
This New Year’s Eve, we’re turning the beach into a vintage 1960s Vegas showroom – think Rat Pack swagger, showgirls, swinging tunes, and big laughs as we count down to midnight together.

Join us for New Year’s Vegas Night on the beach featuring:

• 🎙 Live Rat Pack Tribute – Sinatra, Dean, and Sammy–style hits that will have you snapping your fingers and singing along.
• 😂 Full Comedy Show by Jim Florentine – National headliner comedian best known as a co-host of VH1 Classic’s That Metal Show and for voicing iconic characters on Comedy Central’s Crank Yankers. Wikipedia+1
• 🌴 Dancers & Vegas-Style Atmosphere – High-energy dancers and a classic lounge-show vibe, right on the sand.
• 🍽 Beachfront Buffet – Served from 8:30 PM – 11:00 PM.
• 🥂 Midnight Toast & Party Favors – Ring in the New Year with a bubbly toast and festive party gear.
• 📺 Live Stream of the NYC Ball Drop – Watch the Times Square countdown on a big screen while your toes are in the sand.
• 🚗 Free Parking – Park, party, and relax.

All of this happens right on the beach, under the night sky, with the ocean as your backdrop.

Our comedy headliner, Jim Florentine, has been making audiences laugh around the world for more than two decades. He’s:

• A former co-host of VH1 Classic’s That Metal Show, the beloved talk show for hard rock and heavy metal fans. Wikipedia+1
• The voice behind memorable characters on Comedy Central’s Crank Yankers, including Special Ed and Bobby Fletcher. Wikipedia+1
• Appeared in hit TV shows and films like Louie, Inside Amy Schumer, and Trainwreck. Wikipedia+1
• A prolific stand-up with multiple comedy albums and specials, as well as the author of the bestselling book Everybody Is Awful (Except You!). Wikipedia+2Uncle Vinnie's Comedy Club+2
• Host of his own SiriusXM radio show and popular podcast. Uncle Vinnie's Comedy Club+1

Expect sharp, smart, no-holds-barred comedy – classic Vegas edge with a modern twist.

Date: Wednesday, December 31
Time:

• Doors open: 7:30 PM
• Event starts: 8:00 PM
• Buffet: 8:30 PM – 11:00 PM
• Midnight toast & NYC ball drop live stream: 12:00 AM

Location:
On the beach at Island Grill (85501 Overseas Hwy, Islamorada, FL).

Adults: $125

• Includes Rat Pack live tribute, Jim Florentine comedy show, dancers, buffet (8:30 PM–11 PM), midnight toast, party favors, and access to the NYC ball drop live stream.

Kids (11 years and younger): $29

• Includes buffet (8:30 PM–11 PM)

🎟 Tickets available online only. Capacity is limited – once we’re sold out, we’re sold out.

• 🪑 Seating is first come, first served.
• There are no table reservations for this event.
• If you’d like to sit together as a group, we recommend arriving when doors open at 7:30 PM.
• 🌴 This is a beachfront event, so expect a relaxed, resort-style setting with a Vegas twist.
• 👗 Dress code: Resort-casual to Vegas chic. Cocktail attire, fun Vegas-inspired outfits, or dressed-up Keys casual are all welcome.

• 1960s Vegas-style New Year’s Eve right on the sand
• Rat Pack live tribute
• Full stand-up comedy show by Jim Florentine
• Dancers and vintage showroom energy
• Buffet from 8:30 PM – 11:00 PM
• Midnight champagne toast (for adults)
• Party favors for extra sparkle
• Free parking
• Live stream of the NYC Times Square ball drop on a big screen

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Host or Publisher ISLAND GRILL ISLAMORADA