Upcoming Events

This page shows the upcoming events in chronological order.

ISLANDFEST WEEKEND, Jul 20 - 22

20 July 2018

Come join us for a taste of the Islands - the music, the food, the dance, the fun, the relaxation - we've got it all for you! We're getting you warmed up for Parrothead, which is only a week away! One thing you don't want to miss is the chance to win a tent for Parrothead right next to DJ Xavier's cabana. How do you win that? You enter the Lip Sync Battle Contest on Friday night. Winner gets the use of the air-conditioned tent for the duration of Parrothead, along with Dinner for Two at Cheeks! 

Weekend Highlights:

Friday

  • Welcome Beach Party w/ DJ Shawn, South Beach, 2 PM
  • Streak at Cheeks & Lip Sync Contest w/ DJ Xavier, Cheeks, 7 PM

Saturday

  • Pool Party w/ DJ Xavier, West Pool, 12 PM
  • Islandfest Dance w/ The Craig Thompson Project, Lakeside Restaurant, 7 PM
  • Late Night Streak at Cheeks w/ DJ Ty, Cheeks, 10 PM

Sunday

  • Live Music by the Pool w/ Del, West Pool, 12 PM

PARROTHEAD WEEKEND, July 26 - 29

26 July 2018

Ahhhhh, Parrothead Weekend ... THE PARTY event of the year at Cypress Cove Resort! So much fun that we had to extend the weekend to begin on Thursday in order to fit it all in! What's a Parrothead? Parrotheads love Jimmy Buffett music. Parrotheads love that laid back island culture ... and Parrotheads love to PARTY! Are you READY?

Weekend Highlights:

Thursday

  • Parrothead Kick Off Pool Party w/ DJ Shawn, West Pool, 1 PM
  • Parrothead Pool Party w/ DJ Xavier, West Pool, 7 PM

Friday

  • Parrothead Pool Party w/ DJ Xavier, West Pool, 12 PM
  • Welcome Beach Party w/ DJ Shawn, South Beach, 2 PM
  • Streak at Cheeks w/ DJ Greg, Cheeks, 7 PM

Saturday

  • Parrothead Pool Party w/ DJ Xavier, West Pool, 12 PM
  • Parrothead Parade, Cove Wide, 1 PM 
  • Parrothead Beach Party w/ DJ Shawn, South Beach, 2 PM
  • Crafts & Cocktails w/ Melanie, Scuttlebutts, 4 PM
  • Parrothead Dance w/ The Conch Man Band, Lakeside Restaurant, 7 PM
  • Late Night Streak at Cheeks w/ DJ Ty, Cheeks, 10 PM

Sunday

  • Live Music by the Pool w/ Jim, West Pool, 12 PM

ANYTHING BUT CLOTHES WEEKEND, Aug 3 - 5

3 August 2018

What could we wear if we didn't have fabric? Obviously, we enjoy being nude - but sometimes we want to "dress up"! So, what would you wear if there were no such thing as clothes? It's always fun to see the interesting creations people come up with! 

Weekend Highlights:

Friday

  • Welcome Beach Party w/ DJ Shawn, South Beach, 2 PM
  • Magic/Comedy Night w/ TBA, Lakeside, 8 PM

Saturday

  • Pool Party w/ DJ Xavier, West Pool, 12 PM
  • Anything But Clothes Dance w/ DJ Greg, Lakeside Restaurant, 7 PM
  • Late Night Streak at Cheeks w/ DJ Ty, Cheeks, 10 PM

Sunday

  • Live Music by the Pool w/ Peter, West Pool, 12 PM

BRITISH INVASION WEEKEND, Aug 10 - 12

10 August 2018

The Brits are coming! Well, their music is coming and we love it! Yeah, yeah, yeah! 

Weekend Highlights:

Friday

  • Welcome Beach Party w/ DJ Shawn, South Beach, 2 PM
  • Karaoke Party w/ Mr. Breezz, Scuttlebutts, 7 PM

Saturday

  • Pool Party w/ DJ Xavier, West Pool, 12 PM
  • Superstar Nights featuring a Tribute to the British Invasion, Lakeside Restaurant, 8 PM
  • Late Night Streak at Cheeks w/ DJ Ty, Cheeks, 10 PM

Sunday

  • Live Music by the Pool w/ Jon, West Pool, 12 PM

PROFESSIONAL BODY PAINTING WEEKEND, Aug 17 - 19

17 August 2018

We are happy to invite you to our 7th Annual Professional Body Painting Contest! This year's theme is "Animal Instincts" - come see what these talented artists create with a human canvas! You can watch them paint during the day on Saturday - and see the finished artistic expressions at the dance Saturday night at Lakeside Restaurant. For more information or to sign up to enter the contest, click here

Weekend Highlights:

Friday

  • Welcome Beach Party w/ DJ Shawn, South Beach, 2 PM
  • Streak at Cheeks w/ DJ TBA, Cheeks, 7 PM

Saturday

  • Pool Party w/ DJ Greg, West Pool, 12 PM
  • Professional Body Painting Contest & Dance w/ DJ Xavier, Lakeside Restaurant, 7 PM
  • Late Night Streak at Cheeks w/ DJ Ty, Cheeks, 10 PM

Sunday

  • Live Music by the Pool w/ Rick, West Pool, 12 PM